Synthesis and Characterization of Thienorphine and Its Glucuronide Conjugate

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 e...

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Bibliographic Details
Published in:Synthetic communications 2005-03, Vol.35 (5), p.701-710
Main Authors: Liu, Chun-He, Liu, He, Han, Xiang-Yu, Wu, Bo, Zhong, Bo-Hua, Gong, Ze-Hui
Format: Article
Language:English
Subjects:
glucuronide conjugate
Thienorphine
X-ray analysis
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-200050367