Salvinorin B ethoxymethyl ether
|Systematic (IUPAC) name|
|(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(ethoxymethoxy)-2-(3-furanyl)dodecahydro -6a,10b-dimethyl-4,10-dioxo-2H-naphtho-[2,1-c]pyran-7-carboxylic acid methyl ester|
|Mol. mass||448.505 g/mol|
Salvinorin B ethoxymethyl ether (2-O-ethoxymethylsalvinorin B, symmetry) is a semi-synthetic analogue of the natural product salvinorin A, with a longer duration of action of around 3 hours (compared to less than 30 minutes for salvinorin A), and increased affinity and intrinsic activity at the κ-opioid receptor. Like the related compound herkinorin, 2-ethoxymethyl salvinorin B is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.
Salvinorin B ethoxymethyl ether has a Ki of 0.32 nM at the κ-opioid receptor, and around 3,000 times selectivity over the μ- and δ-opioid receptors, making it one of the most potent and selective kappa agonists yet discovered. In animal studies it fully substituted for salvinorin A and the synthetic kappa agonist U-69593, and was active at doses as low as 0.005 mg/kg. Human bioassays found the compound to be active at 50 μg.
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