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567:
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.
35:
1139:
569:
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
566:
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
572:
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
531:
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".
267:
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Very little data, even on toxicity, is available about its effects on humans other than that it activates the human TAAR1 receptor.
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or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see
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97 °C (207 °F; 370 K) / 5 mmHg (270.7984 °C / 760 mmHg) Experimental
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570:β-PEA. In both cases of β-substitution, enantiomeric selectivity was demonstrated.
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Except where otherwise noted, data are given for materials in their
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References for all endogenous human TAAR1 ligands are provided at
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The
Journal of Pharmacology and Experimental Therapeutics
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References for synthetic TAAR1 agonists can be found at
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434:(TAAR1) agonist, a property which it shares with its
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331:Clear colorless liquid at room temp
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904:Ralmitaront (RG-7906, RO-6889450)
432:trace amine associated receptor 1
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308:
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386:(at 25 °C , 100 kPa).
52:2-(2-Methylphenyl)ethan-1-amine
671:Norepinephrine (noradrenaline)
504:"2-(2-Methylphenyl)ethanamine"
484:. National Library of Medicine
363:Occupational safety and health
296:
1:
1119:Receptor/signaling modulators
436:monomethylated phenethylamine
412:with the chemical formula of
1153:. You can help Knowledge by
61:2-(2-Methylphenyl)ethanamine
651:monoamine neurotransmitters
1226:
1132:
442:(α-methylphenethylamine),
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380:
360:
355:
283:
263:
74:
63:2-Methylbenzeneethanamine
58:
46:
41:
32:
666:Epinephrine (adrenaline)
482:"2-Methylphenethylamine"
376:Corrosive; causes burns
801:-Dimethylphenethylamine
546:10.1124/jpet.106.112532
28:2-Methylphenethylamine
1145:This article about an
924:Ulotaront (SEP-363856)
866:β-Methylphenethylamine
861:4-Methylphenethylamine
856:3-Methylphenethylamine
851:2-Methylphenethylamine
451:N-methylphenethylamine
445:β-methylphenethylamine
402:2-Methylphenethylamine
18:2-methylphenethylamine
846:MDMA (midomafetamine)
772:Synthetic and natural
701:-Methylphenethylamine
1090:List of trace amines
826:4-Hydroxyamphetamine
69:-Tolyl)ethan-1-amine
48:Preferred IUPAC name
1051:Neutral antagonists
1037:-Dimethylethylamine
996:Neutral antagonists
938:Neutral antagonists
841:MDA (tenamfetamine)
831:Isopropyloctopamine
430:. 2MPEA is a human
323: g·mol
29:
735:Phenylethanolamine
390:Infobox references
27:
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1072:3-Iodothyronamine
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964:EPPTB (RO5212773)
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693:3-Methoxytyramine
688:3-Iodothyronamine
438:isomers, such as
398:Chemical compound
396:
395:
232:CompTox Dashboard
116:Interactive image
16:(Redirected from
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881:Norfenfluramine
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919:Solriamfetol
891:
850:
836:Isoprenaline
811:Halostachine
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683:Trace amines
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533:
511:. Retrieved
507:
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486:. Retrieved
460:
405:
401:
400:
372:Main hazards
361:
136:ChEMBL451372
75:Identifiers
66:
59:Other names
1210:Amine stubs
946:RTI-7470-44
886:Phentermine
779:Amphetamine
725:-Octopamine
717:-Octopamine
456:trace amine
440:amphetamine
366:(OHS/OSH):
341:0.96 g/cm3
328:Appearance
284:Properties
174:100.199.500
1194:Categories
914:Selegiline
816:Higenamine
806:Guanfacine
745:Tryptamine
740:Synephrine
649:Classical
642:Endogenous
508:Chemspider
465:References
316:Molar mass
220:B2VHM2W3X9
147:ChemSpider
103:3D model (
92:55755-16-3
82:CAS Number
1116:See also:
909:RO5166017
821:Hordenine
761:-Tyramine
753:-Tyramine
676:Serotonin
661:Histamine
1023:Agonists
986:Agonists
656:Dopamine
633:Agonists
562:10829497
554:17038507
408:) is an
356:Hazards
616:ligands
488:24 June
337:Density
321:135.210
200:2063868
187:PubChem
156:1554538
1057:
1002:
990:
560:
552:
513:27 May
448:, and
268:SMILES
127:ChEMBL
42:Names
1149:is a
1147:amine
1101:TAAR1
1015:TAAR5
978:TAAR2
876:3-MMA
624:TAAR1
558:S2CID
406:2MPEA
105:JSmol
1151:stub
1105:TAAR
894:-PIT
789:DOET
573:not.
550:PMID
515:2014
490:2023
211:UNII
784:DOB
542:doi
538:320
458:).
454:(a
237:EPA
190:CID
65:2-(
1196::
564:.
556:.
548:.
536:.
523:^
506:.
473:^
424:13
306:13
1182:e
1175:t
1168:v
1157:.
1035:N
1033:,
1031:N
892:o
799:N
797:,
795:N
759:p
751:m
723:p
715:m
707:N
699:N
605:e
598:t
591:v
544::
517:.
492:.
427:N
421:H
418:9
415:C
404:(
309:N
303:H
300:9
297:C
239:)
235:(
107:)
67:o
20:)
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