Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. 111.’ Alcohols of the 6,14-endo-EthenotetrahydrooripavinSee ries and Derived Analogs of N- Allylnormorphine and -norcodeine

Abstract

Secondary and tertiary alcohols of general structures IV and V have been prepared by the demethylation of the corresponding bases I and I1 described in part I1 of this series. The phenols so obtained are analgesics of extremely high potency, up to an unprecedented 12,000 times that of morphine. The bases of this and earlier series have been converted into analogs of N-allylnormorphine and N-allylnorcodeine of general structures XI and XI1 via the N-cyanonor compounds and via novel N,N’-methylenebis compounds XI11 resulting from the reaction of the bases I and I1 with methyl azodicarboxylate. Some bases of the series XI1 are morphine antagonists of unprecedented potency, up to 150 times that of N-allylnormorphine