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Salvinorin B methoxymethyl ether

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Chemical compound

Pharmaceutical compound
Salvinorin B methoxymethyl ether
Clinical data
ATC code
  • none
Legal status
Legal status
  • Unknown/Depends on country
Identifiers
  • methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-(methoxymethoxy)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
CAS Number
PubChemCID
ChemSpider
ChEMBL
PDB ligand
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H30O8
Molar mass434.485 g·mol−1
3D model (JSmol)
  • C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]1C(=O)[C@H](C[C@H]2C(=O)OC)OCOC)C)C4=COC=C4
  • InChI=1S/C23H30O8/c1-22-7-5-14-21(26)31-17(13-6-8-29-11-13)10-23(14,2)19(22)18(24)16(30-12-27-3)9-15(22)20(25)28-4/h6,8,11,14-17,19H,5,7,9-10,12H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1 checkY
  • Key:KFVUSZPWUZBAPF-AGQYDFLVSA-N checkY
  (verify)

Salvinorin B methoxymethyl ether (2-O-methoxymethylsalvinorin B) is a semi-syntheticanalogue of the natural productsalvinorin 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 theκ-opioidreceptor. It is prepared fromsalvinorin B.[4] Thecrystal 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 aKi 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 etherhomolog, 'symmetry'.[7][8][9]

See also

[edit]

References

[edit]
  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):263–270.doi:10.1007/s00210-008-0358-8.PMID 18925386.S2CID 8123431.
  2. ^McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, et al. (December 2008)."Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways".Journal of Neurochemistry.107 (6):1753–1765.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, et al. (March 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):1073–1083.doi:10.1124/jpet.107.132142.PMC 2519046.PMID 18089845.
  4. ^Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, et al. (August 2005). "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues".Bioorganic & Medicinal Chemistry Letters.15 (16):3744–3747.doi:10.1016/j.bmcl.2005.05.048.PMID 15993589.
  5. ^Munro TA, Ho DM, Cohen BM (2012)."Salvinorin B methoxymethyl ether".Acta Crystallographica Section E.68 (11):o3225 –o3226.Bibcode:2012AcCrE..68o3225M.doi:10.1107/s1600536812043449.PMC 3515309.PMID 23284529.
  6. ^Han J, Zhang J, Nazarova AL, Bernhard SM, Krumm BE, Zhao L, et al. (May 2023)."Ligand and G-protein selectivity in the κ-opioid receptor".Nature.617 (7960):417–425.Bibcode:2023Natur.617..417H.doi:10.1038/s41586-023-06030-7.PMC 10172140.PMID 37138078.
  7. ^abMunro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, et al. (February 2008)."Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers".Bioorganic & Medicinal Chemistry.16 (3):1279–1286.doi:10.1016/j.bmc.2007.10.067.PMC 2568987.PMID 17981041.
  8. ^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):203–211.doi:10.1007/s00213-008-1458-3.PMID 19153716.
  9. ^Mercury D, Feelodd D (2008)."First look at a new psychoactive drug: symmetry (salvinorin B ethoxymethyl ether)".Entheogen Review.16 (4):136–145.ISSN 1066-1913.
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