3-Methylphenethylamine

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3-Methylphenethylamine
200px
Identifiers
CAS number 55755-17-4 7pxY
PubChem 410085
ChemSpider 362941 7pxY
ChEMBL CHEMBL448576 7pxY
Jmol-3D images Image 1
Properties
Molecular formula C9H13N
Molar mass Script error g mol−1
Appearance clear liquid at room temp.
Density 1.0±0.1 g/cm3
Boiling point 110 °C / 20 mmHg
240.9519 °C / 760 mmHg Experimental[1]
Hazards
Main hazards Corrossive
Flash point 90.5±6.3 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

Very little data, even on toxicity, is available about its effects on humans other than the fact that it is corrosive and activates the human TAAR1 receptor.[1]

References

  1. 1.0 1.1 "2-(3-Methylphenyl)ethanamine". Chemspider. Retrieved 30 May 2014. 
  2. 2.0 2.1 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. PMID 17038507. doi:10.1124/jpet.106.112532. "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."
     


      
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