Salvinorin B methoxymethyl ether

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]

Other names2-O-Methoxymethylsalvinorin B; 2-MMSB

Drug classκ-Opioid receptor agonist; Hallucinogen

ATC code

• None

Legal status

• Unknown/Depends on country

Quick facts Clinical data, Other names ...

Salvinorin B methoxymethyl ether

Clinical data
Other names	2-O-Methoxymethylsalvinorin B; 2-MMSB
Drug class	κ-Opioid receptor agonist; Hallucinogen
ATC code	None
Legal status
Legal status	Unknown/Depends on country
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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It has a longer duration of action of around 2 to 3 hours,^[3] compared to less than 30 minutes for salvinorin A,^[4] and has increased affinity and potency at the κ-opioid receptor. It is prepared from salvinorin B.^[5] The crystal structure is almost superimposable with that of salvinorin A.^[6] Structures bound to the κ-opioid receptor have also been reported.^[7]

Salvinorin B methoxymethyl ether has a K_i of 0.60 nM at the κ opioid receptor,^[8] 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]

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