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{{Short description|Chemical compound}} |
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{{drugbox | verifiedrevid = 411540333 |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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| IUPAC_name = (2''S'',4a''R'',6a''R'',7''R'',9''S'',10a''S'',10b''R'')- 9-(methoxymethoxy)- 2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2''H''-naphtho-pyran-7-carboxylic acid methyl ester |
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| image = 2-MeOMeSalB.png |
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| verifiedrevid = 411541279 |
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| IUPAC_name = 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-benzoisochromene-7-carboxylate |
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| width = 200 |
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| image = Salvinorin B methoxymethyl ether Structure.svg |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| image_class = skin-invert-image |
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| ChemSpiderID = 23323947 |
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| width = <!--Clinical data--> |
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| InChI = 1/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 |
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| tradename = |
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| InChIKey = KFVUSZPWUZBAPF-AGQYDFLVBU |
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| legal_status = Legal/Uncontrolled |
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| smiles1 = C12CC3C(=O)O(C3(1C(=O)(C2C(=O)OC)OCOC)C)c4ccoc4 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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<!--Identifiers-->| ATC_prefix = none |
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| ChEMBL = 258098 |
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| CAS_number = 864378-87-0 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem = 44456192 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23323947 |
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| StdInChIKey = KFVUSZPWUZBAPF-AGQYDFLVSA-N |
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| CAS_number = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ATC_prefix = none |
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| PDB_ligand = U99 |
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| ATC_suffix = |
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| ChEMBL = 258098 |
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| PubChem = 11407876 |
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| C = 23 | H = 30 | O = 8 |
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<!--Chemical data-->| C = 23 |
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| H = 30 |
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| molecular_weight = 434 g/mol |
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| O = 8 |
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| smiles = COCO1C(2(CC3C(=O)O(C3(2C1=O)C)C4=COC=C4)C)C(=O)OC |
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| bioavailability = |
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| molecular_weight = |
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| smiles = C12CC3C(=O)O(C3(1C(=O)(C2C(=O)OC)OCOC)C)C4=COC=C4 |
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| protein_bound = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| metabolism = |
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| StdInChI = 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 |
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| elimination_half-life = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| excretion = |
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| StdInChIKey = KFVUSZPWUZBAPF-AGQYDFLVSA-N |
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| pregnancy_category= |
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| legal_status = Legal/Uncontrolled |
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| routes_of_administration = |
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}} |
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}} |
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'''2-Methoxymethyl salvinorin B''' is a semi-synthetic ] of the natural product ] which is used in scientific research.<ref name="pmid18925386">{{cite journal |author=Inan S, Lee DY, Liu-Chen LY, Cowan A |title=Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |volume=379 |issue=3 |pages=263–70 |year=2009 |month=March |pmid=18925386 |doi=10.1007/s00210-008-0358-8 |url=}}</ref><ref name="pmid19014370">{{cite journal |author=McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ |title=Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways |journal=Journal of Neurochemistry |volume=107 |issue=6 |pages=1753–65 |year=2008 |month=December |pmid=19014370 |pmc=2606093 |doi=10.1111/j.1471-4159.2008.05745.x |url=}}</ref> It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A,<ref name="pmid18089845">{{cite journal |author=Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY |title=2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=324 |issue=3 |pages=1073–83 |year=2008 |month=March |pmid=18089845 |pmc=2519046 |doi=10.1124/jpet.107.132142 |url=}}</ref> and has increased affinity and efficacy at the ] ]. Like the related compound ], 2-methoxymethyl salvinorin B is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation,<ref name="pmid15993589">{{cite journal |author=Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B |title=Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues |journal=Bioorganic & Medicinal Chemistry Letters |volume=15 |issue=16 |pages=3744–7 |year=2005 |month=August |pmid=15993589 |doi=10.1016/j.bmcl.2005.05.048 |url=}}</ref> as while both salvinorin A and salvinorin B are found in the plant '']'', salvinorin A is present in larger quantities.<ref name="pmid16331747">{{cite journal |author=Medana C, Massolino C, Pazzi M, Baiocchi C |title=Determination of salvinorins and divinatorins in Salvia divinorum leaves by liquid chromatography/multistage mass spectrometry |journal=Rapid Communications in Mass Spectrometry : RCM |volume=20 |issue=2 |pages=131–6 |year=2006 |pmid=16331747 |doi=10.1002/rcm.2288 |url=}}</ref> |
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'''Salvinorin B methoxymethyl ether''' ('''2-''O''-methoxymethylsalvinorin B''') is a semi-synthetic ] of the natural product ] used in scientific research.<ref name="pmid18925386">{{cite journal | vauthors = Inan S, Lee DY, Liu-Chen LY, Cowan A | title = Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 379 | issue = 3 | pages = 263–270 | date = March 2009 | pmid = 18925386 | doi = 10.1007/s00210-008-0358-8 | s2cid = 8123431 }}</ref><ref name="pmid19014370">{{cite journal | vauthors = McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ | display-authors = 6 | title = Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways | journal = Journal of Neurochemistry | volume = 107 | issue = 6 | pages = 1753–1765 | date = December 2008 | pmid = 19014370 | pmc = 2606093 | doi = 10.1111/j.1471-4159.2008.05745.x }}</ref> It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A,<ref name="pmid18089845">{{cite journal | vauthors = Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY | display-authors = 6 | title = 2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 324 | issue = 3 | pages = 1073–1083 | date = March 2008 | pmid = 18089845 | pmc = 2519046 | doi = 10.1124/jpet.107.132142 }}</ref> and has increased affinity and potency at the ] ]. It is prepared from ].<ref name="pmid15993589">{{cite journal | vauthors = Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B | display-authors = 6 | title = Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 16 | pages = 3744–3747 | date = August 2005 | pmid = 15993589 | doi = 10.1016/j.bmcl.2005.05.048 }}</ref> The ] is almost superimposable with that of salvinorin A.<ref>{{cite journal |vauthors=Munro TA, Ho DM, Cohen BM |date=2012 |title=Salvinorin B methoxymethyl ether |journal=Acta Crystallographica Section E |volume=68 |issue=11 |pages=o3225–o3226 |doi=10.1107/s1600536812043449 |pmc=3515309 |pmid=23284529|bibcode=2012AcCrE..68o3225M }}</ref> Structures bound to the κ-opioid receptor have also been reported.<ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Ligand and G-protein selectivity in the κ-opioid receptor | journal = Nature | volume = 617 | issue = 7960 | pages = 417–425 | date = May 2023 | pmid = 37138078 | pmc = 10172140 | doi = 10.1038/s41586-023-06030-7 | bibcode = 2023Natur.617..417H }}</ref> |
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2-Methoxymethyl salvinorin B has a ] of 0.60 nM at the κ opioid receptor,<ref name="pmid17981041">{{cite journal |author=Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C |title=Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers |journal=Bioorganic & Medicinal Chemistry |volume=16 |issue=3 |pages=1279–86 |year=2008 |month=February |pmid=17981041 |pmc=2568987 |doi=10.1016/j.bmc.2007.10.067 |url=}}</ref> and is around 5x more potent than Salvinorin A in animal studies, although it is still only half as potent as its stronger homologue ].<ref name="pmid19153716">{{cite journal |author=Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL |title=Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats |journal=Psychopharmacology |volume=203 |issue=2 |pages=203–11 |year=2009 |month=April |pmid=19153716 |doi=10.1007/s00213-008-1458-3 |url=}}</ref> |
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Salvinorin B methoxymethyl ether has a ] of 0.60 nM at the κ opioid receptor,<ref name="pmid17981041">{{cite journal | vauthors = Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C | display-authors = 6 | title = Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 3 | pages = 1279–1286 | date = February 2008 | pmid = 17981041 | pmc = 2568987 | doi = 10.1016/j.bmc.2007.10.067 }}</ref> 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 ], 'symmetry'.<ref name="pmid17981041" /><ref name="pmid19153716">{{cite journal | vauthors = Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL | title = Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats | journal = Psychopharmacology | volume = 203 | issue = 2 | pages = 203–211 | date = April 2009 | pmid = 19153716 | doi = 10.1007/s00213-008-1458-3 | doi-access = free }}</ref><ref>{{Cite journal | vauthors = Mercury D, Feelodd D |date=2008 |title=First look at a new psychoactive drug: symmetry (salvinorin B ethoxymethyl ether) |url=https://www.erowid.org/chemicals/salvinorin_b_ethoxymethyl_ether/salvinorin_b_ethoxymethyl_ether_article1.shtml |journal=Entheogen Review |volume=16 |issue=4 |pages=136–145 |issn=1066-1913 |via=}}</ref> |
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== See also == |
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== See also == |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist}} |
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{{Hallucinogens}} |
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{{Hallucinogens}} |
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{{Opioidergics}} |
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{{DEFAULTSORT:Methoxymethyl salvinorin B, 2-}} |
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