Salvinorin B ethoxymethyl ether
 | It has been suggested that this article be merged into Salvinorin B methoxymethyl ether. (Discuss) Proposed since May 2014. |
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| Formula | C24H32O8 |
| Molar mass | 448.505 g/mol g·mol−1 |
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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,[1] as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.[2]
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.[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.[5]
See also
References
- ^ Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B (August 2005). "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues". Bioorganic & Medicinal Chemistry Letters. 15 (16): 3744–7. doi:10.1016/j.bmcl.2005.05.048. PMID 15993589.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C (February 2008). "Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry. 16 (3): 1279–86. doi:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL (April 2009). "Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats". Psychopharmacology. 203 (2): 203–11. doi:10.1007/s00213-008-1458-3. PMID 19153716.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ First Look at a New Psychoactive Drug:Symmetry (salvinorin B ethoxymethyl ether). The Entheogen Review. 2008;16(4):136-45.