2-Ethoxymethyl salvinorin B
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Systematic (IUPAC) name | |
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(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 | |
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Identifiers | |
ATC code | none |
PubChem | CID 24873526 |
Chemical data | |
Formula | C24H32O8 |
Molar mass | 448.505 g/mol[[Script error: No such module "String".]] |
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2-Ethoxymethyl salvinorin B (symmetry, 2-EtOMe-Sal B) 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,[1] as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.[2]
2-Ethoxymethyl salvinorin B 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.[3] 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.[4] Human bioassays found the compound to be active at 50 μg, but generally unpleasant in effects.[5]
See also
References
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- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Medana C, Massolino C, Pazzi M, Baiocchi C (2006). "Determination of salvinorins and divinatorins in Salvia divinorum leaves by liquid chromatography/multistage mass spectrometry". Rapid Communications in Mass Spectrometry : RCM. 20 (2): 131–6. doi:10.1002/rcm.2288. PMID 16331747.
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- ↑ First Look at a New Psychoactive Drug:Symmetry (salvinorin B ethoxymethyl ether). The Entheogen Review. 2008;16(4):136-45.
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