8-epi-Salvinorin B: crystal structure and affinity at the kappa opioid receptor.

 

8-epi-Salvinorin B: crystal structure and affinity at the kappa opioid receptor.

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Title: 8-epi-Salvinorin B: crystal structure and affinity at the kappa opioid receptor.
Author: Munro, Thomas A; Duncan, Katharine K; Staples, Richard J; Xu, Wei; Liu-Chen, Lee-Yuan; Béguin, Cécile; Carlezon, William A; Cohen, Bruce M
Abstract: There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopts a boat conformation with the furan equatorial. Several lines of evidence suggest that epimerization proceeds via enolization of the lactone rather than a previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity.
Citation: Beilstein journal of organic chemistry. 2007 Jan 09;3: 1.
PMC: http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=17212822

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