methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

• ChemBase ID: 129366
• Molecular Formular: C23H28O8
• Molecular Mass: 432.46362
• Monoisotopic Mass: 432.17841786
• SMILES: O=C(OC)[C@H]1[C@@]2(CC[C@H]3C(=O)O[C@H](c4ccoc4)C[C@@]3([C@H]2C(=O)[C@@H](OC(=O)C)C1)C)C
• Canonical SMILES: COC(=O)[C@@H]1C[C@H](OC(=O)C)C(=O)[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)C[C@H](OC1=O)c1cocc1
• InChI: InChI=1S/C23H28O8/c1-12(24)30-16-9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(22)18(16)25/h6,8,11,14-17,19H,5,7,9-10H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1
• InChIKey: OBSYBRPAKCASQB-AGQYDFLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate
• IUPAC Traditional name: salvinorin A
• Synonyms: Salvinorin A; (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(3-furanyl)dodechydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester; Salvinorin A; (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic Acid Methyl Ester; (-)-Salvinorin A; Divinorin A; Salvinorin; [2S-(2α,4aα,6aβ,7β,9β,10aα,10bβ)]-9-(Acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 83729-01-5
• MDL Number: MFCD05664742
• PubChem SID: 162223660; 24899776
• PubChem CID: 128563
• CHEMBL: 445332
• Chemspider ID: 113947
• IUPHAR ligand ID: 1666
• Wikipedia Title: Salvinorin_A

CALCULATED PROPERTIES

• Acid pKa: 16.451683
• H Donor: 0
• LogD (pH = 5.5): 2.3890138
• LogD (pH = 7.4): 2.3890138
• Log P: 2.3890138
• Molar Refractivity: 105.9954 cm^3
• Polarizability: 42.497757 Å^3
• Polar Surface Area: 109.11 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• H Acceptors: 4

PROPERTIES

Physical Property

• Solubility: 25.07 mg/L at 25 °C (water, est); DMSO: ≥10 mg/mL; ethanol: ~3 mg/mL
• Apperance: white film
• Melting Point: 238-240 °C (460.4-464°F) (also reported 242-244 °C)
• Boiling Point: 760.2°C (1400.36°F)
• Optical Rotation: -45.3 °C at 22 deg C/D (c = 8.530 CHCl3); -41 °C at 25° C/D (c = 1 in CHCl3)

Safety Information

• Storage Condition: protect from light
• RTECS: QL6127142
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Buccal/Sublingual, Smoked
• Protein Bound: κ-opioid receptor
• Legal Status: Uncontrolled (though Salvia divinorum is controlled in some parts of the world, such as in certain states in the US)
• Gene Information: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprk1(29335)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H28O8

DETAILS

Sigma Aldrich - S8071

Biochem/physiol Actions
Salvinorin A is a potent, non-nitrogenous κ opioid selective receptor agonist. Salvinorin A is isolated from Salvia divinorum. Salvinorin A displays high affinity at both native (Ki=4.3 nm) and cloned (Ki=16 nm) κ -opioid receptors. Preliminary studies suggest that Salvanorin A is chemically unique among the psychtropic drugs and does not bind to any known receptor.

Toronto Research Chemicals - S100900

Salvinorin A is a potent and selective kappa-opioid receptor agonist. Salvinorin A has been reported to be brain-penetrant and displays psychoactive properties; hallucinogen.

REFERENCES

• Stewart, D. et al.: Arzneim. Forsch., 56, 269 (2006)
• Rothman, R.B. et al.: J. Pharmacol. Exp. Therap., 320, 801 (2006)
• Sheffler, D. et al.: Trends Pharamacol. Sci., 24, 107 (2006)