β-Methylphenethylamine

Source: Wikipedia, the free encyclopedia.

β-Methylphenethylamine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2-Phenylpropan-1-amine
JSmol)
Density0.93 g/cm3
Boiling point80 °C (176 °F) (at 10 mm Hg)
SMILES
  • NCC(c1ccccc1)C
  • InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 checkY
  • Key:AXORVIZLPOGIRG-UHFFFAOYSA-N checkY
  (verify)

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

positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 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 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.).[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 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.).[4]

Synthesis

β-Methylphenethylamine can be made by the

Pd/C in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.[3]

Presence

In 2015, 52% of supplements labeled as containing

Acacia 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 in Acacia rigidula leaves.[7] This question was litigated during the trial of Hi Tech Pharmaceuticals Inc vs. Cohen.[8][9] Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.[10]

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 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]

See also

References

  1. FDA
    . 22 February 2023. Retrieved 9 June 2023.
  2. S2CID 10829497
    . 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.
  3. ^
    doi:10.1021/ja01356a036
    .
  4. doi:10.1021/ie50422a010
    .
  5. ^
    PMID 25847603
    .
  6. ^ The Editorial Board (13 April 2015). "Conflicts of Interest at the F.D.A." The New York Times. Retrieved 13 April 2015. they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.
  7. ^ Goodman B (7 April 2015). "Untested Stimulant Still in Dietary Supplements". WebMD.
  8. PMID 29114742
    .
  9. ^ "BMPEA and Acacia Rigidula: Hi-Tech Pharmaceuticals Fights Back". PricePlow. 26 October 2015. Retrieved 27 October 2015.
  10. PMID 30422217
    .
  11. PMID 26075771
    .
  12. PMID 24633566
    .
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