4-Methylphenethylamine
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| 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) |
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| ChemSpider | |
| ECHA InfoCard | 100.019.878 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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). | |
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]
References
- ^ a b c d e "4-Methylphenethylamine". Chemical Book. Retrieved 21 July 2014.
- ^ 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. 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. - ^ "4-Methylphenethylamine". PubChem Compound. National Center for Biotechnology Information. Retrieved 21 July 2014.