Title: Salvinorins
Additional Names: Divinorins
Literature References: Family of neoclerodane diterpenes isolated from the hallucinogenic Mexican mint Salvia divinorum. Traditional medicine used by the Mazatec people of Oaxaca, Mexico. Isoln of Salvinorin A: A. Ortega et al., J. Chem. Soc. Perkin Trans. 1 1982, 2505; of A and B and biologic activity: L. J. Valdés, III et al., J. Org. Chem. 49, 4716 (1984); of C: L. J. Valdés, III et al., Org. Lett. 3, 3935 (2001). Stereochemistry: M. Koreeda et al., Chem. Lett. 1990, 2015. Pharmacologic effects: D. J. Siebert, J. Ethnopharmacol. 43, 53 (1994). Review: L. J. Valdés III, J. Psychoactive Drugs 26, 277-283 (1994).
Derivative Type: Salvinorin A
CAS Registry Number: 83729-01-5
CAS Name: (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
Additional Names: divinorin A
Molecular Formula: C23H28O8
Molecular Weight: 432.46
Percent Composition: C 63.88%, H 6.53%, O 29.60%
Literature References: One of the most potent natural hallucinogens known. First naturally occurring non-nitrogenous k opioid receptor (KOR) agonist identified. HPLC quantification in S. divinorum extracts: J. W. Gruber et al., Phytochem. Anal. 10, 22 (1999). LC determn in biological fluids: M. S. Schmidt et al., J. Chromatogr. B 818, 221 (2005). KOR binding profile: B. L. Roth et al., Proc. Natl. Acad. Sci. USA 99, 11934 (2002). Brief review: D. J. Sheffler, B. L. Roth, Trends Pharmacol. Sci. 24, 107-109 (2003).
Properties: Colorless crystals from methanol, mp 238-240° (Ortega); also reported as mp 242-244° (Valdes, 1984). [a]D22 -45.3° (c = 8.530 in CHCl3). [a]D25 -41° (c = 1 in CHCl3).
Melting point: mp 238-240° (Ortega); mp 242-244° (Valdes, 1984)
Optical Rotation: [a]D22 -45.3° (c = 8.530 in CHCl3); [a]D25 -41° (c = 1 in CHCl3)
Use: In traditional medicine, the leaves are used for divination and for treatment of anemia and excretory functions. |