Salvinorin B methoxymethyl ether ATC code Legal status
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
PubChem CID ChemSpider ChEMBL Formula C 23 H 30 O 8 Molar mass 434.485 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
Y Key:KFVUSZPWUZBAPF-AGQYDFLVSA-N
Y
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 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 [ ]
Salvinorin B ethoxymethyl ether
RB-64
References [ ]
^ 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 . S2CID 8123431 .
^ 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): 1753–65. doi :10.1111/j.1471-4159.2008.05745.x . PMC 2606093 . PMID 19014370 .
^ 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): 1073–83. doi :10.1124/jpet.107.132142 . PMC 2519046 . PMID 18089845 .
^ 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): 3744–7. doi :10.1016/j.bmcl.2005.05.048 . PMID 15993589 .
^ Munro TA, Ho DM, Cohen BM (November 2012). "Salvinorin B methoxymethyl ether" . Acta Crystallographica Section E . 68 (Pt 11): o3225-6. doi :10.1107/s1600536812043449 . PMC 3515309 . PMID 23284529 .
^ Munro 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): 1279–86. doi :10.1016/j.bmc.2007.10.067 . PMC 2568987 . PMID 17981041 .
^ 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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