Chemistry:Salvinorin B methoxymethyl ether
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| Formula | C23H30O8 |
| Molar mass | 434.485 g·mol−1 |
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Salvinorin B methoxymethyl ether (2-O-methoxymethylsalvinorin B) is a semi-synthetic analogue of the natural product salvinorin A used in scientific research.[1][2] It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A,[3] and has increased affinity and potency at the κ-opioid receptor. It is prepared from salvinorin B.[4] The crystal structure is almost superimposable with that of salvinorin A.[5] Structures bound to the κ-opioid receptor have also been reported.[6]
Salvinorin B methoxymethyl ether has a Ki of 0.60 nM at the κ opioid receptor,[7] and is around five times more potent than salvinorin A in animal studies, although it is still only half as potent as its ethoxymethyl ether homolog, 'symmetry'.[7][8][9]
See also
References
- ↑ "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): 263–270. March 2009. doi:10.1007/s00210-008-0358-8. PMID 18925386.
- ↑ "Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways". Journal of Neurochemistry 107 (6): 1753–1765. December 2008. doi:10.1111/j.1471-4159.2008.05745.x. PMID 19014370.
- ↑ "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): 1073–1083. March 2008. doi:10.1124/jpet.107.132142. PMID 18089845.
- ↑ "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues". Bioorganic & Medicinal Chemistry Letters 15 (16): 3744–3747. August 2005. doi:10.1016/j.bmcl.2005.05.048. PMID 15993589.
- ↑ "Salvinorin B methoxymethyl ether". Acta Crystallographica Section E 68 (11): o3225–o3226. 2012. doi:10.1107/s1600536812043449. PMID 23284529. Bibcode: 2012AcCrE..68O3225M.
- ↑ "Ligand and G-protein selectivity in the κ-opioid receptor". Nature 617 (7960): 417–425. May 2023. doi:10.1038/s41586-023-06030-7. PMID 37138078. Bibcode: 2023Natur.617..417H.
- ↑ 7.0 7.1 "Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry 16 (3): 1279–1286. February 2008. doi:10.1016/j.bmc.2007.10.067. PMID 17981041.
- ↑ "Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats". Psychopharmacology 203 (2): 203–211. April 2009. doi:10.1007/s00213-008-1458-3. PMID 19153716.
- ↑ "First look at a new psychoactive drug: symmetry (salvinorin B ethoxymethyl ether)". Entheogen Review 16 (4): 136–145. 2008. ISSN 1066-1913. https://www.erowid.org/chemicals/salvinorin_b_ethoxymethyl_ether/salvinorin_b_ethoxymethyl_ether_article1.shtml.
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