title: Hashish. Unsaturated side-chain analogues of delta8-tetrahydrocannabinol with potent biological activity.
abstract: Two delta8-THC derivatives, 4a and 4b, with functionalized side chains were synthesized. Treatment of (+)-trans-p-mentha-2,8-dien-1-ol with the resorcinal 2b followed by removal of the dithiol group with HgO--BF3-Et2O gave the aldehyde 3b. A Wittig reaction of dimethyl (2-oxoheptyl)phosphate with 3b furnished 4a, which was reduced to 4b. Compounds 4a and 4b showed potent cannabinoid-like activity in mice.
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D004295:Dihydroxyphenylalanine / Q000494:pharmacology; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004357:Drug Synergism; D051379:Mice; D011619:Psychotropic Drugs / Q000138:chemical synthesis* / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D011619:Psychotropic Drugs; D004295:Dihydroxyphenylalanine; D013759:Dronabinol