Salvinorin B methoxymethyl ether

Effects

Overview

Salvinorin B methoxymethyl ether (2-O-methoxymethylsalvinorin B, or 2-MMSB) is a semi-synthetic analogue of the natural product Salvinorin A which is used in scientific research. It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A, 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, as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities. PW

Salvinorin B methoxymethyl ether, also known as 2-O-methoxymethylsalvinorin B (2-MMSB) is a semisynthetic analogue of the natural product salvinorin A which is used in scientific research.[1][2][3] WP

It has a longer duration of action of around 2 to 3 hours, compared to less than 30 minutes for salvinorin A, and has increased affinity and potency at the κ-opioid receptor. It is prepared from salvinorin B. The crystal structure is almost superimposable with that of salvinorin A. Structures bound to the κ-opioid receptor have also been reported.[3–7] WP

Salvinorin B methoxymethyl ether has a Kᵢ of 0.60 nM at the κ opioid receptor, 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 homologue, salvinorin B ethoxymethyl ether (2-O-ethoxymethylsalvinorin B; 2-EMSB; "symmetry").[8][9][10] WP⚠ A word may be missing here. It reads this way in the source too.

The drug was encountered online as a novel designer drug in 2020.[3] WP

History

Legal status

Pharmacology

Chemistry

Formula

C23H30O8 PC

Molar mass (g/mol)

434.5 PC

IUPAC name (computed by PubChem)

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 PC

SMILES

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 PC

InChIKey

KFVUSZPWUZBAPF-AGQYDFLVSA-N PC

PubChem CID

44456192

Pop culture

No references added yet.

References

1. Journal / agency Inan S, Lee DY, Liu-Chen LY, Cowan A. 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. March 2009. doi:10.1007/s00210-008-0358-8 · PMID 18925386
2. Journal / agency McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ. Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways. Journal of Neurochemistry. December 2008. doi:10.1111/j.1471-4159.2008.05745.x · PMID 19014370 · PMC2606093
3. Other 2-О-Метоксиметилсальвинорин B (Salvinorin B methoxymethyl ether)
4. Journal / agency Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY. 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. March 2008. doi:10.1124/jpet.107.132142 · PMID 18089845 · PMC2519046
5. Journal / agency Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B. Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues. Bioorganic & Medicinal Chemistry Letters. August 2005. doi:10.1016/j.bmcl.2005.05.048 · PMID 15993589
6. Journal / agency Munro TA, Ho DM, Cohen BM. Salvinorin B methoxymethyl ether. Acta Crystallographica Section E. 2012. doi:10.1107/s1600536812043449 · PMID 23284529 · PMC3515309
7. Journal / agency Han J, Zhang J, Nazarova AL, Bernhard SM, Krumm BE, Zhao L, Lam JH, Rangari VA, Majumdar S, Nichols DE, Katritch V, Yuan P, Fay JF, Che T. Ligand and G-protein selectivity in the κ-opioid receptor. Nature. May 2023. doi:10.1038/s41586-023-06030-7 · PMID 37138078 · PMC10172140
8. Journal / agency Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C. Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers. Bioorganic & Medicinal Chemistry. February 2008. doi:10.1016/j.bmc.2007.10.067 · PMID 17981041 · PMC2568987
9. Journal / agency Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL. Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats. Psychopharmacology. April 2009. doi:10.1007/s00213-008-1458-3 · PMID 19153716
10. Journal / agency Mercury D, Feelodd D. First Look at a New Psychoactive Drug: Symmetry (Salvinorin B Ethoxymethyl Ether). The Entheogen Review. 2008

Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.