9-Nor-9-hydroxyhexahydrocannabinols. Synthesis, Some behavioral and analgesic properties, and comparison with the tetrahydrocannabinols.
The racemic mixture and levo isomer of both 9-nor-9alpha-hydroxyhexahydrocannabinol and its 9beta-hydroxy isomer were prepared. Both alpha-and beta-hydroxy compounds were active in the dog ataxia test and depressed spontaneous activity in mice. However, only the beta-hydroxy compound was an analgesic in mice morphine-like potency. The behavioral and analgesic properties of these compounds may be mediated through different sites or mechanisms and may, therefore, be separable.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects*; D002186:Cannabinoids / Q000138:chemical synthesis*; D002187:Cannabinol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D004285:Dogs; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013997:Time Factors
D000700:Analgesics; D002186:Cannabinoids; D013759:Dronabinol; D002187:Cannabinol