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Revision as of 08:19, 2 February 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharmacology|errors)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound | |
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| Formula | C23H30O8 |
| Molar mass | 434 g/mol g·mol |
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2-Methoxymethyl salvinorin B is a semi-synthetic analogue of the natural product salvinorin A which is used in scientific research. It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A, and has increased affinity and efficacy at the κ-opioid receptor. Like the related compound herkinorin, 2-methoxymethyl 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.
2-Methoxymethyl salvinorin B has a Ki of 0.60 nM at the κ opioid receptor, and is around 5x more potent than Salvinorin A in animal studies, although it is still only half as potent as its stronger homologue 2-Ethoxymethyl Salvinorin B.
See also
References
- Inan S, Lee DY, Liu-Chen LY, Cowan A (2009). "Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A". Naunyn-Schmiedeberg's Archives of Pharmacology. 379 (3): 263–70. doi:10.1007/s00210-008-0358-8. PMID 18925386.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ (2008). "Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways". Journal of Neurochemistry. 107 (6): 1753–65. doi:10.1111/j.1471-4159.2008.05745.x. PMC 2606093. PMID 19014370.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY (2008). "2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A". The Journal of Pharmacology and Experimental Therapeutics. 324 (3): 1073–83. doi:10.1124/jpet.107.132142. PMC 2519046. PMID 18089845.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B (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}}: Unknown parameter|month=ignored (help)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 (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}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL (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}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link)