2-Methylphenethylamine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2-Methylphenethylamine
2-Methylphenethylamine.svg
Identifiers
CAS number 55755-16-3 YesY
PubChem 2063868 YesY
ChemSpider 1554538 YesY
ChEMBL CHEMBL451372 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H13N
Molar mass 135.21 g mol−1
Appearance Clear colorless liquid at room temp[1]
Density 0.96 g/cm3[1]
Boiling point 97 °C (207 °F; 370 K) / 5 mmHg (270.7984 °C / 760 mmHg) Experimental[2]
Hazards
Main hazards Corrosive; causes burns
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

2-Methylphenethylamine (2MPEA) is an organic compound with the chemical formula of C9H13N. 2MPEA is a human trace amine associated receptor 1 (TAAR1) agonist,[3] a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine (a trace amine).[3]

Very little data, even on toxicity, is available about its effects on humans other than the fact that it activates the human TAAR1 receptor.

References[edit]

  1. ^ a b "2-Methylphenethylamine". Chemical Book. Retrieved 27 May 2014. 
  2. ^ "2-(2-Methylphenyl)ethanamine". Chemspider. Retrieved 27 May 2014. 
  3. ^ a b 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". The Journal of Pharmacology and Experimental Therapeutics 320 (1): 475–85. doi:10.1124/jpet.106.112532. PMID 17038507. 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.