576. Amoxapine

Nomenclature

CAS number: 14028-44-5
2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine; CL-67772; Asendin (Lederle); Asendis (Wyeth); Defanyl (Lederle); Demolox (Am. Cyanamid); Moxadil (Lederle).
C17H16ClN3O; mol wt 313.78.
C 65.07%, H 5.14%, Cl 11.30%, N 13.39%, O 5.10%.

Description and references

Prepn: J. Schmutz et al., Helv. Chim. Acta 50, 245 (1967); eidem, Chim. Ther. 2, 424 (1967); C. F. Howell et al., FR 1508536; eidem, US 3663696 (1968, 1972 both to Am. Cyanamid). Analysis of amoxapine and its metabolites by GLC: T. B. Cooper, R. G. Kelly, J. Pharm. Sci. 68, 216 (1979). X-ray crystallography: D. B. Cosulich, F. M. Lovell, Acta Crystallogr. B33, 1147 (1977). Pharmacology: E. N. Greenblatt et al., Arch. Int. Pharmacodyn. Ther. 233, 107 (1978). Clinical study: R. Takahashi et al., J. Int. Med. Res. 7, 7 (1979). Review: T. A. Ban, Psychopharmacol. Bull. 15, 22-25 (1979); E. N. Greenblatt et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 1-18. Review of pharmacology and therapeutic efficacy: S. G. Jue et al., Drugs 24, 1-23 (1982).

Chemical structure

Properties

Crystals from benzene/petr ether, mp 175-176°. Freely sol in chloroform; sol in tetrahydrofuran; sparingly sol in methanol, toluene; slightly sol in acetone. Practically insol in water. LD50 in mice (mg/kg): 122 i.p.; 112 orally (Howell, 1972).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics