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| Names | |
|---|---|
| Preferred IUPAC name
2-(2-Methylphenyl)ethan-1-amine | |
| Other names
2-(2-Methylphenyl)ethanamine | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.199.500 
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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 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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Corrosive; causes burns |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 (atrace amine).[3]
Very little data, even on toxicity, is available about its effects on humans other than that it activates the human TAAR1 receptor.
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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| TAAR1 |
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| TAAR2 |
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| TAAR5 |
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† References for all endogenous human TAAR1 ligands are provided at List of trace amines
‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.
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