8344. Salvinorins

Nomenclature

Divinorins.

Description and 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).

Chemical structure

Derivative

Salvinorin A.

Nomenclature

CAS number: 83729-01-5
(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; divinorin A.
C23H28O8; mol wt 432.46.
C 63.88%, H 6.53%, O 29.60%.

Description and references

One of the most potent natural hallucinogens known. First naturally occurring non-nitrogenous κ 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). [α]D22 -45.3° (c = 8.530 in CHCl3). [α]D25 -41° (c = 1 in CHCl3).

Use

In traditional medicine, the leaves are used for divination and for treatment of anemia and excretory functions.