2710. Cyclizine

Nomenclature

CAS number: 82-92-8
1-Diphenylmethyl-4-methylpiperazine; N-benzhydryl-N′-methylpiperazine; N-methyl-N′-benzhydrylpiperazine; (N-benzhydryl)(N′-methyl)diethylenediamine; Compd 47-83; Wellcome prepn 47-83; Marzine (GlaxoWellcome); Marezine (Himmel).
C18H22N2; mol wt 266.38.
C 81.16%, H 8.32%, N 10.52%.

Description and references

Prepn: R. Baltzly et al., J. Org. Chem. 14, 775 (1949); eidem, US 2630435 (1953 to Burroughs Wellcome). Metabolism: R. Kuntzman et al., Ann. N.Y. Acad. Sci. 226, 131 (1973). Physical properties and analysis: S. A. Benezra, Anal. Profiles Drug Subs. 6, 83 (1977). Crystallographic study: V. Bertolasi et al., Acta Crystallogr. B36, 1975 (1980). HPLC determn: R. B. Walker, I. Kanfer, J. Chromatogr. B 672, 172 (1995). Clinical antiemetic efficacy: G. Rowlands, W. J. Currie, Br. J. Clin. Pract. 30, 197 (1976); W. N. Chestnutt et al., Eur. J. Anaesthesiol. 3, 27 (1986).

Chemical structure

Properties

Light-sensitive crystals from petr ether, mp 105.5-107.5°. uv max (0.1N HCl): 269, 263, 258, 225 (ε 540, 742, 694, 11300). Soly in g/ml at 25°: chloroform 1.1; ether 0.17; ethanol 0.17; in mg/ml: water <0.1.

Derivative

Hydrochloride.

Nomenclature

CAS number: 303-25-3
Valoid (Glaxo Wellcome).
C18H22N2.HCl; mol wt 302.84.
C 71.39%, H 7.66%, N 9.25%, Cl 11.71%.

Properties

Crystals, moderately sol in water. Protect from light.

Therapeutic Category

Antiemetic.

Therapeutic Category (Veterinary)

Antiemetic.

Keywords

Antiemetic