Preparation and analgesic activity of 3,6-diacetylnormorphine and 6-acetylnormorphine.
3,6-Diacetylnormorphine (norheroin) and 6-acetylnormorphine have been prepared in excellent yield through the 3,N-bis(tert-butoxycarbonyl) derivative of normorphine via acetylation and selective removal of protecting groups. This general procedure would be applicable to the preparation of various 3,6-diesters or 6-monoesters of normorphine. The analgesic potency of norheroin was found to be the same as that of 6-acetylnormorphine, about 0.05 that of heroin. The onset, peak, and duration of action of these compounds were nearly identical and comparable with morphine.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D003932:Heroin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D006358:Hot Temperature; D051379:Mice; D009022:Morphine Derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D011930:Reaction Time / Q000187:drug effects
D000700:Analgesics; D009022:Morphine Derivatives; D003932:Heroin