β-Methylphenethylamine

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β-Methylphenethylamine
Beta-methylphenethylamine.png
Systematic (IUPAC) name
2-phenylpropan-1-amine
Clinical data
Legal status Uncontrolled
Identifiers
CAS number 582-22-9
ATC code ?
PubChem CID 11398
ChemSpider 10920 YesY
ChEMBL CHEMBL158578
Chemical data
Formula C9H13N 
Mol. mass 135.21 g/mol
 YesY (what is this?)  (verify)

β-Methylphenethylamine (β-Me-PEA), 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 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 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.).1

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.).2

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°.1

B.p. = 80°C at 10 mm Hg pressure.

Density = 0.93 g/mL

See also

References

  1. ^ a b W. H. Hartung and J. C. Munch (1931). "Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines." J. Am. Chem. Soc. 53 1875-1879.
  2. ^ B. E. Graham, G. F. Cartland and E. H. Woodruff (1945). "Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen." Ind. Eng. Chem. 37 149-151.