464. 4-Amino-3-phenylbutyric Acid

Nomenclature

CAS number: 1078-21-3
β-(Aminomethyl)benzenepropanoic acid; β-(aminomethyl)hydrocinnamic acid; 4-amino-3-phenylbutanoic acid; β-phenyl-γ-aminobutyric acid; fenibut; phenibut; phenigamma; phenygam; PhGABA.
C10H13NO2; mol wt 179.22.
C 67.02%, H 7.31%, N 7.82%, O 17.85%.

Description and references

Prepn starting with α,γ-diamino-β-phenylpropane: Jackson, Kenner, J. Chem. Soc. 1928, 1657. Alternate prepn: Cologne, Pouchol, Bull. Soc. Chim. Fr. 1962, 598. Pharmacology: R. A. Khaunina, Bull. Exp. Biol. Med. 57, 52 (1964). Structure-activity studies: idem, Farmakol. Toksikol. 31, 202 (1968). Activity studies of the isomers: eidem, Byull. Eksp. Biol. Med. 72, 49 (1971), C.A. 76, 81208t (1972). Review of pharmacology and clinical experience: I. Lapin, CNS Drug Rev. 7, 471-481 (2001).

Chemical structure

Properties

mp 250-253° (dec).

Derivative

Hydrobromide.

Nomenclature

CAS number: 103095-38-1
C10H13NO2.HBr; mol wt 260.13.
C 46.17%, H 5.42%, N 5.38%, O 12.30%, Br 30.72%.

Properties

Irregular platelets from benzene, mp 114°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 3060-41-1
C10H13NO2.HCl.

Properties

LD50 in mice, rats (mg/kg): 900, 700 i.p. (Khaunina, 1964).

Therapeutic Category

Anxiolytic.

Keywords

Phenibut: Anxiolytic