Synthesis and Characterization of Thienorphine and Its Glucuronide Conjugate

Abstract

Abstract Thienorphine (1) is a very potent oripavine derivative with mixed agonist and antagonist opioid receptor activities. It was prepared with 7α‐acetyl‐6,14‐ endoethenotetrahydrothebaine as stated material by Grignard reaction, cyanidation, demethylation, and N‐alkylation. The structure of 1 · HCl was elucidated by X‐ray analysis. As part of a continuing program to define the metabolism and distribution of thienorphine in animals and man, the putative metabolite, 3‐glucuronide, was synthesized.