Salvinorin B

Salvinorin B
Clinical data
Other names	Divinorin B; Desacetyldivinorin A; Desacetylsalvinorin A; SB; SalB
ATC code	None;
Identifiers
	IUPAC name methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate;
CAS Number	92545-30-7;
PubChem CID	11440685;
ChemSpider	9615549;
UNII	6HNB6FRT7X;
ChEBI	CHEBI:177592;
ChEMBL	ChEMBL424698;
CompTox Dashboard (EPA)	DTXSID50465988 ;
Chemical and physical data
Formula	C21H26O7
Molar mass	390.432 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)O)C)C4=COC=C4;
	InChI InChI=1S/C21H26O7/c1-20-6-4-12-19(25)28-15(11-5-7-27-10-11)9-21(12,2)17(20)16(23)14(22)8-13(20)18(24)26-3/h5,7,10,12-15,17,22H,4,6,8-9H2,1-3H3/t12-,13-,14-,15-,17-,20-,21-/m0/s1; Key:BLTMVAIOAAGYAR-CEFSSPBYSA-N;

Salvinorin B is a naturally occurring terpene of the salvinorin family and constituent of Salvia divinorum.^[1] In contrast to salvinorin A, salvinorin B is inactive at the κ-opioid receptor.^[2] Accordingly, unlike salvinorin A, salvinorin B is inactive in producing effects in rodents.^[1]^[3] Salvinorin B was first described in the scientific literature by Leander J. Valdes and colleagues by 1984.^[1] Although salvinorin B is inactive, two derivatives, salvinorin B methoxymethyl ether (2-MMSB) and salvinorin B ethoxymethyl ether (2-EMSB), are highly potent κ-opioid receptor agonists with greater activity than salvinorin A.^[4]^[5]^[6]

References

1 2 3 Valdes LJ, Butler WM, Hatfield GM, Paul AG, Koreeda M (1984). "Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum". The Journal of Organic Chemistry. 49 (24): 4716–4720. Bibcode:1984JOrgC..49.4716V. doi:10.1021/jo00198a026. ISSN 0022-3263.
↑ Munro TA, Rizzacasa MA, Roth BL, Toth BA, Yan F (January 2005). "Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist". Journal of Medicinal Chemistry. 48 (2): 345–348. doi:10.1021/jm049438q. PMC 2777653. PMID 15658846.
↑ Siebert DJ (June 1994). "Salvia divinorum and salvinorin A: new pharmacologic findings". Journal of Ethnopharmacology. 43 (1): 53–56. Bibcode:1994JEthn..43...53S. doi:10.1016/0378-8741(94)90116-3. PMID 7526076.
↑ Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, et al. (February 2008). "Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry. 16 (3): 1279–1286. doi:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.
↑ Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, et al. (March 2008). "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. 324 (3): 1073–1083. doi:10.1124/jpet.107.132142. PMC 2519046. PMID 18089845.
↑ Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, et al. (April 2009). "Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats". Psychopharmacology. 203 (2): 203–211. doi:10.1007/s00213-008-1458-3. PMID 19153716.

External links

Salvinorin B - Isomer Design

[ValdesButlerHatfield1984-1] 1 2 3 Valdes LJ, Butler WM, Hatfield GM, Paul AG, Koreeda M (1984). "Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum". The Journal of Organic Chemistry. 49 (24): 4716–4720. Bibcode:1984JOrgC..49.4716V. doi:10.1021/jo00198a026. ISSN 0022-3263.

[MunroRizzacasaRoth2005-2] Munro TA, Rizzacasa MA, Roth BL, Toth BA, Yan F (January 2005). "Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist". Journal of Medicinal Chemistry. 48 (2): 345–348. doi:10.1021/jm049438q. PMC 2777653. PMID 15658846.

[Siebert1994-3] Siebert DJ (June 1994). "Salvia divinorum and salvinorin A: new pharmacologic findings". Journal of Ethnopharmacology. 43 (1): 53–56. Bibcode:1994JEthn..43...53S. doi:10.1016/0378-8741(94)90116-3. PMID 7526076.

[MunroDuncanXu2008-4] Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, et al. (February 2008). "Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry. 16 (3): 1279–1286. doi:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.

[WangChenXu2008-5] Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, et al. (March 2008). "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. 324 (3): 1073–1083. doi:10.1124/jpet.107.132142. PMC 2519046. PMID 18089845.

[BakerPanosKillinger2009-6] Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, et al. (April 2009). "Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats". Psychopharmacology. 203 (2): 203–211. doi:10.1007/s00213-008-1458-3. PMID 19153716.

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See also

References

External links