255:
180:
37:
556:
hydroxyl substituent, the C2-substituted compound had 8- to 27-fold higher potency than the C4-substituted compound. The C3-substituted compound in each homologous series was typically 2- to 5-fold less potent than the 2-substituted compound, except for the hydroxyl substituent. The most potent of the 2-substituted phenylethylamines was 2-chloro-β-PEA, followed by 2-fluoro-β-PEA, 2-bromo-β-PEA, 2-methoxy-β-PEA, 2-methyl-β-PEA, and then 2-hydroxy-β-PEA.
1128:
558:
The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(−)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1. β-Hydroxyl substitution was, however, not tolerated compared with
555:
Several series of substituted phenylethylamines were investigated for activity at the human TAAR1 (Table 2). A surprising finding was the potency of phenylethylamines with substituents at the phenyl C2 position relative to their respective C4-substituted congeners. In each case, except for the
561:
In contrast to a methyl substitution on the β-carbon, an α-methyl substitution reduced potency by ~10-fold for d-amphetamine and 16-fold for l-amphetamine relative to β-PEA (Table 4). N-Methyl substitution was fairly well tolerated; however, N,N-dimethyl substitution was
520:
Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1".
269:
472:
Very little data, even on toxicity, is available about its effects on humans other than that it is corrosive and activates the human TAAR1 receptor.
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601:
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442:
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772:
1093:
363:
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233:
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782:
639:
585:
400:
854:
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1162:
864:
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1193:
879:
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814:
446:
49:
250:
1155:
819:
83:
926:
723:
546:
570:
1092:
or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see
1060:
681:
676:
538:
36:
694:
530:
420:
387:
90.5 ± 6.3 °C (194.9 ± 11.3 °F; 363.6 ± 6.3 K)
292:
157:
492:
221:
93:
944:
887:
869:
859:
710:
702:
254:
179:
1139:
1030:
718:
659:
394:
17:
1182:
746:
738:
345:
168:
550:
907:
824:
799:
201:
1127:
559:β-PEA. In both cases of β-substitution, enantiomeric selectivity was demonstrated.
1078:
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Except where otherwise noted, data are given for materials in their
1135:
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References for all endogenous human TAAR1 ligands are provided at
1003:
966:
952:
612:
116:
106:
834:
574:
238:
523:
The
Journal of Pharmacology and Experimental Therapeutics
1088:
References for synthetic TAAR1 agonists can be found at
1143:
445:(TAAR1) agonist, a property which it shares with its
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1002:
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350:110 °C (230 °F; 383 K) / 20 mmHg
200:
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8:
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1008:
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602:Human trace amine-associated receptor
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7:
1124:
1122:
487:
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352:240.9519 °C / 760 mmHg Experimental
191:
25:
893:Ralmitaront (RG-7906, RO-6889450)
443:trace amine associated receptor 1
1126:
310:
304:
35:
397:(at 25 °C , 100 kPa).
54:2-(3-Methylphenyl)ethan-1-amine
660:Norepinephrine (noradrenaline)
493:"2-(3-Methylphenyl)ethanamine"
364:Occupational safety and health
298:
1:
1108:Receptor/signaling modulators
447:monomethylated phenethylamine
423:with the chemical formula of
1142:. You can help Knowledge by
63:2-(3-Methylphenyl)ethanamine
640:monoamine neurotransmitters
330:clear liquid at room temp.
1220:
1121:
453:(α-methylphenethylamine),
1073:
391:
361:
356:
285:
265:
76:
65:3-Methylbenzeneethanamine
60:
48:
43:
34:
655:Epinephrine (adrenaline)
790:-Dimethylphenethylamine
535:10.1124/jpet.106.112532
322:135.20622
30:3-Methylphenethylamine
1134:This article about an
913:Ulotaront (SEP-363856)
855:β-Methylphenethylamine
850:4-Methylphenethylamine
845:3-Methylphenethylamine
840:2-Methylphenethylamine
462:N-methylphenethylamine
456:β-methylphenethylamine
413:3-Methylphenethylamine
18:3-methylphenethylamine
835:MDMA (midomafetamine)
761:Synthetic and natural
690:-Methylphenethylamine
1079:List of trace amines
815:4-Hydroxyamphetamine
441:. 3MPEA is a human
71:-Tolyl)ethan-1-amine
50:Preferred IUPAC name
1040:Neutral antagonists
1026:-Dimethylethylamine
985:Neutral antagonists
927:Neutral antagonists
830:MDA (tenamfetamine)
820:Isopropyloctopamine
31:
724:Phenylethanolamine
401:Infobox references
29:
1199:3-Tolyl compounds
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1150:
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1111:
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1068:
1061:3-Iodothyronamine
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997:
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953:EPPTB (RO5212773)
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920:
682:3-Methoxytyramine
677:3-Iodothyronamine
449:isomers, such as
409:Chemical compound
407:
406:
277:CC1=CC(=CC=C1)CCN
234:CompTox Dashboard
118:Interactive image
16:(Redirected from
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1054:Inverse agonists
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1189:Phenethylamines
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1096:for references.
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888:Propylhexedrine
870:Norfenfluramine
860:Methamphetamine
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170:ECHA InfoCard
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908:Solriamfetol
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844:
825:Isoprenaline
800:Halostachine
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783:
747:
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703:
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672:Trace amines
554:
526:
522:
500:. Retrieved
496:
471:
416:
412:
411:
373:Main hazards
362:
138:ChEMBL448576
77:Identifiers
68:
61:Other names
26:
1204:Amine stubs
935:RTI-7470-44
875:Phentermine
768:Amphetamine
714:-Octopamine
706:-Octopamine
467:trace amine
451:amphetamine
383:Flash point
377:Corrossive
367:(OHS/OSH):
327:Appearance
286:Properties
176:100.189.789
1183:Categories
903:Selegiline
805:Higenamine
795:Guanfacine
734:Tryptamine
729:Synephrine
638:Classical
631:Endogenous
497:Chemspider
476:References
318:Molar mass
222:46YT56V48J
149:ChemSpider
105:3D model (
94:55755-17-4
84:CAS Number
1105:See also:
898:RO5166017
810:Hordenine
750:-Tyramine
742:-Tyramine
665:Serotonin
650:Histamine
1012:Agonists
975:Agonists
645:Dopamine
622:Agonists
551:10829497
543:17038507
419:) is an
357:Hazards
605:ligands
336:Density
189:PubChem
1046:
991:
979:
549:
541:
502:30 May
459:, and
270:SMILES
202:410085
158:362941
129:ChEMBL
44:Names
1138:is a
1136:amine
1090:TAAR1
1004:TAAR5
967:TAAR2
865:3-MMA
613:TAAR1
547:S2CID
417:3MPEA
107:JSmol
1140:stub
1094:TAAR
883:-PIT
778:DOET
562:not.
539:PMID
504:2014
213:UNII
773:DOB
531:doi
527:320
469:).
465:(a
239:EPA
192:CID
67:2-(
1185::
553:.
545:.
537:.
525:.
512:^
495:.
484:^
435:13
308:13
1171:e
1164:t
1157:v
1146:.
1024:N
1022:,
1020:N
881:o
788:N
786:,
784:N
748:p
740:m
712:p
704:m
696:N
688:N
594:e
587:t
580:v
533::
506:.
438:N
432:H
429:9
426:C
415:(
311:N
305:H
302:9
299:C
241:)
237:(
109:)
69:m
20:)
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