Neuropharmacology
September 1, 2007
Catherine B Willmore-Fordham, Daniel M Krall, Christopher R Mccurdy et al.
49 citations
Data from clinical and preclinical studies converge implicating the plant-derived hallucinogen salvinorin A as an important pharmacologic tool; this psychoactive compound may expand scientific understandings on mammalian kappa-opioid receptor systems. Human salvinorin A effects, consistent with kappa-opioid receptor agonism, include antinociception, sedation, dysphoria and distorted...
Planta Medica
August 1, 2007
Oliver Grundmann, Stephen M Phipps, Immo Zadezensky et al.
81 citations
Salvia divinorum L. (Lamiaceae) has been used for centuries by the Mazatecan culture and has gained popularity as a recreational drug in recent years. Its potent hallucinogenic effects seen in case reports has triggered research and led to the discovery of the first highly selective non-nitrogenous kappa opioid receptor agonist salvinorin A. This review critically evaluates the reported...
Tetrahedron Letters
July 30, 2007
Zhongze Ma, David Y W Lee
In comparison with the NMR data of salvinorin A and its 8-epimer, the published structure of deacetyl-1,10-didehydrosalvinorin G was revised to its 8-epimer. The stereochemistry of 8-epi-deacetyl-1,10-didehydrosalvinorin G was further confirmed by NOESY and chemical synthesis.
Journal of Medicinal Chemistry
July 26, 2007
Denise S Simpson, Peter L Katavic, Anthony Lozama et al.
Further modification of salvinorin A (1a), the major active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study that oxadiazole 11a and salvidivin A (12a), a photooxygenation product of 1a, have been identified as the first neoclerodane diterpenes with kappa antagonist activity. This...
Phytochemistry
July 1, 2007
Lukasz Kutrzeba, Franck E Dayan, J'Lynn Howell et al.
45 citations
Salvinorin A, a neoclerodane diterpenoid, isolated from the Mexican hallucinogenic plant Salvia divinorum, is a potent kappa-opioid receptor agonist. Its biosynthetic route was studied by NMR and HR-ESI-MS analysis of the products of the incorporation of [1-(13)C]-glucose, [Me-(13)C]-methionine, and [1-(13)C;3,4-(2)H2]-1-deoxy-D-xylulose into its structure. While the use of cuttings and...
Journal of Psychoactive Drugs
June 1, 2007
Phil Dalgarno
21 citations
Salvia divinorum is a hallucinogenic plant native to Mexico, where the Mazatec Indians use it in divinatory rituals as a facilitator for contacting the spirits of the dead. A number of traditions surrounding the ritualistic use of Salvia are still observed. Generally the leaves are chewed for the visionary effects. Salvia has recently been embraced by Western drug cultures, where the...
Bioorganic & Medicinal Chemistry Letters
April 15, 2007
Ruslan V Bikbulatov, Feng Yan, Bryan L. Roth et al.
To study drug-receptor interactions, new thio-derivatives of salvinorin A, an extremely potent natural kappa-opioid receptor (KOR) agonist, were synthesized. Obtained compounds were examined for receptor binding affinity. Analogs with the same configuration at carbon atom C-2 as in natural salvinorin A showed higher affinity to KOR than their corresponding epimers.
Magnetic resonance in chemistry : MRC
April 1, 2007
José-luis Giner, David J Kiemle, Lukasz Kutrzeba et al.
14 citations
The complete assignments of the (1)H and (13)C NMR spectra of the hallucinogenic neoclerodane diterpenoid salvinorin A were determined in three different NMR solvents using HSQC, HMBC and COSY. Solvent systems are described that allow the resolution of all (1)H signals. Virtual coupling was observed for the protons at C-2, C-3 and C-4 in the 600 MHz (1)H spectrum in CDCl(3). The complete...
Psychopharmacology
March 2007
Daniela Braida, Valeria Limonta, Simona Pegorini et al.
The hallucinatory effect and potential abuse of salvinorin A, the major ingredient of Salvia divinorum, has not been documented in animals. The effects of salvinorin A on the zebrafish (Danio rerio) model, through its swimming behavior and conditioned place preference (CPP) task, was studied. Swimming activity was determined in a squared observational chamber after an i.m. treatment of...
Journal of Biological Chemistry
February 2, 2007
Timothy A Vortherms, Philip D Mosier, Richard B Westkaemper et al.
40 citations
Salvinorin A, the active component of the hallucinogenic sage Salvia divinorum, is an apparently selective and highly potent kappa-opioid receptor (KOR) agonist. Salvinorin A is unique among ligands for peptidergic G protein-coupled receptors in being nonnitrogenous and lipid-like in character. To examine the molecular basis for the subtype-selective binding of salvinorin A, we utilized an...