7225. Phenethylamine

Nomenclature

CAS number: 64-04-0
Benzeneethanamine; β-phenylethylamine; 1-amino-2-phenylethane; β-aminoethylbenzene; PEA.
C8H11N; mol wt 121.18.
C 79.29%, H 9.15%, N 11.56%.

Description and references

Endogenous amine related structurally and pharmacologically to amphetamine: P. Mantegazza, M. Riva, J. Pharm. Pharmacol. 15, 472 (1963). Present in oil of bitter almonds. Found in normal human urine (about 30 μg/liter). Prepn: Johnson, Guest, Am. Chem. J. 42, 346 (1909); Robinson, Snyder, Org. Synth. coll. vol. III, 720 (1955). Elevated levels in urine due to paranoid chronic schizophrenia: S. G. Potkin et al., Science 206, 470 (1979); due to stress: M. A. Paulos, R. E. Tessel, ibid. 215, 1127 (1982).

Chemical structure

Properties

Liquid. Fishy odor. Absorbs CO2 from air. Does not solidify when cooled in an ice-salt mixture. Strong base. d425 0.9640; bp 194.5-195°. Sol in water. Freely sol in alc, ether.

Derivative

Hydrochloride.

Nomenclature

CAS number: 156-28-5
C8H11N.HCl; mol wt 157.64.
C 60.95%, H 7.67%, N 8.89%, Cl 22.49%.

Properties

Orthorhombic bipyramidal platelets from abs alcohol, mp 217°. Freely sol in water (100 parts H2O will dissolve 80 parts at 15°). Sol in alc. Insol in ether. LD50 s.c. in mice: 470 mg/kg (Mantegazza, Riva).

Caution

Skin irritant and possible sensitizer.