1458. Bucetin

Nomenclature

CAS number: 1083-57-4
N-(4-Ethoxyphenyl)-3-hydroxybutanamide; 3-hydroxy-p-butyrophenetidide; β-hydroxybutyric acid p-phenetidide; p-ethoxy-N-(β-hydroxybutyryl)aniline.
C12H17NO3; mol wt 223.27.
C 64.55%, H 7.67%, N 6.27%, O 21.50%.

Description and references

Phenetidine derivative with analgesic and antipyretic activity. Prepn: G. Ehrhart et al., US 2830087 (1958 to Hoechst); and pharmacology: eidem, Arzneim.-Forsch. 15, 727 (1965). Toxicity data: H. Fujimura, Folia Pharmacol. Jpn. 62, 123 (1966). Metabolism in rabbits: J. Shibasaki et al., Chem. Pharm. Bull. 16, 1726, 2269 (1968). Synergistic effect with ethenzamide, q.v.: H. Kojima et al., Oyo Yakuri 16, 549 (1978), C.A. 90, 81035y (1979). TLC determn in saliva: P. Rohdewald, G. Drehsen, J. Chromatogr. 225, 427 (1981).

Chemical structure

Properties

Crystals from isopropanol, mp 160°. Sparingly sol in water. LD50 in mice (mg/kg): 790 i.p., 2800 orally (Fujimura).

Note

Component in combination analgesics also containing ethenzamide, caffeine and vitamin B1, e.g. Butylon, Bucetalon.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Non-opioids; Anilides