308:
47:
546:
33:
61:
74:
929:. 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
1174:
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
1631:"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)"
884:
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).
1175:
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
1201:
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.
769:
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
2711:
921:-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
1507:
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-
1149:
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
2704:
1124:
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.
824:, a metabolic disorder that leads to intellectual deficits unless treated by dietary manipulation. Catecholamine synthesis is usually considered to begin with tyrosine. The enzyme
1221:
497:
490:
2697:
307:
1334:
1985:
1141:"They have been found in 44 plant families, but no essential metabolic function has been established for them. They are precursors of benzophenanthridine
876:(DBH), which converts dopamine to yield norepinephrine, is also present. In still other neurons in which epinephrine is the transmitter, a third enzyme
1554:
Eisenhofer, G.; Kopin, I. J.; Goldstein, D. S. (2004). "Catecholamine metabolism: a contemporary view with implications for physiology and medicine".
778:(not shown in the diagram). The rate limiting step in catecholamine biosynthesis through the predominant metabolic pathway is the hydroxylation of
1187:
that don't adequately respond to treatment. Each of the tests measure the amount of adrenaline and noradrenaline metabolites, respectively called
241:
and then to dopamine. Depending on the cell type, dopamine may be further converted to norepinephrine or even further converted to epinephrine.
3073:
877:
746:
657:
483:
476:
469:
462:
234:. Tyrosine is also ingested directly from dietary protein. Catecholamine-secreting cells use several reactions to convert tyrosine serially to
3082:
1777:
1687:
1318:
2103:
845:
622:
448:
441:
434:
986:
is a neuromodulator of the peripheral sympathetic nervous system but is also present in the blood (mostly through "spillover" from the
2886:
2838:
1226:
3258:
3253:
1117:-inhibitor), raise the levels of all the catecholamines. Increased catecholamines may also cause an increased respiratory rate (
3574:
2868:
2795:
1978:
567:
893:
Catecholamines have a half-life of a few minutes when circulating in the blood. They can be degraded either by methylation by
2863:
2800:
2402:
3025:
3310:
2072:
1212:
894:
1309:
Purves, D.; Augustine, G. J.; Fitzpatrick, D.; Hall, W. C.; LaMantia, A. S.; McNamara, J. O.; White, L. E., eds. (2008).
852:(AADC; see Cooper et al., 2002) to the transmitter dopamine. This step occurs so rapidly that it is difficult to measure
3588:
2422:
2397:
2037:
520:
2896:
2853:
3030:
2958:
1058:. As MAO-A is one of the enzymes responsible for degradation of these neurotransmitters, its deficiency increases the
926:
571:
3614:
3263:
3120:
3066:
2963:
2843:
1971:
1342:
1106:
1025:
706:
142:
3335:
3007:
2490:
2177:
2108:
873:
817:
642:
534:
527:
231:
3624:
3345:
2427:
1957:
1179:
or the urine metanephrines are used to confirm or exclude certain diseases when the doctor identifies signs of
1090:
220:
3619:
3609:
3360:
2540:
2432:
2098:
771:
587:
249:
3499:
3330:
3325:
3320:
3167:
2723:
2545:
2412:
2392:
2357:
2257:
1017:
1013:
979:
934:
722:
718:
599:
390:
2968:
3085:
3059:
3035:
2858:
2535:
2452:
2067:
1261:
942:
930:
665:
3040:
3295:
2805:
2462:
2437:
2057:
2052:
1629:
Manor, I.; Tyano, S.; Mel, E.; Eisenberg, J.; Bachner-Melman, R.; Kotler, M.; Ebstein, R. P. (2002).
1154:
1125:
1067:
1036:
998:
922:
864:-DOPA to dopamine is the final step in formation of the transmitter; however, in those neurons using
825:
798:
702:
633:
as the cofactor. Dopamine itself is also used as precursor in the synthesis of the neurotransmitters
1434:
Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family".
1089:
Catecholamines cause general physiological changes that prepare the body for physical activity (the
3300:
3002:
2940:
1074:, but it looks similar to carcinoid syndrome with symptoms such as facial flushing and aggression.
1051:
820:, found in large amounts in the liver. Insufficient amounts of phenylalanine hydroxylase result in
775:
630:
603:
583:
3407:
3204:
2442:
2283:
2262:
2211:
1835:
1670:
Brunner, H. G. (1996). "MAOA Deficiency and
Abnormal Behaviour: Perspectives on an Association".
1579:
1536:
1381:
1071:
1029:
938:
745:
is produced in small groups of neurons in the human brain which express its synthesizing enzyme,
3051:
1902:
3573:
or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see
1356:
Joh, T. H.; Hwang, O. (1987). "Dopamine Beta-Hydroxylase: Biochemistry and
Molecular Biology".
46:
3541:
3162:
3157:
2994:
2820:
2815:
2252:
2226:
1773:
1742:
1693:
1683:
1652:
1606:
1597:
Chu, Brianna; Marwaha, Komal; Sanvictores, Terrence; Awosika, Ayoola O.; Ayers, Derek (2024),
1571:
1528:
1486:
1451:
1416:
1373:
1314:
994:
950:
902:
427:
1853:
3175:
2720:
2656:
2613:
2407:
1994:
1827:
1793:
1732:
1724:
1675:
1642:
1563:
1520:
1478:
1443:
1408:
1365:
1256:
1129:
1063:
1055:
1044:
1012:
Extremely high levels of catecholamines (also known as catecholamine toxicity) can occur in
726:
714:
694:
400:
276:
group. Phenylethanolamines such as norepinephrine have a hydroxyl group on the ethyl chain.
146:
90:
2689:
911:
bind to MAO, thereby preventing it from breaking down catecholamines and other monoamines.
816:
and the brain. In mammals, tyrosine can be formed from dietary phenylalanine by the enzyme
3425:
3368:
3350:
3340:
3191:
3183:
2848:
2608:
1953:
1251:
1241:
1192:
1146:
1059:
1040:
1002:
975:
821:
734:
698:
212:
1469:
Wang X, Li J, Dong G, Yue J (February 2014). "The endogenous substrates of brain CYP2D".
1283:
1511:-methyltransferase (PNMT): discovery of a new group in the nucleus tractus solitarius".
812:
are precursors for catecholamines. Both amino acids are found in high concentrations in
192:. Catecholamines are water-soluble and are 50% bound to plasma proteins in circulation.
3511:
3199:
3140:
2830:
2810:
2764:
2670:
2288:
2231:
2196:
2062:
1877:
1737:
1712:
1369:
1246:
1236:
1198:
Blood tests are also done to analyze the amount of catecholamines present in the body.
1098:
997:, which can be induced from psychological reactions or environmental stressors such as
983:
967:
865:
758:
738:
634:
382:
355:
200:
51:
32:
17:
1161:
biosynthesis. They have also been shown to enhance synergistically various effects of
3603:
3227:
3219:
2748:
2661:
2588:
2303:
2032:
1524:
1412:
1176:
1150:
1102:
805:
754:
650:
316:
227:
216:
189:
1839:
1583:
1385:
3388:
3305:
3280:
2891:
2642:
2622:
2477:
2344:
2267:
2169:
1540:
1399:
Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines".
1188:
1180:
1006:
813:
730:
261:
2129:
1926:
60:
1482:
721:, is largely produced in neuronal cell bodies in two areas of the brainstem: the
3559:
3415:
3373:
3355:
3248:
3152:
3135:
3111:
3017:
2878:
2768:
2467:
2139:
2042:
1184:
1162:
869:
742:
638:
300:
296:
269:
196:
175:
37:
1598:
1447:
753:; these neurons project from a nucleus that is adjacent (ventrolateral) to the
3383:
3285:
3275:
3214:
3209:
2950:
2935:
2914:
2778:
2509:
2457:
2417:
2298:
2293:
2275:
2221:
2002:
1679:
1094:
914:
551:
420:
410:
347:
182:
162:
3393:
3378:
3290:
3145:
3130:
2986:
2982:
2927:
2918:
2740:
2526:
2330:
2236:
2149:
1765:
1728:
1118:
1110:
1078:
1021:
733:-pigmented neurons. The similarly neuromelanin-pigmented cell bodies of the
245:
1746:
1656:
1610:
1575:
1490:
1455:
1420:
1697:
1647:
1630:
1532:
1377:
73:
3125:
2787:
2760:
2752:
2447:
2311:
2216:
2027:
1158:
1142:
971:
809:
710:
656:
as cofactors. Norepinephrine is converted into epinephrine by the enzyme
373:
362:
326:
265:
204:
185:
171:
158:
150:
77:
65:
178:
of a larger molecule, where it represents a 1,2-dihydroxybenzene group.
3102:
2647:
2563:
2159:
2144:
2134:
2124:
2077:
2047:
1831:
1769:
1231:
987:
611:
208:
154:
1567:
2756:
2154:
2082:
1713:"Acute intermittent porphyria and phaeochromocytoma: shared features"
1674:. Ciba Foundation Symposium. Vol. 194. Wiley. pp. 155–167.
1062:
of these neurotransmitters considerably. It occurs in the absence of
857:
575:
506:
336:
235:
1963:
3570:
3558:
References for all endogenous human TAAR1 ligands are provided at
3484:
3447:
3433:
3093:
2376:
2182:
946:
273:
188:, which is derived from dietary sources as well as synthesis from
165:
1818:
Kuklin, A. I.; Conger, B. V. (1995). "Catecholamines in Plants".
550:
In humans, catecholamines (shown in yellow) are derived from the
3315:
1114:
908:
794:
614:
545:
3055:
2693:
1967:
126:
1035:
Extremely high levels of catecholamine can also be caused by
1032:, this occurrence is widely known as a "catecholamine dump".
840:-tyrosine by TH results in the formation of the DA precursor
982:
and as hormones in the blood circulation. The catecholamine
917:
of catecholamines is mediated by two main enzymes: catechol-
774:(not shown in the diagram) and DOPA decarboxylase requires
641:. Dopamine is converted into norepinephrine by the enzyme
120:
114:
105:
1341:. San Diego, CA: University of California. Archived from
99:
3569:
References for synthetic TAAR1 agonists can be found at
1711:
Stewart, M. F.; Croft, J.; Reed, P.; New, J. P. (2006).
993:
High catecholamine levels in blood are associated with
941:. The end product of epinephrine and norepinephrine is
860:
that use DA as the transmitter, the decarboxylation of
1313:(4th ed.). Sinauer Associates. pp. 137–138.
1222:
Catecholaminergic polymorphic ventricular tachycardia
1145:, which are the active principal ingredients of many
856:-DOPA in the brain without first inhibiting AADC. In
789:
Catecholamine synthesis is inhibited by alpha-methyl-
129:
111:
96:
93:
1502:
1500:
1050:
High levels of catecholamines can also be caused by
284:
117:
102:
3534:
3520:
3492:
3483:
3465:
3455:
3446:
3424:
3406:
3241:
3110:
3101:
3092:
3016:
2981:
2949:
2926:
2913:
2877:
2829:
2786:
2777:
2739:
2730:
2635:
2601:
2581:
2574:
2562:
2525:
2518:
2508:
2476:
2385:
2375:
2343:
2323:
2245:
2204:
2195:
2168:
2117:
2091:
2020:
2011:
2001:
1153:from in vitro cultures, and flowering. CAs inhibit
123:
108:
2887:3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)
2839:3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL)
2811:Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET)
949:. Dopamine catabolism leads to the production of
2864:3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG)
260:Catecholamines have the distinct structure of a
1605:, Treasure Island (FL): StatPearls Publishing,
1139:
757:and from a nucleus in the dorsal region of the
621:-DOPA is converted into dopamine by the enzyme
1854:"Plasma Free Metanephrines | Lab Tests Online"
1288:Greenspan's Basic & Clinical Endocrinology
3067:
3026:3-Methoxy-4-hydroxyphenylacetaldehyde (HMPAL)
2869:3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
2705:
1979:
1672:Genetics of Criminal and Antisocial Behaviour
1284:"Chapter 11. Adrenal Medulla and Paraganglia"
8:
1024:, in particular, those nuclei affecting the
832:-tyrosine into 3,4-dihydroxyphenylalanine (
3489:
3452:
3107:
3098:
3074:
3060:
3052:
2923:
2783:
2736:
2712:
2698:
2690:
2632:
2598:
2578:
2569:
2522:
2515:
2482:
2382:
2349:
2201:
2017:
2008:
1986:
1972:
1964:
1762:Health assessment and physical examination
1358:Annals of the New York Academy of Sciences
693:Catecholamines are produced mainly by the
226:Tyrosine is created from phenylalanine by
2897:3-Methoxy-4-hydroxymandelaldehyde (MHMAL)
2854:3-Methoxy-4-hydroxymandelaldehyde (MHMAL)
1956:at the U.S. National Library of Medicine
1736:
1646:
1286:. In Gardner, D. G.; Shoback, D. (eds.).
1093:). Some typical effects are increases in
872:(adrenaline) as transmitters, the enzyme
1878:"Urine Metanephrines | Lab Tests Online"
211:epinephrine and norepinephrine from the
72:
29:
2796:3,4-Dihydroxyphenylacetaldehyde (DOPAL)
1903:"Catecholamine Urine & Blood Tests"
1274:
1016:trauma due to stimulation or damage of
2801:3,4-Dihydroxyphenylacetic acid (DOPAC)
1105:levels, and a general reaction of the
568:aromatic amino acid hydroxylase (AAAH)
161:side groups next to each other) and a
3083:Human trace amine-associated receptor
1290:(9th ed.). New York: McGraw-Hill
7:
3008:5-Methoxyindoleacetaldehyde (5-MIAL)
2998:-Acetylserotonin (NAS; normelatonin)
2959:5-Hydroxyindoleacetaldehyde (5-HIAL)
1128:for catecholamine is used to detect
181:Catecholamines are derived from the
31:
2964:5-Hydroxyindoleacetic acid (5-HIAA)
1081:can cause elevated catecholamines.
174:can be either a free molecule or a
3031:4-Hydroxyphenylacetaldehyde (HPAL)
1820:Journal of Plant Growth Regulation
1436:Trends in Pharmacological Sciences
1370:10.1111/j.1749-6632.1987.tb27217.x
195:Included among catecholamines are
25:
3374:Ralmitaront (RG-7906, RO-6889450)
2844:3,4-Dihydroxymandelic acid (DHMA)
1227:History of catecholamine research
1043:, a treatable condition known as
562:-Phenylalanine is converted into
1471:European Journal of Pharmacology
1413:10.1016/j.pharmthera.2009.11.005
627:-amino acid decarboxylase (AADC)
544:
306:
89:
59:
45:
1401:Pharmacology & Therapeutics
844:-DOPA, which is metabolized by
729:, the latter of which contains
252:) are catecholamine analogues.
3141:Norepinephrine (noradrenaline)
2232:Norepinephrine (noradrenaline)
598:-DOPA by another AAAH enzyme (
1:
3589:Receptor/signaling modulators
1717:Journal of Clinical Pathology
1599:"Physiology, Stress Reaction"
925:as a cofactor while MAO uses
836:-DOPA). The hydroxylation of
828:(TH) converts the amino acid
2969:5-Hydroxytryptophol (5-HTOL)
1525:10.1016/0304-3940(85)90555-5
1483:10.1016/j.ejphar.2013.12.025
990:of the sympathetic system).
643:dopamine β-hydroxylase (DBH)
594:-Tyrosine is converted into
3121:monoamine neurotransmitters
2941:5-Hydroxytryptophan (5-HTP)
2859:Vanillylmandelic acid (VMA)
1052:monoamine oxidase A (MAO-A)
943:vanillylmandelic acid (VMA)
572:phenylalanine 4-hydroxylase
248:drugs (such as a number of
27:Class of chemical compounds
3641:
3003:5-Methoxytryptamine (5-MT)
1448:10.1016/j.tips.2005.03.007
1282:Fitzgerald, P. A. (2011).
1170:Testing for catecholamines
1107:sympathetic nervous system
1026:sympathetic nervous system
899:-methyltransferases (COMT)
707:sympathetic nervous system
291:Biosynthetic pathways for
280:Production and degradation
143:monoamine neurotransmitter
3554:
2485:
2352:
2038:Glutamic acid (glutamate)
2033:Aspartic acid (aspartate)
1794:"Catecholamines in Urine"
1680:10.1002/9780470514825.ch9
945:which is excreted in the
882:-methyltransferase (PNMT)
850:-amino acid decarboxylase
818:phenylalanine hydroxylase
232:phenylalanine hydroxylase
3136:Epinephrine (adrenaline)
3036:Indoleacetaldehyde (IAL)
2816:3-Methoxytyramine (3-MT)
2222:Epinephrine (adrenaline)
1958:Medical Subject Headings
1091:fight-or-flight response
903:monoamine oxidases (MAO)
268:groups, an intermediate
250:substituted amphetamines
221:fight-or-flight response
3271:-Dimethylphenethylamine
2821:Homovanillic acid (HVA)
2724:metabolic intermediates
1729:10.1136/jcp.2005.032722
1556:Pharmacological Reviews
951:homovanillic acid (HVA)
18:Catecholamine synthesis
3394:Ulotaront (SEP-363856)
3336:β-Methylphenethylamine
3331:4-Methylphenethylamine
3326:3-Methylphenethylamine
3321:2-Methylphenethylamine
3041:Phenacetaldehyde (PAL)
2657:Carbonyl sulfide (COS)
2258:N-Methylphenethylamine
1167:
1157:oxidation and enhance
1014:central nervous system
1007:low blood sugar levels
980:central nervous system
935:aldehyde dehydrogenase
874:dopamine β-hydroxylase
723:ventral tegmental area
719:central nervous system
600:tyrosine 3-hydroxylase
272:chain, and a terminal
80:
3316:MDMA (midomafetamine)
3242:Synthetic and natural
3171:-Methylphenethylamine
2398:2-AGE (noladin ether)
1648:10.1038/sj.mp.4001037
1262:Vanillylmandelic acid
1068:neuroendocrine tumors
1054:deficiency, known as
1037:neuroendocrine tumors
999:elevated sound levels
931:alcohol dehydrogenase
901:or by deamination by
703:postganglionic fibers
394:-Methylphenethylamine
203:(noradrenaline), and
76:
3560:List of trace amines
3296:4-Hydroxyamphetamine
2806:Homovanillyl alcohol
2609:Carbon monoxide (CO)
1760:Estes, Mary (2016).
1635:Molecular Psychiatry
1513:Neuroscience Letters
1155:indole-3-acetic acid
966:Two catecholamines,
826:tyrosine hydroxylase
799:tyrosine hydroxylase
3521:Neutral antagonists
3507:-Dimethylethylamine
3466:Neutral antagonists
3408:Neutral antagonists
3311:MDA (tenamfetamine)
3301:Isopropyloctopamine
2614:Hydrogen sulfide (H
2468:Virodhamine (O-AEA)
1217:-methyl transferase
1109:. Some drugs, like
878:phenylethanolamine
868:(noradrenaline) or
747:phenylethanolamine
658:phenylethanolamine
631:pyridoxal phosphate
617:(Fe) as cofactors.
604:tetrahydrobiopterin
584:tetrahydrobiopterin
3205:Phenylethanolamine
2671:Sulfur dioxide (SO
2582:Cholinergic system
2284:Phenylethanolamine
2263:N-Methyltryptamine
2227:NAS (normelatonin)
2014:inhibitory systems
2012:Major excitatory /
1931:labtestsonline.org
1882:labtestsonline.org
1858:labtestsonline.org
1832:10.1007/BF00203119
1136:Function in plants
1072:carcinoid syndrome
1030:emergency medicine
939:aldehyde reductase
797:), which inhibits
751:-methyltransferase
713:, which acts as a
662:-methyltransferase
574:), with molecular
81:
3615:Neurotransmitters
3597:
3596:
3592:
3578:
3562:
3550:
3549:
3542:3-Iodothyronamine
3479:
3478:
3442:
3441:
3434:EPPTB (RO5212773)
3402:
3401:
3163:3-Methoxytyramine
3158:3-Iodothyronamine
3049:
3048:
2977:
2976:
2909:
2908:
2905:
2904:
2687:
2686:
2683:
2682:
2631:
2630:
2623:Nitric oxide (NO)
2597:
2596:
2570:
2558:
2557:
2554:
2553:
2504:
2503:
2500:
2499:
2371:
2370:
2367:
2366:
2339:
2338:
2253:3-Iodothyronamine
2191:
2190:
1995:Neurotransmitters
1884:. 6 December 2019
1779:978-0-17-035484-4
1689:978-0-470-51482-5
1568:10.1124/pr.56.3.1
1345:on July 16, 2011.
1320:978-0-87893-697-7
863:
855:
849:
843:
839:
835:
831:
785:
781:
682:
681:
672:
653:
626:
620:
597:
593:
565:
561:
556:
428:3-Methoxytyramine
339:
329:
319:
238:
207:. Release of the
71:
70:
16:(Redirected from
3632:
3583:
3568:
3557:
3535:Inverse agonists
3490:
3453:
3426:Inverse agonists
3108:
3099:
3076:
3069:
3062:
3053:
2924:
2784:
2737:
2721:Neurotransmitter
2714:
2707:
2700:
2691:
2662:Nitrous oxide (N
2633:
2602:Gasotransmitters
2599:
2579:
2523:
2516:
2483:
2418:Anandamide (AEA)
2386:Endocannabinoids
2383:
2350:
2237:Serotonin (5-HT)
2202:
2021:Glutamate system
2018:
2009:
1988:
1981:
1974:
1965:
1941:
1940:
1938:
1937:
1927:"Catecholamines"
1923:
1917:
1916:
1914:
1913:
1899:
1893:
1892:
1890:
1889:
1874:
1868:
1867:
1865:
1864:
1850:
1844:
1843:
1815:
1809:
1808:
1806:
1804:
1790:
1784:
1783:
1764:(2nd ed.).
1757:
1751:
1750:
1740:
1708:
1702:
1701:
1667:
1661:
1660:
1650:
1626:
1620:
1619:
1618:
1617:
1594:
1588:
1587:
1551:
1545:
1544:
1504:
1495:
1494:
1466:
1460:
1459:
1431:
1425:
1424:
1396:
1390:
1389:
1353:
1347:
1346:
1335:"Catecholamines"
1331:
1325:
1324:
1306:
1300:
1299:
1297:
1295:
1279:
1257:Sympathomimetics
1130:pheochromocytoma
1064:pheochromocytoma
1056:Brunner syndrome
1045:pheochromocytoma
861:
853:
847:
841:
837:
833:
829:
804:The amino acids
783:
779:
727:substantia nigra
715:neurotransmitter
695:chromaffin cells
675:as the cofactor.
670:
651:
624:
618:
595:
591:
566:-tyrosine by an
563:
559:
554:
548:
547:
537:
530:
523:
516:
509:
500:
493:
486:
479:
472:
465:
458:
451:
444:
437:
430:
423:
416:
406:
396:
386:
385:
377:
376:
368:
358:
351:
350:
342:
337:
332:
327:
322:
317:
310:
285:
236:
147:organic compound
136:
135:
132:
131:
128:
125:
122:
119:
116:
113:
110:
107:
104:
101:
98:
95:
63:
54:(Noradrenaline)
49:
35:
30:
21:
3640:
3639:
3635:
3634:
3633:
3631:
3630:
3629:
3625:Stress hormones
3600:
3599:
3598:
3593:
3581:
3579:
3577:for references.
3565:
3563:
3546:
3530:
3516:
3475:
3461:
3438:
3420:
3398:
3369:Propylhexedrine
3351:Norfenfluramine
3341:Methamphetamine
3237:
3179:-Methyltyramine
3088:
3080:
3050:
3045:
3012:
2973:
2945:
2901:
2873:
2849:Normetanephrine
2825:
2773:
2757:DOPA (levodopa)
2726:
2718:
2688:
2679:
2674:
2665:
2651:
2627:
2617:
2593:
2550:
2496:
2472:
2363:
2335:
2319:
2241:
2197:Biogenic amines
2187:
2164:
2113:
2087:
2013:
1997:
1992:
1950:
1945:
1944:
1935:
1933:
1925:
1924:
1920:
1911:
1909:
1901:
1900:
1896:
1887:
1885:
1876:
1875:
1871:
1862:
1860:
1852:
1851:
1847:
1817:
1816:
1812:
1802:
1800:
1792:
1791:
1787:
1780:
1772:. p. 143.
1759:
1758:
1754:
1710:
1709:
1705:
1690:
1669:
1668:
1664:
1628:
1627:
1623:
1615:
1613:
1596:
1595:
1591:
1562:(56): 331–349.
1553:
1552:
1548:
1506:
1505:
1498:
1468:
1467:
1463:
1433:
1432:
1428:
1398:
1397:
1393:
1355:
1354:
1350:
1333:
1332:
1328:
1321:
1308:
1307:
1303:
1293:
1291:
1281:
1280:
1276:
1271:
1266:
1252:Steroid hormone
1247:Phenethylamines
1242:Peptide hormone
1208:
1193:normetanephrine
1172:
1147:medicinal plant
1138:
1121:) in patients.
1087:
1060:bioavailability
1041:adrenal medulla
976:neuromodulators
964:
959:
891:
822:phenylketonuria
767:
735:locus coeruleus
699:adrenal medulla
691:
685:
683:
678:
677:
676:
648:
609:
581:
558:
557:-phenylalanine.
549:
541:
540:
539:
538:
533:
531:
526:
524:
519:
517:
514:
512:
510:
505:
503:
501:
496:
494:
489:
487:
482:
480:
475:
473:
468:
466:
461:
459:
456:
454:
452:
447:
445:
440:
438:
433:
431:
426:
424:
419:
417:
409:
407:
404:-Methyltyramine
399:
397:
389:
387:
381:
380:
378:
372:
371:
369:
361:
359:
354:
352:
346:
345:
343:
335:
333:
325:
323:
315:
311:
303:
282:
258:
219:is part of the
213:adrenal medulla
92:
88:
64:
50:
36:
28:
23:
22:
15:
12:
11:
5:
3638:
3636:
3628:
3627:
3622:
3620:TAAR1 agonists
3617:
3612:
3610:Catecholamines
3602:
3601:
3595:
3594:
3567:
3556:
3555:
3552:
3551:
3548:
3547:
3545:
3544:
3538:
3536:
3532:
3531:
3529:
3528:
3524:
3522:
3518:
3517:
3515:
3514:
3512:Trimethylamine
3509:
3496:
3494:
3487:
3481:
3480:
3477:
3476:
3474:
3473:
3469:
3467:
3463:
3462:
3459:
3457:
3450:
3444:
3443:
3440:
3439:
3437:
3436:
3430:
3428:
3422:
3421:
3419:
3418:
3412:
3410:
3404:
3403:
3400:
3399:
3397:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3358:
3353:
3348:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3308:
3303:
3298:
3293:
3288:
3283:
3278:
3273:
3261:
3256:
3251:
3245:
3243:
3239:
3238:
3236:
3235:
3234:
3233:
3225:
3217:
3212:
3207:
3202:
3200:Phenethylamine
3197:
3189:
3181:
3173:
3165:
3160:
3150:
3149:
3148:
3143:
3138:
3133:
3128:
3116:
3114:
3105:
3096:
3090:
3089:
3081:
3079:
3078:
3071:
3064:
3056:
3047:
3046:
3044:
3043:
3038:
3033:
3028:
3022:
3020:
3014:
3013:
3011:
3010:
3005:
3000:
2991:
2989:
2979:
2978:
2975:
2974:
2972:
2971:
2966:
2961:
2955:
2953:
2947:
2946:
2944:
2943:
2938:
2932:
2930:
2921:
2911:
2910:
2907:
2906:
2903:
2902:
2900:
2899:
2894:
2889:
2883:
2881:
2875:
2874:
2872:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2835:
2833:
2831:Norepinephrine
2827:
2826:
2824:
2823:
2818:
2813:
2808:
2803:
2798:
2792:
2790:
2781:
2775:
2774:
2772:
2771:
2765:Norepinephrine
2745:
2743:
2734:
2732:Catecholamines
2728:
2727:
2719:
2717:
2716:
2709:
2702:
2694:
2685:
2684:
2681:
2680:
2678:
2677:
2672:
2668:
2663:
2659:
2654:
2649:
2645:
2639:
2637:
2629:
2628:
2626:
2625:
2620:
2615:
2611:
2605:
2603:
2595:
2594:
2592:
2591:
2585:
2583:
2576:
2572:
2571:
2567:
2560:
2559:
2556:
2555:
2552:
2551:
2549:
2548:
2543:
2538:
2532:
2530:
2520:
2513:
2506:
2505:
2502:
2501:
2498:
2497:
2495:
2494:
2486:
2480:
2474:
2473:
2471:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2389:
2387:
2380:
2373:
2372:
2369:
2368:
2365:
2364:
2362:
2361:
2353:
2347:
2341:
2340:
2337:
2336:
2334:
2333:
2327:
2325:
2321:
2320:
2318:
2317:
2309:
2301:
2296:
2291:
2289:Phenethylamine
2286:
2281:
2273:
2265:
2260:
2255:
2249:
2247:
2243:
2242:
2240:
2239:
2234:
2229:
2224:
2219:
2214:
2208:
2206:
2199:
2193:
2192:
2189:
2188:
2186:
2185:
2180:
2174:
2172:
2166:
2165:
2163:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2121:
2119:
2118:Glycine system
2115:
2114:
2112:
2111:
2106:
2101:
2095:
2093:
2089:
2088:
2086:
2085:
2080:
2075:
2070:
2065:
2063:Kynurenic acid
2060:
2055:
2050:
2045:
2040:
2035:
2030:
2024:
2022:
2015:
2006:
1999:
1998:
1993:
1991:
1990:
1983:
1976:
1968:
1962:
1961:
1954:Catecholamines
1949:
1948:External links
1946:
1943:
1942:
1918:
1894:
1869:
1845:
1810:
1785:
1778:
1752:
1723:(8): 935–936.
1703:
1688:
1662:
1641:(6): 626–632.
1621:
1589:
1546:
1519:(3): 303–308.
1496:
1461:
1442:(5): 274–281.
1426:
1407:(3): 363–375.
1391:
1348:
1339:Health Library
1326:
1319:
1301:
1273:
1272:
1270:
1267:
1265:
1264:
1259:
1254:
1249:
1244:
1239:
1237:Julius Axelrod
1234:
1229:
1224:
1219:
1209:
1207:
1204:
1171:
1168:
1137:
1134:
1099:blood pressure
1086:
1083:
984:norepinephrine
968:norepinephrine
963:
960:
958:
955:
890:
887:
866:norepinephrine
766:
763:
759:solitary tract
739:norepinephrine
690:
687:
680:
679:
654:-ascorbic acid
646:
635:norepinephrine
607:
579:
543:
542:
532:
525:
518:
511:
502:
495:
488:
481:
474:
467:
460:
453:
446:
439:
432:
425:
418:
408:
398:
388:
383:Norepinephrine
379:
370:
360:
356:Phenethylamine
353:
344:
334:
324:
320:-Phenylalanine
314:
313:
312:
305:
304:
293:catecholamines
290:
289:
288:
283:
281:
278:
257:
254:
230:by the enzyme
217:adrenal glands
201:norepinephrine
199:(adrenaline),
137:; abbreviated
69:
68:
56:
55:
52:Norepinephrine
42:
41:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3637:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3607:
3605:
3591:
3590:
3587:
3582:
3576:
3572:
3566:
3561:
3553:
3543:
3540:
3539:
3537:
3533:
3526:
3525:
3523:
3519:
3513:
3510:
3508:
3506:
3502:
3498:
3497:
3495:
3491:
3488:
3486:
3482:
3471:
3470:
3468:
3464:
3458:
3454:
3451:
3449:
3445:
3435:
3432:
3431:
3429:
3427:
3423:
3417:
3414:
3413:
3411:
3409:
3405:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3363:
3359:
3357:
3354:
3352:
3349:
3347:
3344:
3342:
3339:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3270:
3266:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3246:
3244:
3240:
3232:
3230:
3226:
3224:
3222:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3194:
3190:
3188:
3186:
3182:
3180:
3178:
3174:
3172:
3170:
3166:
3164:
3161:
3159:
3156:
3155:
3154:
3151:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3123:
3122:
3118:
3117:
3115:
3113:
3109:
3106:
3104:
3100:
3097:
3095:
3091:
3087:
3084:
3077:
3072:
3070:
3065:
3063:
3058:
3057:
3054:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3023:
3021:
3019:
3015:
3009:
3006:
3004:
3001:
2999:
2997:
2993:
2992:
2990:
2988:
2984:
2980:
2970:
2967:
2965:
2962:
2960:
2957:
2956:
2954:
2952:
2948:
2942:
2939:
2937:
2934:
2933:
2931:
2929:
2925:
2922:
2920:
2916:
2912:
2898:
2895:
2893:
2890:
2888:
2885:
2884:
2882:
2880:
2876:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2836:
2834:
2832:
2828:
2822:
2819:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2793:
2791:
2789:
2785:
2782:
2780:
2776:
2770:
2766:
2762:
2758:
2754:
2750:
2749:Phenylalanine
2747:
2746:
2744:
2742:
2738:
2735:
2733:
2729:
2725:
2722:
2715:
2710:
2708:
2703:
2701:
2696:
2695:
2692:
2676:
2669:
2667:
2660:
2658:
2655:
2653:
2646:
2644:
2641:
2640:
2638:
2634:
2624:
2621:
2619:
2612:
2610:
2607:
2606:
2604:
2600:
2590:
2589:Acetylcholine
2587:
2586:
2584:
2580:
2577:
2575:Miscellaneous
2573:
2568:
2565:
2561:
2547:
2544:
2542:
2539:
2537:
2534:
2533:
2531:
2528:
2524:
2521:
2517:
2514:
2511:
2507:
2492:
2488:
2487:
2484:
2481:
2479:
2478:Neurosteroids
2475:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2390:
2388:
2384:
2381:
2378:
2374:
2359:
2355:
2354:
2351:
2348:
2346:
2345:Neuropeptides
2342:
2332:
2329:
2328:
2326:
2322:
2316:
2314:
2310:
2308:
2306:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2278:
2274:
2272:
2270:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2250:
2248:
2244:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2209:
2207:
2203:
2200:
2198:
2194:
2184:
2181:
2179:
2176:
2175:
2173:
2171:
2167:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2122:
2120:
2116:
2110:
2107:
2105:
2102:
2100:
2097:
2096:
2094:
2090:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2051:
2049:
2046:
2044:
2041:
2039:
2036:
2034:
2031:
2029:
2026:
2025:
2023:
2019:
2016:
2010:
2007:
2004:
2000:
1996:
1989:
1984:
1982:
1977:
1975:
1970:
1969:
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1199:
1196:
1194:
1190:
1186:
1182:
1178:
1177:metanephrines
1169:
1166:
1164:
1160:
1156:
1152:
1151:embryogenesis
1148:
1144:
1135:
1133:
1131:
1127:
1126:Urine testing
1122:
1120:
1116:
1112:
1108:
1104:
1103:blood glucose
1100:
1096:
1092:
1084:
1082:
1080:
1075:
1073:
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1065:
1061:
1057:
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1046:
1042:
1038:
1033:
1031:
1027:
1023:
1019:
1015:
1010:
1008:
1004:
1003:intense light
1000:
996:
991:
989:
985:
981:
977:
973:
969:
961:
956:
954:
952:
948:
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932:
928:
924:
920:
916:
912:
910:
906:
904:
900:
898:
888:
886:
883:
881:
875:
871:
867:
859:
851:
827:
823:
819:
815:
811:
807:
806:phenylalanine
802:
800:
796:
792:
787:
782:-tyrosine to
777:
773:
764:
762:
760:
756:
755:area postrema
752:
750:
744:
740:
736:
732:
728:
724:
720:
716:
712:
708:
704:
700:
696:
688:
686:
674:
668:
663:
661:
655:
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640:
636:
632:
628:
616:
613:
605:
601:
589:
585:
577:
573:
569:
553:
536:
529:
522:
508:
499:
492:
485:
478:
471:
464:
450:
443:
436:
429:
422:
415:
413:
405:
403:
395:
393:
384:
375:
367:
365:
357:
349:
341:
331:
321:
309:
302:
298:
294:
287:
286:
279:
277:
275:
271:
267:
263:
255:
253:
251:
247:
242:
240:
233:
229:
228:hydroxylation
224:
222:
218:
214:
210:
206:
202:
198:
193:
191:
190:phenylalanine
187:
184:
179:
177:
173:
169:
167:
164:
160:
156:
152:
148:
144:
140:
134:
86:
85:catecholamine
79:
75:
67:
62:
58:
57:
53:
48:
44:
43:
40:(Adrenaline)
39:
34:
19:
3585:
3584:
3580:
3564:
3504:
3500:
3389:Solriamfetol
3361:
3306:Isoprenaline
3281:Halostachine
3268:
3264:
3228:
3220:
3192:
3184:
3176:
3168:
3153:Trace amines
3018:Trace amines
2995:
2892:Metanephrine
2731:
2643:Acetaldehyde
2312:
2304:
2276:
2268:
2246:Trace amines
1934:. Retrieved
1930:
1921:
1910:. Retrieved
1906:
1897:
1886:. Retrieved
1881:
1872:
1861:. Retrieved
1857:
1848:
1826:(2): 91–97.
1823:
1819:
1813:
1801:. Retrieved
1797:
1788:
1761:
1755:
1720:
1716:
1706:
1671:
1665:
1638:
1634:
1624:
1614:, retrieved
1602:
1592:
1559:
1555:
1549:
1516:
1512:
1508:
1474:
1470:
1464:
1439:
1435:
1429:
1404:
1400:
1394:
1361:
1357:
1351:
1343:the original
1338:
1329:
1311:Neuroscience
1310:
1304:
1292:. Retrieved
1287:
1277:
1214:
1200:
1197:
1189:metanephrine
1181:hypertension
1173:
1163:gibberellins
1140:
1123:
1088:
1076:
1049:
1034:
1011:
992:
965:
918:
913:
907:
896:
892:
879:
814:blood plasma
803:
790:
788:
768:
765:Biosynthesis
748:
731:neuromelanin
692:
684:
666:
664:(PNMT) with
659:
411:
401:
391:
363:
297:trace amines
292:
262:benzene ring
259:
243:
225:
194:
180:
170:
138:
84:
82:
3416:RTI-7470-44
3356:Phentermine
3249:Amphetamine
3195:-Octopamine
3187:-Octopamine
2879:Epinephrine
2769:Epinephrine
2648:Ammonia (NH
2519:Nucleosides
2279:-Octopamine
2271:-Octopamine
2183:T-HCA (GHC)
2140:Hypotaurine
2092:GABA system
2043:Glutathione
1477:: 211–218.
1364:: 342–350.
1294:October 26,
1185:tachycardia
1113:(a central
889:Degradation
870:epinephrine
793:-tyrosine (
743:Epinephrine
673:-methionine
639:epinephrine
414:-Octopamine
348:Epinephrine
301:human brain
197:epinephrine
176:substituent
149:that has a
38:Epinephrine
3604:Categories
3384:Selegiline
3286:Higenamine
3276:Guanfacine
3215:Tryptamine
3210:Synephrine
3119:Classical
3112:Endogenous
2951:Catabolism
2936:Tryptophan
2915:Tryptophan
2779:Catabolism
2636:Candidates
2510:Nucleobase
2299:Tryptamine
2294:Synephrine
2205:Monoamines
2170:GHB system
2003:Amino acid
1936:2019-10-09
1912:2019-10-09
1888:2019-12-24
1863:2019-12-24
1616:2024-06-28
1603:StatPearls
1269:References
1119:tachypnoea
1095:heart rate
915:Catabolism
669:-adenosyl-
552:amino acid
421:Synephrine
183:amino acid
163:side-chain
3586:See also:
3379:RO5166017
3291:Hordenine
3231:-Tyramine
3223:-Tyramine
3146:Serotonin
3131:Histamine
2987:Melatonin
2983:Serotonin
2928:Anabolism
2919:Serotonin
2741:Anabolism
2527:Adenosine
2331:Histamine
2315:-Tyramine
2307:-Tyramine
2150:Sarcosine
2130:β-Alanine
2125:α-Alanine
1798:webmd.com
1766:Melbourne
1213:Catechol-
1143:alkaloids
1111:tolcapone
1079:porphyria
1022:brainstem
974:, act as
895:catechol-
846:aromatic
623:aromatic
588:cofactors
366:-Tyramine
330:-Tyrosine
264:with two
256:Structure
246:stimulant
157:with two
3493:Agonists
3456:Agonists
3126:Dopamine
3103:Agonists
2788:Dopamine
2761:Dopamine
2753:Tyrosine
2566:-derived
2512:-derived
2493:instead.
2448:Oleamide
2379:-derived
2360:instead.
2217:Dopamine
2028:Agmatine
2005:-derived
1840:41493767
1747:17660335
1657:12140786
1611:31082164
1584:12825309
1576:15317907
1491:24374199
1456:15860375
1421:19948186
1386:86229251
1206:See also
1159:ethylene
988:synapses
972:dopamine
962:Modality
957:Function
810:tyrosine
772:cofactor
737:produce
725:and the
711:Dopamine
701:and the
689:Location
645:, with O
570:enzyme (
374:Dopamine
266:hydroxyl
244:Various
209:hormones
205:dopamine
186:tyrosine
172:Catechol
159:hydroxyl
151:catechol
78:Catechol
66:Dopamine
3086:ligands
2564:Vitamin
2458:RVD-Hpα
2413:AA-5-HT
2160:Taurine
2145:Proline
2135:Glycine
2078:Proline
2048:Glycine
1770:Cengage
1738:1994495
1698:8862875
1541:2578817
1533:3885079
1378:3473965
1232:Hormone
1085:Effects
1039:in the
1020:in the
978:in the
858:neurons
786:-DOPA.
717:in the
705:of the
697:of the
629:, with
612:ferrous
602:) with
515:pathway
457:pathway
455:primary
299:in the
215:of the
155:benzene
141:) is a
3527:
3472:
3460:
2529:system
2403:2-ALPI
2324:Others
2155:Serine
2083:Serine
1960:(MeSH)
1838:
1776:
1745:
1735:
1696:
1686:
1655:
1609:
1582:
1574:
1539:
1531:
1489:
1454:
1419:
1384:
1376:
1317:
1077:Acute
1070:, and
1018:nuclei
995:stress
610:, and
582:) and
576:oxygen
507:CYP2D6
3571:TAAR1
3485:TAAR5
3448:TAAR2
3346:3-MMA
3094:TAAR1
2438:NAGly
2377:Lipid
2212:6-OHM
2104:GABOB
1907:WebMD
1836:S2CID
1803:4 May
1580:S2CID
1537:S2CID
1382:S2CID
1028:. In
1005:, or
947:urine
909:MAOIs
513:minor
504:brain
340:-DOPA
274:amine
270:ethyl
239:-DOPA
166:amine
145:, an
3575:TAAR
3364:-PIT
3259:DOET
2491:here
2489:See
2433:NADA
2408:2-OG
2393:2-AG
2358:here
2356:See
2099:GABA
2073:NAAG
2058:GSSG
2053:GSNO
1805:2017
1774:ISBN
1743:PMID
1694:PMID
1684:ISBN
1653:PMID
1607:PMID
1572:PMID
1529:PMID
1487:PMID
1452:PMID
1417:PMID
1374:PMID
1315:ISBN
1296:2011
1191:and
1183:and
1115:COMT
970:and
937:and
808:and
795:AMPT
649:and
637:and
615:iron
521:COMT
498:AAAH
491:AAAH
484:PNMT
477:PNMT
470:PNMT
463:PNMT
449:AADC
442:AADC
435:AADC
295:and
3254:DOB
2546:ATP
2541:AMP
2536:ADP
2463:SEA
2453:PEA
2443:OEA
2428:LPI
2423:DEA
2178:GHB
2109:GHB
2068:NAA
1828:doi
1733:PMC
1725:doi
1676:doi
1643:doi
1564:doi
1521:doi
1479:doi
1475:724
1444:doi
1409:doi
1405:125
1366:doi
1362:493
927:FAD
776:PLP
606:, O
586:as
535:DBH
528:DBH
3606::
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1515:.
1499:^
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1372:.
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1337:.
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741:.
709:.
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578:(O
223:.
168:.
139:CA
127:iː
115:oʊ
83:A
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3269:N
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3265:N
3229:p
3221:m
3193:p
3185:m
3177:N
3169:N
3075:e
3068:t
3061:v
2996:N
2985:→
2917:→
2713:e
2706:t
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2673:2
2664:2
2652:)
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2616:2
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1973:v
1939:.
1915:.
1891:.
1866:.
1842:.
1830::
1807:.
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1678::
1659:.
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1388:.
1368::
1323:.
1298:.
1215:O
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897:O
880:N
862:L
854:L
848:L
842:L
838:L
834:L
830:L
791:p
784:L
780:L
749:N
671:L
667:S
660:N
652:L
647:2
625:L
619:L
608:2
596:L
592:L
580:2
564:L
560:L
555:L
412:p
402:N
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364:p
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153:(
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130:n
124:m
121:ə
118:l
112:k
109:ˈ
106:ə
103:t
100:æ
97:k
94:ˌ
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87:(
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