Salvinorin B methoxymethyl ether

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 made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation.[4] The crystal structure reveals that the methoxy group overlaps with the acetyl group of salvinorin A, but with a different orientation.[5]

Salvinorin B methoxymethyl ether
Clinical data
ATC code
  • none
Legal status
Legal status
  • Legal/Uncontrolled
Identifiers
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC23H30O8
Molar mass434.485 g·mol−1
3D model (JSmol)
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Salvinorin B methoxymethyl ether has a Ki of 0.60 nM at the κ opioid receptor,[6] and is around five times more potent than salvinorin A in animal studies, although it is still only half as potent as its stronger homolog salvinorin B ethoxymethyl ether (symmetry).[7]

See also

References
  1. Inan S; Lee DY; Liu-Chen LY; Cowan A (March 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.
  2. McLennan GP; Kiss A; Miyatake M; Belcheva MM; Chambers KT; Pozek JJ; Mohabbat Y; Moyer RA; Bohn LM; Coscia CJ (December 2008). "Kappa opioids promote the proliferation of astrocytes via Gβγ and β-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.
  3. Wang Y; Chen Y; Xu W; Lee DY; Ma Z; Rawls SM; Cowan A; Liu-Chen LY (March 2008). "2-Methoxymethyl-Salvinorin B Is a Potent κ 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.
  4. 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.
  5. Munro, Thomas A.; Ho, Douglas M.; Cohen, Bruce M. (2012-11-01). "Salvinorin B methoxymethyl ether". Acta Crystallographica Section E. 68 (11): o3225–o3226. doi:10.1107/s1600536812043449. ISSN 1600-5368. PMC 3515309. PMID 23284529.
  6. 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.
  7. 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.
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