title: 2,6-Methano-3-benzazocine-11-ropanols. Lack of antagonism between optical antipodes and observation of potent narcotic antagonism by two n-methyl derivatives.
abstract: Resolution of a 2,6-methano-3-benzazocine-11-propanol analogue of buprenorphine showed that the biological activity resides in the levo antipode. An attempt to enhance agonist activity by preparation of N-methyl derivatives resulted in two compounds three and five times as potent as nalorphine as antagonists of phenazocine. These compounds are the most potent N-methyl narcotic antagonists reported to date.
mesh_terms: D000818:Animals; D001392:Azocines / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D009292:Narcotic Antagonists / Q000138:chemical synthesis*; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D001392:Azocines; D009292:Narcotic Antagonists