N-methylphenethylamine
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| Names | |
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Preferred IUPAC name
N-Methyl-2-phenylethan-1-amine
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| Other names
N-Methyl-2-phenylethanamine
N-Methylphenethylamine N-Methyl-β-phenethylamine |
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| Identifiers | |
| 589-08-2 | |
| 3D model (Jmol) | Interactive image |
| ChEMBL |
ChEMBL45763 
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| ChemSpider |
11019
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| ECHA InfoCard | 100.008.758 |
| PubChem | 11503 |
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| Properties | |
| C9H13N | |
| Molar mass | 135.21 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.93 g/mL |
| Boiling point | 203 °C (397 °F; 476 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
N-Methylphenethylamine (NMPEA) is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1 μg over 24 hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate. PEA and NMPEA are both alkaloids that are found in a number of different plant species as well. Some Acacia species, such as A. rigidula, contain remarkably high levels of NMPEA (~2300–5300 ppm). NMPEA is also present at low concentrations (< 10 ppm) in a wide range of foodstuffs.
NMPEA is a positional isomer of amphetamine.
In appearance, NMPEA is a colorless liquid. NMPEA is a weak base, with pKa = 10.14; pKb = 3.86 (calculated from data given as Kb). It forms a hydrochloride salt, m.p. 162–164°C.
Although NMPEA is available commercially, it may be synthesized by various methods. An early synthesis reported by Carothers and co-workers involved conversion of phenethylamine to its p-toluenesulfonamide, followed by N-methylation using methyl iodide, then hydrolysis of the sulfonamide. A more recent method, similar in principle, and used for making NMPEA radio-labeled with 14C in the N-methyl group, started with the conversion of phenethylamine to its trifluoroacetamide. This was N-methylated (in this particular case using 14C – labeled methyl iodide), and then the amide hydrolyzed.
NMPEA is a substrate for both MAO-A (KM = 58.8 μM) and MAO-B (KM = 4.13 μM) from rat brain mitochondria.
NMPEA is a pressor, with 1/350 x the potency of epinephrine.
Like its parent compound, PEA, and isomer, amphetamine, NMPEA is a potent agonist of human TAAR1. It has comparable pharmacodynamic and toxicodynamic properties to that of phenethylamine, amphetamine, and other methylphenethylamines in rats.
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