β-Methylphenethylamine (β-Me-PEA, BMPEA, or 1-amino-2-phenylpropane) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

of the phenethylamine class, and a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term meta ...

of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human

TAAR1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is an intracellular amine-activated and G protein-coupled receptor (GPCR) that is primarily ex ...

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 An antihypotensive agent, also known as a vasopressor agent or simply vasopressor, or pressor, is any substance, whether endogeny (biology), endogenous or a medication, that tends to raise low blood pressure. Some antihypotensive drugs act as vas ...

(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 many 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.).

Synthesis

β-Methylphenethylamine can be made by the

catalytic Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organ ...

of 2-phenylpropionitrile with Pd/C in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the 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 question was litigated during the trial of Hi Tech Pharmaceuticals Inc vs. Cohen. Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.

Safety

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 Swedish

food supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

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. Use of β-Methylphenethylamine is also prohibited in sport.

References

{{DEFAULTSORT:Methylphenethylamine, Beta- Stimulants Phenethylamines TAAR1 agonists Norepinephrine releasing agents

Synthesis

Presence

Safety

See also

References