|Preferred IUPAC name
|Jmol 3D model||Interactive image|
|Molar mass||135.21 g·mol−1|
|Appearance||Clear colorless to light yellow liquid|
|Boiling point||214 °C (417 °F; 487 K) |
|Flash point||91 °C (196 °F)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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, a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine (a trace amine). 4MPEA also appears to inhibit the human cytochrome P450 enzymes CYP1A2 and CYP2A6, based upon the published literature.
- "4-Methylphenethylamine". Chemical Book. Retrieved 21 July 2014.
- 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.
- "4-Methylphenethylamine". PubChem Compound. National Center for Biotechnology Information. Retrieved 21 July 2014.
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