315:
54:
553:
40:
68:
81:
936:. The first step of the catabolic process is mediated by either MAO or COMT which depends on the tissue and location of catecholamines (for example degradation of catecholamines in the synaptic cleft is mediated by COMT because MAO is a mitochondrial enzyme). The next catabolic steps in the pathway involve
1181:
Catecholamines are secreted by cells in tissues of different systems of the human body, mostly by the nervous and the endocrine systems. The adrenal glands secrete certain catecholamines into the blood when the person is physically or mentally stressed and this is usually a healthy physiological
1638:"Family-Based and Association Studies of Monoamine Oxidase A and Attention Deficit Hyperactivity Disorder (ADHD): Preferential Transmission of the Long Promoter-Region Repeat and its Association with Impaired Performance on a Continuous Performance Test (TOVA)"
891:
converts norepinephrine into epinephrine. Thus, a cell that uses epinephrine as its transmitter contains four enzymes (TH, AADC, DBH, and PNMT), whereas norepinephrine neurons contain only three enzymes (lacking PNMT) and dopamine cells only two (TH and AADC).
1182:
response. However, acute or chronic excess of circulating catecholamines can potentially increase blood pressure and heart rate to very high levels and eventually provoke dangerous effects. Tests for fractionated plasma free
1208:
Catecholamine tests are done to identify rare tumors at the adrenal gland or in the nervous system. Catecholamine tests provide information relative to tumors such as: pheochromocytoma, paraganglioma, and neuroblastoma.
776:
Dopamine is the first catecholamine synthesized from DOPA. In turn, norepinephrine and epinephrine are derived from further metabolic modification of dopamine. The enzyme dopamine hydroxylase requires copper as a
928:-methyltransferase (COMT) which is present in the synaptic cleft and cytosol of the cell and monoamine oxidase (MAO) which is located in the mitochondrial membrane. Both enzymes require cofactors: COMT uses
1514:
Kitahama, K.; Pearson, J.; Denoroy, L.; Kopp, N.; Ulrich, J.; Maeda, T.; Jouvet, M. (1985). "Adrenergic neurons in human brain demonstrated by immunohistochemistry with antibodies to phenylethanolamine-
2409:
1156:
extracts. CAs have been implicated to have a possible protective role against insect predators, injuries, and nitrogen detoxification. They have been shown to promote plant tissue growth, somatic
3032:
2903:
2860:
2718:
1131:
Catecholamine is secreted into urine after being broken down, and its secretion level can be measured for the diagnosis of illnesses associated with catecholamine levels in the body.
831:, a metabolic disorder that leads to intellectual deficits unless treated by dietary manipulation. Catecholamine synthesis is usually considered to begin with tyrosine. The enzyme
3014:
314:
2711:
1341:
2975:
1228:
1148:"They have been found in 44 plant families, but no essential metabolic function has been established for them. They are precursors of benzophenanthridine
504:
497:
883:(DBH), which converts dopamine to yield norepinephrine, is also present. In still other neurons in which epinephrine is the transmitter, a third enzyme
3047:
2704:
1561:
Eisenhofer, G.; Kopin, I. J.; Goldstein, D. S. (2004). "Catecholamine metabolism: a contemporary view with implications for physiology and medicine".
785:(not shown in the diagram). The rate limiting step in catecholamine biosynthesis through the predominant metabolic pathway is the hydroxylation of
1194:
that don't adequately respond to treatment. Each of the tests measure the amount of adrenaline and noradrenaline metabolites, respectively called
248:
and then to dopamine. Depending on the cell type, dopamine may be further converted to norepinephrine or even further converted to epinephrine.
3581:
241:. Tyrosine is also ingested directly from dietary protein. Catecholamine-secreting cells use several reactions to convert tyrosine serially to
1992:
993:
is a neuromodulator of the peripheral sympathetic nervous system but is also present in the blood (mostly through "spillover" from the
1124:-inhibitor), raise the levels of all the catecholamines. Increased catecholamines may also cause an increased respiratory rate (
3080:
884:
753:
664:
490:
483:
476:
469:
900:
Catecholamines have a half-life of a few minutes when circulating in the blood. They can be degraded either by methylation by
3089:
1784:
1694:
1325:
2110:
1316:
Purves, D.; Augustine, G. J.; Fitzpatrick, D.; Hall, W. C.; LaMantia, A. S.; McNamara, J. O.; White, L. E., eds. (2008).
859:(AADC; see Cooper et al., 2002) to the transmitter dopamine. This step occurs so rapidly that it is difficult to measure
852:
629:
455:
448:
441:
1065:. As MAO-A is one of the enzymes responsible for degradation of these neurotransmitters, its deficiency increases the
2893:
2845:
1233:
3265:
3260:
1349:
2875:
2802:
1985:
574:
2870:
2807:
1186:
or the urine metanephrines are used to confirm or exclude certain diseases when the doctor identifies signs of
17:
3317:
2079:
1219:
901:
3595:
2429:
2404:
2044:
527:
3037:
2965:
933:
578:
3621:
3270:
3127:
3073:
2970:
2850:
1978:
1113:
1032:
713:
149:
2497:
2184:
2115:
1636:
Manor, I.; Tyano, S.; Mel, E.; Eisenberg, J.; Bachner-Melman, R.; Kotler, M.; Ebstein, R. P. (2002).
880:
871:-DOPA to dopamine is the final step in formation of the transmitter; however, in those neurons using
824:
649:
640:
as the cofactor. Dopamine itself is also used as precursor in the synthesis of the neurotransmitters
541:
534:
238:
3342:
1441:
Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family".
1096:
Catecholamines cause general physiological changes that prepare the body for physical activity (the
3631:
3352:
2434:
1964:
1097:
1081:, but it looks similar to carcinoid syndrome with symptoms such as facial flushing and aggression.
827:, found in large amounts in the liver. Insufficient amounts of phenylalanine hydroxylase result in
227:
3626:
3616:
3367:
2547:
2439:
2105:
1677:
Brunner, H. G. (1996). "MAOA Deficiency and
Abnormal Behaviour: Perspectives on an Association".
778:
752:
is produced in small groups of neurons in the human brain which express its synthesizing enzyme,
594:
256:
3058:
1909:
3580:
or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see
3506:
3337:
3332:
3327:
3174:
2730:
2552:
2419:
2399:
2364:
2264:
1363:
Joh, T. H.; Hwang, O. (1987). "Dopamine Beta-Hydroxylase: Biochemistry and
Molecular Biology".
1024:
1020:
986:
941:
729:
725:
606:
397:
1604:
Chu, Brianna; Marwaha, Komal; Sanvictores, Terrence; Awosika, Ayoola O.; Ayers, Derek (2024),
3092:
3066:
3042:
2865:
2542:
2459:
2074:
1860:
1268:
949:
937:
672:
1800:
1019:
Extremely high levels of catecholamines (also known as catecholamine toxicity) can occur in
283:
group. Phenylethanolamines such as norepinephrine have a hydroxyl group on the ethyl chain.
3302:
2812:
2696:
2469:
2444:
2064:
2059:
1161:
1132:
1074:
1043:
1005:
929:
918:
bind to MAO, thereby preventing it from breaking down catecholamines and other monoamines.
832:
823:
and the brain. In mammals, tyrosine can be formed from dietary phenylalanine by the enzyme
805:
709:
1960:
8:
3307:
3009:
2947:
1476:
Wang X, Li J, Dong G, Yue J (February 2014). "The endogenous substrates of brain CYP2D".
1290:
1058:
782:
637:
610:
590:
1518:-methyltransferase (PNMT): discovery of a new group in the nucleus tractus solitarius".
819:
are precursors for catecholamines. Both amino acids are found in high concentrations in
199:. Catecholamines are water-soluble and are 50% bound to plasma proteins in circulation.
3414:
3211:
2449:
2290:
2269:
2218:
1884:
1842:
1744:
1719:
1586:
1543:
1388:
1376:
1205:
Blood tests are also done to analyze the amount of catecholamines present in the body.
1078:
1036:
1004:, which can be induced from psychological reactions or environmental stressors such as
945:
1168:
biosynthesis. They have also been shown to enhance synergistically various effects of
3548:
3169:
3164:
3001:
2827:
2822:
2259:
2233:
1780:
1749:
1700:
1690:
1659:
1613:
1578:
1535:
1531:
1493:
1458:
1423:
1419:
1380:
1321:
1001:
957:
909:
434:
1846:
1590:
1392:
3182:
2727:
2663:
2620:
2414:
2001:
1834:
1739:
1731:
1682:
1649:
1570:
1547:
1527:
1485:
1450:
1415:
1406:
Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines".
1372:
1263:
1136:
1070:
1062:
1051:
733:
721:
701:
407:
153:
97:
1933:
3432:
3375:
3357:
3347:
3198:
3190:
2855:
2615:
1489:
1258:
1248:
1199:
1153:
1066:
1047:
1009:
982:
828:
741:
728:, is largely produced in neuronal cell bodies in two areas of the brainstem: the
705:
219:
3518:
3206:
3147:
2837:
2817:
2771:
2677:
2295:
2238:
2203:
2069:
1605:
1454:
1253:
1243:
1105:
990:
974:
872:
765:
760:; these neurons project from a nucleus that is adjacent (ventrolateral) to the
745:
641:
389:
362:
207:
58:
53:
3566:
1686:
3610:
3234:
3226:
2755:
2668:
2595:
2310:
2039:
1183:
1157:
1109:
812:
761:
657:
323:
234:
223:
196:
1735:
740:-pigmented neurons. The similarly neuromelanin-pigmented cell bodies of the
3395:
3312:
3287:
2898:
2649:
2629:
2484:
2351:
2274:
2176:
1753:
1663:
1617:
1582:
1497:
1462:
1427:
1195:
1187:
1013:
820:
737:
268:
2136:
1704:
1654:
1637:
1539:
1384:
3422:
3380:
3362:
3255:
3159:
3142:
3118:
3024:
2885:
2775:
2474:
2146:
2049:
1191:
1169:
876:
749:
663:
as cofactors. Norepinephrine is converted into epinephrine by the enzyme
645:
307:
303:
276:
203:
182:
44:
39:
185:
of a larger molecule, where it represents a 1,2-dihydroxybenzene group.
3390:
3292:
3282:
3221:
3216:
2957:
2942:
2921:
2785:
2516:
2424:
2305:
2300:
2282:
2228:
2009:
1838:
1101:
921:
558:
427:
417:
354:
189:
169:
2464:
1574:
3400:
3385:
3297:
3152:
3137:
2993:
2989:
2934:
2925:
2747:
2533:
2337:
2243:
2156:
1772:
1720:"Acute intermittent porphyria and phaeochromocytoma: shared features"
1681:. Ciba Foundation Symposium. Vol. 194. Wiley. pp. 155–167.
1125:
1117:
1085:
1069:
of these neurotransmitters considerably. It occurs in the absence of
1028:
252:
67:
1970:
3132:
2794:
2767:
2759:
2454:
2318:
2223:
2034:
1165:
1149:
978:
816:
717:
380:
369:
333:
272:
211:
192:
178:
165:
157:
84:
72:
3565:
References for all endogenous human TAAR1 ligands are provided at
1469:
195:, which is derived from dietary sources as well as synthesis from
3109:
3088:
2654:
2570:
2166:
2151:
2141:
2131:
2084:
2054:
1825:
Kuklin, A. I.; Conger, B. V. (1995). "Catecholamines in Plants".
1776:
1238:
994:
618:
557:
In humans, catecholamines (shown in yellow) are derived from the
215:
161:
552:
2763:
2161:
2089:
864:
582:
513:
343:
242:
80:
1315:
133:
3577:
3491:
3454:
3440:
3100:
2383:
2189:
1042:
Extremely high levels of catecholamine can also be caused by
1039:, this occurrence is widely known as a "catecholamine dump".
953:
847:-tyrosine by TH results in the formation of the DA precursor
280:
172:
2726:
1603:
989:
and as hormones in the blood circulation. The catecholamine
924:
of catecholamines is mediated by two main enzymes: catechol-
3322:
1121:
915:
801:
781:(not shown in the diagram) and DOPA decarboxylase requires
648:. Dopamine is converted into norepinephrine by the enzyme
621:
127:
121:
112:
1513:
1348:. San Diego, CA: University of California. Archived from
106:
3576:
References for synthetic TAAR1 agonists can be found at
1718:
Stewart, M. F.; Croft, J.; Reed, P.; New, J. P. (2006).
1560:
1000:
High catecholamine levels in blood are associated with
948:. The end product of epinephrine and norepinephrine is
867:
that use DA as the transmitter, the decarboxylation of
1635:
1320:(4th ed.). Sinauer Associates. pp. 137–138.
1434:
1399:
1229:
Catecholaminergic polymorphic ventricular tachycardia
1152:, which are the active principal ingredients of many
863:-DOPA in the brain without first inhibiting AADC. In
796:
Catecholamine synthesis is inhibited by alpha-methyl-
136:
118:
103:
100:
1509:
1507:
1057:
High levels of catecholamines can also be caused by
291:
124:
109:
1717:
1160:from in vitro cultures, and flowering. CAs inhibit
130:
115:
2894:3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)
2846:3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)
2818:Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET)
2588:
1504:
956:. Dopamine catabolism leads to the production of
3608:
2871:3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG)
267:Catecholamines have the distinct structure of a
2608:
2532:
2392:
1612:, Treasure Island (FL): StatPearls Publishing,
1440:
764:and from a nucleus in the dorsal region of the
628:-DOPA is converted into dopamine by the enzyme
1861:"Plasma Free Metanephrines | Lab Tests Online"
1676:
1295:Greenspan's Basic & Clinical Endocrinology
3074:
3033:3-Methoxy-4-hydroxyphenylacetaldehyde (HMPAL)
2876:3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
2712:
1986:
1679:Genetics of Criminal and Antisocial Behaviour
1475:
1291:"Chapter 11. Adrenal Medulla and Paraganglia"
1176:
286:
1824:
1031:, in particular, those nuclei affecting the
839:-tyrosine into 3,4-dihydroxyphenylalanine (
3081:
3067:
2719:
2705:
2525:
1993:
1979:
1769:Health assessment and physical examination
1365:Annals of the New York Academy of Sciences
1288:
700:Catecholamines are produced mainly by the
233:Tyrosine is created from phenylalanine by
2904:3-Methoxy-4-hydroxymandelaldehyde (MHMAL)
2861:3-Methoxy-4-hydroxymandelaldehyde (MHMAL)
2642:
1963:at the U.S. National Library of Medicine
1743:
1653:
1293:. In Gardner, D. G.; Shoback, D. (eds.).
1100:). Some typical effects are increases in
879:(adrenaline) as transmitters, the enzyme
1885:"Urine Metanephrines | Lab Tests Online"
1405:
1362:
218:epinephrine and norepinephrine from the
79:
2803:3,4-Dihydroxyphenylacetaldehyde (DOPAL)
1910:"Catecholamine Urine & Blood Tests"
1023:trauma due to stimulation or damage of
14:
3609:
2808:3,4-Dihydroxyphenylacetic acid (DOPAC)
1112:levels, and a general reaction of the
575:aromatic amino acid hydroxylase (AAAH)
539:
532:
525:
518:
509:
488:
481:
474:
460:
453:
446:
432:
425:
415:
405:
386:
377:
367:
168:side groups next to each other) and a
3090:Human trace amine-associated receptor
3062:
2700:
2000:
1974:
1766:
1309:
1297:(9th ed.). New York: McGraw-Hill
1142:
502:
467:
439:
395:
360:
351:
341:
331:
3015:5-Methoxyindoleacetaldehyde (5-MIAL)
3005:-Acetylserotonin (NAS; normelatonin)
2966:5-Hydroxyindoleacetaldehyde (5-HIAL)
1135:for catecholamine is used to detect
495:
321:
188:Catecholamines are derived from the
2971:5-Hydroxyindoleacetic acid (5-HIAA)
1088:can cause elevated catecholamines.
181:can be either a free molecule or a
24:
3038:4-Hydroxyphenylacetaldehyde (HPAL)
1827:Journal of Plant Growth Regulation
1443:Trends in Pharmacological Sciences
1377:10.1111/j.1749-6632.1987.tb27217.x
202:Included among catecholamines are
25:
3643:
3381:Ralmitaront (RG-7906, RO-6889450)
2851:3,4-Dihydroxymandelic acid (DHMA)
1954:
1234:History of catecholamine research
1050:, a treatable condition known as
569:-Phenylalanine is converted into
1478:European Journal of Pharmacology
1420:10.1016/j.pharmthera.2009.11.005
634:-amino acid decarboxylase (AADC)
551:
313:
96:
66:
52:
38:
1926:
1902:
1877:
1853:
1818:
1793:
1760:
1711:
1670:
1629:
1597:
1408:Pharmacology & Therapeutics
851:-DOPA, which is metabolized by
771:
736:, the latter of which contains
259:) are catecholamine analogues.
3148:Norepinephrine (noradrenaline)
2239:Norepinephrine (noradrenaline)
1554:
1356:
1334:
1282:
895:
605:-DOPA by another AAAH enzyme (
13:
1:
3596:Receptor/signaling modulators
1724:Journal of Clinical Pathology
1606:"Physiology, Stress Reaction"
1275:
932:as a cofactor while MAO uses
843:-DOPA). The hydroxylation of
835:(TH) converts the amino acid
2976:5-Hydroxytryptophol (5-HTOL)
1532:10.1016/0304-3940(85)90555-5
1490:10.1016/j.ejphar.2013.12.025
997:of the sympathetic system).
650:dopamine β-hydroxylase (DBH)
601:-Tyrosine is converted into
262:
7:
3128:monoamine neurotransmitters
2948:5-Hydroxytryptophan (5-HTP)
2866:Vanillylmandelic acid (VMA)
1212:
1059:monoamine oxidase A (MAO-A)
968:
963:
950:vanillylmandelic acid (VMA)
695:
579:phenylalanine 4-hydroxylase
255:drugs (such as a number of
27:Class of chemical compounds
10:
3648:
3010:5-Methoxytryptamine (5-MT)
1455:10.1016/j.tips.2005.03.007
1289:Fitzgerald, P. A. (2011).
1177:Testing for catecholamines
1114:sympathetic nervous system
1091:
1033:sympathetic nervous system
906:-methyltransferases (COMT)
714:sympathetic nervous system
298:Biosynthetic pathways for
287:Production and degradation
150:monoamine neurotransmitter
3561:
3541:
3527:
3499:
3490:
3472:
3462:
3453:
3431:
3413:
3248:
3117:
3108:
3099:
3023:
2988:
2956:
2933:
2920:
2884:
2836:
2793:
2784:
2746:
2737:
2581:
2569:
2515:
2492:
2483:
2382:
2359:
2350:
2330:
2252:
2211:
2202:
2175:
2124:
2098:
2045:Glutamic acid (glutamate)
2040:Aspartic acid (aspartate)
2027:
2018:
2008:
1801:"Catecholamines in Urine"
1687:10.1002/9780470514825.ch9
952:which is excreted in the
889:-methyltransferase (PNMT)
857:-amino acid decarboxylase
825:phenylalanine hydroxylase
239:phenylalanine hydroxylase
3143:Epinephrine (adrenaline)
3043:Indoleacetaldehyde (IAL)
2823:3-Methoxytyramine (3-MT)
2229:Epinephrine (adrenaline)
1965:Medical Subject Headings
1098:fight-or-flight response
910:monoamine oxidases (MAO)
275:groups, an intermediate
257:substituted amphetamines
228:fight-or-flight response
3278:-Dimethylphenethylamine
2828:Homovanillic acid (HVA)
2731:metabolic intermediates
1736:10.1136/jcp.2005.032722
1563:Pharmacological Reviews
958:homovanillic acid (HVA)
3401:Ulotaront (SEP-363856)
3343:β-Methylphenethylamine
3338:4-Methylphenethylamine
3333:3-Methylphenethylamine
3328:2-Methylphenethylamine
3048:Phenacetaldehyde (PAL)
2664:Carbonyl sulfide (COS)
2265:N-Methylphenethylamine
1174:
1164:oxidation and enhance
1021:central nervous system
1014:low blood sugar levels
987:central nervous system
942:aldehyde dehydrogenase
881:dopamine β-hydroxylase
730:ventral tegmental area
726:central nervous system
607:tyrosine 3-hydroxylase
279:chain, and a terminal
87:
3323:MDMA (midomafetamine)
3249:Synthetic and natural
3178:-Methylphenethylamine
2405:2-AGE (noladin ether)
1655:10.1038/sj.mp.4001037
1269:Vanillylmandelic acid
1146:
1075:neuroendocrine tumors
1061:deficiency, known as
1044:neuroendocrine tumors
1006:elevated sound levels
938:alcohol dehydrogenase
908:or by deamination by
710:postganglionic fibers
401:-Methylphenethylamine
210:(noradrenaline), and
83:
3567:List of trace amines
3303:4-Hydroxyamphetamine
2813:Homovanillyl alcohol
2616:Carbon monoxide (CO)
1767:Estes, Mary (2016).
1642:Molecular Psychiatry
1520:Neuroscience Letters
1162:indole-3-acetic acid
973:Two catecholamines,
833:tyrosine hydroxylase
806:tyrosine hydroxylase
3528:Neutral antagonists
3514:-Dimethylethylamine
3473:Neutral antagonists
3415:Neutral antagonists
3318:MDA (tenamfetamine)
3308:Isopropyloctopamine
2621:Hydrogen sulfide (H
2475:Virodhamine (O-AEA)
1224:-methyl transferase
1116:. Some drugs, like
885:phenylethanolamine
875:(noradrenaline) or
754:phenylethanolamine
665:phenylethanolamine
638:pyridoxal phosphate
624:(Fe) as cofactors.
611:tetrahydrobiopterin
591:tetrahydrobiopterin
3212:Phenylethanolamine
2678:Sulfur dioxide (SO
2589:Cholinergic system
2291:Phenylethanolamine
2270:N-Methyltryptamine
2234:NAS (normelatonin)
2021:inhibitory systems
2019:Major excitatory /
1938:labtestsonline.org
1889:labtestsonline.org
1865:labtestsonline.org
1839:10.1007/BF00203119
1143:Function in plants
1079:carcinoid syndrome
1037:emergency medicine
946:aldehyde reductase
804:), which inhibits
758:-methyltransferase
720:, which acts as a
669:-methyltransferase
581:), with molecular
88:
3622:Neurotransmitters
3604:
3603:
3599:
3585:
3569:
3557:
3556:
3549:3-Iodothyronamine
3486:
3485:
3449:
3448:
3441:EPPTB (RO5212773)
3409:
3408:
3170:3-Methoxytyramine
3165:3-Iodothyronamine
3056:
3055:
2984:
2983:
2916:
2915:
2912:
2911:
2694:
2693:
2690:
2689:
2638:
2637:
2630:Nitric oxide (NO)
2604:
2603:
2577:
2565:
2564:
2561:
2560:
2511:
2510:
2507:
2506:
2378:
2377:
2374:
2373:
2346:
2345:
2260:3-Iodothyronamine
2198:
2197:
2002:Neurotransmitters
1891:. 6 December 2019
1786:978-0-17-035484-4
1696:978-0-470-51482-5
1575:10.1124/pr.56.3.1
1352:on July 16, 2011.
1327:978-0-87893-697-7
870:
862:
856:
850:
846:
842:
838:
792:
788:
689:
688:
679:
660:
633:
627:
604:
600:
572:
568:
563:
435:3-Methoxytyramine
346:
336:
326:
245:
214:. Release of the
78:
77:
16:(Redirected from
3639:
3590:
3575:
3564:
3542:Inverse agonists
3497:
3496:
3460:
3459:
3433:Inverse agonists
3115:
3114:
3106:
3105:
3083:
3076:
3069:
3060:
3059:
2931:
2930:
2791:
2790:
2744:
2743:
2728:Neurotransmitter
2721:
2714:
2707:
2698:
2697:
2669:Nitrous oxide (N
2640:
2639:
2609:Gasotransmitters
2606:
2605:
2586:
2585:
2576:
2530:
2529:
2523:
2522:
2490:
2489:
2425:Anandamide (AEA)
2393:Endocannabinoids
2390:
2389:
2357:
2356:
2244:Serotonin (5-HT)
2209:
2208:
2028:Glutamate system
2025:
2024:
2016:
2015:
1995:
1988:
1981:
1972:
1971:
1948:
1947:
1945:
1944:
1934:"Catecholamines"
1930:
1924:
1923:
1921:
1920:
1906:
1900:
1899:
1897:
1896:
1881:
1875:
1874:
1872:
1871:
1857:
1851:
1850:
1822:
1816:
1815:
1813:
1811:
1797:
1791:
1790:
1771:(2nd ed.).
1764:
1758:
1757:
1747:
1715:
1709:
1708:
1674:
1668:
1667:
1657:
1633:
1627:
1626:
1625:
1624:
1601:
1595:
1594:
1558:
1552:
1551:
1511:
1502:
1501:
1473:
1467:
1466:
1438:
1432:
1431:
1403:
1397:
1396:
1360:
1354:
1353:
1342:"Catecholamines"
1338:
1332:
1331:
1313:
1307:
1306:
1304:
1302:
1286:
1264:Sympathomimetics
1137:pheochromocytoma
1071:pheochromocytoma
1063:Brunner syndrome
1052:pheochromocytoma
868:
860:
854:
848:
844:
840:
836:
811:The amino acids
790:
786:
734:substantia nigra
722:neurotransmitter
702:chromaffin cells
682:as the cofactor.
677:
658:
631:
625:
602:
598:
573:-tyrosine by an
570:
566:
561:
555:
554:
544:
537:
530:
523:
516:
507:
500:
493:
486:
479:
472:
465:
458:
451:
444:
437:
430:
423:
413:
403:
393:
392:
384:
383:
375:
365:
358:
357:
349:
344:
339:
334:
329:
324:
317:
292:
243:
154:organic compound
143:
142:
139:
138:
135:
132:
129:
126:
123:
120:
117:
114:
111:
108:
105:
102:
70:
61:(Noradrenaline)
56:
42:
30:
29:
21:
3647:
3646:
3642:
3641:
3640:
3638:
3637:
3636:
3632:Stress hormones
3607:
3606:
3605:
3600:
3588:
3586:
3584:for references.
3572:
3570:
3553:
3537:
3523:
3482:
3468:
3445:
3427:
3405:
3376:Propylhexedrine
3358:Norfenfluramine
3348:Methamphetamine
3244:
3186:-Methyltyramine
3095:
3087:
3057:
3052:
3019:
2980:
2952:
2908:
2880:
2856:Normetanephrine
2832:
2780:
2764:DOPA (levodopa)
2733:
2725:
2695:
2686:
2681:
2672:
2658:
2634:
2624:
2600:
2557:
2503:
2479:
2370:
2342:
2326:
2248:
2204:Biogenic amines
2194:
2171:
2120:
2094:
2020:
2004:
1999:
1957:
1952:
1951:
1942:
1940:
1932:
1931:
1927:
1918:
1916:
1908:
1907:
1903:
1894:
1892:
1883:
1882:
1878:
1869:
1867:
1859:
1858:
1854:
1823:
1819:
1809:
1807:
1799:
1798:
1794:
1787:
1779:. p. 143.
1765:
1761:
1716:
1712:
1697:
1675:
1671:
1634:
1630:
1622:
1620:
1602:
1598:
1569:(56): 331–349.
1559:
1555:
1512:
1505:
1474:
1470:
1439:
1435:
1404:
1400:
1361:
1357:
1340:
1339:
1335:
1328:
1314:
1310:
1300:
1298:
1287:
1283:
1278:
1273:
1259:Steroid hormone
1254:Phenethylamines
1249:Peptide hormone
1215:
1200:normetanephrine
1179:
1154:medicinal plant
1145:
1128:) in patients.
1094:
1067:bioavailability
1048:adrenal medulla
983:neuromodulators
971:
966:
898:
829:phenylketonuria
774:
742:locus coeruleus
706:adrenal medulla
698:
692:
690:
685:
684:
683:
655:
616:
588:
565:
564:-phenylalanine.
556:
548:
547:
546:
545:
540:
538:
533:
531:
526:
524:
521:
519:
517:
512:
510:
508:
503:
501:
496:
494:
489:
487:
482:
480:
475:
473:
468:
466:
463:
461:
459:
454:
452:
447:
445:
440:
438:
433:
431:
426:
424:
416:
414:
411:-Methyltyramine
406:
404:
396:
394:
388:
387:
385:
379:
378:
376:
368:
366:
361:
359:
353:
352:
350:
342:
340:
332:
330:
322:
318:
310:
289:
265:
226:is part of the
220:adrenal medulla
99:
95:
71:
57:
43:
33:Catecholamines
28:
23:
22:
15:
12:
11:
5:
3645:
3635:
3634:
3629:
3627:TAAR1 agonists
3624:
3619:
3617:Catecholamines
3602:
3601:
3574:
3563:
3562:
3559:
3558:
3555:
3554:
3552:
3551:
3545:
3543:
3539:
3538:
3536:
3535:
3531:
3529:
3525:
3524:
3522:
3521:
3519:Trimethylamine
3516:
3503:
3501:
3494:
3488:
3487:
3484:
3483:
3481:
3480:
3476:
3474:
3470:
3469:
3466:
3464:
3457:
3451:
3450:
3447:
3446:
3444:
3443:
3437:
3435:
3429:
3428:
3426:
3425:
3419:
3417:
3411:
3410:
3407:
3406:
3404:
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3268:
3263:
3258:
3252:
3250:
3246:
3245:
3243:
3242:
3241:
3240:
3232:
3224:
3219:
3214:
3209:
3207:Phenethylamine
3204:
3196:
3188:
3180:
3172:
3167:
3157:
3156:
3155:
3150:
3145:
3140:
3135:
3123:
3121:
3112:
3103:
3097:
3096:
3086:
3085:
3078:
3071:
3063:
3054:
3053:
3051:
3050:
3045:
3040:
3035:
3029:
3027:
3021:
3020:
3018:
3017:
3012:
3007:
2998:
2996:
2986:
2985:
2982:
2981:
2979:
2978:
2973:
2968:
2962:
2960:
2954:
2953:
2951:
2950:
2945:
2939:
2937:
2928:
2918:
2917:
2914:
2913:
2910:
2909:
2907:
2906:
2901:
2896:
2890:
2888:
2882:
2881:
2879:
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2842:
2840:
2838:Norepinephrine
2834:
2833:
2831:
2830:
2825:
2820:
2815:
2810:
2805:
2799:
2797:
2788:
2782:
2781:
2779:
2778:
2772:Norepinephrine
2752:
2750:
2741:
2739:Catecholamines
2735:
2734:
2724:
2723:
2716:
2709:
2701:
2692:
2691:
2688:
2687:
2685:
2684:
2679:
2675:
2670:
2666:
2661:
2656:
2652:
2646:
2644:
2636:
2635:
2633:
2632:
2627:
2622:
2618:
2612:
2610:
2602:
2601:
2599:
2598:
2592:
2590:
2583:
2579:
2578:
2574:
2567:
2566:
2563:
2562:
2559:
2558:
2556:
2555:
2550:
2545:
2539:
2537:
2527:
2520:
2513:
2512:
2509:
2508:
2505:
2504:
2502:
2501:
2493:
2487:
2481:
2480:
2478:
2477:
2472:
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2432:
2427:
2422:
2417:
2412:
2407:
2402:
2396:
2394:
2387:
2380:
2379:
2376:
2375:
2372:
2371:
2369:
2368:
2360:
2354:
2348:
2347:
2344:
2343:
2341:
2340:
2334:
2332:
2328:
2327:
2325:
2324:
2316:
2308:
2303:
2298:
2296:Phenethylamine
2293:
2288:
2280:
2272:
2267:
2262:
2256:
2254:
2250:
2249:
2247:
2246:
2241:
2236:
2231:
2226:
2221:
2215:
2213:
2206:
2200:
2199:
2196:
2195:
2193:
2192:
2187:
2181:
2179:
2173:
2172:
2170:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2128:
2126:
2125:Glycine system
2122:
2121:
2119:
2118:
2113:
2108:
2102:
2100:
2096:
2095:
2093:
2092:
2087:
2082:
2077:
2072:
2070:Kynurenic acid
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2031:
2029:
2022:
2013:
2006:
2005:
1998:
1997:
1990:
1983:
1975:
1969:
1968:
1961:Catecholamines
1956:
1955:External links
1953:
1950:
1949:
1925:
1901:
1876:
1852:
1817:
1792:
1785:
1759:
1730:(8): 935–936.
1710:
1695:
1669:
1648:(6): 626–632.
1628:
1596:
1553:
1526:(3): 303–308.
1503:
1468:
1449:(5): 274–281.
1433:
1414:(3): 363–375.
1398:
1355:
1346:Health Library
1333:
1326:
1308:
1280:
1279:
1277:
1274:
1272:
1271:
1266:
1261:
1256:
1251:
1246:
1244:Julius Axelrod
1241:
1236:
1231:
1226:
1216:
1214:
1211:
1178:
1175:
1144:
1141:
1106:blood pressure
1093:
1090:
991:norepinephrine
975:norepinephrine
970:
967:
965:
962:
897:
894:
873:norepinephrine
773:
770:
766:solitary tract
746:norepinephrine
697:
694:
687:
686:
661:-ascorbic acid
653:
642:norepinephrine
614:
586:
550:
549:
390:Norepinephrine
363:Phenethylamine
327:-Phenylalanine
320:
319:
312:
311:
300:catecholamines
297:
296:
295:
290:
288:
285:
264:
261:
237:by the enzyme
224:adrenal glands
208:norepinephrine
206:(adrenaline),
144:; abbreviated
76:
75:
63:
62:
59:Norepinephrine
49:
48:
35:
34:
26:
18:Catecholamines
9:
6:
4:
3:
2:
3644:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3614:
3612:
3598:
3597:
3594:
3589:
3583:
3579:
3573:
3568:
3560:
3550:
3547:
3546:
3544:
3540:
3533:
3532:
3530:
3526:
3520:
3517:
3515:
3513:
3509:
3505:
3504:
3502:
3498:
3495:
3493:
3489:
3478:
3477:
3475:
3471:
3465:
3461:
3458:
3456:
3452:
3442:
3439:
3438:
3436:
3434:
3430:
3424:
3421:
3420:
3418:
3416:
3412:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3370:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3277:
3273:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3253:
3251:
3247:
3239:
3237:
3233:
3231:
3229:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3201:
3197:
3195:
3193:
3189:
3187:
3185:
3181:
3179:
3177:
3173:
3171:
3168:
3166:
3163:
3162:
3161:
3158:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3130:
3129:
3125:
3124:
3122:
3120:
3116:
3113:
3111:
3107:
3104:
3102:
3098:
3094:
3091:
3084:
3079:
3077:
3072:
3070:
3065:
3064:
3061:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3030:
3028:
3026:
3022:
3016:
3013:
3011:
3008:
3006:
3004:
3000:
2999:
2997:
2995:
2991:
2987:
2977:
2974:
2972:
2969:
2967:
2964:
2963:
2961:
2959:
2955:
2949:
2946:
2944:
2941:
2940:
2938:
2936:
2932:
2929:
2927:
2923:
2919:
2905:
2902:
2900:
2897:
2895:
2892:
2891:
2889:
2887:
2883:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2843:
2841:
2839:
2835:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2800:
2798:
2796:
2792:
2789:
2787:
2783:
2777:
2773:
2769:
2765:
2761:
2757:
2756:Phenylalanine
2754:
2753:
2751:
2749:
2745:
2742:
2740:
2736:
2732:
2729:
2722:
2717:
2715:
2710:
2708:
2703:
2702:
2699:
2683:
2676:
2674:
2667:
2665:
2662:
2660:
2653:
2651:
2648:
2647:
2645:
2641:
2631:
2628:
2626:
2619:
2617:
2614:
2613:
2611:
2607:
2597:
2596:Acetylcholine
2594:
2593:
2591:
2587:
2584:
2582:Miscellaneous
2580:
2575:
2572:
2568:
2554:
2551:
2549:
2546:
2544:
2541:
2540:
2538:
2535:
2531:
2528:
2524:
2521:
2518:
2514:
2499:
2495:
2494:
2491:
2488:
2486:
2485:Neurosteroids
2482:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2406:
2403:
2401:
2398:
2397:
2395:
2391:
2388:
2385:
2381:
2366:
2362:
2361:
2358:
2355:
2353:
2352:Neuropeptides
2349:
2339:
2336:
2335:
2333:
2329:
2323:
2321:
2317:
2315:
2313:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2285:
2281:
2279:
2277:
2273:
2271:
2268:
2266:
2263:
2261:
2258:
2257:
2255:
2251:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2216:
2214:
2210:
2207:
2205:
2201:
2191:
2188:
2186:
2183:
2182:
2180:
2178:
2174:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2129:
2127:
2123:
2117:
2114:
2112:
2109:
2107:
2104:
2103:
2101:
2097:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
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2058:
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2048:
2046:
2043:
2041:
2038:
2036:
2033:
2032:
2030:
2026:
2023:
2017:
2014:
2011:
2007:
2003:
1996:
1991:
1989:
1984:
1982:
1977:
1976:
1973:
1966:
1962:
1959:
1958:
1939:
1935:
1929:
1915:
1911:
1905:
1890:
1886:
1880:
1866:
1862:
1856:
1848:
1844:
1840:
1836:
1832:
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1802:
1796:
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1778:
1774:
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1529:
1525:
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1479:
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1359:
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1225:
1223:
1218:
1217:
1210:
1206:
1203:
1201:
1197:
1193:
1189:
1185:
1184:metanephrines
1173:
1171:
1167:
1163:
1159:
1158:embryogenesis
1155:
1151:
1140:
1138:
1134:
1133:Urine testing
1129:
1127:
1123:
1119:
1115:
1111:
1110:blood glucose
1107:
1103:
1099:
1089:
1087:
1082:
1080:
1076:
1072:
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1064:
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1055:
1053:
1049:
1045:
1040:
1038:
1034:
1030:
1026:
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1017:
1015:
1011:
1010:intense light
1007:
1003:
998:
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988:
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976:
961:
959:
955:
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939:
935:
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927:
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917:
913:
911:
907:
905:
893:
890:
888:
882:
878:
874:
866:
858:
834:
830:
826:
822:
818:
814:
813:phenylalanine
809:
807:
803:
799:
794:
789:-tyrosine to
784:
780:
769:
767:
763:
762:area postrema
759:
757:
751:
747:
743:
739:
735:
731:
727:
723:
719:
715:
711:
707:
703:
693:
681:
675:
670:
668:
662:
651:
647:
643:
639:
635:
623:
620:
612:
608:
596:
592:
584:
580:
576:
560:
543:
536:
529:
515:
506:
499:
492:
485:
478:
471:
457:
450:
443:
436:
429:
422:
420:
412:
410:
402:
400:
391:
382:
374:
372:
364:
356:
348:
338:
328:
316:
309:
305:
301:
294:
293:
284:
282:
278:
274:
270:
260:
258:
254:
249:
247:
240:
236:
235:hydroxylation
231:
229:
225:
221:
217:
213:
209:
205:
200:
198:
197:phenylalanine
194:
191:
186:
184:
180:
176:
174:
171:
167:
163:
159:
155:
151:
147:
141:
93:
92:catecholamine
86:
82:
74:
69:
65:
64:
60:
55:
51:
50:
47:(Adrenaline)
46:
41:
37:
36:
32:
31:
19:
3592:
3591:
3587:
3571:
3511:
3507:
3396:Solriamfetol
3368:
3313:Isoprenaline
3288:Halostachine
3275:
3271:
3235:
3227:
3199:
3191:
3183:
3175:
3160:Trace amines
3025:Trace amines
3002:
2899:Metanephrine
2738:
2650:Acetaldehyde
2319:
2311:
2283:
2275:
2253:Trace amines
1941:. Retrieved
1937:
1928:
1917:. Retrieved
1913:
1904:
1893:. Retrieved
1888:
1879:
1868:. Retrieved
1864:
1855:
1833:(2): 91–97.
1830:
1826:
1820:
1808:. Retrieved
1804:
1795:
1768:
1762:
1727:
1723:
1713:
1678:
1672:
1645:
1641:
1631:
1621:, retrieved
1609:
1599:
1566:
1562:
1556:
1523:
1519:
1515:
1481:
1477:
1471:
1446:
1442:
1436:
1411:
1407:
1401:
1368:
1364:
1358:
1350:the original
1345:
1336:
1318:Neuroscience
1317:
1311:
1299:. Retrieved
1294:
1284:
1221:
1207:
1204:
1196:metanephrine
1188:hypertension
1180:
1170:gibberellins
1147:
1130:
1095:
1083:
1056:
1041:
1018:
999:
972:
925:
920:
914:
903:
899:
886:
821:blood plasma
810:
797:
795:
775:
772:Biosynthesis
755:
738:neuromelanin
699:
691:
673:
671:(PNMT) with
666:
418:
408:
398:
370:
304:trace amines
299:
269:benzene ring
266:
250:
232:
201:
187:
177:
145:
91:
89:
3423:RTI-7470-44
3363:Phentermine
3256:Amphetamine
3202:-Octopamine
3194:-Octopamine
2886:Epinephrine
2776:Epinephrine
2655:Ammonia (NH
2526:Nucleosides
2286:-Octopamine
2278:-Octopamine
2190:T-HCA (GHC)
2147:Hypotaurine
2099:GABA system
2050:Glutathione
1484:: 211–218.
1371:: 342–350.
1301:October 26,
1192:tachycardia
1120:(a central
896:Degradation
877:epinephrine
800:-tyrosine (
750:Epinephrine
680:-methionine
646:epinephrine
421:-Octopamine
355:Epinephrine
308:human brain
204:epinephrine
183:substituent
156:that has a
45:Epinephrine
3611:Categories
3391:Selegiline
3293:Higenamine
3283:Guanfacine
3222:Tryptamine
3217:Synephrine
3126:Classical
3119:Endogenous
2958:Catabolism
2943:Tryptophan
2922:Tryptophan
2786:Catabolism
2643:Candidates
2517:Nucleobase
2306:Tryptamine
2301:Synephrine
2212:Monoamines
2177:GHB system
2010:Amino acid
1943:2019-10-09
1919:2019-10-09
1895:2019-12-24
1870:2019-12-24
1623:2024-06-28
1610:StatPearls
1276:References
1126:tachypnoea
1102:heart rate
922:Catabolism
676:-adenosyl-
559:amino acid
428:Synephrine
190:amino acid
170:side-chain
3593:See also:
3386:RO5166017
3298:Hordenine
3238:-Tyramine
3230:-Tyramine
3153:Serotonin
3138:Histamine
2994:Melatonin
2990:Serotonin
2935:Anabolism
2926:Serotonin
2748:Anabolism
2534:Adenosine
2338:Histamine
2322:-Tyramine
2314:-Tyramine
2157:Sarcosine
2137:β-Alanine
2132:α-Alanine
1805:webmd.com
1773:Melbourne
1220:Catechol-
1150:alkaloids
1118:tolcapone
1086:porphyria
1029:brainstem
981:, act as
902:catechol-
853:aromatic
630:aromatic
595:cofactors
373:-Tyramine
337:-Tyrosine
271:with two
263:Structure
253:stimulant
164:with two
3500:Agonists
3463:Agonists
3133:Dopamine
3110:Agonists
2795:Dopamine
2768:Dopamine
2760:Tyrosine
2573:-derived
2519:-derived
2500:instead.
2455:Oleamide
2386:-derived
2367:instead.
2224:Dopamine
2035:Agmatine
2012:-derived
1847:41493767
1754:17660335
1664:12140786
1618:31082164
1591:12825309
1583:15317907
1498:24374199
1463:15860375
1428:19948186
1393:86229251
1213:See also
1166:ethylene
995:synapses
979:dopamine
969:Modality
964:Function
817:tyrosine
779:cofactor
744:produce
732:and the
718:Dopamine
708:and the
696:Location
652:, with O
577:enzyme (
381:Dopamine
273:hydroxyl
251:Various
216:hormones
212:dopamine
193:tyrosine
179:Catechol
166:hydroxyl
158:catechol
85:Catechol
73:Dopamine
3093:ligands
2571:Vitamin
2465:RVD-Hpα
2420:AA-5-HT
2167:Taurine
2152:Proline
2142:Glycine
2085:Proline
2055:Glycine
1777:Cengage
1745:1994495
1705:8862875
1548:2578817
1540:3885079
1385:3473965
1239:Hormone
1092:Effects
1046:in the
1027:in the
985:in the
865:neurons
793:-DOPA.
724:in the
712:of the
704:of the
636:, with
619:ferrous
609:) with
522:pathway
464:pathway
462:primary
306:in the
222:of the
162:benzene
148:) is a
3534:
3479:
3467:
2536:system
2410:2-ALPI
2331:Others
2162:Serine
2090:Serine
1967:(MeSH)
1845:
1783:
1752:
1742:
1703:
1693:
1662:
1616:
1589:
1581:
1546:
1538:
1496:
1461:
1426:
1391:
1383:
1324:
1084:Acute
1077:, and
1025:nuclei
1002:stress
617:, and
589:) and
583:oxygen
514:CYP2D6
3578:TAAR1
3492:TAAR5
3455:TAAR2
3353:3-MMA
3101:TAAR1
2445:NAGly
2384:Lipid
2219:6-OHM
2111:GABOB
1914:WebMD
1843:S2CID
1810:4 May
1587:S2CID
1544:S2CID
1389:S2CID
1035:. In
1012:, or
954:urine
916:MAOIs
520:minor
511:brain
347:-DOPA
281:amine
277:ethyl
246:-DOPA
173:amine
152:, an
3582:TAAR
3371:-PIT
3266:DOET
2498:here
2496:See
2440:NADA
2415:2-OG
2400:2-AG
2365:here
2363:See
2106:GABA
2080:NAAG
2065:GSSG
2060:GSNO
1812:2017
1781:ISBN
1750:PMID
1701:PMID
1691:ISBN
1660:PMID
1614:PMID
1579:PMID
1536:PMID
1494:PMID
1459:PMID
1424:PMID
1381:PMID
1322:ISBN
1303:2011
1198:and
1190:and
1122:COMT
977:and
944:and
815:and
802:AMPT
656:and
644:and
622:iron
528:COMT
505:AAAH
498:AAAH
491:PNMT
484:PNMT
477:PNMT
470:PNMT
456:AADC
449:AADC
442:AADC
302:and
3261:DOB
2553:ATP
2548:AMP
2543:ADP
2470:SEA
2460:PEA
2450:OEA
2435:LPI
2430:DEA
2185:GHB
2116:GHB
2075:NAA
1835:doi
1740:PMC
1732:doi
1683:doi
1650:doi
1571:doi
1528:doi
1486:doi
1482:724
1451:doi
1416:doi
1412:125
1373:doi
1369:493
934:FAD
783:PLP
613:, O
593:as
542:DBH
535:DBH
3613::
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2770:→
2766:→
2762:→
2758:→
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2625:S)
1936:.
1912:.
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1863:.
1841:.
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1775::
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1728:60
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1658:.
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1534:.
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1522:.
1506:^
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1480:.
1457:.
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1410:.
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1379:.
1367:.
1344:.
1202:.
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1139:.
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1016:.
1008:,
960:.
940:,
930:Mg
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808:.
768:.
748:.
716:.
597:.
585:(O
230:.
175:.
146:CA
134:iː
122:oʊ
90:A
3512:N
3510:,
3508:N
3369:o
3276:N
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3272:N
3236:p
3228:m
3200:p
3192:m
3184:N
3176:N
3082:e
3075:t
3068:v
3003:N
2992:→
2924:→
2720:e
2713:t
2706:v
2682:)
2680:2
2671:2
2659:)
2657:3
2623:2
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1994:e
1987:t
1980:v
1946:.
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1898:.
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1849:.
1837::
1814:.
1789:.
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1666:.
1652::
1646:7
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1567:3
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1516:N
1500:.
1488::
1465:.
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1430:.
1418::
1395:.
1375::
1330:.
1305:.
1222:O
926:O
904:O
887:N
869:L
861:L
855:L
849:L
845:L
841:L
837:L
798:p
791:L
787:L
756:N
678:L
674:S
667:N
659:L
654:2
632:L
626:L
615:2
603:L
599:L
587:2
571:L
567:L
562:L
419:p
409:N
399:N
371:p
345:L
335:L
325:L
244:L
160:(
140:/
137:n
131:m
128:ə
125:l
119:k
116:ˈ
113:ə
110:t
107:æ
104:k
101:ˌ
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94:(
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