Synthesis and analgesic activity of some 14.beta.-substituted analogs of morphine

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Abstract
Treatment ot 14.beta.-nitrocodeinone with sodium borohydride gave the codeine derivative which was reduced with Zn 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. The 14.beta.-substituted codeine and codeinones were O-demethylated to the corresponding morphine analog with boron tribromide. With the exception of 14.beta.-nitromorphinone, which was weak in activity, all other 14.beta.-substituted morphine derivatives were approximately equal in potency to normorphine in the guinea pig ileum preparation.