51:
5309:
lipophilicity increasing brain penetration. For several classes of CNS active substances, Hansch and Leo54 found that blood-brain barrier penetration is optimal when the LogP values are in the range of 1.5-2.7, with the mean value of 2.1. An analysis of small drug-like molecules suggested that for better brain permeation46 and for good intestinal permeability55 the LogD values need to be greater than 0 and less than 3. In comparison, the mean value for ClogP for the marketed CNS drugs is 2.5, which is in good agreement with the range found by Hansch et al.22
603:
580:
2025:
1997:
42:
1817:
2508:(FDA) issued a public health advisory against the use of the drug in November 2000. In this advisory, the FDA requested but did not require that all drug companies discontinue marketing products containing PPA. The agency estimates that PPA caused between 200 and 500 strokes per year among 18-to-49-year-old users. In 2005, the FDA removed PPA from over-the-counter sale and removed its "generally recognized as safe and effective" (GRASE) status. Under the 2020
6176:
4608:
man. ... The lack of effect of administration of neomycin to one patient indicates that the hydroxylation occurs in body tissues. ... a major portion of the β-hydroxylation of hydroxyamphetamine occurs in non-adrenal tissue. Unfortunately, at the present time one cannot be completely certain that the hydroxylation of hydroxyamphetamine in vivo is accomplished by the same enzyme which converts dopamine to noradrenaline.
4916:β-Phenylethylamine (Table 12–1) can be viewed as the parent compound of the sympathomimetic amines, consisting of a benzene ring and an ethylamine side chain. The structure permits substitutions to be made on the aromatic ring, the α- and β-carbon atoms, and the terminal amino group to yield a variety of compounds with sympathomimetic activity. ...N-methylation increases the potency of primary amines ...
4755:
The observed lack of a significant accumulation of PHN in brain following the intraventricular administration of (+)-amphetamine and the formation of appreciable amounts of PHN from (+)-POH in brain tissue in vivo supports the view that the aromatic hydroxylation of amphetamine following its systemic
1398:
Many sympathetic hormones and neurotransmitters are based on the phenethylamine skeleton, and function generally in "fight or flight" type responses, such as increasing heart rate, blood pressure, dilating the pupils, increased energy, drying of mucous membranes, increased sweating, and a significant
5308:
Lipophilicity was the first of the descriptors to be identified as important for CNS penetration. Hansch and Leo54 reasoned that highly lipophilic molecules will partitioned into the lipid interior of membranes and will be retained there. However, ClogP correlates nicely with LogBBB with increasing
4702:
The biologic significance of the different levels of serum DβH activity was studied in two ways. First, in vivo ability to β-hydroxylate the synthetic substrate hydroxyamphetamine was compared in two subjects with low serum DβH activity and two subjects with average activity. ... In one study,
4655:
Figure 1. Glycine conjugation of benzoic acid. The glycine conjugation pathway consists of two steps. First benzoate is ligated to CoASH to form the high-energy benzoyl-CoA thioester. This reaction is catalyzed by the HXM-A and HXM-B medium-chain acid:CoA ligases and requires energy in the form of
4925:
Substitution of a hydroxyl group on the β carbon generally decreases actions within the CNS, largely because it lowers lipid solubility. However, such substitution greatly enhances agonist activity at both α- and β- adrenergic receptors. Although ephedrine is less potent than methamphetamine as a
4607:
Hydroxyamphetamine was administered orally to five human subjects ... Since conversion of hydroxyamphetamine to hydroxynorephedrine occurs in vitro by the action of dopamine-β-oxidase, a simple method is suggested for measuring the activity of this enzyme and the effect of its inhibitors in
4920:
This substitution blocks oxidation by MAO, greatly prolonging the duration of action of non-catecholamines because their degradation depends largely on the action of this enzyme. The duration of action of drugs such as ephedrine or amphetamine is thus measured in hours rather than in minutes.
4356:
The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class
3568:
Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, et al. (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates".
2425:
Brand names of PPA have included
Acutrim, Appedrine, Capton Diet, Control, Dexatrim, Emagrin Plus A.P., Glifentol, Kontexin, Merex, Monydrin, Mydriatine, Prolamine, Propadrine, Propagest, Recatol, Rinexin, Tinaroc, and Westrim, among many others. It has also been used in
5032:
Metamfetamine acts in a manner similar to amfetamine, but with the addition of the methyl group to the chemical structure. It is more lipophilic (Log p value 2.07, compared with 1.76 for amfetamine), thereby enabling rapid and extensive transport across the blood–brain
4703:
hydroxyamphetamine (Paredrine), a synthetic substrate for DβH, was administered to subjects with either low or average levels of serum DβH activity. The percent of the drug hydroxylated to hydroxynorephedrine was comparable in all subjects (6.5-9.62) (Table 3).
4656:
ATP. ... The benzoyl-CoA is then conjugated to glycine by GLYAT to form hippuric acid, releasing CoASH. In addition to the factors listed in the boxes, the levels of ATP, CoASH, and glycine may influence the overall rate of the glycine conjugation pathway.
4753:-hydroxylation and β-hydroxylation reactions is important in species where aromatic hydroxylation of amphetamine is the predominant pathway of metabolism. Following systemic administration of amphetamine to rats, POH has been found in urine and in plasma.
4756:
administration occurs predominantly in the periphery, and that POH is then transported through the blood-brain barrier, taken up by noradrenergic neurones in brain where (+)-POH is converted in the storage vesicles by dopamine β-hydroxylase to PHN.
971:
occurring in the user, resulting in a strong sensation that an event or experience currently being experienced has already been experienced in the past. Some pharmaceutical drugs, when taken together, have also been implicated in the cause of
2535:
4084:
Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin".
4921:
Similarly, compounds with an α-methyl substituent persist in the nerve terminals and are more likely to release NE from storage sites. Agents such as metaraminol exhibit a greater degree of indirect sympathomimetic activity.
4620:
Badenhorst CP, van der Sluis R, Erasmus E, van Dijk AA (September 2013). "Glycine conjugation: importance in metabolism, the role of glycine N-acyltransferase, and factors that influence interindividual variation".
984:
and PPA together to relieve flu symptoms. He found the experience so interesting that he completed the full course of his treatment and reported it to the psychologists to write up as a case study. Because of the
4500:
Cashman JR, Xiong YN, Xu L, Janowsky A (March 1999). "N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication".
4357:(39). ... The phase 1 metabolism of amphetamine analogs is catalyzed by two systems: cytochrome P450 and flavin monooxygenase. ... Amphetamine can also undergo aromatic hydroxylation to
3927:
Greenway F, Herber D, Raum W, Herber D, Morales S (July 1999). "Double-blind, randomized, placebo-controlled clinical trials with non-prescription medications for the treatment of obesity".
218:
6106:
4527:
Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection".
2180:
PPA, structurally, is in the substituted phenethylamine class, consisting of a cyclic benzene or phenyl group, a two carbon ethyl moiety, and a terminal nitrogen, hence the name
4898:
Westfall DP, Westfall TC (2010). "Chapter 12: Adrenergic
Agonists and Antagonists: CLASSIFICATION OF SYMPATHOMIMETIC DRUGS". In Brunton LL, Chabner BA, Knollmann BC (eds.).
5399:
11735:
2541:
Drugs containing PPA were banned in India on 27 January 2011. On 13 September 2011, Madras High Court revoked a ban on manufacture and sale of pediatric drugs PPA and
1539:(CNS) effects. Hence, PPA crosses into the brain only to some extent, has only weak CNS effects, and most of its effects are peripheral. In any case, PPA can produce
2774:
2501:
and could also be purchased on its own; however, it is no longer approved for human use. A European
Category 1 Licence is required to purchase PPA for academic use.
7491:
13614:
2769:[Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
14225:
2207:
to be active at all but the highest doses. However, the addition of the α-methyl group allows the compound to avoid metabolism and confer an effect. In general,
13609:
5534:
3404:
Yoon BW, Bae HJ, Hong KS, Lee SM, Park BJ, Yu KH, et al. (January 2007). "Phenylpropanolamine contained in cold remedies and risk of hemorrhagic stroke".
163:
3252:
Salerno SM, Jackson JL, Berbano EP (August 2005). "The impact of oral phenylpropanolamine on blood pressure: a meta-analysis and review of the literature".
2257:
than other amphetamines. The lipophilicity of amphetamines is closely related to their brain permeability. For comparison to PPA, the experimental log P of
9843:
4966:
Bharate SS, Mignani S, Vishwakarma RA (December 2018). "Why Are the
Majority of Active Compounds in the CNS Domain Natural Products? A Critical Analysis".
3962:
Taiminen T, Jääskeläinen SK (September 2001). "Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male".
2467:
6026:
4668:
Horwitz D, Alexander RW, Lovenberg W, Keiser HR (May 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity".
870:
from many markets starting in 2000 following findings that it was associated with increased risk of hemorrhagic stroke. It was previously available both
4005:
Bancaud J, Brunet-Bourgin F, Chauvel P, Halgren E (February 1994). "Anatomical origin of déjà vu and vivid 'memories' in human temporal lobe epilepsy".
14155:
7568:
6715:
5499:
4715:
Freeman JJ, Sulser F (December 1974). "Formation of p-hydroxynorephedrine in brain following intraventricular administration of p-hydroxyamphetamine".
4269:
Patrick KS, Markowitz JS (1997). "Pharmacology of methylphenidate, amphetamine enantiomers and pemoline in attention-deficit hyperactivity disorder".
231:
4768:
Matsuda LA, Hanson GR, Gibb JW (December 1989). "Neurochemical effects of amphetamine metabolites on central dopaminergic and serotonergic systems".
243:
6066:
5477:
8433:
8413:
5321:
105:
4282:
11908:
7484:
7263:
7175:
6212:
5854:
3502:
Rothman RB, Baumann MH (December 2005). "Targeted screening for biogenic amine transporters: potential applications for natural products".
680:
14160:
12333:
2722:
2520:
2211:-methylation of primary amines increases their potency, whereas β-hydroxylation decreases CNS activity, but conveys more selectivity for
13644:
13639:
11464:
12692:
12642:
4122:"Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products"
3212:
Ioannides-Demos LL, Proietto J, Tonkin AM, McNeil JJ (2006). "Safety of drug therapies used for weight loss and treatment of obesity".
2342:, human use of PPA and its formulations was banned on 10 February 2011, but the ban was overturned by the judiciary in September 2011.
13659:
13634:
5546:
12378:
12373:
12368:
12363:
12353:
12348:
12343:
12338:
12328:
12318:
12308:
12288:
12278:
12273:
12268:
12083:
12023:
13654:
13649:
13629:
13624:
14190:
12248:
12243:
12193:
11986:
9836:
9799:
7171:
6021:
666:
12213:
12103:
12093:
12088:
11790:
7477:
1492:
5580:
5172:"Substitution of phenylephrine for pseudoephedrine as a nasal decongeststant. An illogical way to control methamphetamine abuse"
14200:
12662:
11970:
9781:
9772:
6708:
3818:
725:
14220:
14195:
13187:
9763:
7435:
6659:
5677:
5640:
5613:
4830:
3622:
3174:
3129:
2680:
4098:
2478:
In Sweden, PPA is still available in prescription decongestants; PPA is also still available in
Germany. It is used in some
2338:, it was withdrawn from the market on 31 May 2001. It was voluntarily withdrawn from the Australian market by July 2001. In
11609:
10901:
10249:
1072:
4749:-hydroxynorephedrine (PHN) may contribute to the pharmacological profile of the parent drug. ... The location of the
2766:
2319:
effects of PPA were characterized in the late 1920s and the 1930s. PPA was first introduced for medical use by the 1930s.
14029:
10815:
10127:
9829:
9790:
5517:
4171:"The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue"
2381:
14165:
12559:
11619:
10926:
10269:
6632:
5369:
2762:
1362:
14145:
12687:
12677:
12657:
11664:
6701:
5960:
5955:
4907:
4349:
2512:, it requires FDA approval before it can be marketed again effectively banning the drug even as a prescription drug.
2363:
1957:
700:
5416:
Jones G (2008). "Caffeine and other sympathomimetic stimulants: modes of action and effects on sports performance".
5400:"Madras High Court revokes ban on manufacture and sale of paediatric drugs nimesulide and PPA – India Medical Times"
2993:
Bouchard R, Weber AR, Geiger JD (July 2002). "Informed decision-making on sympathomimetic use in sport and health".
13197:
13015:
12682:
12667:
12652:
12435:
11624:
10931:
10274:
7452:
6676:
6205:
4449:"Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism"
6031:
14185:
14140:
13310:
13010:
12960:
12672:
11795:
11316:
10561:
7121:
6126:
4365:-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
1476:
389:
203:
6094:
5221:"The cerebrovascular response to norepinephrine: A scoping systematic review of the animal and human literature"
1711:
urinary pH, the elimination of PPA is accelerated and its half-life and duration are shortened, whereas at more
14125:
13750:
13619:
13604:
13599:
13182:
11990:
11760:
11604:
11167:
11136:
10911:
10430:
10404:
10259:
9808:
1392:
1044:
788:
3043:
Gentile DA, Friday GA, Skoner DP (2000). "Management of allergic rhinitis: antihistamines and decongestants".
2130:
of PPA have varied in their stereoisomer composition in different countries, which may explain differences in
976:. reported the case of an otherwise healthy male who started experiencing intense and recurrent sensations of
13594:
13589:
13177:
13172:
12937:
12016:
11649:
11599:
11594:
11311:
10906:
10254:
8799:
6624:
6036:
4344:(7th ed.). Philadelphia, US: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648.
4304:
2767:"RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
2748:
1816:
1570:
of PPA is approximately 20%. However, it has been said that no recent studies have substantiated this value.
1436:
994:
5503:
4926:
central stimulant, it is more powerful in dilating bronchioles and increasing blood pressure and heart rate.
13551:
12554:
11966:
11775:
11765:
11745:
11704:
11679:
11629:
11539:
11146:
11141:
10936:
10414:
10409:
10279:
9754:
6636:
6516:
4794:-OHNor is well documented and dopamine-β hydroxylase present in noradrenergic neurons could easily convert
3745:
Mersfelder TL (March 2001). "Phenylpropanolamine and stroke: the study, the FDA ruling, the implications".
2770:
2531:
2505:
1630:
598:
499:
17:
989:
action of the drugs and previous findings from electrode stimulation of the brain, it was speculated that
14135:
14024:
13531:
13526:
12571:
11785:
11780:
11755:
11709:
11419:
11151:
11131:
10755:
10683:
10052:
9982:
8633:
8183:
7923:
7511:
6198:
2282:
2278:
866:
were first characterized around 1930. It was introduced for medical use by the 1930s. The medication was
559:
548:
5548:
Implementation of the international drug control treaties: changes in the scope of control of substances
4361:-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords
14175:
13162:
12040:
12032:
11336:
11286:
8088:
7179:
6640:
6628:
6434:
5945:
5932:
2927:
Chua SS, Benrimoj SI, Triggs EJ (1989). "Pharmacokinetics of non-prescription sympathomimetic agents".
2451:
2394:
2049:
1728:
1700:
1540:
762:
354:
14215:
14210:
13475:
13305:
9860:
9852:
7183:
6620:
5670:
1985:
1942:
1935:
934:. However, these forms have all been discontinued. PPA remains available in certain other countries.
12502:
10750:
10047:
5329:
2006:
575:
12009:
11534:
11257:
10810:
10530:
10107:
8106:
7275:
7246:
7046:
6644:
6190:
5965:
2463:
2281:
is -1.2. Methamphetamine has high brain permeability, whereas phenylephrine and norepinephrine are
1751:
1626:
1391:
and has been instead characterized as exclusively an indirectly acting sympathomimetic. It acts by
1048:
1024:
8754:
1064:
1060:
14180:
14170:
13541:
13500:
13224:
13092:
13087:
13077:
13005:
12995:
12749:
12739:
12722:
12581:
11821:
11699:
11514:
11474:
11439:
11429:
10703:
10693:
10002:
9992:
7440:
7286:
6724:
6664:
6495:
6156:
4488:
2608:; however, other evidence from animal studies suggests that this reaction is catalyzed by DBH in
2189:
2153:)-phenylpropanolamine, appears to be the most commonly used formulation of PPA pharmaceutically.
2053:
1981:
1532:
1488:
1388:
1384:
1056:
804:
149:
63:
2462:. However, clinical studies suggest that PPA is not effective in this regard. PPA is not on the
14150:
13701:
13669:
13578:
13217:
12985:
12622:
12531:
12523:
12515:
12507:
11982:
11978:
11846:
11750:
11714:
11689:
11126:
11011:
10399:
10307:
8519:
8211:
8201:
7772:
7529:
6912:
6577:
6469:
6081:
5883:
5630:
5566:
2536:
United
Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
2489:, PPA was available in many "all in one" cough and cold medications which usually also feature
1825:
1567:
1536:
1504:
1403:
1361:
The smaller the value, the more strongly the substance releases the neurotransmitter. See also
1052:
927:
280:
5603:
5006:
Schep LJ, Slaughter RJ, Beasley DM (August 2010). "The clinical toxicology of metamfetamine".
4337:
4169:
Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, et al. (April 2012).
3701:
Bravo EL (March 1988). "Phenylpropanolamine and other over-the-counter vasoactive compounds".
3612:
3164:
2670:
2249:
of 0.67, while its predicted log P values range from 0.57 to 0.89. The compound is relatively
13536:
13480:
13353:
13338:
13327:
12980:
12717:
12697:
11841:
11684:
11003:
10961:
10299:
10217:
8718:
8494:
8137:
6146:
6089:
6000:
5950:
5916:
5912:
5908:
5900:
5896:
5873:
5480:["Rinexin" from the Pharmaceutical Specialties of Sweden] (drug catalog) (in Swedish)
4820:
3119:
2403:
2372:
2246:
2060:
1874:
1673:
1606:
1583:
1418:(noradrenaline) in its sympathomimetic effects, although responses are variable depending on
1205:
871:
759:
743:
312:
6107:
Neurobiological effects of physical exercise § Attention deficit hyperactivity disorder
5551:. Vienna: Commission on Narcotic Drugs, Forty-third session. 6–15 March 2000. Archived from
3785:
3458:
Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates".
2285:. The optimal log P for brain permeation and central activity is about 2.1 (range 1.5–2.7).
1715:
urinary pH, the elimination of PPA is reduced and its half-life and duration are extended.
799:. It was previously thought to act as a mixed acting sympathomimetic with additional direct
13857:
13716:
13711:
13368:
13358:
13348:
13212:
13000:
12952:
12897:
12887:
12637:
11974:
11694:
11669:
11529:
11484:
11434:
11049:
10993:
10875:
10805:
10520:
10315:
10177:
10102:
9377:
7016:
6390:
6366:
6234:
6179:
5995:
5940:
5904:
5892:
5663:
5552:
2558:
2524:
2095:
1867:
1308:
899:
751:
508:
423:
337:
4120:
Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, et al. (2013).
2334:, however, it is still available either by prescription or sometimes over-the-counter. In
803:
actions on adrenergic receptors, but this proved not to be the case. Chemically, PPA is a
602:
579:
488:
186:
8:
14205:
14130:
14019:
13765:
13568:
13515:
13167:
13082:
13072:
12990:
12926:
12813:
12744:
12734:
12617:
11836:
11574:
11424:
11266:
10966:
10800:
10698:
10688:
10611:
10545:
10222:
10112:
9997:
9987:
9910:
8922:
8304:
7607:
7500:
7296:
6961:
6933:
6763:
6541:
6465:
6282:
6051:
2554:
2439:
2327:
2124:
2056:
1642:
1448:
1440:
1376:
1228:
1041:
879:
792:
766:
414:
325:
156:
3347:
13378:
13373:
12475:
11851:
11187:
11182:
10678:
10445:
9977:
7503:
7381:
7027:
6956:
6843:
6475:
5889:
5294:
5269:
5245:
5220:
5196:
5171:
4871:
4741:
In species where aromatic hydroxylation of amphetamine is the major metabolic pathway,
4693:
4646:
4593:
4584:
4568:
4473:
4448:
4246:
4219:
4195:
4170:
4146:
4121:
3987:
3940:
3869:
3844:
3429:
3417:
2304:
2088:
2064:
1771:
1740:
1732:
959:
859:
848:
784:
123:
6693:
4540:
4398:
3334:
O'Donnell SR (March 1995). "Sympathomimetic vasoconstrictors as nasal decongestants".
3056:
2188:(the first carbon before the nitrogen group) also makes this compound a member of the
13706:
13453:
13443:
13413:
13343:
13035:
12778:
12450:
11062:
10886:
10733:
10348:
10182:
10031:
9487:
9462:
9382:
8260:
8010:
7875:
7355:
6833:
6828:
6561:
5879:
5836:
5779:
5636:
5609:
5433:
5299:
5250:
5201:
5187:
5023:
4983:
4903:
4863:
4826:
4777:
4732:
4728:
4685:
4638:
4598:
4544:
4509:
4478:
4464:
4403:
4345:
4286:
4251:
4200:
4151:
4102:
4057:
4022:
3979:
3944:
3909:
3905:
3874:
3762:
3718:
3678:
3618:
3586:
3519:
3475:
3433:
3421:
3381:
3351:
3305:
3269:
3229:
3225:
3170:
3125:
3010:
3006:
2944:
2870:
2742:
2676:
2430:
under brand names including
Allerest, Demazin, Dimetapp, and Sinarest, among others.
2226:
2222:
2204:
2154:
1724:
1677:
1622:
1548:
1444:
1126:
875:
755:
115:
4875:
4697:
4650:
3296:
Johnson DA, Hricik JG (1993). "The pharmacology of alpha-adrenergic decongestants".
3121:
The
Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies
2600:
metabolism in humans suggests that a different enzyme may mediate the conversion of
50:
33:
13448:
13428:
13268:
12932:
12907:
12851:
12491:
11740:
11584:
11494:
11383:
11247:
11121:
11034:
10891:
10627:
10515:
10394:
10338:
10187:
9926:
9457:
9021:
8864:
8663:
8241:
8003:
7993:
7554:
6883:
6808:
5920:
5848:
5807:
5425:
5289:
5281:
5240:
5232:
5191:
5183:
5145:
5015:
4975:
4855:
4724:
4677:
4630:
4588:
4580:
4536:
4468:
4460:
4393:
4278:
4241:
4231:
4190:
4182:
4141:
4133:
4094:
4049:
4040:
Rothman RB, Baumann MH (2003). "Monoamine transporters and psychostimulant drugs".
4014:
3991:
3971:
3936:
3901:
3864:
3856:
3754:
3710:
3670:
3578:
3511:
3467:
3413:
3343:
3261:
3221:
3052:
3002:
2936:
2609:
2427:
2415:
2292:
2238:
2127:
1775:
1712:
1689:
1468:
1460:
1419:
1013:
923:
919:
895:
615:
262:
176:
5520:(Press release). US Food and Drug Administration. 23 December 2005. Archived from
4941:
14044:
13887:
13808:
13055:
13040:
12947:
12922:
12847:
12782:
12627:
12539:
11674:
11519:
11262:
11177:
11067:
10956:
10738:
10601:
10540:
10535:
10440:
10353:
10212:
10036:
9900:
8255:
7563:
7469:
7092:
7067:
7062:
7022:
6898:
6893:
6755:
6616:
6593:
6312:
6287:
6243:
6076:
6071:
6046:
5869:
5767:
5502:(Press release). US Food and Drug Administration. 6 November 2000. Archived from
5120:
5095:
5070:
5045:
5019:
4979:
4634:
4053:
3892:
Ioannides-Demos LL, Proietto J, McNeil JJ (2005). "Pharmacotherapy for obesity".
3714:
2270:
2258:
2170:
2162:
2139:
2110:
1790:
1544:
1380:
1342:
943:
824:
812:
796:
448:
320:
290:
270:
5377:
4378:
2596:. Evidence from studies that measured the effect of serum DBH concentrations on
2523:. It is still available for veterinary use in dogs, however, as a treatment for
2024:
1747:
can reduce the excretion of these agents and thereby increase exposure to them.
14078:
13959:
13872:
13202:
12823:
12486:
11509:
11272:
11202:
11024:
10921:
10835:
10470:
10328:
10207:
10137:
9367:
9036:
9001:
8722:
8478:
8388:
8141:
8006:
7726:
7681:
7446:
7072:
6848:
6670:
6521:
6426:
6358:
6337:
6327:
6257:
6131:
6116:
3471:
2486:
2219:
2076:
1638:
1528:
1524:
1415:
1091:
955:
867:
780:
5521:
5451:
4859:
4569:"Dopamine-beta-oxidase activity in man, using hydroxyamphetamine as substrate"
3860:
3515:
14119:
14094:
14089:
14004:
13913:
13892:
13866:
13824:
13689:
13433:
13288:
13137:
13060:
12798:
12420:
12405:
11242:
11232:
11172:
11095:
10973:
10951:
10760:
10606:
10510:
10500:
10435:
10368:
10229:
10062:
9905:
9821:
9517:
9357:
9041:
8985:
8942:
8603:
8527:
8393:
8332:
8221:
8110:
8022:
7776:
7696:
7691:
7635:
7622:
7401:
7232:
7077:
6918:
6793:
6606:
6490:
6454:
6439:
6371:
6307:
6302:
6141:
5858:
5325:
4290:
4283:
10.1002/(SICI)1099-1077(199711/12)12:6<527::AID-HUP932>3.0.CO;2-U
4018:
3682:
2412:
2323:
2289:
2274:
1846:
1832:
1744:
1720:
1614:
1591:
1560:
1001:
931:
591:
306:
5285:
4681:
3582:
2861:
Kanfer I, Dowse R, Vuma V (1993). "Pharmacokinetics of oral decongestants".
1770:
As PPA is not extensively metabolized, it would probably not be affected by
708:
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
14084:
13999:
13877:
13832:
13780:
13721:
13679:
13418:
13065:
12843:
12838:
12788:
12769:
12445:
11945:
11872:
11816:
11811:
11559:
11459:
11449:
11414:
11217:
11197:
11100:
10845:
10840:
10825:
10745:
10718:
10586:
10581:
10485:
10465:
10373:
10147:
10142:
10122:
10042:
10017:
9885:
9880:
9542:
9527:
9472:
8967:
8789:
8734:
8726:
8698:
8658:
8577:
8543:
8358:
8153:
8145:
8126:
8114:
7998:
7867:
7843:
7803:
7271:
7227:
7097:
7042:
7037:
6923:
6858:
6788:
6773:
6750:
6732:
6480:
6395:
6381:
6272:
6225:
6221:
5437:
5303:
5254:
5205:
5027:
4987:
4867:
4642:
4602:
4548:
4513:
4482:
4255:
4204:
4155:
4106:
4061:
3983:
3975:
3948:
3913:
3878:
3766:
3590:
3523:
3479:
3425:
3273:
3265:
3233:
3014:
2940:
2359:
2185:
2115:
2084:
2068:
1839:
1618:
1021:
986:
967:
891:
747:
181:
171:
5535:
Over-the-Counter (OTC) Drug Review | OTC Monograph Reform in the CARES Act
5270:"Medicinal chemical properties of successful central nervous system drugs"
4781:
4736:
4689:
4407:
4026:
3758:
3722:
3674:
3385:
3355:
3309:
2948:
2874:
14104:
14069:
14039:
13969:
13964:
13939:
13837:
13740:
13393:
13383:
13363:
13317:
13298:
13278:
13257:
13045:
13030:
12965:
12917:
12857:
12828:
12808:
12774:
12702:
12496:
12430:
11940:
11925:
11770:
11654:
11564:
11504:
11212:
11057:
11039:
10855:
10850:
10795:
10790:
10728:
10723:
10662:
10642:
10480:
10343:
10239:
10157:
10152:
10092:
10087:
10027:
10022:
9961:
9941:
9667:
9642:
9637:
9632:
9522:
9497:
9482:
9467:
9432:
9417:
9397:
9392:
9362:
9342:
9317:
9302:
9247:
9192:
9121:
9116:
9111:
9071:
9066:
8972:
8957:
8927:
8917:
8902:
8873:
8844:
8688:
8678:
8653:
8643:
8608:
8551:
8514:
8443:
8438:
8418:
8383:
8319:
8294:
8284:
8265:
8226:
8096:
7973:
7968:
7928:
7903:
7893:
7883:
7853:
7848:
7823:
7798:
7792:
7757:
7716:
7711:
7676:
7661:
7656:
7602:
7592:
7573:
7534:
7391:
7327:
7322:
7252:
7242:
7237:
7222:
7211:
7206:
7136:
7107:
7102:
7032:
7002:
6971:
6946:
6908:
6863:
6823:
6813:
6783:
6778:
6459:
6449:
6410:
6322:
6317:
6297:
6277:
6267:
6252:
6161:
6136:
5705:
5686:
4331:
4329:
4236:
4186:
4137:
2534:
session called for including the stereoisomer norephedrine in Table I of
2516:
2490:
2316:
2262:
2254:
2166:
2135:
2002:
1853:
1786:
1598:
1556:
1552:
1411:
947:
903:
863:
816:
772:
3075:
468:
14074:
14009:
13989:
13984:
13979:
13974:
13954:
13944:
13918:
13897:
13852:
13847:
13816:
13785:
13770:
13760:
13674:
13505:
13468:
13458:
13438:
13398:
13388:
13243:
13239:
13229:
13025:
12975:
12970:
12902:
12892:
12877:
12872:
12862:
12793:
12764:
12759:
12632:
12566:
12549:
12460:
12455:
12425:
11915:
11856:
11639:
11634:
11589:
11579:
11569:
11479:
11469:
11398:
11393:
11227:
11222:
11207:
11076:
11072:
11029:
10998:
10978:
10946:
10896:
10865:
10770:
10765:
10713:
10708:
10652:
10647:
10637:
10495:
10490:
10475:
10460:
10333:
10323:
10294:
10234:
10202:
10192:
10167:
10097:
10067:
10057:
10012:
10007:
9951:
9946:
9936:
9732:
9722:
9712:
9697:
9692:
9677:
9657:
9652:
9627:
9622:
9607:
9587:
9582:
9577:
9547:
9537:
9532:
9502:
9492:
9452:
9442:
9422:
9372:
9352:
9332:
9327:
9307:
9292:
9287:
9277:
9257:
9252:
9242:
9237:
9232:
9212:
9197:
9187:
9167:
9146:
9131:
9106:
9101:
9096:
9081:
9076:
9061:
9046:
9031:
9026:
9016:
9006:
8962:
8947:
8937:
8912:
8907:
8888:
8878:
8859:
8854:
8834:
8829:
8819:
8814:
8804:
8794:
8784:
8774:
8769:
8713:
8703:
8693:
8683:
8623:
8613:
8593:
8588:
8573:
8547:
8539:
8535:
8509:
8504:
8453:
8448:
8428:
8423:
8378:
8368:
8363:
8353:
8314:
8299:
8289:
8250:
8236:
8132:
8122:
8083:
8078:
8068:
8063:
8053:
8038:
8014:
7988:
7978:
7963:
7958:
7948:
7943:
7913:
7898:
7871:
7833:
7819:
7815:
7811:
7788:
7784:
7747:
7706:
7686:
7666:
7651:
7617:
7597:
7549:
7544:
7416:
7406:
7396:
7376:
7337:
7317:
7301:
7201:
7196:
7161:
7156:
7151:
7146:
7052:
7007:
6966:
6873:
6768:
6556:
6536:
6531:
6526:
6485:
6444:
6415:
6405:
6400:
6376:
6332:
6292:
6101:
6056:
5429:
4914:
CHEMISTRY AND STRUCTURE-ACTIVITY RELATIONSHIP OF SYMPATHOMIMETIC AMINES
4846:
Balint EE, Falkay G, Balint GA (2009). "Khat - a controversial plant".
2542:
2250:
2212:
2131:
1782:
1666:
1602:
1587:
1579:
981:
951:
844:
776:
642:
479:
300:
4619:
4326:
1383:, However, PPA was subsequently found to show only weak or negligible
1020:
was found to quadruple caffeine levels. In another study, PPA reduced
41:
14054:
13949:
13862:
13842:
13775:
13664:
13495:
13463:
13408:
13403:
12912:
12882:
12833:
12818:
12754:
12481:
12440:
12071:
12066:
12061:
12056:
12051:
11935:
11930:
11903:
11877:
11831:
11826:
11644:
11357:
11252:
11237:
10983:
10941:
10870:
10820:
10785:
10525:
10505:
10284:
10197:
10172:
10117:
10082:
9727:
9717:
9702:
9682:
9672:
9647:
9617:
9597:
9592:
9572:
9567:
9562:
9512:
9507:
9477:
9447:
9437:
9402:
9387:
9347:
9337:
9322:
9312:
9297:
9272:
9267:
9262:
9227:
9222:
9202:
9172:
9136:
9091:
9086:
9051:
9011:
8952:
8932:
8893:
8839:
8824:
8809:
8779:
8740:
8708:
8673:
8668:
8638:
8583:
8565:
8561:
8531:
8523:
8463:
8403:
8373:
8348:
8309:
8275:
8231:
8169:
8100:
8092:
8073:
8058:
8048:
8043:
8028:
8018:
7983:
7953:
7938:
7933:
7918:
7908:
7887:
7858:
7838:
7827:
7780:
7767:
7762:
7752:
7742:
7671:
7612:
7583:
7539:
7386:
7371:
7347:
7216:
7141:
7131:
7087:
7012:
6976:
6951:
6941:
6888:
6838:
6803:
6741:
6728:
6601:
6546:
6511:
6262:
6151:
6111:
5518:"Phenylpropanolamine (PPA) Information Page – FDA moves PPA from OTC"
5236:
3661:
Johnson DA (1991). "Pharmacology and safety of phenylpropanolamine".
3166:
Concise
Dictionary of Pharmacological Agents: Properties and Synonyms
2509:
2494:
2312:
2266:
2193:
2174:
2158:
1798:
1794:
1716:
1654:
1595:
1170:
1149:
1111:
820:
808:
434:
368:
109:
6220:
3207:
3205:
3203:
3201:
3199:
3197:
3195:
3193:
14059:
13905:
13745:
13726:
13556:
13546:
13490:
13485:
13423:
13293:
13283:
13273:
13050:
12942:
12867:
12415:
11950:
11730:
11554:
11549:
11499:
11489:
11388:
11116:
11090:
11085:
11019:
10988:
10860:
10830:
10775:
10657:
10632:
10596:
10591:
10389:
10363:
10358:
10289:
10162:
10132:
10072:
9956:
9931:
9895:
9890:
9612:
9602:
9552:
9427:
9412:
9407:
9217:
9182:
9177:
9151:
9126:
8993:
8883:
8849:
8730:
8628:
8618:
8598:
8569:
8555:
8499:
8473:
8458:
8340:
8270:
8159:
8149:
8033:
7879:
7863:
7807:
7643:
7578:
7411:
7332:
7057:
6997:
6903:
6868:
6853:
6818:
6347:
6041:
5744:
5374:
Dte.GHS, Ministry of Health and Family
Welfare, Government of India
4526:
4099:
10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3
4004:
3211:
2586:
2498:
2479:
2455:
1101:
1017:
528:
459:
12001:
5343:
4379:"Dopamine-beta-hydroxylase. Stereochemical course of the reaction"
665:
14099:
14064:
13994:
13755:
13157:
13122:
12803:
12727:
12712:
12358:
12323:
12313:
12303:
12298:
12293:
12283:
10780:
10077:
9707:
9687:
9662:
9557:
9282:
9207:
9141:
8648:
8468:
8216:
8164:
8118:
7721:
7191:
6980:
6798:
6551:
6121:
6061:
5975:
5970:
5567:"Unsafe Drugs- nimesulide, Cisapride, Phenylpropanolamine Banned"
3885:
3190:
2592:
2106:
1736:
1372:
1289:
907:
800:
3845:"Centrally Acting Agents for Obesity: Past, Present, and Future"
2668:
1996:
14014:
13934:
13799:
13790:
13731:
13234:
13152:
13142:
13132:
13117:
13107:
13102:
12707:
12607:
12410:
12388:
12383:
12263:
12258:
12253:
12238:
12233:
12228:
12203:
12168:
12163:
12158:
12153:
12148:
12143:
12138:
11454:
11444:
10880:
10450:
8977:
8324:
8206:
7627:
4822:
Forensic Chemistry of Substance Misuse: A Guide to Drug Control
4667:
2459:
2335:
2331:
2308:
2203:
Exogenous compounds in this family are degraded too rapidly by
1909:
1902:
998:
539:
5655:
5219:
Froese L, Dian J, Gomez A, Unger B, Zeiler FA (October 2020).
4119:
3076:"Phenylpropanolamine: Uses, Interactions, Mechanism of Action"
2675:. Index nominum. Medpharm Scientific Publishers. p. 828.
14049:
13207:
13127:
13097:
12647:
12597:
12592:
12465:
12393:
12218:
12183:
12123:
12108:
11659:
11524:
11367:
11352:
11326:
11306:
11192:
10455:
10244:
7421:
5844:
5376:. Central Drugs Standard Control Organization. Archived from
4959:
4489:
Table 5: N-containing drugs and xenobiotics oxygenated by FMO
4338:"Phenylisopropylamine stimulants: amphetamine-related agents"
3891:
2339:
1774:. Conversely, there is likely to be accumulation of PPA with
1727:
can increase the excretion of and thereby reduce exposure to
1658:
1516:
1512:
1071:
Monoamine release by phenylpropanolamine and related agents (
1055:. The stereoisomers of the drug have only weak or negligible
656:
373:
5001:
4999:
4997:
4900:
Goodman & Gilman's Pharmacological Basis of Therapeutics
3247:
3245:
3243:
1586:. Only about 3 to 4% of an oral dose of PPA is metabolized.
1073:
564:
84:)-Phenylpropanolamine; dl-Norephedrine; (±)-Norephedrine; (1
13561:
13192:
13147:
13112:
12612:
12602:
12398:
12223:
12208:
12198:
12188:
12178:
12173:
12133:
12128:
12118:
12113:
12098:
12078:
11614:
11544:
11362:
11331:
11321:
10916:
10264:
8408:
6878:
5581:"Madras High Court Revokes Ban on Manufacture and Sale PPA"
4079:
4077:
4075:
4073:
4071:
2120:
1708:
1520:
519:
4613:
4211:
4168:
4162:
4083:
3836:
2988:
2986:
2984:
2982:
2980:
2978:
14034:
4994:
4965:
4113:
3563:
3561:
3559:
3557:
3555:
3553:
3240:
3038:
3036:
3034:
3032:
3030:
3028:
3026:
3024:
2976:
2974:
2972:
2970:
2968:
2966:
2964:
2962:
2960:
2958:
2922:
2920:
2918:
2916:
2914:
2912:
2910:
2908:
2906:
2904:
2729:. 24 March 2015. Archived from the original on 6 May 2015
2364:
4419:
Dopamine-β-hydroxylase catalyzed the removal of the pro-
4068:
3926:
3551:
3549:
3547:
3545:
3543:
3541:
3539:
3537:
3535:
3533:
2902:
2900:
2898:
2896:
2894:
2892:
2890:
2888:
2886:
2884:
1547:
effects at very high doses. PPA is more lipophilic than
1491:
of PPA at steady state in terms of peak levels, whereas
1471:
of PPA are linear across an oral dose range of 25 to 100
1395:
and thereby indirectly activating adrenergic receptors.
10562:
6723:
5088:
1704:
1665:
hours. About 4% of excreted material is in the form of
5138:
4499:
4423:
hydrogen atom and the production of 1-norephedrine, (2
4217:
3920:
3842:
3021:
2955:
2856:
2854:
2852:
2850:
2848:
2846:
2844:
2842:
2840:
2838:
2836:
2834:
2832:
2830:
2828:
2826:
2824:
2822:
2820:
2818:
2816:
2814:
2812:
2626:
2382:
2288:
PPA has been used pharmaceutically exclusively as the
1684:
hours, with a range in different studies of 3.7 to 4.9
1563:
and has greater brain permeability than these agents.
5113:
5005:
4770:
Journal of Pharmacology and Experimental Therapeutics
4566:
4502:
Journal of Pharmacology and Experimental Therapeutics
4340:. In Lemke TL, Williams DA, Roche VF, Zito W (eds.).
3567:
3530:
3497:
3495:
3493:
3491:
3489:
3453:
3451:
3449:
3447:
3445:
3443:
3251:
2881:
2810:
2808:
2806:
2804:
2802:
2800:
2798:
2796:
2794:
2792:
2307:
in the early 20th century, in or around 1910. It was
783:, among others. Rarely, PPA has been associated with
5605:
Veterinary Toxicology: Basic and Clinical Principles
5218:
4297:
4262:
3961:
3617:. Lippincott Williams & Wilkins. pp. 643–.
3606:
3604:
3602:
3600:
3291:
3289:
3287:
3285:
3283:
2326:, PPA is no longer sold due to an increased risk of
2005:. The β-hydroxylation of amphetamine is mediated by
1804:
6391:
mast cell stabilizer (some are also antihistamines)
5212:
5038:
4271:
Human Psychopharmacology: Clinical and Experimental
3042:
2992:
2530:Internationally, an item on the agenda of the 2000
1793:, as shown below. It is also a minor metabolite of
11287:
7499:
5478:"Rinexin in Farmaceutiska Specialiteter i Sverige"
4845:
4623:Expert Opinion on Drug Metabolism & Toxicology
4033:
3813:
3811:
3809:
3807:
3486:
3440:
3399:
3397:
3395:
2926:
2789:
2664:
2662:
2660:
2658:
2656:
2654:
2652:
2650:
2648:
2646:
2395:
2001:In humans, norephedrine occurs as a metabolite of
958:. It has been associated rarely with incidence of
9861:
5622:
5261:
5063:
4767:
4529:Journal of Pharmaceutical and Biomedical Analysis
3843:Coulter AA, Rebello CJ, Greenway FL (July 2018).
3740:
3738:
3736:
3734:
3732:
3597:
3280:
3158:
3156:
3154:
3152:
3150:
3148:
910:and has shown effectiveness for this indication.
14117:
4897:
4661:
4573:British Journal of Pharmacology and Chemotherapy
4370:
4268:
2672:Index Nominum 2000: International Drug Directory
447:
6067:History and culture of substituted amphetamines
4562:
4560:
4558:
4446:
3804:
3656:
3654:
3392:
3329:
3327:
3325:
3323:
3321:
3319:
3045:Immunology and Allergy Clinics of North America
2860:
2643:
2590:and it is presumed to be metabolized similarly
1463:forms of PPA reach peak levels after 3.0 to 4.5
422:
14226:World Anti-Doping Agency prohibited substances
9851:
4039:
3729:
3652:
3650:
3648:
3646:
3644:
3642:
3640:
3638:
3636:
3634:
3501:
3457:
3403:
3145:
1641:at the β carbon of PPA also helps to increase
1371:PPA was originally thought to act as a direct
12017:
9837:
7485:
6709:
6206:
5671:
5628:
5267:
4802:-OHNor after intraventricular administration.
4714:
4314:. Shire US Inc. December 2013. pp. 12–13
3610:
3333:
3295:
2404:
2373:
1551:sympathomimetics with hydroxyl groups on the
1459:hours) following administration. Conversely,
1363:Monoamine releasing agent § Activity profiles
5411:
5409:
4893:
4891:
4889:
4887:
4885:
4839:
4825:. Royal Society of Chemistry. pp. 53–.
4555:
4493:
3780:
3778:
3776:
3696:
3694:
3692:
3372:Aaron CK (August 1990). "Sympathomimetics".
3367:
3365:
3316:
1778:due to its dependence on urinary excretion.
1621:at the α carbon of PPA blocks metabolism by
1495:levels are not increased with steady state.
1406:as a sympathomimetic. It is about 100 to 200
1081:Tooltip half maximal effective concentration
576:DTXSID70859305 DTXSID4023466, DTXSID70859305
4814:
4812:
4810:
4761:
4708:
4520:
4431:)-2-amino-1-hydroxyl-1-phenylpropane, from
3631:
3304:(6 Pt 2): 110S–115S, discussion 143S–146S.
2869:(6 Pt 2): 116S–128S, discussion 143S–146S.
2717:
2715:
2713:
2711:
2709:
2707:
2705:
2703:
2701:
2699:
2521:Combat Methamphetamine Epidemic Act of 2005
2040:)-α-methyl-β-hydroxyphenethylamine or as (1
2028:Space-filling model of phenylpropanolamine.
1811:Metabolic pathways of amphetamine in humans
878:. PPA remains available for medical and/or
185:
12024:
12010:
9844:
9830:
7492:
7478:
6716:
6702:
6213:
6199:
5678:
5664:
5163:
4936:
4934:
4567:Sjoerdsma A, von Studnitz W (April 1963).
4335:
4312:United States Food and Drug Administration
3744:
3162:
3113:
3111:
3109:
3107:
3105:
3103:
3101:
3099:
3097:
3070:
3068:
3066:
2612:within noradrenergic neurons in the brain.
601:
578:
487:
49:
40:
14156:Drugs acting on the cardiovascular system
5635:. John Wiley & Sons. pp. 1309–.
5595:
5406:
5322:"Advisories, Warnings and Recalls – 2001"
5293:
5244:
5195:
4882:
4592:
4472:
4397:
4376:
4245:
4235:
4218:Głowacka K, Wiela-Hojeńska A (May 2021).
4194:
4145:
3868:
3773:
3689:
3362:
2669:Schweizerischer Apotheker-Verein (2000).
2369:Tooltip International Nonproprietary Name
1483:hours when the drug is taken once every 4
507:
5632:Veterinary Pharmacology and Therapeutics
5444:
5176:British Journal of Clinical Pharmacology
4902:(12th ed.). New York: McGraw-Hill.
4807:
4342:Foye's principles of medicinal chemistry
3819:"Search Results for phenylpropanolamine"
3614:Foye's Principles of Medicinal Chemistry
2696:
2023:
1365:for a larger table with more compounds.
10567:Tooltip Norepinephrine releasing agents
5629:Riviere JE, Papich MG (17 March 2009).
4931:
3660:
3094:
3063:
2482:medications like Wick DayMed capsules.
1758:L/h/kg, while renal clearance was 0.432
1582:. It also does not undergo significant
1016:with PPA. In one study, PPA taken with
1012:There has been very little research on
574:
467:
14:
14118:
5169:
2761:
2580:has been shown to be metabolized into
2519:manufacture, PPA is controlled by the
2445:
2438:PPA remains available for medical and
2387:Tooltip Dénomination Commune Française
2345:
1979:
1972:
1967:
1962:
1955:
1948:
1933:
1919:
1914:
1907:
1900:
1893:
1886:
1879:
1858:
1844:
1837:
1830:
1653:Approximately 90% of a dose of PPA is
1092:
965:Certain drugs increase the chances of
795:. As such, it is an indirectly acting
592:
92:)-α-Methyl-β-hydroxyphenethylamine; (1
12005:
9825:
7473:
6697:
6194:
5859:
5659:
5601:
5415:
5268:Pajouhesh H, Lenz GR (October 2005).
4447:Krueger SK, Williams DE (June 2005).
4305:"Adderall XR Prescribing Information"
3700:
3371:
3169:. Springer Netherlands. p. 219.
2105:-Norpseudoephedrine is also known as
1940:
1926:
1872:
1865:
1851:
1531:, reduces its permeation through the
1527:of PPA at the β carbon increases its
1110:
1100:
1090:
754:. It was previously commonly used in
742:), sold under many brand names, is a
547:
249:
114:
4818:
4220:"Pseudoephedrine—Benefits and Risks"
3117:
2450:There has been interest in PPA as a
1823:
1754:of PPA has been reported to be 0.546
1479:levels of PPA are achieved within 12
175:
14030:Lysergic acid 2,4-dimethylazetidide
12031:
4440:
3348:10.5694/j.1326-5377.1995.tb139882.x
2777:from the original on 27 August 2023
2584:by dopamine beta-hydroxylase (DBH)
1425:
1379:and hence to act as a mixed acting
1035:
527:
438:
24:
14161:Drugs acting on the nervous system
11292:Tooltip Serotonin releasing agents
4585:10.1111/j.1476-5381.1963.tb01467.x
3941:10.1002/j.1550-8528.1999.tb00420.x
3418:10.1212/01.wnl.0000250351.38999.f2
2619:
2418:. It is also known by the synonym
2400:Tooltip United States Adopted Name
913:
25:
14237:
9866:Tooltip Dopamine releasing agents
5608:. Academic Press. pp. 458–.
4923:Substitution on the β-Carbon Atom
4918:Substitution on the α-Carbon Atom
2553:PPA remains available for use in
2548:
2391:phenylpropanolamine hydrochloride
1112:
212:
134:
6175:
6174:
5348:Therapeutic Goods Administration
5328:. 7 January 2009. Archived from
5188:10.1111/j.1365-2125.2006.02833.x
4465:10.1016/j.pharmthera.2005.01.001
3964:Journal of Clinical Neuroscience
3906:10.2165/00003495-200565100-00006
3226:10.2165/00002018-200629040-00001
3007:10.1097/00042752-200207000-00003
2515:Because of its potential use in
1995:
1815:
1765:
1102:
791:, thereby indirectly activating
632:
626:
14191:Norepinephrine releasing agents
12961:N,alpha-Diethylphenylethylamine
11987:Monoamine metabolism modulators
9800:Monoamine metabolism modulators
6127:Performance-enhancing substance
5685:
5583:. Scribd.com. 13 September 2011
5573:
5559:
5539:
5528:
5510:
5492:
5470:
5392:
5362:
5336:
5314:
4453:Pharmacology & Therapeutics
4386:Journal of Biological Chemistry
3998:
3955:
3786:"Drugs@FDA: FDA-Approved Drugs"
2571:
2473:
2433:
2059:. It is closely related to the
1703:of PPA is dependent on urinary
1498:
1393:inducing norepinephrine release
1030:
1007:
937:
885:
713:Key:DLNKOYKMWOXYQA-CBAPKCEASA-N
6224:and other nasal preparations (
4848:Wiener Klinische Wochenschrift
4745:-hydroxyamphetamine (POH) and
3792:. Food and Drug Administration
3611:Lemke TL, Williams DA (2008).
2755:
2245:g/mol. It has an experimental
1692:PPA has ranged from 4.3 to 5.8
1648:
1515:are about 40% of those in the
1399:number of additional effects.
1045:norepinephrine releasing agent
789:norepinephrine releasing agent
635:
620:
238:
225:
13:
1:
14201:Recreational drug metabolites
11971:Monoamine reuptake inhibitors
11967:Receptor/signaling modulators
9782:Monoamine reuptake inhibitors
9755:Receptor/signaling modulators
6037:Benzedrine in popular culture
5500:"Phenylpopanolamine Advisory"
4541:10.1016/S0731-7085(02)00330-8
4399:10.1016/S0021-9258(19)43051-2
3057:10.1016/S0889-8561(05)70152-1
2636:
2468:list of prohibited substances
2409:Tooltip British Approved Name
2378:Tooltip British Approved Name
2048:)-β-hydroxyamphetamine, is a
1573:
1430:
918:PPA was previously available
405:)-2-amino-1-phenylpropan-1-ol
14221:Withdrawn anti-obesity drugs
14196:Peripherally selective drugs
11923:Adrenergic release blockers:
6517:Calcium hexamine thiocyanate
5020:10.3109/15563650.2010.516752
4980:10.1021/acs.jmedchem.7b01922
4729:10.1016/0028-3908(74)90069-0
4635:10.1517/17425255.2013.796929
4054:10.1016/j.ejphar.2003.08.054
3715:10.1161/01.hyp.11.3_pt_2.ii7
2532:Commission on Narcotic Drugs
2506:Food and Drug Administration
2283:peripherally selective drugs
2019:
234:(Prohibited drug precursors)
7:
14025:Lysergic acid 2-butyl amide
8865:Deoxyepinephrine (epinine,
8242:Deoxyepinephrine (epinine,
8089:Tetracyclic antidepressants
7555:Deoxyepinephrine (epinine,
5344:"Alert Phenylpropanolamine"
3163:Morton IK, Hall JM (2012).
3124:. Springer US. p. 71.
1733:urinary alkalinizing agents
1511:L/kg. Levels of PPA in the
898:. It has also been used to
763:cough and cold preparations
116:Multum Consumer Information
10:
14242:
14035:Lysergic acid diethylamide
9853:Monoamine releasing agents
9791:Monoamine releasing agents
6435:Beclometasone dipropionate
5602:Gupta RC (23 April 2012).
4377:Taylor KB (January 1974).
3472:10.2174/156802606778249766
2773:(published 25 July 2023).
2504:In the United States, the
2452:performance-enhancing drug
2298:
2184:. The methyl group on the
2050:substituted phenethylamine
1797:and a major metabolite of
1625:(MAOs). PPA is also not a
1447:forms of the drug reached
1051:with around 10-fold lower
807:and is closely related to
765:. The medication is taken
610:Chemical and physical data
14166:Drugs developed by Unilab
13927:
13688:
13577:
13514:
13326:
13256:
12580:
12039:
11959:
11890:
11865:
11804:
11723:
11407:
11376:
11345:
11299:
11285:
11160:
11109:
10671:
10620:
10574:
10560:
10423:
10382:
9970:
9919:
9873:
9859:
9745:
9160:
8762:
8753:
8487:
8194:
8182:
8107:Tricyclic antidepressants
7735:
7522:
7510:
7430:
7364:
7346:
7310:
7285:
7262:
7170:
7120:
6990:
6932:
6749:
6740:
6654:
6590:
6570:
6504:
6425:
6352:excluding corticosteroids
6346:
6242:
6233:
6170:
6014:
5988:
5930:
5835:
5828:
5806:
5778:
5766:
5704:
5693:
5170:Eccles R (January 2007).
4860:10.1007/s00508-009-1259-7
3861:10.1007/s40265-018-0946-y
3663:Drug Development Research
3516:10.1016/j.lfs.2005.09.001
2747:: CS1 maint: unfit URL (
2200:-methyl analogue of PPA.
1717:Urinary acidifying agents
1578:PPA is not substantially
1360:
864:effects on blood pressure
775:of PPA include increased
721:
696:
676:
654:
641:
614:
609:
590:
558:
538:
518:
498:
478:
458:
433:
413:
385:
380:
367:
353:
336:
319:
299:
289:
279:
269:
261:
202:
197:
162:
148:
122:
104:
72:
62:
57:
48:
39:
14146:Beta-Hydroxyamphetamines
12925:(Dextromethamphetamine,
11258:Phthalimidopropiophenone
10531:Phthalimidopropiophenone
6505:Other nasal preparations
5740:Mixed amphetamine salts
5456:World Anti Doping Agency
3753:(3): 208–9, 213–9, 223.
2564:
2557:. It is used to control
2464:World Anti-Doping Agency
2350:
2330:. In a few countries in
1781:Norephedrine is a minor
1688:hours. The half-life of
1519:and 20% of those in the
1292:((+)-norpseudoephedrine)
1049:dopamine releasing agent
1040:PPA acts primarily as a
995:hyperdopaminergic action
823:. It is most commonly a
13579:Phenylalkylpyrrolidines
13501:Methylenedioxycathinone
13178:3,4-MDA (tenamfetamine)
8520:Atypical antipsychotics
7773:Atypical antipsychotics
6496:Triamcinolone acetonide
6157:Substituted amphetamine
5370:"Drugs Banned In India"
5286:10.1602/neurorx.2.4.541
4682:10.1161/01.RES.32.5.594
4175:Neuropsychopharmacology
4126:Neuropsychopharmacology
3583:10.1124/jpet.103.053975
3374:Emerg Med Clin North Am
2771:Diário Oficial da União
2190:substituted amphetamine
2138:profiles. In any case,
1731:including PPA, whereas
1455:hours (range 1.0 to 2.3
1410:times less potent than
1402:PPA has relatively low
1271:(–)-Phenylpropanolamine
1252:(+)-Phenylpropanolamine
805:substituted amphetamine
14186:Human drug metabolites
14141:Antihypotensive agents
12503:β-Methylphenethylamine
12497:α-Methylphenethylamine
8719:Typical antipsychotics
8202:(R)-3-Nitrobiphenyline
8138:Typical antipsychotics
6578:Olopatadine/mometasone
6470:Fluticasone propionate
5225:Pharmacol Res Perspect
4019:10.1093/brain/117.1.71
3976:10.1054/jocn.2000.0810
3266:10.1038/sj.jhh.1001869
2941:10.1002/bdd.2510100102
2442:in certain countries.
2063:(β-ketoamphetamines).
2029:
2007:dopamine β-hydroxylase
1826:4-Hydroxyphenylacetone
1568:plasma protein binding
1537:central nervous system
1505:volume of distribution
1309:(–)-Norpseudoephedrine
1097:Tooltip Norepinephrine
1065:β-adrenergic receptors
993:occurs as a result of
980:upon taking the drugs
946:effects and can cause
100:)-β-Hydroxyamphetamine
14126:Amphetamine alkaloids
13694:(and close relatives)
13193:MDMA (midomafetamine)
12535:-Methylphenethylamine
12527:-Methylphenethylamine
12519:-Methylphenethylamine
12511:-Methylphenethylamine
11991:Monoamine neurotoxins
11615:MDMA (midomafetamine)
10962:Dextromethamphetamine
10917:MDMA (midomafetamine)
10265:MDMA (midomafetamine)
10218:Dextromethamphetamine
9809:Monoamine neurotoxins
7311:Absorption inhibitors
6367:histamine antagonists
6147:Recreational drug use
6090:Motivational salience
6085:-Methylphenethylamine
6032:Amphetamine psychosis
6001:4-Hydroxynorephedrine
5884:competitive inhibitor
5864:Tooltip messenger RNA
5452:"The Prohibited List"
4942:"Phenylpropanolamine"
3759:10.3949/ccjm.68.3.208
3675:10.1002/ddr.430220302
2723:"Phenylpropanolamine"
2606:4-hydroxynorephedrine
2582:4-hydroxynorephedrine
2032:PPA, also known as (1
2027:
1875:4-Hydroxynorephedrine
1674:elimination half-life
1607:4-hydroxynorephedrine
1584:first-pass metabolism
1345:((+)-pseudoephedrine)
1206:Dextromethamphetamine
851:and is also known as
744:sympathomimetic agent
313:4-Hydroxynorephedrine
76:PPA; Norephedrine; (1
27:Sympathomimetic agent
13858:N,N-Dimethyldopamine
13516:Phenylisobutylamines
13213:Naphthylaminopropane
12898:Isopropylamphetamine
12888:4-Hydroxyamphetamine
10994:Naphthylaminopropane
10876:4-Hydroxyamphetamine
10521:Naphthylaminopropane
10178:4-Hydroxyamphetamine
9378:Dichloroisoprenaline
6571:Combination products
5996:4-Hydroxyamphetamine
5837:Biomolecular targets
5008:Clin Toxicol (Phila)
4670:Circulation Research
4237:10.3390/ijms22105146
4187:10.1038/npp.2011.304
4138:10.1038/npp.2012.204
3571:J Pharmacol Exp Ther
2929:Biopharm Drug Dispos
2602:4-hydroxyamphetamine
2598:4-hydroxyamphetamine
2578:4-Hydroxyamphetamine
2559:urinary incontinence
2525:urinary incontinence
2362:of the drug and its
2145:-norephedrine, or (1
2065:β-Hydroxyamphetamine
1868:4-Hydroxyamphetamine
1549:structurally related
1507:of PPA is 3.0 to 4.5
1493:area-under-the-curve
1487:hours. There is 62%
1435:PPA is readily- and
1377:adrenergic receptors
1235:(–)-methamphetamine)
1212:(+)-methamphetamine)
1047:. It also acts as a
1004:areas of the brain.
906:in the treatment of
862:around 1910 and its
849:β-hydroxyamphetamine
793:adrenergic receptors
752:appetite suppressant
14020:Lysergic acid amide
13766:Ethylnorepinephrine
13569:Phenylisobutylamine
13021:Phenylpropanolamine
12956:-Norpseudoephedrine
12927:Levomethamphetamine
12814:Dimethylamphetamine
11600:MDA (tenamfetamine)
11267:Levopropylhexedrine
11045:Phenylpropanolamine
10967:Levomethamphetamine
10907:MDA (tenamfetamine)
10801:Dimethylamphetamine
10612:Pseudophenmetrazine
10546:Levopropylhexedrine
10255:MDA (tenamfetamine)
10223:Levomethamphetamine
10113:Dimethylamphetamine
9911:Pseudophenmetrazine
9057:Phenylpropanolamine
8923:Ethylnorepinephrine
8399:Phenylpropanolamine
8305:Ethylnorepinephrine
7702:Phenylpropanolamine
7608:Ethylnorepinephrine
7501:Adrenergic receptor
7083:Phenylpropanolamine
6962:Levopropylhexedrine
6934:Adrenergic agonists
6764:4-Methylamphetamine
6633:+dexbrompheniramine
6612:Phenylpropanolamine
6542:Ipratropium bromide
6466:Fluticasone furoate
6052:Executive functions
5890:Carbonic anhydrases
5524:on 12 January 2009.
5506:on 26 January 2010.
4974:(23): 10345–10374.
4336:Glennon RA (2013).
2555:veterinary medicine
2446:Exercise and sports
2411:in the case of the
2356:Phenylpropanolamine
2346:Society and culture
2328:haemorrhagic stroke
2253:, but is also more
2125:Pharmaceutical drug
2099:-norpseudoephedrine
1661:unchanged within 24
1643:metabolic stability
1533:blood–brain barrier
1441:oral administration
1326:(–)-Pseudoephedrine
1229:Levomethamphetamine
1084:
882:in some countries.
746:which is used as a
736:Phenylpropanolamine
254: Rx-Only
221:(Prescription only)
36:
34:Phenylpropanolamine
14136:Anti-obesity drugs
12476:Phenylethanolamine
7457:Never to phase III
7382:Desiccated thyroid
7028:Dexmethylphenidate
6725:Antiobesity agents
6681:Never to phase III
6476:Mometasone furoate
6095:Incentive salience
5989:Active metabolites
5569:. 27 January 2011.
5555:on 14 August 2003.
5430:10.1042/BSE0440109
5380:on 13 October 2013
4854:(19–20): 604–614.
4786:The metabolism of
3790:accessdata.fda.gov
3709:(3 Pt 2): II7–10.
2030:
1772:hepatic impairment
1741:sodium bicarbonate
1635:-methyltransferase
1623:monoamine oxidases
1273:((–)-norephedrine)
1254:((+)-norephedrine)
1070:
960:hemorrhagic stroke
950:such as increased
785:hemorrhagic stroke
355:Duration of action
32:
14176:Enantiopure drugs
14113:
14112:
13454:N-Ethylpentedrone
13414:Dimethylcathinone
13036:Propylamphetamine
12779:Dextroamphetamine
12451:Methallylescaline
11999:
11998:
11994:
11886:
11885:
11281:
11280:
11063:Propylamphetamine
10887:Iofetamine (123I)
10734:Dextroamphetamine
10556:
10555:
10349:Propylamphetamine
10183:Iofetamine (123I)
10032:Dextroamphetamine
9819:
9818:
9812:
9803:
9794:
9785:
9776:
9767:
9758:
9741:
9740:
9488:Iodocyanopindolol
9463:Hydroxytertatolol
9383:Dihydroalprenolol
8996:
8988:
8980:
8897:
8749:
8748:
8343:
8335:
8327:
8279:
8261:Dihydroergotamine
8178:
8177:
8011:hydroxynefazodone
7876:dihydroergotamine
7646:
7638:
7630:
7587:
7467:
7466:
7356:2,4-Dinitrophenol
7289:receptor agonists
7184:glucagon agonists
7116:
7115:
6834:Dimethylcathinone
6829:Dextroamphetamine
6691:
6690:
6586:
6585:
6188:
6187:
5984:
5983:
5829:Neuropharmacology
5824:
5823:
5780:Dextroamphetamine
5642:978-0-8138-2061-3
5615:978-0-12-385927-3
5096:"Pseudoephedrine"
4832:978-0-85404-178-7
4723:(12): 1187–1190.
4717:Neuropharmacology
4042:Eur. J. Pharmacol
3855:(11): 1113–1132.
3624:978-0-7817-6879-5
3466:(17): 1845–1859.
3460:Curr Top Med Chem
3176:978-94-011-4439-1
3131:978-1-4757-2085-3
2682:978-3-88763-075-1
2610:synaptic vesicles
2227:molecular formula
2205:monoamine oxidase
2016:
2015:
1725:ammonium chloride
1678:immediate-release
1559:(adrenaline) and
1535:, and limits its
1445:Immediate-release
1369:
1368:
1127:Dextroamphetamine
1117:Tooltip Serotonin
1014:drug interactions
924:combination forms
900:suppress appetite
890:PPA is used as a
733:
732:
667:Interactive image
560:CompTox Dashboard
376:: 90% (unchanged)
253:
241:
229:
216:
138:
16:(Redirected from
14233:
14216:Veterinary drugs
14211:Sympathomimetics
13819:
13811:
13802:
13793:
13734:
13695:
13449:N-Ethylhexedrone
13429:Hydroxybupropion
13269:Chlorphentermine
13246:
12955:
12933:Methoxyphenamine
12908:Lisdexamfetamine
12852:Levofenfluramine
12492:Phenpromethamine
12026:
12019:
12012:
12003:
12002:
11961:
11913:Antagonist-like:
11585:Levofenfluramine
11495:Chlorphentermine
11412:Phenethylamines:
11384:4-Methylaminorex
11297:
11296:
11293:
11289:
11248:Methylhexanamine
11079:
11035:Phenpromethamine
10892:Lisdexamfetamine
10676:Phenethylamines:
10572:
10571:
10568:
10564:
10516:Methylhexanamine
10339:Phenpromethamine
10188:Lisdexamfetamine
9975:Phenethylamines:
9871:
9870:
9867:
9863:
9846:
9839:
9832:
9823:
9822:
9806:
9797:
9788:
9779:
9770:
9761:
9749:
9458:Hydroxycarteolol
9022:Methoxyphenamine
8994:
8986:
8981:-DOPA (levodopa)
8978:
8895:
8869:-methyldopamine)
8760:
8759:
8664:Phenoxybenzamine
8341:
8333:
8328:-DOPA (levodopa)
8325:
8277:
8246:-methyldopamine)
8192:
8191:
8004:Phenylpiperazine
7994:Phenoxybenzamine
7644:
7636:
7631:-DOPA (levodopa)
7628:
7585:
7569:Dexisometheptene
7559:-methyldopamine)
7520:
7519:
7494:
7487:
7480:
7471:
7470:
6884:Lisdexamfetamine
6809:Chlorphentermine
6747:
6746:
6718:
6711:
6704:
6695:
6694:
6594:Sympathomimetics
6396:Cromoglicic acid
6283:Levmetamfetamine
6244:Sympathomimetics
6240:
6239:
6215:
6208:
6201:
6192:
6191:
6178:
6177:
6015:Related articles
5921:enzyme activator
5865:
5861:
5833:
5832:
5808:Lisdexamfetamine
5751:Adderall XR
5726:Dyanavel XR
5721:
5702:
5701:
5680:
5673:
5666:
5657:
5656:
5647:
5646:
5626:
5620:
5619:
5599:
5593:
5592:
5590:
5588:
5577:
5571:
5570:
5563:
5557:
5556:
5543:
5537:
5532:
5526:
5525:
5514:
5508:
5507:
5496:
5490:
5489:
5487:
5485:
5474:
5468:
5467:
5465:
5463:
5458:. 1 January 2024
5448:
5442:
5441:
5413:
5404:
5403:
5396:
5390:
5389:
5387:
5385:
5366:
5360:
5359:
5357:
5355:
5340:
5334:
5333:
5318:
5312:
5311:
5297:
5265:
5259:
5258:
5248:
5237:10.1002/prp2.655
5216:
5210:
5209:
5199:
5167:
5161:
5160:
5158:
5156:
5146:"Norepinephrine"
5142:
5136:
5135:
5133:
5131:
5117:
5111:
5110:
5108:
5106:
5092:
5086:
5085:
5083:
5081:
5067:
5061:
5060:
5058:
5056:
5042:
5036:
5035:
5003:
4992:
4991:
4963:
4957:
4956:
4954:
4952:
4938:
4929:
4928:
4895:
4880:
4879:
4843:
4837:
4836:
4819:King LA (2009).
4816:
4805:
4804:
4765:
4759:
4758:
4712:
4706:
4705:
4665:
4659:
4658:
4629:(9): 1139–1153.
4617:
4611:
4610:
4596:
4564:
4553:
4552:
4524:
4518:
4517:
4508:(3): 1251–1260.
4497:
4491:
4486:
4476:
4444:
4438:
4437:
4416:
4414:
4401:
4383:
4374:
4368:
4367:
4333:
4324:
4323:
4321:
4319:
4309:
4301:
4295:
4294:
4266:
4260:
4259:
4249:
4239:
4215:
4209:
4208:
4198:
4166:
4160:
4159:
4149:
4117:
4111:
4110:
4081:
4066:
4065:
4037:
4031:
4030:
4002:
3996:
3995:
3959:
3953:
3952:
3924:
3918:
3917:
3900:(10): 1391–418.
3889:
3883:
3882:
3872:
3840:
3834:
3833:
3831:
3829:
3815:
3802:
3801:
3799:
3797:
3782:
3771:
3770:
3747:Cleve Clin J Med
3742:
3727:
3726:
3698:
3687:
3686:
3658:
3629:
3628:
3608:
3595:
3594:
3565:
3528:
3527:
3499:
3484:
3483:
3455:
3438:
3437:
3401:
3390:
3389:
3369:
3360:
3359:
3331:
3314:
3313:
3293:
3278:
3277:
3249:
3238:
3237:
3209:
3188:
3187:
3185:
3183:
3160:
3143:
3142:
3140:
3138:
3115:
3092:
3091:
3089:
3087:
3072:
3061:
3060:
3040:
3019:
3018:
2995:Clin J Sport Med
2990:
2953:
2952:
2924:
2879:
2878:
2858:
2787:
2786:
2784:
2782:
2765:(24 July 2023).
2759:
2753:
2752:
2746:
2738:
2736:
2734:
2719:
2694:
2693:
2691:
2689:
2666:
2630:
2613:
2607:
2603:
2599:
2583:
2579:
2575:
2410:
2406:
2401:
2397:
2388:
2384:
2379:
2375:
2370:
2366:
2277:is -0.3, and of
2244:
2239:molecular weight
2182:phen-ethyl-amine
2071:, which include
1999:
1998:
1988:
1977:
1970:
1965:
1960:
1953:
1946:
1938:
1931:
1924:
1917:
1912:
1905:
1898:
1891:
1884:
1877:
1870:
1863:
1856:
1849:
1842:
1835:
1828:
1819:
1805:
1776:renal impairment
1761:
1757:
1695:
1690:extended-release
1687:
1683:
1664:
1510:
1486:
1482:
1474:
1469:pharmacokinetics
1466:
1461:extended-release
1458:
1454:
1451:levels about 1.5
1426:Pharmacokinetics
1414:(adrenaline) or
1409:
1133:(+)-amphetamine)
1118:
1114:
1108:
1107:Tooltip Dopamine
1104:
1098:
1094:
1085:
1082:
1078:
1069:
1036:Pharmacodynamics
920:over-the-counter
896:nasal congestion
872:over-the-counter
787:. PPA acts as a
760:over-the-counter
729:
728:
669:
649:
637:
634:
628:
622:
605:
594:
583:
582:
568:
566:
551:
531:
511:
491:
471:
451:
441:
440:
426:
362:
348:
341:
331:
251:
248:
240:
237:
227:
224:
214:
211:
189:
179:
136:
133:
118:
53:
44:
37:
35:
31:
21:
14241:
14240:
14236:
14235:
14234:
14232:
14231:
14230:
14116:
14115:
14114:
14109:
14045:Methoxphenidine
13923:
13888:Normetanephrine
13817:
13809:
13800:
13791:
13732:
13693:
13692:
13684:
13573:
13564:
13510:
13471:
13322:
13313:
13301:
13252:
13244:
13220:
13068:
13056:Tranylcypromine
13041:Pseudoephedrine
12953:
12948:Norfenfluramine
12923:Methamphetamine
12848:Dexfenfluramine
12783:Levoamphetamine
12730:
12628:Bromo-DragonFLY
12576:
12562:
12540:Methylphenidate
12471:
12041:Phenethylamines
12035:
12033:Phenethylamines
12030:
12000:
11995:
11955:
11898:DAT modulators:
11882:
11861:
11800:
11719:
11675:Norfenfluramine
11520:Dexfenfluramine
11403:
11372:
11350:Aminotetralins:
11341:
11291:
11277:
11263:Propylhexedrine
11156:
11105:
11077:
11068:Pseudoephedrine
10957:Methamphetamine
10739:Levoamphetamine
10667:
10616:
10602:Phendimetrazine
10566:
10552:
10541:Propylhexedrine
10536:Phenylbiguanide
10419:
10378:
10354:Pseudoephedrine
10213:Methamphetamine
10037:Levoamphetamine
9966:
9915:
9901:Phendimetrazine
9865:
9855:
9850:
9820:
9815:
9737:
9156:
8745:
8483:
8256:Dexmedetomidine
8187:
8174:
8007:antidepressants
7731:
7564:Desglymidodrine
7515:
7506:
7498:
7468:
7463:
7462:
7447:Clinical trials
7426:
7360:
7342:
7306:
7288:
7281:
7258:
7182:
7166:
7123:
7112:
7093:Propylhexedrine
7068:Phendimetrazine
7063:Methylphenidate
7023:Dexfenfluramine
6986:
6928:
6899:Norfenfluramine
6894:Methamphetamine
6756:phenethylamines
6754:
6736:
6722:
6692:
6687:
6686:
6671:Clinical trials
6650:
6617:Pseudoephedrine
6592:
6582:
6566:
6500:
6427:Corticosteroids
6421:
6351:
6342:
6313:Propylhexedrine
6288:Methylephedrine
6229:
6219:
6189:
6184:
6166:
6077:Methylphenidate
6072:Methamphetamine
6047:Doping in sport
6027:ADHD management
6010:
5980:
5926:
5870:5-HT1A receptor
5863:
5820:
5802:
5774:
5768:Levoamphetamine
5762:
5736:Evekeo ODT
5719:
5714:Adzenys ER
5698:pharmaceuticals
5697:
5695:
5689:
5684:
5653:
5651:
5650:
5643:
5627:
5623:
5616:
5600:
5596:
5586:
5584:
5579:
5578:
5574:
5565:
5564:
5560:
5545:
5544:
5540:
5533:
5529:
5516:
5515:
5511:
5498:
5497:
5493:
5483:
5481:
5476:
5475:
5471:
5461:
5459:
5450:
5449:
5445:
5414:
5407:
5398:
5397:
5393:
5383:
5381:
5368:
5367:
5363:
5353:
5351:
5342:
5341:
5337:
5320:
5319:
5315:
5266:
5262:
5217:
5213:
5168:
5164:
5154:
5152:
5144:
5143:
5139:
5129:
5127:
5121:"Phenylephrine"
5119:
5118:
5114:
5104:
5102:
5094:
5093:
5089:
5079:
5077:
5069:
5068:
5064:
5054:
5052:
5044:
5043:
5039:
5004:
4995:
4964:
4960:
4950:
4948:
4940:
4939:
4932:
4924:
4922:
4919:
4917:
4915:
4910:
4896:
4883:
4844:
4840:
4833:
4817:
4808:
4766:
4762:
4754:
4713:
4709:
4666:
4662:
4618:
4614:
4565:
4556:
4525:
4521:
4498:
4494:
4487:
4445:
4441:
4412:
4410:
4381:
4375:
4371:
4352:
4334:
4327:
4317:
4315:
4307:
4303:
4302:
4298:
4267:
4263:
4216:
4212:
4181:(5): 1192–203.
4167:
4163:
4118:
4114:
4082:
4069:
4038:
4034:
4013:(Pt 1): 71–90.
4003:
3999:
3960:
3956:
3925:
3921:
3890:
3886:
3841:
3837:
3827:
3825:
3817:
3816:
3805:
3795:
3793:
3784:
3783:
3774:
3743:
3730:
3699:
3690:
3659:
3632:
3625:
3609:
3598:
3566:
3531:
3500:
3487:
3456:
3441:
3402:
3393:
3370:
3363:
3332:
3317:
3298:Pharmacotherapy
3294:
3281:
3254:J Hum Hypertens
3250:
3241:
3210:
3191:
3181:
3179:
3177:
3161:
3146:
3136:
3134:
3132:
3118:Elks J (2014).
3116:
3095:
3085:
3083:
3080:DrugBank Online
3074:
3073:
3064:
3041:
3022:
2991:
2956:
2925:
2882:
2863:Pharmacotherapy
2859:
2790:
2780:
2778:
2760:
2756:
2740:
2739:
2732:
2730:
2727:web.archive.org
2721:
2720:
2697:
2687:
2685:
2683:
2667:
2644:
2639:
2634:
2633:
2627:
2622:
2620:Reference notes
2617:
2616:
2605:
2601:
2597:
2581:
2577:
2576:
2572:
2567:
2551:
2476:
2448:
2436:
2408:
2399:
2386:
2377:
2368:
2353:
2348:
2301:
2271:pseudoephedrine
2259:methamphetamine
2242:
2236:
2232:
2171:methamphetamine
2163:pseudoephedrine
2157:of PPA include
2109:, and is found
2083:-norephedrine (
2067:exists as four
2022:
2017:
2012:
2011:
2010:
2000:
1992:
1991:
1990:
1989:
1984:
1980:
1978:
1975:
1973:
1971:
1968:
1966:
1963:
1961:
1956:
1954:
1951:
1949:
1947:
1945:
1941:
1939:
1934:
1932:
1929:
1927:
1925:
1922:
1920:
1918:
1915:
1913:
1908:
1906:
1901:
1899:
1896:
1894:
1892:
1889:
1887:
1885:
1882:
1880:
1878:
1873:
1871:
1866:
1864:
1859:
1857:
1852:
1850:
1845:
1843:
1838:
1836:
1831:
1829:
1824:
1820:
1812:
1791:methamphetamine
1768:
1759:
1755:
1693:
1685:
1681:
1662:
1651:
1576:
1545:psychostimulant
1508:
1501:
1484:
1480:
1472:
1464:
1456:
1452:
1433:
1428:
1407:
1381:sympathomimetic
1343:Pseudoephedrine
1173:((–)-ephedrine)
1116:
1106:
1096:
1080:
1077:
1038:
1033:
1010:
944:sympathomimetic
940:
922:and in certain
916:
914:Available forms
888:
855:-norephedrine.
825:racemic mixture
813:pseudoephedrine
797:sympathomimetic
724:
722:
717:
714:
709:
704:
703:
692:
689:
688:O(c1ccccc1)(N)C
684:
683:
672:
647:
631:
625:
586:
562:
554:
534:
514:
494:
474:
454:
437:
429:
409:
406:
393:
392:
360:
346:
339:
329:
321:Onset of action
310:
281:Protein binding
271:Bioavailability
263:Pharmacokinetic
257:
193:
151:
144:
125:
28:
23:
22:
15:
12:
11:
5:
14239:
14229:
14228:
14223:
14218:
14213:
14208:
14203:
14198:
14193:
14188:
14183:
14181:Ergogenic aids
14178:
14173:
14171:Drugs in sport
14168:
14163:
14158:
14153:
14148:
14143:
14138:
14133:
14128:
14111:
14110:
14108:
14107:
14102:
14097:
14092:
14087:
14082:
14079:Levosalbutamol
14072:
14067:
14062:
14057:
14052:
14047:
14042:
14037:
14032:
14027:
14022:
14017:
14012:
14007:
14002:
13997:
13992:
13987:
13982:
13977:
13972:
13967:
13962:
13960:Desvenlafaxine
13957:
13952:
13947:
13942:
13937:
13931:
13929:
13925:
13924:
13922:
13921:
13916:
13911:
13903:
13895:
13890:
13885:
13875:
13873:Norepinephrine
13870:
13860:
13855:
13850:
13845:
13840:
13835:
13830:
13822:
13814:
13812:-Phenylalanine
13806:
13797:
13788:
13783:
13778:
13773:
13768:
13763:
13758:
13753:
13748:
13743:
13738:
13729:
13724:
13719:
13714:
13709:
13704:
13698:
13696:
13690:Catecholamines
13686:
13685:
13683:
13682:
13677:
13672:
13667:
13662:
13657:
13652:
13647:
13642:
13637:
13632:
13627:
13622:
13617:
13612:
13607:
13602:
13597:
13592:
13583:
13581:
13575:
13574:
13572:
13571:
13559:
13554:
13549:
13544:
13539:
13534:
13529:
13520:
13518:
13512:
13511:
13509:
13508:
13503:
13498:
13493:
13488:
13483:
13478:
13466:
13461:
13456:
13451:
13446:
13441:
13436:
13431:
13426:
13421:
13416:
13411:
13406:
13401:
13396:
13391:
13386:
13381:
13376:
13371:
13366:
13361:
13356:
13351:
13346:
13341:
13332:
13330:
13324:
13323:
13321:
13320:
13308:
13296:
13291:
13286:
13281:
13276:
13271:
13262:
13260:
13254:
13253:
13251:
13250:
13237:
13232:
13227:
13215:
13210:
13205:
13203:Methamnetamine
13200:
13195:
13190:
13185:
13180:
13175:
13170:
13165:
13160:
13155:
13150:
13145:
13140:
13135:
13130:
13125:
13120:
13115:
13110:
13105:
13100:
13095:
13090:
13085:
13080:
13075:
13063:
13058:
13053:
13048:
13043:
13038:
13033:
13028:
13023:
13018:
13013:
13008:
13003:
12998:
12993:
12988:
12983:
12978:
12973:
12968:
12963:
12958:
12950:
12945:
12940:
12935:
12930:
12920:
12915:
12910:
12905:
12900:
12895:
12890:
12885:
12880:
12875:
12870:
12865:
12860:
12855:
12841:
12836:
12831:
12826:
12824:Etilamfetamine
12821:
12816:
12811:
12806:
12801:
12796:
12791:
12786:
12772:
12767:
12762:
12757:
12752:
12747:
12742:
12737:
12725:
12720:
12715:
12710:
12705:
12700:
12695:
12690:
12685:
12680:
12675:
12670:
12665:
12660:
12655:
12650:
12645:
12640:
12635:
12630:
12625:
12620:
12615:
12610:
12605:
12600:
12595:
12586:
12584:
12578:
12577:
12575:
12574:
12569:
12557:
12552:
12543:
12542:
12537:
12529:
12521:
12513:
12505:
12500:
12494:
12489:
12487:Phenethylamine
12484:
12469:
12468:
12463:
12458:
12453:
12448:
12443:
12438:
12433:
12428:
12423:
12418:
12413:
12408:
12402:
12401:
12396:
12391:
12386:
12381:
12376:
12371:
12366:
12361:
12356:
12351:
12346:
12341:
12336:
12331:
12326:
12321:
12316:
12311:
12306:
12301:
12296:
12291:
12286:
12281:
12276:
12271:
12266:
12261:
12256:
12251:
12246:
12241:
12236:
12231:
12226:
12221:
12216:
12211:
12206:
12201:
12196:
12191:
12186:
12181:
12176:
12171:
12166:
12161:
12156:
12151:
12146:
12141:
12136:
12131:
12126:
12121:
12116:
12111:
12106:
12101:
12096:
12091:
12086:
12081:
12075:
12074:
12069:
12064:
12059:
12054:
12045:
12043:
12037:
12036:
12029:
12028:
12021:
12014:
12006:
11997:
11996:
11960:
11957:
11956:
11954:
11953:
11948:
11943:
11938:
11933:
11928:
11919:
11918:
11906:
11894:
11892:
11888:
11887:
11884:
11883:
11881:
11880:
11875:
11866:
11863:
11862:
11860:
11859:
11854:
11849:
11844:
11839:
11834:
11829:
11824:
11819:
11814:
11805:
11802:
11801:
11799:
11798:
11793:
11788:
11783:
11778:
11773:
11768:
11763:
11758:
11753:
11748:
11743:
11738:
11733:
11724:
11721:
11720:
11718:
11717:
11712:
11707:
11702:
11697:
11692:
11687:
11682:
11677:
11672:
11667:
11662:
11657:
11652:
11647:
11642:
11637:
11632:
11627:
11622:
11617:
11612:
11607:
11602:
11597:
11592:
11587:
11582:
11577:
11572:
11567:
11562:
11557:
11552:
11547:
11542:
11537:
11532:
11527:
11522:
11517:
11512:
11510:Metamfepramone
11507:
11502:
11497:
11492:
11487:
11482:
11477:
11472:
11467:
11462:
11457:
11452:
11447:
11442:
11437:
11432:
11427:
11422:
11417:
11408:
11405:
11404:
11402:
11401:
11396:
11391:
11386:
11377:
11374:
11373:
11371:
11370:
11365:
11360:
11355:
11346:
11343:
11342:
11340:
11339:
11334:
11329:
11324:
11319:
11314:
11309:
11300:
11294:
11283:
11282:
11279:
11278:
11276:
11275:
11273:Tuaminoheptane
11270:
11260:
11255:
11250:
11245:
11240:
11235:
11230:
11225:
11220:
11215:
11210:
11205:
11203:Cyclopentamine
11200:
11195:
11190:
11185:
11180:
11175:
11170:
11161:
11158:
11157:
11155:
11154:
11149:
11144:
11139:
11134:
11129:
11124:
11119:
11110:
11107:
11106:
11104:
11103:
11098:
11093:
11088:
11083:
11070:
11065:
11060:
11055:
11047:
11042:
11037:
11032:
11027:
11025:Phenethylamine
11022:
11017:
11009:
11001:
10996:
10991:
10986:
10981:
10976:
10971:
10970:
10969:
10964:
10954:
10949:
10944:
10939:
10934:
10929:
10924:
10922:Metamfepramone
10919:
10914:
10909:
10904:
10899:
10894:
10889:
10884:
10878:
10873:
10868:
10863:
10858:
10853:
10848:
10843:
10838:
10836:Etilamfetamine
10833:
10828:
10823:
10818:
10813:
10808:
10803:
10798:
10793:
10788:
10783:
10778:
10773:
10768:
10763:
10758:
10753:
10748:
10743:
10742:
10741:
10736:
10726:
10721:
10716:
10711:
10706:
10701:
10696:
10691:
10686:
10681:
10672:
10669:
10668:
10666:
10665:
10660:
10655:
10650:
10645:
10640:
10635:
10630:
10621:
10618:
10617:
10615:
10614:
10609:
10604:
10599:
10594:
10589:
10584:
10575:
10569:
10558:
10557:
10554:
10553:
10551:
10550:
10549:
10548:
10538:
10533:
10528:
10523:
10518:
10513:
10508:
10503:
10498:
10493:
10488:
10483:
10478:
10473:
10471:Cyclopentamine
10468:
10463:
10458:
10453:
10448:
10443:
10438:
10433:
10424:
10421:
10420:
10418:
10417:
10412:
10407:
10402:
10397:
10392:
10383:
10380:
10379:
10377:
10376:
10371:
10366:
10361:
10356:
10351:
10346:
10341:
10336:
10331:
10329:Phenethylamine
10326:
10321:
10313:
10305:
10297:
10292:
10287:
10282:
10277:
10272:
10267:
10262:
10257:
10252:
10247:
10242:
10237:
10232:
10227:
10226:
10225:
10220:
10210:
10208:Metamfepramone
10205:
10200:
10195:
10190:
10185:
10180:
10175:
10170:
10165:
10160:
10155:
10150:
10145:
10140:
10138:Etilamfetamine
10135:
10130:
10125:
10120:
10115:
10110:
10105:
10100:
10095:
10090:
10085:
10080:
10075:
10070:
10065:
10060:
10055:
10050:
10045:
10040:
10034:
10025:
10020:
10015:
10010:
10005:
10000:
9995:
9990:
9985:
9980:
9971:
9968:
9967:
9965:
9964:
9959:
9954:
9949:
9944:
9939:
9934:
9929:
9920:
9917:
9916:
9914:
9913:
9908:
9903:
9898:
9893:
9888:
9883:
9874:
9868:
9857:
9856:
9849:
9848:
9841:
9834:
9826:
9817:
9816:
9814:
9813:
9804:
9795:
9786:
9777:
9768:
9759:
9746:
9743:
9742:
9739:
9738:
9736:
9735:
9730:
9725:
9720:
9715:
9710:
9705:
9700:
9695:
9690:
9685:
9680:
9675:
9670:
9665:
9660:
9655:
9650:
9645:
9640:
9635:
9630:
9625:
9620:
9615:
9610:
9605:
9600:
9595:
9590:
9585:
9580:
9575:
9570:
9565:
9560:
9555:
9550:
9545:
9540:
9535:
9530:
9525:
9520:
9515:
9510:
9505:
9500:
9495:
9490:
9485:
9480:
9475:
9470:
9465:
9460:
9455:
9450:
9445:
9440:
9435:
9430:
9425:
9420:
9415:
9410:
9405:
9400:
9395:
9390:
9385:
9380:
9375:
9370:
9368:Dexpropranolol
9365:
9360:
9355:
9350:
9345:
9340:
9335:
9330:
9325:
9320:
9315:
9310:
9305:
9300:
9295:
9290:
9285:
9280:
9275:
9270:
9265:
9260:
9255:
9250:
9245:
9240:
9235:
9230:
9225:
9220:
9215:
9210:
9205:
9200:
9195:
9190:
9185:
9180:
9175:
9170:
9164:
9162:
9158:
9157:
9155:
9154:
9149:
9144:
9139:
9134:
9129:
9124:
9119:
9114:
9109:
9104:
9099:
9094:
9089:
9084:
9079:
9074:
9069:
9064:
9059:
9054:
9049:
9044:
9039:
9037:Norepinephrine
9034:
9029:
9024:
9019:
9014:
9009:
9004:
9002:Levosalbutamol
8999:
8991:
8989:-Phenylalanine
8983:
8975:
8970:
8965:
8960:
8955:
8950:
8945:
8940:
8935:
8930:
8925:
8920:
8915:
8910:
8905:
8900:
8891:
8886:
8881:
8876:
8871:
8862:
8857:
8852:
8847:
8842:
8837:
8832:
8827:
8822:
8817:
8812:
8807:
8802:
8797:
8792:
8787:
8782:
8777:
8772:
8766:
8764:
8757:
8751:
8750:
8747:
8746:
8744:
8743:
8738:
8723:chlorpromazine
8716:
8711:
8706:
8701:
8696:
8691:
8686:
8681:
8676:
8671:
8666:
8661:
8656:
8651:
8646:
8641:
8636:
8631:
8626:
8621:
8616:
8611:
8606:
8601:
8596:
8591:
8586:
8581:
8559:
8517:
8512:
8507:
8502:
8497:
8491:
8489:
8485:
8484:
8482:
8481:
8479:Xylometazoline
8476:
8471:
8466:
8461:
8456:
8451:
8446:
8441:
8436:
8431:
8426:
8421:
8416:
8411:
8406:
8401:
8396:
8391:
8389:Norepinephrine
8386:
8381:
8376:
8371:
8366:
8361:
8356:
8351:
8346:
8338:
8336:-Phenylalanine
8330:
8322:
8317:
8312:
8307:
8302:
8297:
8292:
8287:
8282:
8273:
8268:
8263:
8258:
8253:
8248:
8239:
8234:
8229:
8224:
8219:
8214:
8209:
8204:
8198:
8196:
8189:
8185:
8180:
8179:
8176:
8175:
8173:
8172:
8167:
8162:
8157:
8142:chlorpromazine
8135:
8130:
8104:
8086:
8081:
8076:
8071:
8066:
8061:
8056:
8051:
8046:
8041:
8036:
8031:
8026:
8001:
7996:
7991:
7986:
7981:
7976:
7971:
7966:
7961:
7956:
7951:
7946:
7941:
7936:
7931:
7926:
7921:
7916:
7911:
7906:
7901:
7896:
7891:
7861:
7856:
7851:
7846:
7841:
7836:
7831:
7801:
7796:
7770:
7765:
7760:
7755:
7750:
7745:
7739:
7737:
7733:
7732:
7730:
7729:
7727:Xylometazoline
7724:
7719:
7714:
7709:
7704:
7699:
7694:
7689:
7684:
7682:Norepinephrine
7679:
7674:
7669:
7664:
7659:
7654:
7649:
7641:
7639:-Phenylalanine
7633:
7625:
7620:
7615:
7610:
7605:
7600:
7595:
7590:
7581:
7576:
7571:
7566:
7561:
7552:
7547:
7542:
7537:
7532:
7526:
7524:
7517:
7513:
7508:
7507:
7497:
7496:
7489:
7482:
7474:
7465:
7464:
7461:
7460:
7459:
7458:
7455:
7444:
7438:
7432:
7431:
7428:
7427:
7425:
7424:
7419:
7414:
7409:
7404:
7399:
7394:
7389:
7384:
7379:
7374:
7368:
7366:
7362:
7361:
7359:
7358:
7352:
7350:
7344:
7343:
7341:
7340:
7335:
7330:
7325:
7320:
7314:
7312:
7308:
7307:
7305:
7304:
7299:
7293:
7291:
7283:
7282:
7280:
7279:
7268:
7266:
7260:
7259:
7257:
7256:
7250:
7240:
7235:
7230:
7225:
7220:
7214:
7209:
7204:
7199:
7194:
7188:
7186:
7168:
7167:
7165:
7164:
7159:
7154:
7149:
7144:
7139:
7134:
7128:
7126:
7118:
7117:
7114:
7113:
7111:
7110:
7105:
7100:
7095:
7090:
7085:
7080:
7075:
7073:Phenethylamine
7070:
7065:
7060:
7055:
7050:
7040:
7035:
7030:
7025:
7020:
7010:
7005:
7000:
6994:
6992:
6988:
6987:
6985:
6984:
6974:
6969:
6964:
6959:
6954:
6949:
6944:
6938:
6936:
6930:
6929:
6927:
6926:
6921:
6916:
6906:
6901:
6896:
6891:
6886:
6881:
6876:
6871:
6866:
6861:
6856:
6851:
6849:Etilamfetamine
6846:
6841:
6836:
6831:
6826:
6821:
6816:
6811:
6806:
6801:
6796:
6791:
6786:
6781:
6776:
6771:
6766:
6760:
6758:
6744:
6738:
6737:
6721:
6720:
6713:
6706:
6698:
6689:
6688:
6685:
6684:
6683:
6682:
6679:
6668:
6662:
6656:
6655:
6652:
6651:
6649:
6648:
6625:+carbinoxamine
6614:
6609:
6604:
6598:
6596:
6588:
6587:
6584:
6583:
6581:
6580:
6574:
6572:
6568:
6567:
6565:
6564:
6559:
6554:
6549:
6544:
6539:
6534:
6529:
6524:
6522:Eucalyptus oil
6519:
6514:
6508:
6506:
6502:
6501:
6499:
6498:
6493:
6488:
6483:
6478:
6473:
6462:
6457:
6452:
6447:
6442:
6437:
6431:
6429:
6423:
6422:
6420:
6419:
6413:
6408:
6403:
6398:
6386:
6385:
6379:
6374:
6362:
6361:
6359:Spaglumic acid
6355:
6353:
6344:
6343:
6341:
6340:
6338:Xylometazoline
6335:
6330:
6328:Tuaminoheptane
6325:
6320:
6315:
6310:
6305:
6300:
6295:
6290:
6285:
6280:
6275:
6270:
6265:
6260:
6258:Cyclopentamine
6255:
6249:
6247:
6237:
6231:
6230:
6218:
6217:
6210:
6203:
6195:
6186:
6185:
6183:
6182:
6171:
6168:
6167:
6165:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6132:Phenethylamine
6129:
6124:
6119:
6117:Norepinephrine
6114:
6109:
6104:
6099:
6098:
6097:
6087:
6079:
6074:
6069:
6064:
6059:
6054:
6049:
6044:
6039:
6034:
6029:
6024:
6018:
6016:
6012:
6011:
6009:
6008:
6003:
5998:
5992:
5990:
5986:
5985:
5982:
5981:
5979:
5978:
5973:
5968:
5963:
5958:
5953:
5948:
5943:
5937:
5935:
5928:
5927:
5925:
5924:
5887:
5877:
5872:(low affinity
5867:
5852:
5841:
5839:
5830:
5826:
5825:
5822:
5821:
5819:
5818:
5812:
5810:
5804:
5803:
5801:
5800:
5795:
5790:
5784:
5782:
5776:
5775:
5772:
5770:
5764:
5763:
5761:
5760:
5759:
5758:
5753:
5748:
5738:
5733:
5728:
5723:
5720:Adzenys XR-ODT
5716:
5710:
5708:
5699:
5694:Main articles
5691:
5690:
5683:
5682:
5675:
5668:
5660:
5649:
5648:
5641:
5621:
5614:
5594:
5572:
5558:
5538:
5527:
5509:
5491:
5469:
5443:
5418:Essays Biochem
5405:
5391:
5361:
5350:. 7 March 2006
5335:
5332:on 3 May 2010.
5313:
5280:(4): 541–553.
5260:
5211:
5162:
5137:
5112:
5087:
5062:
5037:
5014:(7): 675–694.
4993:
4958:
4930:
4908:
4881:
4838:
4831:
4806:
4776:(3): 901–908.
4760:
4707:
4676:(5): 594–599.
4660:
4612:
4579:(2): 278–284.
4554:
4535:(2): 247–255.
4519:
4492:
4459:(3): 357–387.
4439:
4392:(2): 454–458.
4369:
4350:
4325:
4296:
4277:(6): 527–546.
4261:
4210:
4161:
4132:(4): 552–562.
4112:
4067:
4048:(1–3): 23–40.
4032:
3997:
3970:(5): 460–462.
3954:
3935:(4): 370–378.
3919:
3884:
3835:
3803:
3772:
3728:
3688:
3669:(3): 197–207.
3630:
3623:
3596:
3577:(1): 138–145.
3529:
3510:(5): 512–518.
3485:
3439:
3412:(2): 146–149.
3391:
3380:(3): 513–526.
3361:
3342:(5): 264–267.
3315:
3279:
3260:(8): 643–652.
3239:
3220:(4): 277–302.
3189:
3175:
3144:
3130:
3093:
3082:. 29 June 2018
3062:
3051:(2): 355–368.
3020:
3001:(4): 209–224.
2954:
2880:
2788:
2754:
2695:
2681:
2641:
2640:
2638:
2635:
2632:
2631:
2624:
2623:
2621:
2618:
2615:
2614:
2569:
2568:
2566:
2563:
2550:
2549:Veterinary use
2547:
2487:United Kingdom
2475:
2472:
2447:
2444:
2440:veterinary use
2435:
2432:
2352:
2349:
2347:
2344:
2303:PPA was first
2300:
2297:
2279:norepinephrine
2234:
2230:
2220:small-molecule
2077:dextrorotatory
2021:
2018:
2014:
2013:
1994:
1993:
1822:
1821:
1814:
1813:
1810:
1809:
1808:
1803:
1767:
1764:
1680:PPA is about 4
1650:
1647:
1639:hydroxyl group
1575:
1572:
1529:hydrophilicity
1525:hydroxyl group
1500:
1497:
1432:
1429:
1427:
1424:
1416:norepinephrine
1367:
1366:
1358:
1357:
1355:
1352:
1349:
1346:
1339:
1338:
1336:
1333:
1330:
1327:
1323:
1322:
1320:
1317:
1314:
1311:
1305:
1304:
1302:
1299:
1296:
1293:
1286:
1285:
1283:
1280:
1277:
1274:
1267:
1266:
1264:
1261:
1258:
1255:
1248:
1247:
1245:
1242:
1239:
1236:
1225:
1224:
1222:
1219:
1216:
1213:
1202:
1201:
1199:
1196:
1193:
1190:
1186:
1185:
1183:
1180:
1177:
1174:
1167:
1166:
1164:
1161:
1158:
1155:
1146:
1145:
1143:
1140:
1137:
1134:
1123:
1122:
1119:
1109:
1099:
1089:
1075:
1037:
1034:
1032:
1029:
1009:
1006:
956:blood pressure
939:
936:
915:
912:
887:
884:
880:veterinary use
858:PPA was first
781:blood pressure
731:
730:
719:
718:
716:
715:
712:
710:
707:
699:
698:
697:
694:
693:
691:
690:
687:
679:
678:
677:
674:
673:
671:
670:
662:
660:
652:
651:
645:
639:
638:
629:
623:
618:
612:
611:
607:
606:
596:
588:
587:
585:
584:
571:
569:
556:
555:
553:
552:
544:
542:
536:
535:
533:
532:
524:
522:
516:
515:
513:
512:
504:
502:
496:
495:
493:
492:
484:
482:
476:
475:
473:
472:
464:
462:
456:
455:
453:
452:
444:
442:
431:
430:
428:
427:
419:
417:
411:
410:
408:
407:
396:
388:
387:
386:
383:
382:
378:
377:
371:
365:
364:
357:
351:
350:
343:
334:
333:
323:
317:
316:
303:
297:
296:
295:Minimal (3–4%)
293:
287:
286:
283:
277:
276:
273:
267:
266:
259:
258:
256:
255:
246:
235:
222:
208:
206:
200:
199:
195:
194:
192:
191:
168:
166:
160:
159:
154:
152:administration
146:
145:
143:
142:
140:
130:
128:
120:
119:
112:
102:
101:
74:
70:
69:
66:
60:
59:
55:
54:
46:
45:
26:
9:
6:
4:
3:
2:
14238:
14227:
14224:
14222:
14219:
14217:
14214:
14212:
14209:
14207:
14204:
14202:
14199:
14197:
14194:
14192:
14189:
14187:
14184:
14182:
14179:
14177:
14174:
14172:
14169:
14167:
14164:
14162:
14159:
14157:
14154:
14152:
14151:Decongestants
14149:
14147:
14144:
14142:
14139:
14137:
14134:
14132:
14129:
14127:
14124:
14123:
14121:
14106:
14103:
14101:
14098:
14096:
14095:Thiamphenicol
14093:
14091:
14090:Theodrenaline
14088:
14086:
14083:
14080:
14076:
14073:
14071:
14068:
14066:
14063:
14061:
14058:
14056:
14053:
14051:
14048:
14046:
14043:
14041:
14038:
14036:
14033:
14031:
14028:
14026:
14023:
14021:
14018:
14016:
14013:
14011:
14008:
14006:
14005:Fluorolintane
14003:
14001:
13998:
13996:
13993:
13991:
13988:
13986:
13983:
13981:
13978:
13976:
13973:
13971:
13968:
13966:
13963:
13961:
13958:
13956:
13953:
13951:
13948:
13946:
13943:
13941:
13938:
13936:
13933:
13932:
13930:
13928:Miscellaneous
13926:
13920:
13917:
13915:
13914:Phenylephrine
13912:
13910:
13908:
13904:
13902:
13900:
13896:
13894:
13893:Orciprenaline
13891:
13889:
13886:
13883:
13879:
13876:
13874:
13871:
13868:
13867:Levonordefrin
13864:
13861:
13859:
13856:
13854:
13851:
13849:
13846:
13844:
13841:
13839:
13836:
13834:
13831:
13829:
13827:
13823:
13821:
13815:
13813:
13807:
13804:
13798:
13795:
13789:
13787:
13784:
13782:
13779:
13777:
13774:
13772:
13769:
13767:
13764:
13762:
13759:
13757:
13754:
13752:
13749:
13747:
13744:
13742:
13739:
13736:
13730:
13728:
13725:
13723:
13720:
13718:
13715:
13713:
13710:
13708:
13705:
13703:
13700:
13699:
13697:
13691:
13687:
13681:
13678:
13676:
13673:
13671:
13668:
13666:
13663:
13661:
13658:
13656:
13653:
13651:
13648:
13646:
13643:
13641:
13638:
13636:
13633:
13631:
13628:
13626:
13623:
13621:
13618:
13616:
13613:
13611:
13608:
13606:
13603:
13601:
13598:
13596:
13593:
13591:
13588:
13585:
13584:
13582:
13580:
13576:
13570:
13567:
13563:
13560:
13558:
13555:
13553:
13550:
13548:
13545:
13543:
13540:
13538:
13535:
13533:
13530:
13528:
13525:
13522:
13521:
13519:
13517:
13513:
13507:
13504:
13502:
13499:
13497:
13494:
13492:
13489:
13487:
13484:
13482:
13479:
13477:
13474:
13470:
13467:
13465:
13462:
13460:
13457:
13455:
13452:
13450:
13447:
13445:
13442:
13440:
13437:
13435:
13434:Methcathinone
13432:
13430:
13427:
13425:
13422:
13420:
13417:
13415:
13412:
13410:
13407:
13405:
13402:
13400:
13397:
13395:
13392:
13390:
13387:
13385:
13382:
13380:
13377:
13375:
13372:
13370:
13367:
13365:
13362:
13360:
13357:
13355:
13352:
13350:
13347:
13345:
13342:
13340:
13337:
13334:
13333:
13331:
13329:
13325:
13319:
13316:
13312:
13309:
13307:
13304:
13300:
13297:
13295:
13292:
13290:
13289:Mephentermine
13287:
13285:
13282:
13280:
13277:
13275:
13272:
13270:
13267:
13264:
13263:
13261:
13259:
13255:
13248:
13241:
13238:
13236:
13233:
13231:
13228:
13226:
13223:
13219:
13216:
13214:
13211:
13209:
13206:
13204:
13201:
13199:
13196:
13194:
13191:
13189:
13186:
13184:
13181:
13179:
13176:
13174:
13171:
13169:
13166:
13164:
13161:
13159:
13156:
13154:
13151:
13149:
13146:
13144:
13141:
13139:
13138:6-Chloro-MDMA
13136:
13134:
13131:
13129:
13126:
13124:
13121:
13119:
13116:
13114:
13111:
13109:
13106:
13104:
13101:
13099:
13096:
13094:
13091:
13089:
13086:
13084:
13081:
13079:
13076:
13074:
13071:
13067:
13064:
13062:
13061:Xylopropamine
13059:
13057:
13054:
13052:
13049:
13047:
13044:
13042:
13039:
13037:
13034:
13032:
13029:
13027:
13024:
13022:
13019:
13017:
13014:
13012:
13009:
13007:
13004:
13002:
12999:
12997:
12994:
12992:
12989:
12987:
12984:
12982:
12979:
12977:
12974:
12972:
12969:
12967:
12964:
12962:
12959:
12957:
12951:
12949:
12946:
12944:
12941:
12939:
12936:
12934:
12931:
12928:
12924:
12921:
12919:
12916:
12914:
12911:
12909:
12906:
12904:
12901:
12899:
12896:
12894:
12891:
12889:
12886:
12884:
12881:
12879:
12876:
12874:
12871:
12869:
12866:
12864:
12861:
12859:
12856:
12853:
12849:
12845:
12842:
12840:
12837:
12835:
12832:
12830:
12827:
12825:
12822:
12820:
12817:
12815:
12812:
12810:
12807:
12805:
12802:
12800:
12799:Benzphetamine
12797:
12795:
12792:
12790:
12787:
12784:
12780:
12776:
12773:
12771:
12768:
12766:
12763:
12761:
12758:
12756:
12753:
12751:
12748:
12746:
12743:
12741:
12738:
12736:
12733:
12729:
12726:
12724:
12721:
12719:
12716:
12714:
12711:
12709:
12706:
12704:
12701:
12699:
12696:
12694:
12691:
12689:
12686:
12684:
12681:
12679:
12676:
12674:
12671:
12669:
12666:
12664:
12661:
12659:
12656:
12654:
12651:
12649:
12646:
12644:
12641:
12639:
12636:
12634:
12631:
12629:
12626:
12624:
12621:
12619:
12616:
12614:
12611:
12609:
12606:
12604:
12601:
12599:
12596:
12594:
12591:
12590:Psychedelics:
12588:
12587:
12585:
12583:
12579:
12573:
12570:
12568:
12565:
12561:
12558:
12556:
12553:
12551:
12548:
12545:
12544:
12541:
12538:
12536:
12534:
12530:
12528:
12526:
12522:
12520:
12518:
12514:
12512:
12510:
12506:
12504:
12501:
12499:(amphetamine)
12498:
12495:
12493:
12490:
12488:
12485:
12483:
12480:
12479:
12478:
12477:
12474:
12467:
12464:
12462:
12459:
12457:
12454:
12452:
12449:
12447:
12444:
12442:
12439:
12437:
12434:
12432:
12429:
12427:
12424:
12422:
12421:Isoproscaline
12419:
12417:
12414:
12412:
12409:
12407:
12406:Allylescaline
12404:
12403:
12400:
12397:
12395:
12392:
12390:
12387:
12385:
12382:
12380:
12377:
12375:
12372:
12370:
12367:
12365:
12362:
12360:
12357:
12355:
12352:
12350:
12347:
12345:
12342:
12340:
12337:
12335:
12332:
12330:
12327:
12325:
12322:
12320:
12317:
12315:
12312:
12310:
12307:
12305:
12302:
12300:
12297:
12295:
12292:
12290:
12287:
12285:
12282:
12280:
12277:
12275:
12272:
12270:
12267:
12265:
12262:
12260:
12257:
12255:
12252:
12250:
12247:
12245:
12242:
12240:
12237:
12235:
12232:
12230:
12227:
12225:
12222:
12220:
12217:
12215:
12212:
12210:
12207:
12205:
12202:
12200:
12197:
12195:
12192:
12190:
12187:
12185:
12182:
12180:
12177:
12175:
12172:
12170:
12167:
12165:
12162:
12160:
12157:
12155:
12152:
12150:
12147:
12145:
12142:
12140:
12137:
12135:
12132:
12130:
12127:
12125:
12122:
12120:
12117:
12115:
12112:
12110:
12107:
12105:
12102:
12100:
12097:
12095:
12092:
12090:
12087:
12085:
12082:
12080:
12077:
12076:
12073:
12070:
12068:
12065:
12063:
12060:
12058:
12055:
12053:
12050:
12049:Psychedelics:
12047:
12046:
12044:
12042:
12038:
12034:
12027:
12022:
12020:
12015:
12013:
12008:
12007:
12004:
11993:
11992:
11988:
11984:
11983:Serotonergics
11980:
11979:Dopaminergics
11976:
11972:
11968:
11965:
11958:
11952:
11949:
11947:
11944:
11942:
11939:
11937:
11934:
11932:
11929:
11927:
11924:
11921:
11920:
11917:
11914:
11910:
11907:
11905:
11902:
11901:Agonist-like:
11899:
11896:
11895:
11893:
11889:
11879:
11876:
11874:
11871:
11868:
11867:
11864:
11858:
11855:
11853:
11850:
11848:
11845:
11843:
11840:
11838:
11835:
11833:
11830:
11828:
11825:
11823:
11820:
11818:
11815:
11813:
11810:
11807:
11806:
11803:
11797:
11794:
11792:
11789:
11787:
11784:
11782:
11779:
11777:
11774:
11772:
11769:
11767:
11764:
11762:
11759:
11757:
11754:
11752:
11749:
11747:
11744:
11742:
11739:
11737:
11734:
11732:
11729:
11726:
11725:
11722:
11716:
11713:
11711:
11708:
11706:
11703:
11701:
11698:
11696:
11693:
11691:
11688:
11686:
11683:
11681:
11678:
11676:
11673:
11671:
11668:
11666:
11663:
11661:
11658:
11656:
11653:
11651:
11648:
11646:
11643:
11641:
11638:
11636:
11633:
11631:
11628:
11626:
11623:
11621:
11618:
11616:
11613:
11611:
11608:
11606:
11603:
11601:
11598:
11596:
11593:
11591:
11588:
11586:
11583:
11581:
11578:
11576:
11573:
11571:
11568:
11566:
11563:
11561:
11558:
11556:
11553:
11551:
11548:
11546:
11543:
11541:
11538:
11536:
11533:
11531:
11528:
11526:
11523:
11521:
11518:
11516:
11513:
11511:
11508:
11506:
11503:
11501:
11498:
11496:
11493:
11491:
11488:
11486:
11483:
11481:
11478:
11476:
11473:
11471:
11468:
11466:
11463:
11461:
11458:
11456:
11453:
11451:
11448:
11446:
11443:
11441:
11438:
11436:
11433:
11431:
11428:
11426:
11423:
11421:
11418:
11416:
11413:
11410:
11409:
11406:
11400:
11397:
11395:
11392:
11390:
11387:
11385:
11382:
11379:
11378:
11375:
11369:
11366:
11364:
11361:
11359:
11356:
11354:
11351:
11348:
11347:
11344:
11338:
11335:
11333:
11330:
11328:
11325:
11323:
11320:
11318:
11315:
11313:
11310:
11308:
11305:
11304:Aminoindanes:
11302:
11301:
11298:
11295:
11290:
11284:
11274:
11271:
11268:
11264:
11261:
11259:
11256:
11254:
11251:
11249:
11246:
11244:
11243:Isometheptene
11241:
11239:
11236:
11234:
11233:Hexacyclonate
11231:
11229:
11226:
11224:
11221:
11219:
11216:
11214:
11211:
11209:
11206:
11204:
11201:
11199:
11196:
11194:
11191:
11189:
11186:
11184:
11181:
11179:
11176:
11174:
11171:
11169:
11166:
11163:
11162:
11159:
11153:
11150:
11148:
11145:
11143:
11140:
11138:
11135:
11133:
11130:
11128:
11125:
11123:
11120:
11118:
11115:
11112:
11111:
11108:
11102:
11099:
11097:
11096:Xylopropamine
11094:
11092:
11089:
11087:
11084:
11081:
11074:
11071:
11069:
11066:
11064:
11061:
11059:
11056:
11054:
11052:
11048:
11046:
11043:
11041:
11038:
11036:
11033:
11031:
11028:
11026:
11023:
11021:
11018:
11016:
11014:
11010:
11008:
11006:
11002:
11000:
10997:
10995:
10992:
10990:
10987:
10985:
10982:
10980:
10977:
10975:
10974:Methcathinone
10972:
10968:
10965:
10963:
10960:
10959:
10958:
10955:
10953:
10952:Mephentermine
10950:
10948:
10945:
10943:
10940:
10938:
10935:
10933:
10930:
10928:
10925:
10923:
10920:
10918:
10915:
10913:
10910:
10908:
10905:
10903:
10900:
10898:
10895:
10893:
10890:
10888:
10885:
10882:
10879:
10877:
10874:
10872:
10869:
10867:
10864:
10862:
10859:
10857:
10854:
10852:
10849:
10847:
10844:
10842:
10839:
10837:
10834:
10832:
10829:
10827:
10824:
10822:
10819:
10817:
10814:
10812:
10809:
10807:
10804:
10802:
10799:
10797:
10794:
10792:
10789:
10787:
10784:
10782:
10779:
10777:
10774:
10772:
10769:
10767:
10764:
10762:
10761:Benzphetamine
10759:
10757:
10754:
10752:
10749:
10747:
10744:
10740:
10737:
10735:
10732:
10731:
10730:
10727:
10725:
10722:
10720:
10717:
10715:
10712:
10710:
10707:
10705:
10702:
10700:
10697:
10695:
10692:
10690:
10687:
10685:
10682:
10680:
10677:
10674:
10673:
10670:
10664:
10661:
10659:
10656:
10654:
10651:
10649:
10646:
10644:
10641:
10639:
10636:
10634:
10631:
10629:
10626:
10623:
10622:
10619:
10613:
10610:
10608:
10607:Phenmetrazine
10605:
10603:
10600:
10598:
10595:
10593:
10590:
10588:
10585:
10583:
10580:
10577:
10576:
10573:
10570:
10565:
10559:
10547:
10544:
10543:
10542:
10539:
10537:
10534:
10532:
10529:
10527:
10524:
10522:
10519:
10517:
10514:
10512:
10511:Isometheptene
10509:
10507:
10504:
10502:
10501:Hexacyclonate
10499:
10497:
10494:
10492:
10489:
10487:
10484:
10482:
10479:
10477:
10474:
10472:
10469:
10467:
10464:
10462:
10459:
10457:
10454:
10452:
10449:
10447:
10444:
10442:
10439:
10437:
10434:
10432:
10429:
10426:
10425:
10422:
10416:
10413:
10411:
10408:
10406:
10403:
10401:
10398:
10396:
10393:
10391:
10388:
10385:
10384:
10381:
10375:
10372:
10370:
10369:Xylopropamine
10367:
10365:
10362:
10360:
10357:
10355:
10352:
10350:
10347:
10345:
10342:
10340:
10337:
10335:
10332:
10330:
10327:
10325:
10322:
10320:
10318:
10314:
10312:
10310:
10306:
10304:
10302:
10298:
10296:
10293:
10291:
10288:
10286:
10283:
10281:
10278:
10276:
10273:
10271:
10268:
10266:
10263:
10261:
10258:
10256:
10253:
10251:
10248:
10246:
10243:
10241:
10238:
10236:
10233:
10231:
10230:Methcathinone
10228:
10224:
10221:
10219:
10216:
10215:
10214:
10211:
10209:
10206:
10204:
10201:
10199:
10196:
10194:
10191:
10189:
10186:
10184:
10181:
10179:
10176:
10174:
10171:
10169:
10166:
10164:
10161:
10159:
10156:
10154:
10151:
10149:
10146:
10144:
10141:
10139:
10136:
10134:
10131:
10129:
10126:
10124:
10121:
10119:
10116:
10114:
10111:
10109:
10106:
10104:
10101:
10099:
10096:
10094:
10091:
10089:
10086:
10084:
10081:
10079:
10076:
10074:
10071:
10069:
10066:
10064:
10063:Benzphetamine
10061:
10059:
10056:
10054:
10051:
10049:
10046:
10044:
10041:
10038:
10035:
10033:
10029:
10026:
10024:
10021:
10019:
10016:
10014:
10011:
10009:
10006:
10004:
10001:
9999:
9996:
9994:
9991:
9989:
9986:
9984:
9981:
9979:
9976:
9973:
9972:
9969:
9963:
9960:
9958:
9955:
9953:
9950:
9948:
9945:
9943:
9940:
9938:
9935:
9933:
9930:
9928:
9925:
9922:
9921:
9918:
9912:
9909:
9907:
9906:Phenmetrazine
9904:
9902:
9899:
9897:
9894:
9892:
9889:
9887:
9884:
9882:
9879:
9876:
9875:
9872:
9869:
9864:
9858:
9854:
9847:
9842:
9840:
9835:
9833:
9828:
9827:
9824:
9811:
9810:
9805:
9802:
9801:
9796:
9793:
9792:
9787:
9784:
9783:
9778:
9775:
9774:
9773:Serotonergics
9769:
9766:
9765:
9764:Dopaminergics
9760:
9757:
9756:
9753:
9748:
9747:
9744:
9734:
9731:
9729:
9726:
9724:
9721:
9719:
9716:
9714:
9711:
9709:
9706:
9704:
9701:
9699:
9696:
9694:
9691:
9689:
9686:
9684:
9681:
9679:
9676:
9674:
9671:
9669:
9666:
9664:
9661:
9659:
9656:
9654:
9651:
9649:
9646:
9644:
9641:
9639:
9636:
9634:
9631:
9629:
9626:
9624:
9621:
9619:
9616:
9614:
9611:
9609:
9606:
9604:
9601:
9599:
9596:
9594:
9591:
9589:
9586:
9584:
9581:
9579:
9576:
9574:
9571:
9569:
9566:
9564:
9561:
9559:
9556:
9554:
9551:
9549:
9546:
9544:
9541:
9539:
9536:
9534:
9531:
9529:
9526:
9524:
9521:
9519:
9518:Levobetaxolol
9516:
9514:
9511:
9509:
9506:
9504:
9501:
9499:
9496:
9494:
9491:
9489:
9486:
9484:
9481:
9479:
9476:
9474:
9471:
9469:
9466:
9464:
9461:
9459:
9456:
9454:
9451:
9449:
9446:
9444:
9441:
9439:
9436:
9434:
9431:
9429:
9426:
9424:
9421:
9419:
9416:
9414:
9411:
9409:
9406:
9404:
9401:
9399:
9396:
9394:
9391:
9389:
9386:
9384:
9381:
9379:
9376:
9374:
9371:
9369:
9366:
9364:
9361:
9359:
9358:Cyanopindolol
9356:
9354:
9351:
9349:
9346:
9344:
9341:
9339:
9336:
9334:
9331:
9329:
9326:
9324:
9321:
9319:
9316:
9314:
9311:
9309:
9306:
9304:
9301:
9299:
9296:
9294:
9291:
9289:
9286:
9284:
9281:
9279:
9276:
9274:
9271:
9269:
9266:
9264:
9261:
9259:
9256:
9254:
9251:
9249:
9246:
9244:
9241:
9239:
9236:
9234:
9231:
9229:
9226:
9224:
9221:
9219:
9216:
9214:
9211:
9209:
9206:
9204:
9201:
9199:
9196:
9194:
9191:
9189:
9186:
9184:
9181:
9179:
9176:
9174:
9171:
9169:
9166:
9165:
9163:
9159:
9153:
9150:
9148:
9145:
9143:
9140:
9138:
9135:
9133:
9130:
9128:
9125:
9123:
9120:
9118:
9115:
9113:
9110:
9108:
9105:
9103:
9100:
9098:
9095:
9093:
9090:
9088:
9085:
9083:
9080:
9078:
9075:
9073:
9070:
9068:
9065:
9063:
9060:
9058:
9055:
9053:
9050:
9048:
9045:
9043:
9042:Orciprenaline
9040:
9038:
9035:
9033:
9030:
9028:
9025:
9023:
9020:
9018:
9015:
9013:
9010:
9008:
9005:
9003:
9000:
8998:
8992:
8990:
8984:
8982:
8976:
8974:
8971:
8969:
8966:
8964:
8961:
8959:
8956:
8954:
8951:
8949:
8946:
8944:
8943:Hexoprenaline
8941:
8939:
8936:
8934:
8931:
8929:
8926:
8924:
8921:
8919:
8916:
8914:
8911:
8909:
8906:
8904:
8901:
8899:
8892:
8890:
8887:
8885:
8882:
8880:
8877:
8875:
8872:
8870:
8868:
8863:
8861:
8858:
8856:
8853:
8851:
8848:
8846:
8843:
8841:
8838:
8836:
8833:
8831:
8828:
8826:
8823:
8821:
8818:
8816:
8813:
8811:
8808:
8806:
8803:
8801:
8798:
8796:
8793:
8791:
8788:
8786:
8783:
8781:
8778:
8776:
8773:
8771:
8768:
8767:
8765:
8761:
8758:
8756:
8752:
8742:
8739:
8736:
8732:
8728:
8724:
8720:
8717:
8715:
8712:
8710:
8707:
8705:
8702:
8700:
8697:
8695:
8692:
8690:
8687:
8685:
8682:
8680:
8677:
8675:
8672:
8670:
8667:
8665:
8662:
8660:
8657:
8655:
8652:
8650:
8647:
8645:
8642:
8640:
8637:
8635:
8632:
8630:
8627:
8625:
8622:
8620:
8617:
8615:
8612:
8610:
8607:
8605:
8604:Esmirtazapine
8602:
8600:
8597:
8595:
8592:
8590:
8587:
8585:
8582:
8579:
8575:
8571:
8567:
8563:
8560:
8557:
8553:
8549:
8545:
8541:
8537:
8533:
8529:
8528:brexpiprazole
8525:
8521:
8518:
8516:
8513:
8511:
8508:
8506:
8503:
8501:
8498:
8496:
8493:
8492:
8490:
8486:
8480:
8477:
8475:
8472:
8470:
8467:
8465:
8462:
8460:
8457:
8455:
8452:
8450:
8447:
8445:
8442:
8440:
8437:
8435:
8432:
8430:
8427:
8425:
8422:
8420:
8417:
8415:
8412:
8410:
8407:
8405:
8402:
8400:
8397:
8395:
8394:Oxymetazoline
8392:
8390:
8387:
8385:
8382:
8380:
8377:
8375:
8372:
8370:
8367:
8365:
8362:
8360:
8357:
8355:
8352:
8350:
8347:
8345:
8339:
8337:
8331:
8329:
8323:
8321:
8318:
8316:
8313:
8311:
8308:
8306:
8303:
8301:
8298:
8296:
8293:
8291:
8288:
8286:
8283:
8281:
8274:
8272:
8269:
8267:
8264:
8262:
8259:
8257:
8254:
8252:
8249:
8247:
8245:
8240:
8238:
8235:
8233:
8230:
8228:
8225:
8223:
8222:Apraclonidine
8220:
8218:
8215:
8213:
8210:
8208:
8205:
8203:
8200:
8199:
8197:
8193:
8190:
8188:
8181:
8171:
8168:
8166:
8163:
8161:
8158:
8155:
8151:
8147:
8143:
8139:
8136:
8134:
8131:
8128:
8124:
8120:
8116:
8112:
8111:amitriptyline
8108:
8105:
8102:
8098:
8094:
8090:
8087:
8085:
8082:
8080:
8077:
8075:
8072:
8070:
8067:
8065:
8062:
8060:
8057:
8055:
8052:
8050:
8047:
8045:
8042:
8040:
8037:
8035:
8032:
8030:
8027:
8024:
8023:triazoledione
8020:
8016:
8012:
8008:
8005:
8002:
8000:
7997:
7995:
7992:
7990:
7987:
7985:
7982:
7980:
7977:
7975:
7972:
7970:
7967:
7965:
7962:
7960:
7957:
7955:
7952:
7950:
7947:
7945:
7942:
7940:
7937:
7935:
7932:
7930:
7927:
7925:
7922:
7920:
7917:
7915:
7912:
7910:
7907:
7905:
7902:
7900:
7897:
7895:
7892:
7889:
7885:
7881:
7877:
7873:
7869:
7865:
7862:
7860:
7857:
7855:
7852:
7850:
7847:
7845:
7842:
7840:
7837:
7835:
7832:
7829:
7825:
7821:
7817:
7813:
7809:
7805:
7804:Beta blockers
7802:
7800:
7797:
7794:
7790:
7786:
7782:
7778:
7777:brexpiprazole
7774:
7771:
7769:
7766:
7764:
7761:
7759:
7756:
7754:
7751:
7749:
7746:
7744:
7741:
7740:
7738:
7734:
7728:
7725:
7723:
7720:
7718:
7715:
7713:
7710:
7708:
7705:
7703:
7700:
7698:
7697:Phenylephrine
7695:
7693:
7692:Oxymetazoline
7690:
7688:
7685:
7683:
7680:
7678:
7675:
7673:
7670:
7668:
7665:
7663:
7660:
7658:
7655:
7653:
7650:
7648:
7642:
7640:
7634:
7632:
7626:
7624:
7623:Isometheptene
7621:
7619:
7616:
7614:
7611:
7609:
7606:
7604:
7601:
7599:
7596:
7594:
7591:
7589:
7582:
7580:
7577:
7575:
7572:
7570:
7567:
7565:
7562:
7560:
7558:
7553:
7551:
7548:
7546:
7543:
7541:
7538:
7536:
7533:
7531:
7528:
7527:
7525:
7521:
7518:
7516:
7509:
7505:
7502:
7495:
7490:
7488:
7483:
7481:
7476:
7475:
7472:
7456:
7454:
7451:
7450:
7448:
7445:
7442:
7439:
7437:
7434:
7433:
7429:
7423:
7420:
7418:
7415:
7413:
7410:
7408:
7405:
7403:
7402:Setmelanotide
7400:
7398:
7395:
7393:
7390:
7388:
7385:
7383:
7380:
7378:
7375:
7373:
7370:
7369:
7367:
7363:
7357:
7354:
7353:
7351:
7349:
7345:
7339:
7336:
7334:
7331:
7329:
7326:
7324:
7321:
7319:
7316:
7315:
7313:
7309:
7303:
7300:
7298:
7295:
7294:
7292:
7290:
7284:
7277:
7273:
7270:
7269:
7267:
7265:
7261:
7254:
7251:
7248:
7247:+cagrilintide
7244:
7241:
7239:
7236:
7234:
7233:Oxyntomodulin
7231:
7229:
7226:
7224:
7221:
7218:
7215:
7213:
7210:
7208:
7205:
7203:
7200:
7198:
7195:
7193:
7190:
7189:
7187:
7185:
7181:
7177:
7173:
7169:
7163:
7160:
7158:
7155:
7153:
7150:
7148:
7145:
7143:
7140:
7138:
7135:
7133:
7130:
7129:
7127:
7125:
7119:
7109:
7106:
7104:
7101:
7099:
7096:
7094:
7091:
7089:
7086:
7084:
7081:
7079:
7078:Phenmetrazine
7076:
7074:
7071:
7069:
7066:
7064:
7061:
7059:
7056:
7054:
7051:
7048:
7044:
7041:
7039:
7036:
7034:
7031:
7029:
7026:
7024:
7021:
7018:
7014:
7011:
7009:
7006:
7004:
7001:
6999:
6996:
6995:
6993:
6989:
6982:
6978:
6975:
6973:
6970:
6968:
6965:
6963:
6960:
6958:
6955:
6953:
6950:
6948:
6945:
6943:
6940:
6939:
6937:
6935:
6931:
6925:
6922:
6920:
6919:Xylopropamine
6917:
6914:
6910:
6907:
6905:
6902:
6900:
6897:
6895:
6892:
6890:
6887:
6885:
6882:
6880:
6877:
6875:
6872:
6870:
6867:
6865:
6862:
6860:
6857:
6855:
6852:
6850:
6847:
6845:
6842:
6840:
6837:
6835:
6832:
6830:
6827:
6825:
6822:
6820:
6817:
6815:
6812:
6810:
6807:
6805:
6802:
6800:
6797:
6795:
6794:Benzphetamine
6792:
6790:
6787:
6785:
6782:
6780:
6777:
6775:
6772:
6770:
6767:
6765:
6762:
6761:
6759:
6757:
6752:
6748:
6745:
6743:
6739:
6734:
6730:
6726:
6719:
6714:
6712:
6707:
6705:
6700:
6699:
6696:
6680:
6678:
6675:
6674:
6672:
6669:
6666:
6663:
6661:
6658:
6657:
6653:
6646:
6642:
6638:
6637:+fexofenadine
6634:
6630:
6626:
6622:
6618:
6615:
6613:
6610:
6608:
6607:Phenylephrine
6605:
6603:
6600:
6599:
6597:
6595:
6591:Systemic use:
6589:
6579:
6576:
6575:
6573:
6569:
6563:
6560:
6558:
6555:
6553:
6550:
6548:
6545:
6543:
6540:
6538:
6535:
6533:
6530:
6528:
6525:
6523:
6520:
6518:
6515:
6513:
6510:
6509:
6507:
6503:
6497:
6494:
6492:
6491:Triamcinolone
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6471:
6467:
6464:Fluticasone (
6463:
6461:
6458:
6456:
6455:Dexamethasone
6453:
6451:
6448:
6446:
6443:
6441:
6440:Betamethasone
6438:
6436:
6433:
6432:
6430:
6428:
6424:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6393:
6392:
6388:
6387:
6383:
6380:
6378:
6375:
6373:
6372:Levocabastine
6369:
6368:
6364:
6363:
6360:
6357:
6356:
6354:
6349:
6345:
6339:
6336:
6334:
6331:
6329:
6326:
6324:
6321:
6319:
6316:
6314:
6311:
6309:
6308:Phenylephrine
6306:
6304:
6303:Oxymetazoline
6301:
6299:
6296:
6294:
6291:
6289:
6286:
6284:
6281:
6279:
6276:
6274:
6271:
6269:
6266:
6264:
6261:
6259:
6256:
6254:
6251:
6250:
6248:
6245:
6241:
6238:
6236:
6232:
6227:
6223:
6222:Decongestants
6216:
6211:
6209:
6204:
6202:
6197:
6196:
6193:
6181:
6173:
6172:
6169:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6142:Phenylacetone
6140:
6138:
6135:
6133:
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6096:
6093:
6092:
6091:
6088:
6086:
6084:
6080:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6058:
6055:
6053:
6050:
6048:
6045:
6043:
6040:
6038:
6035:
6033:
6030:
6028:
6025:
6023:
6020:
6019:
6017:
6013:
6007:
6004:
6002:
5999:
5997:
5994:
5993:
5991:
5987:
5977:
5974:
5972:
5969:
5967:
5964:
5962:
5959:
5957:
5954:
5952:
5949:
5947:
5944:
5942:
5939:
5938:
5936:
5934:
5929:
5922:
5918:
5914:
5910:
5906:
5902:
5898:
5894:
5891:
5888:
5885:
5881:
5878:
5875:
5871:
5868:
5862:
5856:
5853:
5850:
5846:
5843:
5842:
5840:
5838:
5834:
5831:
5827:
5817:
5814:
5813:
5811:
5809:
5805:
5799:
5796:
5794:
5791:
5789:
5786:
5785:
5783:
5781:
5777:
5771:
5769:
5765:
5757:
5754:
5752:
5749:
5747:
5746:
5742:
5741:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5717:
5715:
5712:
5711:
5709:
5707:
5703:
5700:
5692:
5688:
5681:
5676:
5674:
5669:
5667:
5662:
5661:
5658:
5654:
5644:
5638:
5634:
5633:
5625:
5617:
5611:
5607:
5606:
5598:
5582:
5576:
5568:
5562:
5554:
5550:
5549:
5542:
5536:
5531:
5523:
5519:
5513:
5505:
5501:
5495:
5479:
5473:
5457:
5453:
5447:
5439:
5435:
5431:
5427:
5423:
5419:
5412:
5410:
5401:
5395:
5379:
5375:
5371:
5365:
5349:
5345:
5339:
5331:
5327:
5326:Health Canada
5323:
5317:
5310:
5305:
5301:
5296:
5291:
5287:
5283:
5279:
5275:
5271:
5264:
5256:
5252:
5247:
5242:
5238:
5234:
5231:(5): e00655.
5230:
5226:
5222:
5215:
5207:
5203:
5198:
5193:
5189:
5185:
5181:
5177:
5173:
5166:
5151:
5147:
5141:
5126:
5122:
5116:
5101:
5097:
5091:
5076:
5072:
5066:
5051:
5047:
5046:"Amphetamine"
5041:
5034:
5029:
5025:
5021:
5017:
5013:
5009:
5002:
5000:
4998:
4989:
4985:
4981:
4977:
4973:
4969:
4962:
4947:
4943:
4937:
4935:
4927:
4911:
4909:9780071624428
4905:
4901:
4894:
4892:
4890:
4888:
4886:
4877:
4873:
4869:
4865:
4861:
4857:
4853:
4849:
4842:
4834:
4828:
4824:
4823:
4815:
4813:
4811:
4803:
4801:
4797:
4793:
4789:
4783:
4779:
4775:
4771:
4764:
4757:
4752:
4748:
4744:
4738:
4734:
4730:
4726:
4722:
4718:
4711:
4704:
4699:
4695:
4691:
4687:
4683:
4679:
4675:
4671:
4664:
4657:
4652:
4648:
4644:
4640:
4636:
4632:
4628:
4624:
4616:
4609:
4604:
4600:
4595:
4590:
4586:
4582:
4578:
4574:
4570:
4563:
4561:
4559:
4550:
4546:
4542:
4538:
4534:
4530:
4523:
4515:
4511:
4507:
4503:
4496:
4490:
4484:
4480:
4475:
4470:
4466:
4462:
4458:
4454:
4450:
4443:
4436:
4435:-amphetamine.
4434:
4430:
4426:
4422:
4409:
4405:
4400:
4395:
4391:
4387:
4380:
4373:
4366:
4364:
4360:
4353:
4351:9781609133450
4347:
4343:
4339:
4332:
4330:
4313:
4306:
4300:
4292:
4288:
4284:
4280:
4276:
4272:
4265:
4257:
4253:
4248:
4243:
4238:
4233:
4229:
4225:
4224:Int J Mol Sci
4221:
4214:
4206:
4202:
4197:
4192:
4188:
4184:
4180:
4176:
4172:
4165:
4157:
4153:
4148:
4143:
4139:
4135:
4131:
4127:
4123:
4116:
4108:
4104:
4100:
4096:
4092:
4088:
4080:
4078:
4076:
4074:
4072:
4063:
4059:
4055:
4051:
4047:
4043:
4036:
4028:
4024:
4020:
4016:
4012:
4008:
4001:
3993:
3989:
3985:
3981:
3977:
3973:
3969:
3965:
3958:
3950:
3946:
3942:
3938:
3934:
3930:
3923:
3915:
3911:
3907:
3903:
3899:
3895:
3888:
3880:
3876:
3871:
3866:
3862:
3858:
3854:
3850:
3846:
3839:
3824:
3820:
3814:
3812:
3810:
3808:
3791:
3787:
3781:
3779:
3777:
3768:
3764:
3760:
3756:
3752:
3748:
3741:
3739:
3737:
3735:
3733:
3724:
3720:
3716:
3712:
3708:
3704:
3697:
3695:
3693:
3684:
3680:
3676:
3672:
3668:
3664:
3657:
3655:
3653:
3651:
3649:
3647:
3645:
3643:
3641:
3639:
3637:
3635:
3626:
3620:
3616:
3615:
3607:
3605:
3603:
3601:
3592:
3588:
3584:
3580:
3576:
3572:
3564:
3562:
3560:
3558:
3556:
3554:
3552:
3550:
3548:
3546:
3544:
3542:
3540:
3538:
3536:
3534:
3525:
3521:
3517:
3513:
3509:
3505:
3498:
3496:
3494:
3492:
3490:
3481:
3477:
3473:
3469:
3465:
3461:
3454:
3452:
3450:
3448:
3446:
3444:
3435:
3431:
3427:
3423:
3419:
3415:
3411:
3407:
3400:
3398:
3396:
3387:
3383:
3379:
3375:
3368:
3366:
3357:
3353:
3349:
3345:
3341:
3337:
3330:
3328:
3326:
3324:
3322:
3320:
3311:
3307:
3303:
3299:
3292:
3290:
3288:
3286:
3284:
3275:
3271:
3267:
3263:
3259:
3255:
3248:
3246:
3244:
3235:
3231:
3227:
3223:
3219:
3215:
3208:
3206:
3204:
3202:
3200:
3198:
3196:
3194:
3178:
3172:
3168:
3167:
3159:
3157:
3155:
3153:
3151:
3149:
3133:
3127:
3123:
3122:
3114:
3112:
3110:
3108:
3106:
3104:
3102:
3100:
3098:
3081:
3077:
3071:
3069:
3067:
3058:
3054:
3050:
3046:
3039:
3037:
3035:
3033:
3031:
3029:
3027:
3025:
3016:
3012:
3008:
3004:
3000:
2996:
2989:
2987:
2985:
2983:
2981:
2979:
2977:
2975:
2973:
2971:
2969:
2967:
2965:
2963:
2961:
2959:
2950:
2946:
2942:
2938:
2934:
2930:
2923:
2921:
2919:
2917:
2915:
2913:
2911:
2909:
2907:
2905:
2903:
2901:
2899:
2897:
2895:
2893:
2891:
2889:
2887:
2885:
2876:
2872:
2868:
2864:
2857:
2855:
2853:
2851:
2849:
2847:
2845:
2843:
2841:
2839:
2837:
2835:
2833:
2831:
2829:
2827:
2825:
2823:
2821:
2819:
2817:
2815:
2813:
2811:
2809:
2807:
2805:
2803:
2801:
2799:
2797:
2795:
2793:
2776:
2772:
2768:
2764:
2758:
2750:
2744:
2728:
2724:
2718:
2716:
2714:
2712:
2710:
2708:
2706:
2704:
2702:
2700:
2684:
2678:
2674:
2673:
2665:
2663:
2661:
2659:
2657:
2655:
2653:
2651:
2649:
2647:
2642:
2629:
2625:
2611:
2595:
2594:
2589:
2588:
2574:
2570:
2562:
2560:
2556:
2546:
2544:
2539:
2537:
2533:
2528:
2526:
2522:
2518:
2513:
2511:
2507:
2502:
2500:
2496:
2492:
2488:
2483:
2481:
2471:
2469:
2465:
2461:
2457:
2453:
2443:
2441:
2431:
2429:
2423:
2421:
2417:
2414:
2413:hydrochloride
2407:
2398:
2392:
2385:
2376:
2367:
2361:
2357:
2343:
2341:
2337:
2333:
2329:
2325:
2324:United States
2320:
2318:
2315:in 1913. The
2314:
2310:
2306:
2296:
2294:
2291:
2290:hydrochloride
2286:
2284:
2280:
2276:
2275:phenylephrine
2272:
2268:
2264:
2260:
2256:
2252:
2248:
2240:
2228:
2224:
2221:
2216:
2214:
2210:
2206:
2201:
2199:
2195:
2191:
2187:
2183:
2178:
2176:
2172:
2168:
2164:
2160:
2156:
2152:
2148:
2144:
2141:
2137:
2133:
2129:
2126:
2122:
2118:
2117:
2112:
2108:
2104:
2100:
2098:
2093:
2091:
2086:
2082:
2078:
2074:
2070:
2069:stereoisomers
2066:
2062:
2058:
2055:
2051:
2047:
2043:
2039:
2035:
2026:
2008:
2004:
1987:
1983:
1959:
1944:
1937:
1930:Hydroxylation
1923:Hydroxylation
1911:
1904:
1897:Hydroxylation
1890:Hydroxylation
1883:Hydroxylation
1876:
1869:
1862:
1855:
1848:
1847:Hippuric acid
1841:
1834:
1833:Phenylacetone
1827:
1818:
1807:
1806:
1802:
1800:
1796:
1792:
1788:
1784:
1779:
1777:
1773:
1766:Miscellaneous
1763:
1753:
1748:
1746:
1745:acetazolamide
1742:
1738:
1734:
1730:
1726:
1722:
1721:ascorbic acid
1718:
1714:
1710:
1706:
1702:
1697:
1691:
1679:
1675:
1670:
1668:
1660:
1656:
1646:
1644:
1640:
1636:
1634:
1628:
1624:
1620:
1616:
1615:hydroxylation
1612:
1608:
1604:
1600:
1597:
1593:
1592:hippuric acid
1589:
1585:
1581:
1571:
1569:
1564:
1562:
1561:phenylephrine
1558:
1554:
1550:
1546:
1542:
1538:
1534:
1530:
1526:
1522:
1518:
1514:
1506:
1496:
1494:
1490:
1478:
1470:
1462:
1450:
1446:
1442:
1438:
1437:well-absorbed
1423:
1421:
1417:
1413:
1405:
1400:
1396:
1394:
1390:
1386:
1382:
1378:
1374:
1364:
1359:
1356:
1353:
1350:
1347:
1344:
1341:
1340:
1337:
1334:
1331:
1328:
1325:
1324:
1321:
1318:
1315:
1312:
1310:
1307:
1306:
1303:
1300:
1297:
1294:
1291:
1288:
1287:
1284:
1281:
1278:
1275:
1272:
1269:
1268:
1265:
1262:
1259:
1256:
1253:
1250:
1249:
1246:
1243:
1240:
1237:
1234:
1230:
1227:
1226:
1223:
1220:
1217:
1214:
1211:
1207:
1204:
1203:
1200:
1197:
1194:
1191:
1189:(+)-Ephedrine
1188:
1187:
1184:
1181:
1178:
1175:
1172:
1169:
1168:
1165:
1162:
1159:
1156:
1154:
1153:(–)-Cathinone
1152:
1148:
1147:
1144:
1141:
1138:
1135:
1132:
1128:
1125:
1124:
1120:
1115:
1105:
1095:
1087:
1086:
1079:
1068:
1066:
1062:
1058:
1054:
1050:
1046:
1043:
1028:
1026:
1023:
1019:
1015:
1005:
1003:
1000:
996:
992:
988:
983:
979:
975:
970:
969:
963:
961:
957:
953:
949:
945:
942:PPA produces
935:
933:
932:United States
929:
925:
921:
911:
909:
905:
901:
897:
893:
883:
881:
877:
873:
869:
865:
861:
856:
854:
850:
846:
842:
838:
834:
830:
826:
822:
818:
814:
810:
806:
802:
798:
794:
790:
786:
782:
778:
774:
770:
768:
764:
761:
757:
753:
749:
745:
741:
737:
727:
720:
711:
706:
705:
702:
695:
686:
685:
682:
675:
668:
664:
663:
661:
658:
653:
646:
644:
640:
619:
617:
613:
608:
604:
600:
597:
595:
593:ECHA InfoCard
589:
581:
577:
573:
572:
570:
561:
557:
550:
546:
545:
543:
541:
537:
530:
526:
525:
523:
521:
517:
510:
506:
505:
503:
501:
497:
490:
486:
485:
483:
481:
477:
470:
466:
465:
463:
461:
457:
450:
446:
445:
443:
436:
432:
425:
421:
420:
418:
416:
412:
404:
400:
395:
394:
391:
384:
379:
375:
372:
370:
366:
358:
356:
352:
344:
342:
335:
327:
324:
322:
318:
314:
308:
307:Hippuric acid
304:
302:
298:
294:
292:
288:
284:
282:
278:
274:
272:
268:
264:
260:
247:
245:
236:
233:
223:
220:
210:
209:
207:
205:
201:
196:
188:
183:
178:
173:
170:
169:
167:
165:
161:
158:
155:
153:
147:
141:
132:
131:
129:
127:
121:
117:
113:
111:
107:
103:
99:
95:
91:
87:
83:
79:
75:
71:
67:
65:
61:
58:Clinical data
56:
52:
47:
43:
38:
30:
19:
14085:Solriamfetol
14000:Famprofazone
13906:
13898:
13884:-Octopamine)
13881:
13878:Norfenefrine
13833:Metanephrine
13825:
13781:Isoprenaline
13737:(Dextrodopa)
13722:Adrenochrome
13680:Pyrovalerone
13586:
13565:
13524:Entactogens:
13523:
13473:Entactogens:
13472:
13419:Ethcathinone
13335:
13314:
13303:Entactogens:
13302:
13265:
13258:Phentermines
13221:
13070:Entactogens:
13069:
13066:Zylofuramine
13020:
12844:Fenfluramine
12839:Fenethylline
12789:Amphetaminil
12770:Amfepentorex
12731:
12589:
12582:Amphetamines
12563:
12547:Entactogens:
12546:
12532:
12524:
12516:
12508:
12472:
12470:
12446:Metaescaline
12048:
11963:
11962:
11946:Guanethidine
11922:
11912:
11900:
11897:
11873:Indeloxazine
11869:
11817:4-Methyl-αMT
11812:4-Methyl-αET
11809:Tryptamines:
11808:
11728:Piperazines:
11727:
11560:Fenfluramine
11460:6-Methyl-MDA
11450:5-Methyl-MDA
11415:2-Methyl-MDA
11411:
11380:
11349:
11303:
11218:Feprosidnine
11198:Clofenciclan
11164:
11114:Piperazines:
11113:
11101:Zylofuramine
11050:
11044:
11012:
11004:
10846:Fenethylline
10841:Famprofazone
10826:Ethcathinone
10746:Amphetaminil
10719:Amfepentorex
10675:
10624:
10587:Fenmetramide
10582:Fenbutrazate
10579:Morpholines:
10578:
10486:Feprosidnine
10466:Clofenciclan
10427:
10387:Piperazines:
10386:
10374:Zylofuramine
10316:
10308:
10300:
10148:Fenethylline
10143:Famprofazone
10123:Ethcathinone
10043:Amphetaminil
10018:Amfepentorex
9974:
9923:
9886:Fenmetramide
9881:Fenbutrazate
9878:Morpholines:
9877:
9807:
9798:
9789:
9780:
9771:
9762:
9751:
9750:
9543:Metipranolol
9528:Levomoprolol
9473:Idropranolol
9056:
8968:Isoprenaline
8866:
8790:Arformoterol
8735:thioridazine
8727:fluphenazine
8699:Spiroxatrine
8659:Phentolamine
8578:tandospirone
8544:paliperidone
8434:Tasipimidine
8414:Rezatomidine
8398:
8359:Medetomidine
8243:
8154:thioridazine
8146:fluphenazine
8127:trimipramine
8115:clomipramine
7999:Phentolamine
7868:acetergamine
7844:Corynanthine
7701:
7556:
7276:+semaglutide
7272:Cagrilintide
7228:Orforglipron
7098:Pyrovalerone
7082:
7047:+phentermine
7043:Fenfluramine
7038:Fenbutrazate
6924:Zylofuramine
6859:Fenethylline
6789:Amphetaminil
6774:Amfepentorex
6751:Amphetamines
6611:
6562:Saline water
6481:Prednisolone
6389:
6382:Thonzylamine
6365:
6348:Antiallergic
6273:Fenoxazoline
6082:
6006:Norephedrine
6005:
5933:transporters
5849:full agonist
5815:
5797:
5792:
5787:
5755:
5750:
5743:
5735:
5730:
5725:
5718:
5713:
5652:
5631:
5624:
5604:
5597:
5585:. Retrieved
5575:
5561:
5553:the original
5547:
5541:
5530:
5522:the original
5512:
5504:the original
5494:
5482:. Retrieved
5472:
5460:. Retrieved
5455:
5446:
5421:
5417:
5394:
5382:. Retrieved
5378:the original
5373:
5364:
5352:. Retrieved
5347:
5338:
5330:the original
5316:
5307:
5277:
5273:
5263:
5228:
5224:
5214:
5182:(1): 10–14.
5179:
5175:
5165:
5153:. Retrieved
5149:
5140:
5128:. Retrieved
5124:
5115:
5103:. Retrieved
5099:
5090:
5078:. Retrieved
5074:
5065:
5053:. Retrieved
5049:
5040:
5031:
5011:
5007:
4971:
4967:
4961:
4949:. Retrieved
4945:
4913:
4899:
4851:
4847:
4841:
4821:
4799:
4795:
4791:
4787:
4785:
4773:
4769:
4763:
4750:
4746:
4742:
4740:
4720:
4716:
4710:
4701:
4673:
4669:
4663:
4654:
4626:
4622:
4615:
4606:
4576:
4572:
4532:
4528:
4522:
4505:
4501:
4495:
4456:
4452:
4442:
4432:
4428:
4424:
4420:
4418:
4411:. Retrieved
4389:
4385:
4372:
4362:
4358:
4355:
4341:
4316:. Retrieved
4311:
4299:
4274:
4270:
4264:
4230:(10): 5146.
4227:
4223:
4213:
4178:
4174:
4164:
4129:
4125:
4115:
4093:(1): 32–41.
4090:
4086:
4045:
4041:
4035:
4010:
4006:
4000:
3967:
3963:
3957:
3932:
3928:
3922:
3897:
3893:
3887:
3852:
3848:
3838:
3826:. Retrieved
3822:
3794:. Retrieved
3789:
3750:
3746:
3706:
3703:Hypertension
3702:
3666:
3662:
3613:
3574:
3570:
3507:
3503:
3463:
3459:
3409:
3405:
3377:
3373:
3339:
3335:
3301:
3297:
3257:
3253:
3217:
3213:
3180:. Retrieved
3165:
3135:. Retrieved
3120:
3084:. Retrieved
3079:
3048:
3044:
2998:
2994:
2932:
2928:
2866:
2862:
2779:. Retrieved
2757:
2731:. Retrieved
2726:
2686:. Retrieved
2671:
2628:
2591:
2585:
2573:
2552:
2540:
2529:
2514:
2503:
2484:
2477:
2474:Legal status
2470:as of 2024.
2449:
2437:
2434:Availability
2428:combinations
2424:
2420:norephedrine
2419:
2390:
2360:generic name
2355:
2354:
2321:
2302:
2287:
2217:
2208:
2202:
2197:
2186:alpha carbon
2181:
2179:
2150:
2146:
2142:
2128:preparations
2116:Catha edulis
2114:
2102:
2096:
2089:
2085:levorotatory
2080:
2072:
2045:
2041:
2037:
2033:
2031:
1969:unidentified
1916:unidentified
1861:Norephedrine
1860:
1840:Benzoic acid
1780:
1769:
1749:
1729:amphetamines
1707:. At a more
1698:
1671:
1652:
1632:
1619:methyl group
1610:
1577:
1565:
1502:
1499:Distribution
1489:accumulation
1477:Steady-state
1434:
1401:
1397:
1370:
1270:
1251:
1232:
1209:
1150:
1130:
1039:
1031:Pharmacology
1022:theophylline
1011:
1008:Interactions
990:
987:dopaminergic
977:
973:
966:
964:
948:side effects
941:
938:Side effects
928:prescription
917:
902:and promote
892:decongestant
889:
886:Medical uses
876:prescription
857:
852:
840:
836:
832:
828:
773:Side effects
771:
756:prescription
748:decongestant
739:
735:
734:
723:
549:ChEMBL136560
402:
398:
338:Elimination
204:Legal status
198:Legal status
97:
93:
89:
85:
81:
77:
29:
18:Norephedrine
14105:Venlafaxine
14070:Pronethalol
14040:Methoxamine
13970:Dizocilpine
13965:Diphenidine
13940:Amidephrine
13901:-Octopamine
13838:Metaraminol
13805:(Droxidopa)
13751:Epinephrine
13741:Dimetofrine
13587:Stimulants:
13566:Stimulants:
13394:Brephedrone
13384:Amfepramone
13336:Stimulants:
13318:Cericlamine
13299:Phentermine
13279:Clortermine
13266:Stimulants:
13046:Sibutramine
13031:Prenylamine
12966:Oxifentorex
12918:Metaraminol
12858:Fenproporex
12829:Fencamfamin
12809:Clobenzorex
12775:Amphetamine
12732:Stimulants:
12473:Stimulants:
12431:Macromerine
11975:Adrenergics
11941:Guanazodine
11926:Bethanidine
11771:Mepiprazole
11565:Flephedrone
11505:Amfepramone
11485:Brephedrone
11381:Oxazolines:
11213:Cyprodenate
11058:Prenylamine
11040:Phentermine
10856:Flephedrone
10851:Fenproporex
10796:Clortermine
10791:Clobenzorex
10729:Amphetamine
10724:Amfepramone
10663:Thozalinone
10643:Cyclazodone
10625:Oxazolines:
10481:Cyprodenate
10344:Prenylamine
10158:Flephedrone
10153:Fenproporex
10093:Clortermine
10088:Clobenzorex
10028:Amphetamine
10023:Amfepramone
9962:Thozalinone
9942:Cyclazodone
9924:Oxazolines:
9668:Spirendolol
9643:Propranolol
9638:Propafenone
9633:Pronethalol
9523:Levobunolol
9498:Isoxaprolol
9483:Indopanolol
9468:ICI-118,551
9433:Eugenodilol
9418:Ersentilide
9398:Draquinolol
9393:Diprafenone
9363:Dalbraminol
9343:Cicloprolol
9318:Carpindolol
9303:Butofilolol
9248:Bornaprolol
9193:Alprenoxime
9161:Antagonists
9122:Tulobuterol
9117:Tretoquinol
9112:Terbutaline
9072:Ractopamine
9067:Prenalterol
8973:Isoxsuprine
8958:Indacaterol
8928:Eugenodilol
8918:Etilevodopa
8903:Epinephrine
8894:Droxidopa (
8874:Dipivefrine
8845:Clenbuterol
8689:Setiptiline
8679:Rauwolscine
8654:Pardoprunox
8644:Mirtazapine
8609:Fenmetozole
8552:risperidone
8515:Atipamezole
8488:Antagonists
8444:Tiamenidine
8439:Tetryzoline
8419:Rilmenidine
8384:Naphazoline
8320:Guanoxabenz
8295:Epinephrine
8285:Etilevodopa
8276:Droxidopa (
8266:Dipivefrine
8227:Brimonidine
8097:maprotiline
7974:Pardoprunox
7969:Niguldipine
7929:Mepiprazole
7904:Hydroxyzine
7894:Etoperidone
7884:nicergoline
7854:Domesticine
7849:Dapiprazole
7824:eugenodilol
7799:Benoxathian
7793:risperidone
7758:Anisodamine
7736:Antagonists
7717:Tiamenidine
7712:Tetryzoline
7677:Naphazoline
7662:Methoxamine
7657:Metaraminol
7603:Etilevodopa
7593:Epinephrine
7584:Droxidopa (
7574:Dipivefrine
7535:Amidephrine
7443:from market
7392:Metreleptin
7328:Mitratapide
7323:Dirlotapide
7253:Tirzepatide
7243:Semaglutide
7238:Retatrutide
7223:Liraglutide
7212:Ecnoglutide
7207:Danuglipron
7137:Ibipinabant
7124:antagonists
7122:Cannabinoid
7108:Tesofensine
7103:Sibutramine
7033:Difemetorex
7017:+naltrexone
7003:Atomoxetine
6972:Terbutaline
6947:Clenbuterol
6913:+topiramate
6909:Phentermine
6864:Fenproporex
6824:Clortermine
6814:Clobenzorex
6784:Amphetamine
6779:Amfepramone
6667:from market
6641:+loratadine
6629:+cetirizine
6460:Flunisolide
6450:Ciclesonide
6411:Olopatadine
6323:Tramazoline
6318:Tetryzoline
6298:Naphazoline
6278:Iproheptine
6268:Epinephrine
6253:Amidephrine
6162:Trace amine
6137:Phentermine
5706:Amphetamine
5687:Amphetamine
5424:: 109–123.
5354:31 December
5071:"Ephedrine"
4318:30 December
2935:(1): 1–14.
2517:amphetamine
2493:or another
2491:paracetamol
2305:synthesized
2273:is 0.7, of
2269:is 1.1, of
2265:is 1.8, of
2263:amphetamine
2261:is 2.1, of
2255:hydrophilic
2215:receptors.
2167:amphetamine
2136:side effect
2054:amphetamine
2003:amphetamine
1976:Conjugation
1952:Deamination
1854:Amphetamine
1787:amphetamine
1750:Total body
1743:as well as
1701:elimination
1667:metabolites
1649:Elimination
1599:deamination
1588:Metabolites
1580:metabolized
1557:epinephrine
1553:phenyl ring
1541:amphetamine
1467:hours. The
1412:epinephrine
904:weight loss
860:synthesized
845:enantiomers
817:amphetamine
650: g·mol
599:100.035.349
381:Identifiers
345:4 (3.7–4.9)
301:Metabolites
244:Schedule VI
73:Other names
64:Trade names
14206:Stimulants
14131:Anorectics
14120:Categories
14075:Salbutamol
14010:Hexapradol
13990:Etafedrine
13985:Ephenidine
13980:Dopexamine
13975:Dobutamine
13955:Denopamine
13945:Arbutamine
13919:Synephrine
13853:Methyldopa
13848:Metirosine
13796:(Levodopa)
13786:Isoetarine
13771:Fenclonine
13761:Etilefrine
13675:Prolintane
13506:Mephedrone
13469:Radafaxine
13459:Pentedrone
13439:Methedrone
13399:Buphedrone
13389:Benzedrone
13328:Cathinones
13240:Selegiline
13230:Amiflamine
13026:Pholedrine
12976:Ortetamine
12971:Oxilofrine
12903:Lefetamine
12893:Iofetamine
12878:Furfenorex
12873:Formetorex
12863:Flucetorex
12794:Benfluorex
12765:Amfecloral
12760:Alfetamine
12633:D-Deprenyl
12550:Lophophine
12461:Psi-2C-T-4
12456:Proscaline
12426:Jimscaline
11916:SoRI-20041
11909:SoRI-20040
11857:Tryptamine
11640:Methedrone
11635:Mephedrone
11590:Lophophine
11580:Iofetamine
11570:Flucetorex
11470:Amiflamine
11399:Fluminorex
11394:Clominorex
11228:Heptaminol
11223:Gilutensin
11208:Cypenamine
11073:Selegiline
11030:Pholedrine
10999:Ortetamine
10979:Methedrone
10947:Mephedrone
10897:Lophophine
10866:Furfenorex
10771:Buphedrone
10714:Amfecloral
10709:Alfetamine
10653:Fluminorex
10648:Fenozolone
10638:Clominorex
10496:Heptaminol
10491:Gilutensin
10476:Cypenamine
10461:Amineptine
10334:Pholedrine
10324:Pholedrine
10295:Ortetamine
10235:Methedrone
10203:Mephedrone
10193:Lophophine
10168:Furfenorex
10098:D-Deprenyl
10068:Buphedrone
10013:Amfecloral
10008:Alfetamine
9952:Fluminorex
9947:Fenozolone
9937:Clominorex
9733:Xipranolol
9723:Toliprolol
9713:Tiprenolol
9698:Tienoxolol
9693:Tertatolol
9678:Sulfinalol
9658:Soquinolol
9653:Ronactolol
9628:Procinolol
9623:Primidolol
9608:Penbutolol
9588:Pacrinolol
9583:Oxprenolol
9578:Nipradilol
9548:Metoprolol
9538:Mepindolol
9533:Medroxalol
9503:Isamoltane
9493:Iprocrolol
9453:Flusoxolol
9443:Falintolol
9423:Esatenolol
9373:Diacetolol
9353:Cloranolol
9333:Celiprolol
9328:Carvedilol
9308:Capsinolol
9293:Butaxamine
9288:Bupranolol
9278:Bunitrolol
9258:Bucindolol
9253:Brefonalol
9243:Bopindolol
9238:Bisoprolol
9233:Bevantolol
9213:Arotinolol
9198:Amosulalol
9188:Alprenolol
9168:Acebutolol
9147:Zilpaterol
9132:Vilanterol
9107:Solabegron
9102:Salmeterol
9097:Salbutamol
9082:Reproterol
9077:Procaterol
9062:Pirbuterol
9047:Oxyfedrine
9032:Mirabegron
9027:Methyldopa
9017:Melevodopa
9007:Lubabegron
8963:Isoetarine
8948:Higenamine
8938:Formoterol
8913:Etilefrine
8908:Etafedrine
8889:Dopexamine
8879:Dobutamine
8860:Denopamine
8855:Corbadrine
8835:Carmoterol
8830:Carbuterol
8820:Broxaterol
8815:Bitolterol
8805:Bambuterol
8795:Arotinolol
8785:Arbutamine
8775:Alifedrine
8770:Abediterol
8714:Tolazoline
8704:Sunepitron
8694:Spegatrine
8684:Rotigotine
8624:Ketanserin
8614:Fluparoxan
8594:Cirazoline
8589:Buflomedil
8574:ipsapirone
8562:Azapirones
8548:quetiapine
8540:olanzapine
8536:lurasidone
8510:Aptazapine
8505:Amesergide
8454:Tolonidine
8449:Tizanidine
8429:Talipexole
8424:Romifidine
8379:Moxonidine
8369:Methyldopa
8364:Melevodopa
8354:Lofexidine
8315:Guanfacine
8300:Etilefrine
8290:Ergotamine
8251:Detomidine
8237:Corbadrine
8133:Trimazosin
8123:imipramine
8084:Tolazoline
8079:Tiodazosin
8069:Tamsulosin
8064:Talipexole
8054:Spegatrine
8039:Quinazosin
8015:nefazodone
7989:Phendioxan
7979:Pelanserin
7964:Niaprazine
7959:Neldazosin
7949:Naftopidil
7944:Moxisylyte
7914:Ketanserin
7899:Fenspiride
7872:ergotamine
7834:Buflomedil
7820:carvedilol
7816:arotinolol
7812:amosulalol
7789:quetiapine
7785:olanzapine
7748:Ajmalicine
7707:Synephrine
7687:Octopamine
7667:Methyldopa
7652:Melevodopa
7618:Indanidine
7598:Etilefrine
7550:Corbadrine
7545:Cirazoline
7504:modulators
7417:Zonisamide
7407:Topiramate
7397:Naltrexone
7377:Bimagrumab
7348:Uncouplers
7338:Simmondsin
7318:Cetilistat
7302:Lorcaserin
7202:Cotadutide
7197:Cinchonine
7162:Taranabant
7157:Surinabant
7152:Rosonabant
7147:Rimonabant
7053:Manifaxine
7008:Benfluorex
6967:Synephrine
6874:Furfenorex
6769:Amfecloral
6742:Stimulants
6729:Anorectics
6621:+azatadine
6557:Ritiometan
6537:Hyaluronan
6532:Hexamidine
6527:Framycetin
6486:Tixocortol
6445:Budesonide
6416:Lodoxamide
6406:Azelastine
6401:Nedocromil
6377:Antazoline
6333:Tymazoline
6293:Metizoline
6102:Narcolepsy
6057:Formetorex
5931:Inhibited
4968:J Med Chem
4413:6 November
3336:Med J Aust
2637:References
2543:nimesulide
2251:lipophilic
2213:adrenergic
2061:cathinones
2057:derivative
1783:metabolite
1735:including
1603:side chain
1574:Metabolism
1431:Absorption
1387:for these
1221:736–1291.7
982:amantadine
952:heart rate
777:heart rate
655:3D model (
643:Molar mass
509:33RU150WUN
480:ChemSpider
424:14838-15-4
415:CAS Number
390:IUPAC name
291:Metabolism
14055:PARGY-LAD
13950:Cafedrine
13909:-Tyramine
13863:Nordefrin
13843:Metaterol
13828:-Tyramine
13820:-Tyrosine
13776:Ibopamine
13665:Naphyrone
13496:Methylone
13464:Pentylone
13409:Cathinone
13404:Bupropion
13247:-Deprenyl
12913:Mefenorex
12883:Gepefrine
12834:Fencamine
12819:Ephedrine
12755:Acridorex
12482:Hordenine
12441:Mescaline
12334:2C-T-22.5
12072:25N-NBOMe
12067:25I-NBOMe
12062:25D-NBOMe
12057:25C-NBOMe
12052:25B-NBOMe
11964:See also:
11936:Guanadrel
11931:Bretylium
11904:SoRI-9804
11878:Viqualine
11832:5-MeO-αMT
11827:5-MeO-αET
11645:Methylone
11358:8-OH-DPAT
11253:Octodrine
11238:Indanorex
11080:-Deprenyl
10984:Methylone
10942:Mefenorex
10871:Hordenine
10821:Ephedrine
10786:Cathinone
10526:Octodrine
10506:Indanorex
10285:Methylone
10198:Mefenorex
10173:Hordenine
10118:Ephedrine
10083:Cathinone
9752:See also:
9728:Xibenolol
9718:Tolamolol
9703:Tilisolol
9683:Talinolol
9673:SR 59230A
9648:Ridazolol
9618:Practolol
9598:Pamatolol
9593:Pafenolol
9573:Nifenalol
9568:Nebivolol
9563:Nadoxolol
9513:Landiolol
9508:Labetalol
9478:Indenolol
9448:Flestolol
9438:Exaprolol
9403:Ecastolol
9388:Dilevalol
9348:Cinamolol
9338:Cetamolol
9323:Carteolol
9313:Carazolol
9298:Butidrine
9273:Bufuralol
9268:Bufetolol
9263:Bucumolol
9228:Betaxolol
9223:Befunolol
9203:Ancarolol
9173:Adaprolol
9137:Xamoterol
9092:Ritodrine
9087:Rimiterol
9052:PF-610355
9012:Mabuterol
8997:-Tyrosine
8953:Ibopamine
8933:Fenoterol
8840:Cimaterol
8825:Buphenine
8810:Befunolol
8780:Amibegron
8741:Yohimbine
8709:Terguride
8674:Piribedil
8669:Piperoxan
8639:Mianserin
8584:BRL-44408
8566:buspirone
8532:clozapine
8524:asenapine
8464:Vatinoxan
8404:Piperoxan
8374:Mivazerol
8349:Ibopamine
8344:-Tyrosine
8310:Guanabenz
8232:Clonidine
8170:Zolertine
8101:mianserin
8093:amoxapine
8074:Terazosin
8059:Spiperone
8049:Silodosin
8044:Quinidine
8029:Piperoxan
8019:trazodone
7984:Perlapine
7954:Nantenine
7939:Monatepil
7934:Metazosin
7919:L-765,314
7909:Indoramin
7888:terguride
7864:Ergolines
7859:Doxazosin
7839:Bunazosin
7828:labetalol
7781:clozapine
7768:Atiprosin
7763:Anisodine
7753:Alfuzosin
7743:Abanoquil
7672:Midodrine
7647:-Tyrosine
7613:Ibopamine
7540:Buspirone
7453:Phase III
7441:Withdrawn
7387:Metformin
7372:Beloranib
7217:Exenatide
7142:Otenabant
7132:Drinabant
7088:Pipradrol
7013:Bupropion
6977:Yohimbine
6952:Ephedrine
6942:Albuterol
6889:Mefenorex
6839:Ephedrine
6804:Cathinone
6677:Phase III
6665:Withdrawn
6645:+naproxen
6602:Ephedrine
6547:Mupirocin
6512:Cafaminol
6263:Ephedrine
6152:Serotonin
6112:Nootropic
5793:ProCentra
5788:Dexedrine
5587:7 January
5484:7 January
5384:7 January
4291:0885-6222
3683:0272-4391
3434:211233331
3406:Neurology
2781:27 August
2561:in dogs.
2510:CARES Act
2495:analgesic
2313:mydriatic
2267:ephedrine
2241:of 151.21
2237:NO and a
2225:with the
2218:PPA is a
2194:Ephedrine
2175:cathinone
2159:ephedrine
2155:Analogues
2111:naturally
2020:Chemistry
1982:XM-ligase
1964:Oxidation
1950:Oxidative
1799:cathinone
1795:ephedrine
1752:clearance
1631:catechol
1627:substrate
1596:oxidative
1389:receptors
1354:>10000
1335:>10000
1319:>10000
1301:>10000
1282:>10000
1263:>10000
1215:12.3–13.8
1198:>10000
1182:>10000
1176:43.1–72.4
1171:Ephedrine
1042:selective
1025:clearance
894:to treat
868:withdrawn
835:)- and (1
827:of the (1
821:cathinone
809:ephedrine
369:Excretion
340:half-life
150:Routes of
124:Pregnancy
110:Drugs.com
14060:Phenibut
13746:Dopamine
13727:Ciladopa
13717:a-Me-TRA
13557:Eutylone
13547:Butylone
13491:Ethylone
13486:Butylone
13476:3,4-DMMC
13424:Eutylone
13374:4-MeMABP
13294:Pentorex
13284:Etolorex
13274:Cloforex
13051:Tiflorex
12943:Morforex
12868:Fludorex
12623:Beatrice
12416:Escaline
11951:Guanoxan
11731:2C-B-BZP
11555:Etolorex
11550:Ethylone
11500:Cloforex
11490:Butylone
11389:Aminorex
11117:2C-B-BZP
11091:Tyramine
11086:Tiflorex
11020:Pentorex
10989:Morforex
10861:Fludorex
10831:Ethylone
10776:Butylone
10751:β-Me-PEA
10679:2-OH-PEA
10658:Pemoline
10633:Aminorex
10597:Morforex
10592:Morazone
10390:2C-B-BZP
10364:Tyramine
10359:Tiflorex
10290:Morforex
10163:Fludorex
10133:Ethylone
10073:Butylone
10048:β-Me-PEA
9978:2-OH-PEA
9957:Pemoline
9932:Aminorex
9896:Morforex
9891:Morazone
9613:Pindolol
9603:Pargolol
9553:Moprolol
9428:Esprolol
9413:Ericolol
9408:Epanolol
9218:Atenolol
9183:Afurolol
9178:Adimolol
9152:Zinterol
9127:Vibegron
8884:Dopamine
8850:Colterol
8763:Agonists
8731:loxapine
8629:Lisuride
8619:Idazoxan
8599:Efaroxan
8570:gepirone
8556:zotepine
8500:Adimolol
8474:Xylazine
8459:Urapidil
8271:Dopamine
8195:Agonists
8160:Urapidil
8150:loxapine
8034:Prazosin
7880:lisuride
7808:adimolol
7579:Dopamine
7523:Agonists
7412:ZGN-1061
7333:Orlistat
7180:and / or
7058:Mazindol
6998:Aminorex
6904:Pentorex
6869:Fludorex
6854:Etolorex
6819:Cloforex
6180:Category
6042:Dopamine
5866:inducer)
5745:Adderall
5462:1 August
5438:18384286
5304:16489364
5255:32965778
5206:17116124
5105:1 August
5033:barrier.
5028:20849327
4988:29989814
4951:1 August
4876:22816940
4868:19921126
4798:-OHA to
4790:-OHA to
4698:28641000
4651:23738007
4643:23650932
4603:13977820
4549:12191709
4514:10027866
4483:15922018
4256:34067981
4205:22169943
4156:23072836
4107:11071707
4062:14612135
3984:11535020
3949:10440593
3929:Obes Res
3914:15977970
3879:30014268
3828:1 August
3823:DailyMed
3796:1 August
3767:11263849
3591:12954796
3524:16202429
3504:Life Sci
3480:17017961
3426:17210897
3274:15944721
3234:16569079
3214:Drug Saf
3182:1 August
3137:1 August
3086:1 August
3015:12131054
2775:Archived
2743:cite web
2733:1 August
2688:1 August
2587:in vitro
2499:caffeine
2480:polypill
2456:exercise
2389:, while
2309:patented
2223:compound
1762:L/h/kg.
1737:antacids
1655:excreted
1590:include
1385:affinity
1218:8.5–24.5
1179:236–1350
1142:698–1765
1139:5.8–24.8
1088:Compound
1057:affinity
1027:by 50%.
1018:caffeine
1002:temporal
767:by mouth
726:(verify)
460:DrugBank
232:Class F3
182:QG04BX91
164:ATC code
157:By mouth
139: B2
126:category
14100:UWA-101
14065:PRO-LAD
13995:ETH-LAD
13756:Epinine
13712:a-Me-DA
13635:4-MePPP
13630:4-MePHP
13625:4-MePBP
13537:Ariadne
13315:Others:
13225:3,4-DCA
13222:Others:
13173:2,3-MDA
13158:6-MAPDB
13123:5-MAPDB
12804:Cathine
12728:ZDCM-04
12713:Psi-DOM
12698:Ganesha
12564:Others:
12379:2C-T-33
12374:2C-T-32
12369:2C-T-31
12364:2C-T-30
12359:2C-T-28
12354:2C-T-27
12349:2C-T-25
12344:2C-T-24
12339:2C-T-23
12329:2C-T-22
12324:2C-T-21
12319:2C-T-20
12314:2C-T-19
12309:2C-T-18
12304:2C-T-17
12299:2C-T-16
12294:2C-T-15
12289:2C-T-14
12284:2C-T-13
12279:2C-T-12
12274:2C-T-11
12269:2C-T-10
12084:2C-B-AN
11870:Others:
11736:3-MeOPP
11165:Others:
10781:Cathine
10428:Others:
10078:Cathine
9708:Timolol
9688:Tazolol
9663:Sotalol
9558:Nadolol
9283:Bunolol
9208:Arnolol
9142:XP21279
8721:(e.g.,
8649:NAN-190
8564:(e.g.,
8522:(e.g.,
8469:XP21279
8217:Amitraz
8165:WB-4101
8140:(e.g.,
8119:doxepin
8109:(e.g.,
8091:(e.g.,
8009:(e.g.,
7866:(e.g.,
7806:(e.g.,
7775:(e.g.,
7722:XP21279
7192:AMG 133
6981:Yohimbe
6957:Ephedra
6844:Ephedra
6799:Cathine
6552:Retinol
6350:agents,
6246:, plain
6235:Topical
6122:Obesity
5976:SLC22A5
5971:SLC22A3
5816:Vyvanse
5798:Zenzedi
5756:Mydayis
5295:1201314
5274:NeuroRx
5246:7510331
5197:2000711
5155:26 July
5150:PubChem
5130:21 July
5125:PubChem
5100:PubChem
5080:26 July
5075:PubChem
5055:26 July
5050:PubChem
4946:PubChem
4782:2600821
4737:4457764
4690:4713201
4594:1703637
4474:1828602
4408:4809526
4247:8152226
4196:3306880
4147:3572453
4087:Synapse
4027:8149215
3992:6733989
3870:6095132
3723:3280497
3386:2201518
3356:7534374
3310:7507588
2949:2647163
2875:7507589
2593:in vivo
2485:In the
2466:(WADA)
2393:is its
2358:is the
2322:In the
2317:pressor
2299:History
2196:is the
2192:class.
2140:racemic
2107:cathine
2087:), and
1974:Glycine
1696:hours.
1657:in the
1617:). The
1601:of the
1404:potency
1373:agonist
1290:Cathine
1136:6.6–7.2
1053:potency
997:in the
991:déjà vu
978:déjà vu
974:déjà vu
968:déjà vu
930:in the
908:obesity
874:and by
801:agonist
648:151.209
616:Formula
469:DB00397
435:PubChem
359:Oral: 3
332:minutes
328:: 15–30
242::
184: (
180:)
174: (
172:R01BA01
14015:IP-LAD
13935:AL-LAD
13707:6-OHDA
13242:(also
13235:DiFMDA
13153:6-MAPB
13143:6-EAPB
13133:6-APDB
13118:5-MAPB
13108:5-EAPB
13103:5-APDB
12708:MMDA-2
12608:3C-MAL
12560:MDMPEA
12411:DESOXY
12389:2C-TFM
12384:2C-TFE
12264:2C-T-9
12259:2C-T-8
12254:2C-T-7
12249:2C-T-6
12244:2C-T-5
12239:2C-T-4
12234:2C-T-3
12229:2C-T-2
12204:2C-O-4
12194:2C-NH2
12169:2C-G-N
12164:2C-G-6
12159:2C-G-5
12154:2C-G-4
12149:2C-G-3
12144:2C-G-2
12139:2C-G-1
11891:Others
11791:pTFMPP
11680:4-TFMA
11620:MDMPEA
11455:6-APDB
11445:5-APDB
11075:(also
10927:MDMPEA
10881:5-APDI
10451:5-APDI
10270:MDMPEA
8898:-DOPS)
8280:-DOPS)
8207:4-NEMD
7588:-DOPS)
7436:WHO-EM
7365:Others
7287:5-HT2C
7264:DACRAs
6660:WHO-EM
5915:, and
5882:(weak
5874:ligand
5731:Evekeo
5639:
5612:
5436:
5302:
5292:
5253:
5243:
5204:
5194:
5026:
4986:
4906:
4874:
4866:
4829:
4780:
4735:
4696:
4688:
4649:
4641:
4601:
4591:
4547:
4512:
4481:
4471:
4406:
4348:
4289:
4254:
4244:
4203:
4193:
4154:
4144:
4105:
4060:
4025:
3990:
3982:
3947:
3912:
3877:
3867:
3765:
3721:
3681:
3621:
3589:
3522:
3478:
3432:
3424:
3384:
3354:
3308:
3272:
3232:
3173:
3128:
3013:
2947:
2873:
2763:Anvisa
2679:
2460:sports
2380:, and
2336:Canada
2332:Europe
2243:
2173:, and
2132:misuse
2079:) and
1910:CYP2D6
1903:CYP2D6
1760:
1756:
1709:acidic
1694:
1686:
1682:
1663:
1637:. The
1605:) and
1543:-like
1523:. The
1509:
1485:
1481:
1473:
1465:
1457:
1453:
1420:tissue
1408:
1083:, nM)
999:mesial
819:, and
681:SMILES
540:ChEMBL
529:D08368
361:
347:
330:
230:
217:
14050:MT-45
13803:-DOPS
13794:-DOPA
13735:-DOPA
13702:6-FNE
13645:MOPVP
13640:MOPPP
13615:MDPPP
13610:MDPBP
13605:α-PVP
13600:α-PPP
13595:α-PHP
13590:α-PBP
13532:4-MAB
13527:4-CAB
13481:3-MMC
13379:4-MPD
13369:4-MEC
13364:4-FMC
13359:4-EMC
13354:4-CMC
13349:4-BMC
13339:3-FMC
13311:MDMPH
13208:MMDMA
13188:MDHMA
13128:6-APB
13098:5-APB
13093:4-MTA
13088:4-MMA
13078:4-FMA
12750:3-FMA
12740:2-FMA
12693:DOTFM
12648:DMMDA
12643:DMCPA
12618:Aleph
12598:3C-BZ
12593:3C-AL
12572:DMPEA
12555:MDPEA
12466:TCB-2
12436:MEPEA
12394:2C-YN
12219:2C-SE
12214:2C-Ph
12184:2C-iP
12124:2C-EF
12109:2C-CP
12104:2C-CN
12094:2C-Bu
12089:2C-Bn
11796:TFMPP
11766:MeOPP
11761:MDBZP
11660:MMDMA
11630:MDPEA
11610:MDHMA
11525:DFMDA
11465:AEMMA
11440:4-MTA
11430:4-FMA
11420:4-CAB
11368:MDMAT
11353:6-CAT
11327:MDMAI
11307:5-IAI
11193:5-IAI
11168:2-ADN
11142:MeOPP
11137:MDBZP
10937:MDPEA
10883:(IAP)
10704:4-MMA
10694:4-FMA
10684:4-CAB
10628:4-MAR
10456:5-IAI
10431:2-ADN
10410:MeOPP
10405:MDBZP
10280:MDPEA
10245:MMDMA
10003:4-MMA
9993:4-FMA
9983:4-CAB
9927:4-MAR
8212:6-FNE
7530:6-FNE
7422:Water
7297:5-HTP
7172:GLP-1
6991:Other
6062:ΔFosB
5966:EAAT3
5961:VMAT2
5956:VMAT1
5917:hCA14
5913:hCA13
5909:hCA12
5901:hCA5B
5897:hCA5A
5845:TAAR1
4872:S2CID
4694:S2CID
4647:S2CID
4382:(PDF)
4308:(PDF)
4007:Brain
3988:S2CID
3894:Drugs
3849:Drugs
3430:S2CID
2565:Notes
2351:Names
2340:India
2311:as a
2247:log P
1986:GLYAT
1928:Beta-
1921:Beta-
1895:Para-
1888:Para-
1881:Para-
1739:like
1719:like
1713:basic
1659:urine
1609:(via
1594:(via
1555:like
1521:lungs
1517:heart
1513:brain
1439:with
701:InChI
657:JSmol
374:Urine
363:hours
349:hours
315:(≤1%)
309:(~4%)
13660:MPPP
13655:MPHP
13650:MPBP
13620:MDPV
13562:MBDB
13552:EBDB
13344:4-MC
13306:MDPH
13198:MDOH
13183:MDEA
13148:6-IT
13113:5-IT
13083:4-MA
13073:4-FA
13016:PMMA
13011:PMEA
12996:PFMA
12745:3-FA
12735:2-FA
12723:TeMA
12703:MMDA
12688:DOPR
12668:DOET
12663:DOEF
12613:3C-P
12603:3C-E
12399:2C-V
12224:2C-T
12209:2C-P
12199:2C-O
12189:2C-N
12179:2C-I
12174:2C-H
12134:2C-G
12129:2C-F
12119:2C-E
12114:2C-D
12099:2C-C
12079:2C-B
11837:5-MT
11822:5-CT
11786:pFPP
11781:pCPP
11776:oMPP
11756:mCPP
11751:MBZP
11746:DCPP
11710:PMMA
11705:PMEA
11665:MMMA
11655:MMDA
11625:MDOH
11605:MDEA
11595:MBDB
11545:EDMA
11540:EBDB
11535:DMMA
11435:4-HA
11425:4-FA
11363:MDAT
11332:MMAI
11322:MDAI
11317:ETAI
11312:AMMI
11288:SRAs
11188:4-BP
11183:2-BP
11178:2-AT
11173:2-AI
11152:pFPP
11147:oMPP
11132:mCPP
11127:MBZP
10932:MDOH
10912:MDEA
10902:MBDB
10816:EBDB
10811:DMMA
10699:4-MA
10689:4-FA
10563:NRAs
10446:4-BP
10441:2-AT
10436:2-AI
10415:oMPP
10400:MBZP
10275:MDOH
10260:MDEA
10250:MBDB
10240:MMDA
10128:EBDB
10108:DMMA
9998:4-MA
9988:4-FA
9862:DRAs
8800:BAAM
8634:mCPP
8495:1-PP
8409:PS75
7924:mCPP
6879:Khat
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5951:SERT
5905:hCA7
5893:hCA4
5860:mRNA
5855:CART
5696:and
5637:ISBN
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5589:2014
5486:2014
5464:2024
5434:PMID
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5356:2018
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