2-Methylphenethylamine

changed 2-Methylphenethylamine.svg skin-invert-image 2-(2-Methylphenyl)ethan-1-amine 2-(2-Methylphenyl)ethanamine2-Methylbenzeneethanamine2-(o-Tolyl)ethan-1-amine correct ?? 55755-16-3 correct EBI 451372 correct chemspider 1554538 674-091-6 correct FDA B2VHM2W3X9 2063868 1S/C9H13N/c1-8-4-2-3-5-9(8)6-7-10/h2-5H,6-7,10H2,1H3 OWOUKRYOZIZVFK-UHFFFAOYSA-N CC1=CC=CC=C1CCN 9 13 1 Clear colorless liquid at room temp2-Methylphenethylamine https://pubchem.ncbi.nlm.nih.gov/compound/2063868 24 June 2023 National Library of Medicine 0.96 g/cm3 97 / 5 mmHg (270.7984 °C / 760 mmHg) Experimental2-(2-Methylphenyl)ethanamine http://www.chemspider.com/Chemical-Structure.1554538.html Chemspider 27 May 2014 Corrosive; causes burns 05 07 Danger 314 315 319 335 412 260 261 264 264+265 271 273 280 301+330+331 302+352 302+361+354 304+340 305+351+338 305+354+338 316 317 319 321 332+317 337+317 362+364 363 403+233 405 501 2-Methylphenethylamine (2MPEA) is an organic compound with the chemical formula of C9H13N yes. 2MPEA is a human trace amine associated receptor 1 (TAAR1) agonist,Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1 The Journal of Pharmacology and Experimental Therapeutics 320 1 475–85 January 2007 17038507 10.1124/jpet.106.112532 10829497 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 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.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 β-PEA. In both cases of β-substitution, enantiomeric selectivity was demonstrated.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 not. a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine (a trace amine). Very little data, even on toxicity, is available about its effects on humans other than that it activates the human TAAR1 receptor. References Category:Methyl compounds Category:Phenethylamines Category:TAAR1 agonists