45:
3964:
538:
358:
1829:
4025:
1089:
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.
1236:
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
1183:
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,
1136:
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
1088:
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
837:
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
1184:
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).
1137:
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.
1234:-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.
1237:
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.
1101:
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".
981:
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".
838:(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
1759:
1008:
Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection".
750:
Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection".
3456:
3451:
1679:
1149:
Horwitz D, Alexander RW, Lovenberg W, Keiser HR (May 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity".
239:
4009:
1196:
Freeman JJ, Sulser F (December 1974). "Formation of p-hydroxynorephedrine in brain following intraventricular administration of p-hydroxyamphetamine".
1249:
Matsuda LA, Hanson GR, Gibb JW (December 1989). "Neurochemical effects of amphetamine metabolites on central dopaminergic and serotonergic systems".
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1719:
1507:
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2115:
2110:
1925:
1865:
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2090:
2085:
2035:
1674:
2055:
1945:
1935:
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4100:
4002:
2504:
3029:
1330:
17:
1230:-hydroxynorephedrine (PHN) may contribute to the pharmacological profile of the parent drug. ... The location of the
4059:
3871:
4110:
2401:
4090:
3995:
2529:
2519:
2499:
1613:
1608:
830:
498:
273:
3039:
2857:
2524:
2509:
2494:
2277:
930:"Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism"
1684:
4115:
4095:
3152:
2852:
2802:
2514:
1779:
846:-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
78:
1747:
4052:
3592:
3461:
3446:
3441:
3024:
3436:
3431:
3019:
3014:
2779:
1858:
1689:
825:(7th ed.). Philadelphia, US: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648.
785:
695:
357:
3393:
2396:
1275:-OHNor is well documented and dopamine-β hydroxylase present in noradrenergic neurons could easily convert
160:
33:
3866:
3373:
3368:
2413:
842:-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords
3004:
1882:
1874:
1598:
1585:
4105:
3317:
3147:
1323:
724:
526:
483:
476:
2344:
555:
1851:
1618:
1302:
547:
3383:
3342:
3066:
2934:
2929:
2919:
2847:
2837:
2591:
2581:
2564:
2423:
1809:
1298:
969:
666:
612:; however, other evidence from animal studies suggests that this reaction is catalyzed by DBH in
522:
4040:
3983:
3543:
3511:
3420:
3059:
2827:
2464:
2373:
2365:
2357:
2349:
1734:
1536:
366:
818:
3378:
3322:
3195:
3180:
3169:
2822:
2559:
2539:
1799:
1742:
1603:
1569:
1565:
1561:
1553:
1549:
1526:
149:
1760:
Neurobiological effects of physical exercise § Attention deficit hyperactivity disorder
4085:
3699:
3558:
3553:
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3200:
3190:
3054:
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2794:
2739:
2729:
2479:
1832:
1648:
1593:
1557:
1545:
1316:
543:
408:
169:
8:
3971:
3861:
3607:
3410:
3357:
3009:
2924:
2914:
2862:
2832:
2768:
2655:
2586:
2576:
2459:
1704:
1658:
629:
401:
331:
319:
104:
95:
3220:
3215:
2317:
1542:
1222:
In species where aromatic hydroxylation of amphetamine is the major metabolic pathway,
1174:
1127:
1074:
1065:
1049:
954:
929:
1021:
879:
763:
3548:
3295:
3285:
3255:
3185:
2877:
2620:
2292:
1532:
1489:
1432:
1258:
1213:
1209:
1166:
1119:
1079:
1025:
990:
959:
945:
884:
826:
767:
315:
1178:
1131:
604:
metabolism in humans suggests that a different enzyme may mediate the conversion of
330:
in humans. When it occurs as a metabolite of amphetamine, it is produced from both
129:
4032:
3290:
3270:
3110:
2774:
2749:
2693:
2333:
1573:
1501:
1460:
1205:
1158:
1111:
1069:
1061:
1017:
949:
941:
874:
759:
613:
281:
InChI=1S/C9H13NO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
185:
3886:
3729:
3650:
2897:
2882:
2789:
2764:
2689:
2624:
2469:
2381:
1729:
1724:
1699:
1522:
1420:
1115:
323:
859:
600:. Evidence from studies that measured the effect of serum DBH concentrations on
4036:
3979:
3975:
3920:
3801:
3714:
3044:
2665:
2328:
1784:
1769:
1050:"Dopamine-beta-oxidase activity in man, using hydroxyamphetamine as substrate"
44:
4079:
3936:
3931:
3846:
3755:
3734:
3708:
3666:
3531:
3275:
3130:
2979:
2902:
2640:
2262:
2247:
1794:
1511:
387:
373:
3963:
1162:
3926:
3841:
3719:
3674:
3622:
3563:
3521:
3260:
2907:
2685:
2680:
2630:
2611:
2287:
1123:
1083:
1029:
994:
963:
771:
380:
1262:
1217:
1170:
888:
3946:
3911:
3881:
3811:
3806:
3781:
3679:
3582:
3235:
3225:
3205:
3159:
3140:
3120:
3099:
2887:
2872:
2807:
2759:
2699:
2670:
2650:
2616:
2544:
2338:
2272:
1814:
1789:
1358:
1339:
542:
In humans, para-hydroxynorephedrine is a metabolite of amphetamine. The
394:
327:
812:
810:
3916:
3851:
3831:
3826:
3821:
3816:
3796:
3786:
3760:
3739:
3694:
3689:
3658:
3627:
3612:
3602:
3516:
3347:
3310:
3300:
3280:
3240:
3230:
3085:
3081:
3071:
2867:
2817:
2812:
2744:
2734:
2719:
2714:
2704:
2635:
2606:
2601:
2474:
2408:
2391:
2302:
2297:
2267:
1754:
1709:
215:
140:
1100:
3896:
3791:
3704:
3684:
3617:
3506:
3337:
3305:
3250:
3245:
2754:
2724:
2675:
2660:
2596:
2323:
2282:
1913:
1908:
1903:
1898:
1893:
1804:
1764:
807:
115:
4024:
3901:
3747:
3587:
3568:
3398:
3388:
3332:
3327:
3265:
3135:
3125:
3115:
2892:
2784:
2709:
2257:
1694:
1397:
1007:
749:
590:
1843:
860:"Dopamine-beta-hydroxylase. Stereochemical course of the reaction"
238:
3941:
3906:
3836:
3597:
2999:
2964:
2645:
2569:
2554:
2200:
2165:
2155:
2145:
2140:
2135:
2125:
1774:
1714:
1628:
1623:
596:
537:
3856:
3776:
3641:
3632:
3573:
3076:
2994:
2984:
2974:
2959:
2949:
2944:
2549:
2449:
2252:
2230:
2225:
2105:
2100:
2095:
2080:
2075:
2070:
2045:
2010:
2005:
2000:
1995:
1990:
1985:
1980:
1148:
551:
450:
443:
1308:
3891:
3049:
2969:
2939:
2489:
2439:
2434:
2307:
2235:
2060:
2025:
1965:
1950:
1497:
970:
Table 5: N-containing drugs and xenobiotics oxygenated by FMO
819:"Phenylisopropylamine stimulants: amphetamine-related agents"
229:
3403:
3034:
2989:
2954:
2454:
2444:
2240:
2065:
2050:
2040:
2030:
2020:
2015:
1975:
1970:
1960:
1955:
1940:
1920:
1094:
3876:
900:
Dopamine-β-hydroxylase catalyzed the removal of the pro-
980:
904:
hydrogen atom and the production of 1-norephedrine, (2
642:
1251:
1047:
983:
821:. In Lemke TL, Williams DA, Roche VF, Zito W (eds.).
345:
778:
1104:Expert Opinion on Drug Metabolism & Toxicology
690:
688:
1248:
1010:Journal of Pharmaceutical and Biomedical Analysis
4077:
1142:
1054:British Journal of Pharmacology and Chemotherapy
128:
1720:History and culture of substituted amphetamines
1043:
1041:
1039:
927:
851:
717:
685:
594:and it is presumed to be metabolized similarly
103:
725:"Amphetamine: Biomedical Effects and Toxicity"
4060:
4003:
1859:
1324:
1283:-OHNor after intraventricular administration.
1195:
795:. Shire US Inc. December 2013. pp. 12–13
1036:
705:. United States Food and Drug Administration
1242:
1189:
1001:
974:
912:)-2-amino-1-hydroxyl-1-phenylpropane, from
743:
352:Metabolic pathways of amphetamine in humans
4067:
4053:
4010:
3996:
1866:
1852:
1331:
1317:
1048:Sjoerdsma A, von Studnitz W (April 1963).
816:
793:United States Food and Drug Administration
616:within noradrenergic neurons in the brain.
148:
1301:at the U.S. National Library of Medicine
1073:
953:
878:
857:
340:
168:
823:Foye's principles of medicinal chemistry
14:
4078:
584:has been shown to be metabolized into
520:
513:
508:
503:
496:
489:
474:
460:
455:
448:
441:
434:
427:
420:
399:
385:
378:
371:
1847:
1512:
1312:
928:Krueger SK, Williams DE (June 2005).
786:"Adderall XR Prescribing Information"
696:"Adderall XR Prescribing Information"
481:
467:
413:
406:
392:
4019:
3958:
364:
3872:Lysergic acid 2,4-dimethylazetidide
1873:
588:by dopamine beta-hydroxylase (DBH)
119:
24:
1066:10.1111/j.1476-5381.1963.tb01467.x
921:
25:
4127:
1292:
86:4-(2-amino-1-hydroxypropyl)phenol
4023:
3962:
1828:
1827:
946:10.1016/j.pharmthera.2005.01.001
536:
356:
202:
196:
43:
2803:N,alpha-Diethylphenylethylamine
1780:Performance-enhancing substance
1338:
934:Pharmacology & Therapeutics
867:Journal of Biological Chemistry
652:
575:
286:Key:JAYBQRKXEFDRER-RCOVLWMOSA-N
1226:-hydroxyamphetamine (POH) and
659:
205:
190:
13:
1:
4101:Recreational drug metabolites
1690:Benzedrine in popular culture
1022:10.1016/S0731-7085(02)00330-8
880:10.1016/S0021-9258(19)43051-2
764:10.1016/S0731-7085(02)00330-8
635:
550:in this image is mediated by
4039:. You can help Knowledge by
3982:. You can help Knowledge by
1210:10.1016/0028-3908(74)90069-0
1116:10.1517/17425255.2013.796929
7:
3867:Lysergic acid 2-butyl amide
623:
10:
4132:
4018:
3957:
3877:Lysergic acid diethylamide
858:Taylor KB (January 1974).
180:Chemical and physical data
4111:Nervous system drug stubs
3769:
3530:
3419:
3356:
3168:
3098:
2422:
1881:
1823:
1667:
1641:
1583:
1488:
1481:
1459:
1431:
1419:
1357:
1346:
269:
249:
227:
214:
184:
179:
159:
139:
114:
94:
74:
69:
56:
51:
42:
4091:Beta-Hydroxyamphetamines
3974:article relating to the
2767:(Dextromethamphetamine,
1393:Mixed amphetamine salts
1303:Medical Subject Headings
568:
548:substituted amphetamines
3421:Phenylalkylpyrrolidines
3343:Methylenedioxycathinone
3020:3,4-MDA (tenamfetamine)
1810:Substituted amphetamine
1163:10.1161/01.RES.32.5.594
667:"p-Hydroxynorephedrine"
261:((C)N)(O)C1=CC=C(O)C=C1
4116:Organic compound stubs
4096:Human drug metabolites
4031:This article about an
2345:β-Methylphenethylamine
2339:α-Methylphenethylamine
752:J. Pharm. Biomed. Anal
556:dopamine β-hydroxylase
367:4-Hydroxyphenylacetone
341:Amphetamine metabolism
3536:(and close relatives)
3035:MDMA (midomafetamine)
2377:-Methylphenethylamine
2369:-Methylphenethylamine
2361:-Methylphenethylamine
2353:-Methylphenethylamine
1800:Recreational drug use
1743:Motivational salience
1738:-Methylphenethylamine
1685:Amphetamine psychosis
1654:4-Hydroxynorephedrine
1537:competitive inhibitor
1517:Tooltip messenger RNA
1299:p-Hydroxynorephedrine
610:4-hydroxynorephedrine
586:4-hydroxynorephedrine
546:hydroxylation of the
416:4-Hydroxynorephedrine
308:4-hydroxynorephedrine
60:4-Hydroxynorephedrine
18:4-Hydroxynorephedrine
3700:N,N-Dimethyldopamine
3358:Phenylisobutylamines
3055:Naphthylaminopropane
2740:Isopropylamphetamine
2730:4-Hydroxyamphetamine
1649:4-Hydroxyamphetamine
1490:Biomolecular targets
1151:Circulation Research
606:4-hydroxyamphetamine
602:4-hydroxyamphetamine
582:4-Hydroxyamphetamine
409:4-Hydroxyamphetamine
300:-Hydroxynorephedrine
65:-Hydroxynorephedrine
37:-Hydroxynorephedrine
3862:Lysergic acid amide
3608:Ethylnorepinephrine
3411:Phenylisobutylamine
2863:Phenylpropanolamine
2798:-Norpseudoephedrine
2769:Levomethamphetamine
2656:Dimethylamphetamine
1705:Executive functions
1543:Carbonic anhydrases
817:Glennon RA (2013).
630:Hydroxynorephedrine
335:-hydroxyamphetamine
39:
2318:Phenylethanolamine
1748:Incentive salience
1642:Active metabolites
1267:The metabolism of
731:. Pubchem Compound
673:. PubChem Compound
337:and norephedrine.
32:
4048:
4047:
3991:
3990:
3955:
3954:
3296:N-Ethylpentedrone
3256:Dimethylcathinone
2878:Propylamphetamine
2621:Dextroamphetamine
2293:Methallylescaline
1841:
1840:
1637:
1636:
1482:Neuropharmacology
1477:
1476:
1433:Dextroamphetamine
1204:(12): 1187–1190.
1198:Neuropharmacology
614:synaptic vesicles
565:
564:
294:
293:
240:Interactive image
27:Chemical compound
16:(Redirected from
4123:
4106:Sympathomimetics
4069:
4062:
4055:
4033:organic compound
4027:
4020:
4012:
4005:
3998:
3966:
3959:
3661:
3653:
3644:
3635:
3576:
3537:
3291:N-Ethylhexedrone
3271:Hydroxybupropion
3111:Chlorphentermine
3088:
2797:
2775:Methoxyphenamine
2750:Lisdexamfetamine
2694:Levofenfluramine
2334:Phenpromethamine
1868:
1861:
1854:
1845:
1844:
1831:
1830:
1668:Related articles
1574:enzyme activator
1518:
1514:
1486:
1485:
1461:Lisdexamfetamine
1404:Adderall XR
1379:Dyanavel XR
1374:
1355:
1354:
1333:
1326:
1319:
1310:
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1286:
1285:
1246:
1240:
1239:
1193:
1187:
1186:
1146:
1140:
1139:
1110:(9): 1139–1153.
1098:
1092:
1091:
1077:
1045:
1034:
1033:
1005:
999:
998:
989:(3): 1251–1260.
978:
972:
967:
957:
925:
919:
918:
897:
895:
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855:
849:
848:
814:
805:
804:
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790:
782:
776:
775:
747:
741:
740:
738:
736:
721:
715:
714:
712:
710:
703:Medication Guide
700:
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683:
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678:
663:
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611:
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47:
40:
38:
31:
21:
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4130:
4126:
4125:
4124:
4122:
4121:
4120:
4076:
4075:
4074:
4073:
4017:
4016:
3956:
3951:
3887:Methoxphenidine
3765:
3730:Normetanephrine
3659:
3651:
3642:
3633:
3574:
3535:
3534:
3526:
3415:
3406:
3352:
3313:
3164:
3155:
3143:
3094:
3086:
3062:
2910:
2898:Tranylcypromine
2883:Pseudoephedrine
2795:
2790:Norfenfluramine
2765:Methamphetamine
2690:Dexfenfluramine
2625:Levoamphetamine
2572:
2470:Bromo-DragonFLY
2418:
2404:
2382:Methylphenidate
2313:
1883:Phenethylamines
1877:
1875:Phenethylamines
1872:
1842:
1837:
1819:
1730:Methylphenidate
1725:Methamphetamine
1700:Doping in sport
1680:ADHD management
1663:
1633:
1579:
1523:5-HT1A receptor
1516:
1473:
1455:
1427:
1421:Levoamphetamine
1415:
1389:Evekeo ODT
1372:
1367:Adzenys ER
1351:pharmaceuticals
1350:
1348:
1342:
1337:
1295:
1290:
1289:
1247:
1243:
1235:
1194:
1190:
1147:
1143:
1099:
1095:
1046:
1037:
1006:
1002:
979:
975:
968:
926:
922:
893:
891:
862:
856:
852:
833:
815:
808:
798:
796:
788:
784:
783:
779:
748:
744:
734:
732:
723:
722:
718:
708:
706:
698:
694:
693:
686:
676:
674:
665:
664:
660:
655:
650:
649:
643:
638:
626:
621:
620:
609:
605:
601:
585:
581:
580:
576:
571:
566:
561:
560:
559:
541:
533:
532:
531:
530:
525:
521:
519:
516:
514:
512:
509:
507:
504:
502:
497:
495:
492:
490:
488:
486:
482:
480:
475:
473:
470:
468:
466:
463:
461:
459:
456:
454:
449:
447:
442:
440:
437:
435:
433:
430:
428:
426:
423:
421:
419:
414:
412:
407:
405:
400:
398:
393:
391:
386:
384:
379:
377:
372:
370:
365:
361:
353:
343:
324:sympathomimetic
290:
287:
282:
277:
276:
265:
262:
257:
256:
245:
220:
210:
201:
195:
175:
155:
135:
118:
110:
90:
87:
82:
81:
61:
28:
23:
22:
15:
12:
11:
5:
4129:
4119:
4118:
4113:
4108:
4103:
4098:
4093:
4088:
4072:
4071:
4064:
4057:
4049:
4046:
4045:
4028:
4015:
4014:
4007:
4000:
3992:
3989:
3988:
3976:nervous system
3967:
3953:
3952:
3950:
3949:
3944:
3939:
3934:
3929:
3924:
3921:Levosalbutamol
3914:
3909:
3904:
3899:
3894:
3889:
3884:
3879:
3874:
3869:
3864:
3859:
3854:
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3802:Desvenlafaxine
3799:
3794:
3789:
3784:
3779:
3773:
3771:
3767:
3766:
3764:
3763:
3758:
3753:
3745:
3737:
3732:
3727:
3717:
3715:Norepinephrine
3712:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3664:
3656:
3654:-Phenylalanine
3648:
3639:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3571:
3566:
3561:
3556:
3551:
3546:
3540:
3538:
3532:Catecholamines
3528:
3527:
3525:
3524:
3519:
3514:
3509:
3504:
3499:
3494:
3489:
3484:
3479:
3474:
3469:
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3425:
3423:
3417:
3416:
3414:
3413:
3401:
3396:
3391:
3386:
3381:
3376:
3371:
3362:
3360:
3354:
3353:
3351:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3308:
3303:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3198:
3193:
3188:
3183:
3174:
3172:
3166:
3165:
3163:
3162:
3150:
3138:
3133:
3128:
3123:
3118:
3113:
3104:
3102:
3096:
3095:
3093:
3092:
3079:
3074:
3069:
3057:
3052:
3047:
3045:Methamnetamine
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2792:
2787:
2782:
2777:
2772:
2762:
2757:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2683:
2678:
2673:
2668:
2666:Etilamfetamine
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2628:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2567:
2562:
2557:
2552:
2547:
2542:
2537:
2532:
2527:
2522:
2517:
2512:
2507:
2502:
2497:
2492:
2487:
2482:
2477:
2472:
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2428:
2426:
2420:
2419:
2417:
2416:
2411:
2399:
2394:
2385:
2384:
2379:
2371:
2363:
2355:
2347:
2342:
2336:
2331:
2329:Phenethylamine
2326:
2311:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2244:
2243:
2238:
2233:
2228:
2223:
2218:
2213:
2208:
2203:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2133:
2128:
2123:
2118:
2113:
2108:
2103:
2098:
2093:
2088:
2083:
2078:
2073:
2068:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1978:
1973:
1968:
1963:
1958:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1917:
1916:
1911:
1906:
1901:
1896:
1887:
1885:
1879:
1878:
1871:
1870:
1863:
1856:
1848:
1839:
1838:
1836:
1835:
1824:
1821:
1820:
1818:
1817:
1812:
1807:
1802:
1797:
1792:
1787:
1785:Phenethylamine
1782:
1777:
1772:
1770:Norepinephrine
1767:
1762:
1757:
1752:
1751:
1750:
1740:
1732:
1727:
1722:
1717:
1712:
1707:
1702:
1697:
1692:
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1677:
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1632:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1590:
1588:
1581:
1580:
1578:
1577:
1540:
1530:
1525:(low affinity
1520:
1505:
1494:
1492:
1483:
1479:
1478:
1475:
1474:
1472:
1471:
1465:
1463:
1457:
1456:
1454:
1453:
1448:
1443:
1437:
1435:
1429:
1428:
1425:
1423:
1417:
1416:
1414:
1413:
1412:
1411:
1406:
1401:
1391:
1386:
1381:
1376:
1373:Adzenys XR-ODT
1369:
1363:
1361:
1352:
1347:Main articles
1344:
1343:
1336:
1335:
1328:
1321:
1313:
1307:
1306:
1294:
1293:External links
1291:
1288:
1287:
1257:(3): 901–908.
1241:
1188:
1157:(5): 594–599.
1141:
1093:
1060:(2): 278–284.
1035:
1016:(2): 247–255.
1000:
973:
940:(3): 357–387.
920:
873:(2): 454–458.
850:
831:
806:
777:
742:
716:
684:
657:
656:
654:
651:
648:
647:
640:
639:
637:
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562:
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339:
326:metabolite of
322:and an active
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4008:
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3999:
3994:
3993:
3987:
3985:
3981:
3977:
3973:
3968:
3965:
3961:
3960:
3948:
3945:
3943:
3940:
3938:
3937:Thiamphenicol
3935:
3933:
3932:Theodrenaline
3930:
3928:
3925:
3922:
3918:
3915:
3913:
3910:
3908:
3905:
3903:
3900:
3898:
3895:
3893:
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3885:
3883:
3880:
3878:
3875:
3873:
3870:
3868:
3865:
3863:
3860:
3858:
3855:
3853:
3850:
3848:
3847:Fluorolintane
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3780:
3778:
3775:
3774:
3772:
3770:Miscellaneous
3768:
3762:
3759:
3757:
3756:Phenylephrine
3754:
3752:
3750:
3746:
3744:
3742:
3738:
3736:
3735:Orciprenaline
3733:
3731:
3728:
3725:
3721:
3718:
3716:
3713:
3710:
3709:Levonordefrin
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3678:
3676:
3673:
3671:
3669:
3665:
3663:
3657:
3655:
3649:
3646:
3640:
3637:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3578:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3541:
3539:
3533:
3529:
3523:
3520:
3518:
3515:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3427:
3426:
3424:
3422:
3418:
3412:
3409:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3364:
3363:
3361:
3359:
3355:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3276:Methcathinone
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3176:
3175:
3173:
3171:
3167:
3161:
3158:
3154:
3151:
3149:
3146:
3142:
3139:
3137:
3134:
3132:
3131:Mephentermine
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3106:
3105:
3103:
3101:
3097:
3090:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2980:6-Chloro-MDMA
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
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2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2909:
2906:
2904:
2903:Xylopropamine
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2799:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2770:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2695:
2691:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2641:Benzphetamine
2639:
2637:
2634:
2632:
2629:
2626:
2622:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
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2580:
2578:
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2556:
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2551:
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2533:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2432:Psychedelics:
2430:
2429:
2427:
2425:
2421:
2415:
2412:
2410:
2407:
2403:
2400:
2398:
2395:
2393:
2390:
2387:
2386:
2383:
2380:
2378:
2376:
2372:
2370:
2368:
2364:
2362:
2360:
2356:
2354:
2352:
2348:
2346:
2343:
2341:(amphetamine)
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2321:
2320:
2319:
2316:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2263:Isoproscaline
2261:
2259:
2256:
2254:
2251:
2249:
2248:Allylescaline
2246:
2245:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2119:
2117:
2114:
2112:
2109:
2107:
2104:
2102:
2099:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1918:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1891:Psychedelics:
1889:
1888:
1886:
1884:
1880:
1876:
1869:
1864:
1862:
1857:
1855:
1850:
1849:
1846:
1834:
1826:
1825:
1822:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1796:
1795:Phenylacetone
1793:
1791:
1788:
1786:
1783:
1781:
1778:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1749:
1746:
1745:
1744:
1741:
1739:
1737:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1713:
1711:
1708:
1706:
1703:
1701:
1698:
1696:
1693:
1691:
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1672:
1670:
1666:
1660:
1657:
1655:
1652:
1650:
1647:
1646:
1644:
1640:
1630:
1627:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
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1602:
1600:
1597:
1595:
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1589:
1587:
1582:
1575:
1571:
1567:
1563:
1559:
1555:
1551:
1547:
1544:
1541:
1538:
1534:
1531:
1528:
1524:
1521:
1515:
1509:
1506:
1503:
1499:
1496:
1495:
1493:
1491:
1487:
1484:
1480:
1470:
1467:
1466:
1464:
1462:
1458:
1452:
1449:
1447:
1444:
1442:
1439:
1438:
1436:
1434:
1430:
1424:
1422:
1418:
1410:
1407:
1405:
1402:
1400:
1399:
1395:
1394:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1370:
1368:
1365:
1364:
1362:
1360:
1356:
1353:
1345:
1341:
1334:
1329:
1327:
1322:
1320:
1315:
1314:
1311:
1304:
1300:
1297:
1296:
1284:
1282:
1278:
1274:
1270:
1264:
1260:
1256:
1252:
1245:
1238:
1233:
1229:
1225:
1219:
1215:
1211:
1207:
1203:
1199:
1192:
1185:
1180:
1176:
1172:
1168:
1164:
1160:
1156:
1152:
1145:
1138:
1133:
1129:
1125:
1121:
1117:
1113:
1109:
1105:
1097:
1090:
1085:
1081:
1076:
1071:
1067:
1063:
1059:
1055:
1051:
1044:
1042:
1040:
1031:
1027:
1023:
1019:
1015:
1011:
1004:
996:
992:
988:
984:
977:
971:
965:
961:
956:
951:
947:
943:
939:
935:
931:
924:
917:
916:-amphetamine.
915:
911:
907:
903:
890:
886:
881:
876:
872:
868:
861:
854:
847:
845:
841:
834:
832:9781609133450
828:
824:
820:
813:
811:
794:
787:
781:
773:
769:
765:
761:
758:(2): 247–55.
757:
753:
746:
730:
726:
720:
704:
697:
691:
689:
672:
668:
662:
658:
645:
641:
631:
628:
627:
615:
599:
598:
593:
592:
578:
574:
557:
553:
549:
545:
544:aromatic ring
528:
524:
500:
485:
478:
471:Hydroxylation
464:Hydroxylation
452:
445:
438:Hydroxylation
431:Hydroxylation
424:Hydroxylation
417:
410:
403:
396:
389:
388:Hippuric acid
382:
375:
374:Phenylacetone
368:
359:
348:
347:
338:
336:
334:
329:
325:
321:
317:
313:
309:
305:
301:
299:
284:
279:
278:
275:
268:
259:
258:
255:
248:
241:
237:
236:
234:
231:
226:
219:
217:
213:
189:
187:
183:
178:
171:
167:
166:
164:
162:
158:
151:
147:
146:
144:
142:
138:
131:
127:
126:
124:
117:
113:
106:
102:
101:
99:
97:
93:
84:
83:
80:
73:
68:
64:
59:
55:
52:Clinical data
50:
46:
41:
36:
30:
19:
4041:expanding it
4030:
3984:expanding it
3969:
3927:Solriamfetol
3842:Famprofazone
3748:
3740:
3726:-Octopamine)
3723:
3720:Norfenefrine
3675:Metanephrine
3667:
3623:Isoprenaline
3579:(Dextrodopa)
3564:Adrenochrome
3522:Pyrovalerone
3428:
3407:
3366:Entactogens:
3365:
3315:Entactogens:
3314:
3261:Ethcathinone
3177:
3156:
3145:Entactogens:
3144:
3107:
3100:Phentermines
3063:
2912:Entactogens:
2911:
2908:Zylofuramine
2686:Fenfluramine
2681:Fenethylline
2631:Amphetaminil
2612:Amfepentorex
2573:
2431:
2424:Amphetamines
2405:
2389:Entactogens:
2388:
2374:
2366:
2358:
2350:
2314:
2312:
2288:Metaescaline
1890:
1735:
1659:Norephedrine
1653:
1586:transporters
1502:full agonist
1468:
1450:
1445:
1440:
1408:
1403:
1396:
1388:
1383:
1378:
1371:
1366:
1280:
1276:
1272:
1268:
1266:
1254:
1250:
1244:
1231:
1227:
1223:
1221:
1201:
1197:
1191:
1182:
1154:
1150:
1144:
1135:
1107:
1103:
1096:
1087:
1057:
1053:
1013:
1009:
1003:
986:
982:
976:
937:
933:
923:
913:
909:
905:
901:
899:
892:. Retrieved
870:
866:
853:
843:
839:
836:
822:
797:. Retrieved
792:
780:
755:
751:
745:
733:. Retrieved
728:
719:
707:. Retrieved
702:
675:. Retrieved
670:
661:
644:
595:
589:
577:
510:unidentified
457:unidentified
415:
402:Norephedrine
381:Benzoic acid
332:
320:norephedrine
311:
307:
303:
297:
296:
295:
62:
34:
29:
4086:Amphetamine
3947:Venlafaxine
3912:Pronethalol
3882:Methoxamine
3812:Dizocilpine
3807:Diphenidine
3782:Amidephrine
3743:-Octopamine
3680:Metaraminol
3647:(Droxidopa)
3593:Epinephrine
3583:Dimetofrine
3429:Stimulants:
3408:Stimulants:
3236:Brephedrone
3226:Amfepramone
3178:Stimulants:
3160:Cericlamine
3141:Phentermine
3121:Clortermine
3108:Stimulants:
2888:Sibutramine
2873:Prenylamine
2808:Oxifentorex
2760:Metaraminol
2700:Fenproporex
2671:Fencamfamin
2651:Clobenzorex
2617:Amphetamine
2574:Stimulants:
2315:Stimulants:
2273:Macromerine
1815:Trace amine
1790:Phentermine
1359:Amphetamine
1340:Amphetamine
799:30 December
517:Conjugation
493:Deamination
395:Amphetamine
328:amphetamine
223: g·mol
70:Identifiers
57:Other names
4080:Categories
3917:Salbutamol
3852:Hexapradol
3832:Etafedrine
3827:Ephenidine
3822:Dopexamine
3817:Dobutamine
3797:Denopamine
3787:Arbutamine
3761:Synephrine
3695:Methyldopa
3690:Metirosine
3638:(Levodopa)
3628:Isoetarine
3613:Fenclonine
3603:Etilefrine
3517:Prolintane
3348:Mephedrone
3311:Radafaxine
3301:Pentedrone
3281:Methedrone
3241:Buphedrone
3231:Benzedrone
3170:Cathinones
3082:Selegiline
3072:Amiflamine
2868:Pholedrine
2818:Ortetamine
2813:Oxilofrine
2745:Lefetamine
2735:Iofetamine
2720:Furfenorex
2715:Formetorex
2705:Flucetorex
2636:Benfluorex
2607:Amfecloral
2602:Alfetamine
2475:D-Deprenyl
2392:Lophophine
2303:Psi-2C-T-4
2298:Proscaline
2268:Jimscaline
1755:Narcolepsy
1710:Formetorex
1584:Inhibited
894:6 November
735:12 October
677:25 October
653:References
636:References
228:3D model (
216:Molar mass
170:O6914L7189
141:ChemSpider
96:CAS Number
79:IUPAC name
3897:PARGY-LAD
3792:Cafedrine
3751:-Tyramine
3705:Nordefrin
3685:Metaterol
3670:-Tyramine
3662:-Tyrosine
3618:Ibopamine
3507:Naphyrone
3338:Methylone
3306:Pentylone
3251:Cathinone
3246:Bupropion
3089:-Deprenyl
2755:Mefenorex
2725:Gepefrine
2676:Fencamine
2661:Ephedrine
2597:Acridorex
2324:Hordenine
2283:Mescaline
2176:2C-T-22.5
1914:25N-NBOMe
1909:25I-NBOMe
1904:25D-NBOMe
1899:25C-NBOMe
1894:25B-NBOMe
1805:Serotonin
1765:Nootropic
1446:ProCentra
1441:Dexedrine
709:7 October
523:XM-ligase
505:Oxidation
491:Oxidative
314:-hydroxy
310:) is the
3902:Phenibut
3588:Dopamine
3569:Ciladopa
3559:a-Me-TRA
3399:Eutylone
3389:Butylone
3333:Ethylone
3328:Butylone
3318:3,4-DMMC
3266:Eutylone
3216:4-MeMABP
3136:Pentorex
3126:Etolorex
3116:Cloforex
2893:Tiflorex
2785:Morforex
2710:Fludorex
2465:Beatrice
2258:Escaline
1833:Category
1695:Dopamine
1519:inducer)
1398:Adderall
1279:-OHA to
1271:-OHA to
1179:28641000
1132:23738007
1124:23650932
1084:13977820
1030:12191709
995:10027866
964:15922018
772:12191709
624:See also
591:in vitro
105:771-91-5
3942:UWA-101
3907:PRO-LAD
3837:ETH-LAD
3598:Epinine
3554:a-Me-DA
3477:4-MePPP
3472:4-MePHP
3467:4-MePBP
3379:Ariadne
3157:Others:
3067:3,4-DCA
3064:Others:
3015:2,3-MDA
3000:6-MAPDB
2965:5-MAPDB
2646:Cathine
2570:ZDCM-04
2555:Psi-DOM
2540:Ganesha
2406:Others:
2221:2C-T-33
2216:2C-T-32
2211:2C-T-31
2206:2C-T-30
2201:2C-T-28
2196:2C-T-27
2191:2C-T-25
2186:2C-T-24
2181:2C-T-23
2171:2C-T-22
2166:2C-T-21
2161:2C-T-20
2156:2C-T-19
2151:2C-T-18
2146:2C-T-17
2141:2C-T-16
2136:2C-T-15
2131:2C-T-14
2126:2C-T-13
2121:2C-T-12
2116:2C-T-11
2111:2C-T-10
1926:2C-B-AN
1775:Obesity
1629:SLC22A5
1624:SLC22A3
1469:Vyvanse
1451:Zenzedi
1409:Mydayis
1263:2600821
1218:4457764
1171:4713201
1075:1703637
955:1828602
889:4809526
597:in vivo
515:Glycine
221:167.208
186:Formula
150:5305318
130:6931143
116:PubChem
3857:IP-LAD
3777:AL-LAD
3549:6-OHDA
3084:(also
3077:DiFMDA
2995:6-MAPB
2985:6-EAPB
2975:6-APDB
2960:5-MAPB
2950:5-EAPB
2945:5-APDB
2550:MMDA-2
2450:3C-MAL
2402:MDMPEA
2253:DESOXY
2231:2C-TFM
2226:2C-TFE
2106:2C-T-9
2101:2C-T-8
2096:2C-T-7
2091:2C-T-6
2086:2C-T-5
2081:2C-T-4
2076:2C-T-3
2071:2C-T-2
2046:2C-O-4
2036:2C-NH2
2011:2C-G-N
2006:2C-G-6
2001:2C-G-5
1996:2C-G-4
1991:2C-G-3
1986:2C-G-2
1981:2C-G-1
1568:, and
1535:(weak
1527:ligand
1384:Evekeo
1305:(MeSH)
1261:
1216:
1177:
1169:
1130:
1122:
1082:
1072:
1028:
993:
962:
952:
887:
829:
770:
552:CYP2D6
451:CYP2D6
444:CYP2D6
316:analog
254:SMILES
4035:is a
3978:is a
3970:This
3892:MT-45
3645:-DOPS
3636:-DOPA
3577:-DOPA
3544:6-FNE
3487:MOPVP
3482:MOPPP
3457:MDPPP
3452:MDPBP
3447:α-PVP
3442:α-PPP
3437:α-PHP
3432:α-PBP
3374:4-MAB
3369:4-CAB
3323:3-MMC
3221:4-MPD
3211:4-MEC
3206:4-FMC
3201:4-EMC
3196:4-CMC
3191:4-BMC
3181:3-FMC
3153:MDMPH
3050:MMDMA
3030:MDHMA
2970:6-APB
2940:5-APB
2935:4-MTA
2930:4-MMA
2920:4-FMA
2592:3-FMA
2582:2-FMA
2535:DOTFM
2490:DMMDA
2485:DMCPA
2460:Aleph
2440:3C-BZ
2435:3C-AL
2414:DMPEA
2397:MDPEA
2308:TCB-2
2278:MEPEA
2236:2C-YN
2061:2C-SE
2056:2C-Ph
2026:2C-iP
1966:2C-EF
1951:2C-CP
1946:2C-CN
1936:2C-Bu
1931:2C-Bn
1715:ΔFosB
1619:EAAT3
1614:VMAT2
1609:VMAT1
1570:hCA14
1566:hCA13
1562:hCA12
1554:hCA5B
1550:hCA5A
1498:TAAR1
1175:S2CID
1128:S2CID
863:(PDF)
789:(PDF)
699:(PDF)
569:Notes
527:GLYAT
469:Beta-
462:Beta-
436:Para-
429:Para-
422:Para-
274:InChI
230:JSmol
4037:stub
3980:stub
3972:drug
3502:MPPP
3497:MPHP
3492:MPBP
3462:MDPV
3404:MBDB
3394:EBDB
3186:4-MC
3148:MDPH
3040:MDOH
3025:MDEA
2990:6-IT
2955:5-IT
2925:4-MA
2915:4-FA
2858:PMMA
2853:PMEA
2838:PFMA
2587:3-FA
2577:2-FA
2565:TeMA
2545:MMDA
2530:DOPR
2510:DOET
2505:DOEF
2455:3C-P
2445:3C-E
2241:2C-V
2066:2C-T
2051:2C-P
2041:2C-O
2031:2C-N
2021:2C-I
2016:2C-H
1976:2C-G
1971:2C-F
1961:2C-E
1956:2C-D
1941:2C-C
1921:2C-B
1675:ADHD
1604:SERT
1558:hCA7
1546:hCA4
1513:mRNA
1508:CART
1349:and
1259:PMID
1214:PMID
1167:PMID
1120:PMID
1080:PMID
1026:PMID
991:PMID
960:PMID
896:2014
885:PMID
827:ISBN
801:2013
768:PMID
737:2013
729:NCBI
711:2013
679:2013
671:NCBI
554:and
499:FMO3
312:para
161:UNII
63:para
3512:PEP
3384:BDB
3286:NEB
3060:TAP
3010:IAP
3005:EDA
2848:PMA
2843:PIA
2833:PFA
2828:PCA
2823:PBA
2780:MMA
2560:TMA
2525:DON
2520:DOM
2515:DOI
2500:DOC
2495:DOB
2480:DMA
2409:BOH
1599:NET
1594:DAT
1533:MAO
1426:N/A
1255:251
1206:doi
1159:doi
1112:doi
1070:PMC
1062:doi
1018:doi
987:288
950:PMC
942:doi
938:106
875:doi
871:249
760:doi
608:to
484:DBH
477:DBH
318:of
306:or
304:PHN
120:CID
4082::
2692:,
2623:,
1564:,
1560:,
1556:,
1552:,
1548:,
1265:.
1253:.
1220:.
1212:.
1202:13
1200:.
1181:.
1173:.
1165:.
1155:32
1153:.
1134:.
1126:.
1118:.
1106:.
1086:.
1078:.
1068:.
1058:20
1056:.
1052:.
1038:^
1024:.
1014:30
1012:.
985:.
958:.
948:.
936:.
932:.
908:,1
898:.
883:.
869:.
865:.
835:.
809:^
791:.
766:.
756:30
754:.
727:.
701:.
687:^
669:.
200:13
4068:e
4061:t
4054:v
4043:.
4011:e
4004:t
3997:v
3986:.
3923:)
3919:(
3749:p
3741:p
3724:m
3722:(
3711:)
3707:(
3668:m
3660:L
3652:L
3643:L
3634:L
3575:D
3091:)
3087:D
2796:L
2771:)
2696:)
2688:(
2627:)
2619:(
2375:p
2367:o
2359:N
2351:m
1867:e
1860:t
1853:v
1736:N
1576:)
1572:(
1539:)
1529:)
1510:(
1504:)
1500:(
1332:e
1325:t
1318:v
1281:p
1277:p
1273:p
1269:p
1232:p
1228:p
1224:p
1208::
1161::
1114::
1108:9
1064::
1032:.
1020::
997:.
966:.
944::
914:d
910:R
906:S
902:R
877::
844:p
840:p
803:.
774:.
762::
739:.
713:.
681:.
558:.
333:p
302:(
298:p
232:)
209:2
206:O
203:N
197:H
194:9
191:C
35:p
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
