Salvinorin B methoxymethyl ether

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 prepared from salvinorin B.^[4] The crystal structure is almost superimposable with that of salvinorin A.^[5] Structures bound to the κ-opioid receptor have also been reported.^[6]

Salvinorin B methoxymethyl ether

Clinical data
ATC code	none
Legal status
Legal status	Legal/Uncontrolled
Identifiers
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-benzo[f]isochromene-7-carboxylate
CAS Number	864378-87-0
PubChem CID	44456192
ChemSpider	23323947 Y
ChEMBL	ChEMBL258098 Y
PDB ligand	U99 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID201028497
Chemical and physical data
Formula	C23H30O8
Molar mass	434.485 g·mol−1
3D model (JSmol)	Interactive image
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
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 has a K_i of 0.60 nM at the κ opioid receptor,^[7] 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 homolog, 'symmetry'.^[7][8][9]

See also

• RB-64