Article ; Online: 8-epi-Salvinorin B
Beilstein Journal of Organic Chemistry, Vol 3, Iss 1, p
crystal structure and affinity at the κ opioid receptor
2007 Volume 1
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 ... ...
| 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. |
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| Keywords | Science ; Q ; Organic chemistry ; QD241-441 |
| Language | English |
| Publishing date | 2007-01-01T00:00:00Z |
| Publisher | Beilstein-Institut |
| Document type | Article ; Online |
| Database | BASE - Bielefeld Academic Search Engine (life sciences selection) |
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