B/C-cis- and -trans-1,3,4,9,10,10a-Hexahydro-2H-10,4a-methanoiminoethanophenanthrene (homo- and homoisomorphinan) derivatives as analgesics.
N-Alkyl derivatives of B/C-cis- and B/C-trans-6-hydroxy-1,3,4,9,10,10a-hexahydro-2H-10,4a-methanoimino-ethanophenanthrene have been prepared. The analgesic potency and physical dependence capacity of these compounds were determined. The N-methyl derivatives were analgesically equipotent with morphine. None of these compounds except the N-methyl-B/C-trans isomer 2b suppressed or precipitated the abstinence syndrome. Compound 2b was a narcotic agonist. The N-methyl-B/C-cis compound 2a appears to warrant further examination for its potential as a potent analgesic having no physical dependence liability.
D000700:Analgesics / Q000138:chemical synthesis*; D000701:Analgesics, Opioid / Q000138:chemical synthesis; D000818:Animals; D000882:Haplorhini; D008253:Macaca mulatta; D051379:Mice; D008968:Molecular Conformation; D009019:Morphinans / Q000138:chemical synthesis* / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
D000700:Analgesics; D000701:Analgesics, Opioid; D009019:Morphinans