2-Ethoxymethyl salvinorin B

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2-Ethoxymethyl salvinorin B
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
Legal status
Legal status
  • Legal/Uncontrolled
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


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  2. 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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  5. First Look at a New Psychoactive Drug:Symmetry (salvinorin B ethoxymethyl ether). The Entheogen Review. 2008;16(4):136-45.