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| ECHA InfoCard | 100.008.619 |
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| Formula | C9H13N |
| Molar mass | 135.210 g·mol−1 |
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| Density | 0.93 g/cm3 |
| Boiling point | 80 °C (176 °F) (at 10 mm Hg) |
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β-Methylphenethylamine (β-Me-PEA,BMPEA, or1-amino-2-phenylpropane) is anorganic compound of thephenethylamine class, and apositional isomer of the drugamphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are humanTAAR1 agonists.[2] In appearance, it is a colorless or yellowish liquid.
Relatively little information has been published about this substance. Hartung and Munch reported that it had goodantihypotensive (pressor) activity in experimental animals, and that it was orally active. The MLD (minimum lethal dose) for the HCl salt was given as 500 mg/kg (rat, s.c.) and 50 mg/kg (rabbit, i.v.).[3]
A study by Graham and co-workers at the Upjohn Co., comparing many β-methylphenethylamines substituted on the benzene ring showed that β-methylphenethylamine itself had 1/700 x the pressor activity ofepinephrine, corresponding to ~ 1/3 the potency of amphetamine. The β-methyl compound also had ~ 2 x the broncho-dilating power of amphetamine (as measured using the isolated rabbit lung), and an LD50 of 50 mg/kg (rat, i.v.).[4]
β-Methylphenethylamine can be made by thecatalytichydrogenation of 2-phenylpropionitrile withPd/C in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.[3]
In 2015, 52% of supplements labeled as containingAcacia rigidula were found to contain BMPEA.[5][6] Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day.[5] In 2012, however, the FDA determined that BMPEA was not naturally present inAcacia rigidula leaves.[7] This question was litigated during the trial ofHi Tech Pharmaceuticals Inc vs. Cohen.[8][9] Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.[10]
β-Methylphenethylamine was associated with a case of cerebral hemorrhage in a Swedish athlete and first time user. The female victim with no medical history had taken a Swedishfood supplement with 290 mg β-methylphenethylamine per serving before commencing her usual exercises. After about 30 minutes the first symptoms appeared. The presence of the active ingredient was not declared on the label.[11] Use of β-Methylphenethylamine is also prohibited in sports.[12]
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.
they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.
