4-Methylphenethylamine

4-Methylphenethylamine (4MPEA), also known as para-methylphenethylamine, is an organic compound with the chemical formula of C9H13N. 4MPEA 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] 4MPEA also appears to inhibit the human cytochrome P450 enzymes CYP1A2 and CYP2A6, based upon the published literature.[3]

4-Methylphenethylamine
Names
Preferred IUPAC name
2-(4-Methylphenyl)ethan-1-amine
Other names
2-(4-Methylphenyl)ethanamine
2-(p-Tolyl)ethan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.878
UNII
  • CC1=CC=C(C=C1)CCN
Properties
C9H13N
Molar mass 135.210 g·mol−1
Appearance Clear colorless to light yellow liquid[1]
Density 0.93 g/mL[1]
Boiling point 214 °C (417 °F; 487 K)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive[1]
Flash point 91 °C (196 °F)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "4-Methylphenethylamine". Chemical Book. Retrieved 21 July 2014.
  2. 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. S2CID 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.
  3. "4-Methylphenethylamine". PubChem Compound. National Center for Biotechnology Information. Retrieved 21 July 2014.


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