161. Adiphenine

Nomenclature

CAS number: 64-95-9
α-Phenylbenzeneacetic acid 2-(diethylamino)ethyl ester; 2-diethylaminoethyl diphenylacetate; diphenylacetyldiethylaminoethanol; diphacil; spasmolytin.
C20H25NO2; mol wt 311.42.
C 77.14%, H 8.09%, N 4.50%, O 10.28%.

Description and references

Anticholinergic. Prepn: DE 626539 (1936 to Ciba); and pharmacology: T. Wagner-Jauregg et al., Ber. 72, 1551 (1939); R. R. Burtner, J. W. Cusic, J. Am. Chem. Soc. 65, 262 (1943). Crystal and molecular structure: J. J. Guy, T. A. Hamor, J. Chem. Soc. Perkin Trans. 2 1973, 942. Effect on TSH release: D. Jordan et al., Eur. J. Pharmacol. 41, 53 (1977). HPLC determn in tissues: J. Michelot et al., J. Chromatogr. 257, 395 (1983). Pharmacokinetics: idem et al., Xenobiotica 11, 123 (1981).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 50-42-0
Trasentine (Ciba-Geigy).
C20H25NO2.HCl; mol wt 347.88.
C 69.05%, H 7.53%, N 4.03%, O 9.20%, Cl 10.19%.

Properties

Crystals, mp 113-114°. Readily sol in water; very sparingly sol in alcohol, ether. LD50 i.p. in mice: 0.24 g/kg (Burtner, Cusic).

Therapeutic Category

Antispasmodic.

Keywords

Antispasmodic; Antimuscarinic