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 Y
ChEMBL	CHEMBL258098 Y
Chemical data
Formula	C23H30O8
Molecular 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 Y Key:KFVUSZPWUZBAPF-AGQYDFLVSA-N Y
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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. 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.

Salvinorin B methoxymethyl ether has a K_i 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 stronger homolog salvinorin B ethoxymethyl ether.

See also

• RB-64