Synthesis, Structure Elucidation, and Pharmacological Evaluation of 5‐Methyl‐oxymorphone (= 4,5α‐epoxy‐3,14‐dihydroxy‐5,17‐dimethylmorphinan‐6‐one)

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Abstract
Synthesis of 5‐methyl‐oxymorphone (3) was accomplished by oxidation of 5‐methylthebaine (4) with performic acid, followed by catalytic hydrogenation and cleavage of the 3‐MeO group. X‐Ray analysis confirmed that the 14‐OH group has, like the one in oxymorphone (1), β‐orientation. Pharmacological studies in vivo and in vitro showed 3 to possess slightly less opioid agonistic properties than 1.