1119. Benzquinamide

Nomenclature

CAS number: 63-12-7
2-(Acetyloxy)-N,N-diethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-3-carboxamide; N,N-diethyl-1,3,4,6,7,11b-hexahydro-2-hydroxy-9,10-dimethoxy-2H-benzo[a]quinolizine-3-carboxamide acetate; 2-acetoxy-3-(N,N-diethylcarboxamido)-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzopyridocoline; 2-hydroxy-3-diethylcarbamyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine acetate; BZQ; NSC-64375; P-2647; Emete-Con (Roerig); Promecon (Searle); Quantril (Roerig).
C22H32N2O5; mol wt 404.50.
C 65.32%, H 7.97%, N 6.93%, O 19.78%.

Description and references

Prepn: Trettner, US 3053845 (1962 to Pfizer). Pharmacology: Scriabine et al., J. Am. Med. Assoc. 184, 276 (1963); Kadzielawa, Gumulka, Arch. Int. Pharmacodyn. Ther. 163, 139 (1966). Metabolic studies: Koe, Pinson, J. Med. Chem. 7, 635 (1964); Wiseman et al., Biochem. Pharmacol. 13, 1421 (1964). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Crystals from diisopropyl ether, mp 130-131.5°. LD50 orally in rats: 990 mg/kg; i.p. in mice: 376 mg/kg (Goldenthal).

Therapeutic Category

Antipsychotic, antiemetic.

Keywords

Antiemetic; Antipsychotic; Other Tricyclics