Salvinorin B methoxymethyl ether

Salvinorin B methoxymethyl ether

Systematic (IUPAC) name
(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(methoxymethoxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho-[2,1-c]pyran-7-carboxylic acid methyl ester
Clinical data
Legal status	Legal/Uncontrolled
Identifiers
ATC code	none
PubChem	CID 11407876
ChemSpider	23323947
ChEMBL	CHEMBL258098
Chemical data
Formula	C23H30O8
Molar mass	434 g/mol
SMILES COCO[C@H]1C[C@H]([C@@]2(CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]2C1=O)C)C4=COC=C4)C)C(=O)OC
InChI 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 Key:KFVUSZPWUZBAPF-AGQYDFLVSA-N
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Salvinorin B methoxymethyl ether (2-O-methoxymethylsalvinorin B) is a semi-synthetic analogue of the natural product salvinorin A which is 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. Like the related compound herkinorin, salvinorin B methoxymethyl ether is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation,^[4] as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.^[5]

Salvinorin B methoxymethyl ether has a K_i 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.^[7]

See also

• RB-64

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 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.
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 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.
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. 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.
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.