β-Methylphenethylamine

β-Methylphenethylamine

Systematic (IUPAC) name
2-phenylpropan-1-amine
Clinical data
Legal status	Uncontrolled
Identifiers
CAS Number	582-22-9 Y[PubChem]
ATC code	none
PubChem	CID: 11398
ChemSpider	10920 Y
UNII	6XL7O3V13L Y
ChEMBL	CHEMBL158578
Chemical data
Formula	C9H13N
Molecular mass	135.21 g/mol
SMILES NCC(c1ccccc1)C
InChI InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 Y Key:AXORVIZLPOGIRG-UHFFFAOYSA-N Y
Physical data
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), or 1-amino-2-phenylpropane, is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. 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 good antihypotensive (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.).

A study by Graham and co-workers at the Upjohn Co., comparing a large number of β-methylphenethylamines substituted on the benzene ring showed that β-methylphenethylamine itself had 1/700 x the pressor activity of epinephrine, 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.).

Chemistry

β-Methylphenethylamine has been synthesized by the catalytic hydrogenation of 2-phenylpropionitrile with Pd on charcoal, in absolute ethanol containing 3 equivalents of HCl; the base was isolated in the form of its HCl salt, m.p. 123-124°.

Presence

In 2015, 52% of supplements labeled as containing Acacia rigidula were found to contain BMPEA. Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day. In 2012, however, the FDA determined that BMPEA was not naturally present in Acacia rigidula leaves. This is currently in dispute by Hi-Tech Pharmaceuticals, who claim to have a process of extracting BMPEA from acacia rigidula and have submitted expert witness testimony to the FDA for review.

See also

• Amphetamine
• β-Methylamphetamine
• Phenethylamine