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Synthesis and Characterization of Thienorphine and Its Glucuronide Conjugate

Chun‐He Liu, He Liu, Xiangyu Han, Bo Wu, Bo‐Hua Zhong, Ze‐Hui Gong

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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.

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What this paper is about

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.

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Available 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.

Key concepts: Chemistry, Glucuronide, Conjugate, Demethylation, Alkylation, Metabolite, Agonist, Stereochemistry

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