Synthesis and analgesic activity of some 14 beta-substituted analogues of morphine.
Treatment of 14 beta-nitrocodeinone with sodium borohydride gave the codeine derivative which was reduced with zinc dust in acetic anhydride-acetic acid solution to give 14 beta-acetamidocodeine 6-acetate. 14 beta-Thiocyanatocodeinone was obtained from the reaction of thebaine with thiocyanogen and was reduced to 14 beta-mercaptocodeine with lithium aluminum hydride. 14 beta-Bromo- and 14 beta-chlorocodeinone were prepared by the reaction of thebaine with N-bromosuccinimide and N-chlorosuccinimide, respectively. These 14 beta-substituted codeine and codeinones were O-demethylated to the corresponding morphine analogues with boron tribromide. With the exception of 14 beta-nitromorphinone, which was weak in activity, all the other 14 beta-substituted morphine derivatives were approximately equal in potency to normorphine in the guinea pig ileum preparation.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D009022:Morphine Derivatives / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D009022:Morphine Derivatives