Optical resolution of some homobenzomorphan derivatives and their pharmacological properties.
Racemic 1,4-dimethyl- (1), 1,4,12 alpha-trimethyl- (2), and 1,4,12 beta-trimethyl-10-hydroxy-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine (3) have been optically resolved. The analgesic potency and physical-dependence capacity of the optical isomers and their racemic parents were determined. The levo isomers of compounds 2 and 3 were analgesically much more potent than the dextro isomers and were equipotent with morphine. Optical resolution gave no effect on the activity of compound 1. None of the optical isomers and the racemates suppressed the morphine-withdrawal syndrome in the monkey.
D000700:Analgesics; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D000882:Haplorhini; D006801:Humans; D008253:Macaca mulatta; D051379:Mice; D009019:Morphinans / Q000302:isolation & purification*; D012646:Self Administration; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013375:Substance Withdrawal Syndrome / Q000503:physiopathology; D019966:Substance-Related Disorders / Q000209:etiology
D000700:Analgesics; D001575:Benzomorphans; D009019:Morphinans