Optical resolution of (+/-)-2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans and their pharmacological properties.
The levo and dextro isomers of 2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans have been prepared. The analgesic potency and physical dependence capacity of the optical isomers and their racemic parents were determined. The 9alpha-propyl levo isomer was analgesically equipotent with morphine; the 9beta-propyl levo isomer was considerably more potent subcutaneously and equipotent orally. None of the optical isomers suppressed the withdrawal syndrome; the 9beta-propyl levo isomer exacerbated the withdrawal syndrome.
D000700:Analgesics / Q000138:chemical synthesis; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000882:Haplorhini; D006801:Humans; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis*; D009021:Morphine Dependence / Q000503:physiopathology; D009904:Optical Rotation; D013237:Stereoisomerism; D019966:Substance-Related Disorders / Q000209:etiology
D000700:Analgesics; D001575:Benzomorphans; D009019:Morphinans