Gourt Home::Gourt :: Salvinorin A
| Salvinorin A | |
|---|---|
| Chemical name |
(2S,4aR,6aR,7R,9S,10aS,10bR)-methyl 9-acetoxy-2-(furan-3-yl)-6a,10b- dimethyl-4,10-dioxo-dodecahydro-1H- benzo*isochromene-7-carboxylate |
| Chemical formula | C23H28O8 |
| Molecular mass | 432.46 g/mol |
| Melting point | 238 - 240 °C |
| CAS number | 83729-01-5 |
| SMILES | O=C1*2(*)*(CC*3(*)* 2(C)C*(C4=COC=C4)(*)OC3=O)(C) *(*(OC)=O)C*1OC(C)=O |
Salvinorin A is the main active psychotropic constituent of the plant Salvia divinorum (diviner's sage, Mexican mint), which has a long history of use as an entheogen. Salvinorin A is a dissociative hallucinogenic compound that is active at the extremely low doses of 0.2 - 0.5 mg, near the levels of LSD in quantitative potency, making it the most potent naturally occurring psychoactive drug known to date.Bryan L. Roth, Karen Baner, Richard Westkaemper, Daniel Siebert, Kenner C. Rice, SeAnna Steinberg, Paul Ernsberger, and Richard B. Rothman. Salvinorin A: A potent naturally occurring nonnitrogenous kappa opioid selective agonist. http://www.pnas.org/cgi/content/abstract/99/18/11934 Salvinorin A is found together with several other structurally related salvinorins. Salvinorin is a trans-neoclerodane diterpenoid. It acts as a kappa opioid receptor agonist and is the first known compound acting on this receptor that is not an alkaloid. The psychoactive effects of salvinorin A are similar to those of other kappa opioid receptor agonists.
History
Salvinorin A was isolated independently in 1982 by Alfredo Ortega in Mexico and in 1984 by Leander J. Valdes III in the USA. Its pharmacological mechanism was elucidated in the laboratory of Bryan L. Roth.
Salvinorins A - F
Salvinorin A is one of several structurally related salvinorins. The des-acetylated analog salvinorin B is devoid of human activity. It was speculated that salvinorin C might be even more potent than salvinorin A, but human tests and receptor binding assays could not confirm this. Salvinorin A seems to be the only active naturally occurring salvinorin.
| Name | R1 | R2 | Structure | Activity |
|---|---|---|---|---|
| Salvinorin A | -OCOCH3 | - | 1 | active |
| Salvinorin B | -OH | - | 1 | inactive |
| Salvinorin C | -OCOCH3 | -OCOCH3 | 2 | inactive |
| Salvinorin D | -OH | -OCOCH3 | 2 | inactive |
| Salvinorin E | -OCOCH3 | -OH | 2 | inactive |
| Salvinorin F | -H | -OH | 2 | unknown |
Chemistry
Salvinorin A can be synthesized from the inactive Salvinorin B by acetylation.
Mechanism of Action
Salvinorin A is a potent kappa opioid receptor agonist in humans, which is primarily responsible for its psychoactive activity. Salvinorin A has no actions at the 5-HT2A serotonin receptor, the principal molecular target responsible for the actions of classical hallucinogens.ibid.
See also
External links
- Erowid Salvia divinorum vault
- Lycaeum Salvinorin A
- Photographs of Crystalline Salvinorin-A and .PDF Extraction Articles.
- Tryptamind Salvinorin A Downloadable salvinorin extraction photos.
- The Salvia divinorum Research and Information Center (Daniel Siebert)
- Salvinorin A: A potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proc. Natl. Acad. Sci. U.S.A. 99(18):11934-11939 (2002) PMID 12192085
References
- Charles Chavkin, Sumit Sud, Wenzhen Jin, Jeremy Stewart, Jordan K. Zjawiony, Daniel J. Siebert, Beth Ann Toth, Sandra J. Hufeisen, and Bryan L. Roth. "Salvinorin A, an Active Component of the Hallucinogenic Sage Salvia divinorum Is a Highly Efficacious kappa-Opioid Receptor Agonist: Structural and Functional Considerations." The Journal of Pharmacology and Experimental Therapeutics 2004, 308 (3), 1197-1203.
- Thomas A. Munro, Mark A. Rizzacasa, Bryan L. Roth, Beth A. Toth, and Feng Yan. "Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist." J. Med. Chem. 2005, 48 (2), 345-348. PMID 15658846
Terpenes and terpenoids | Acetates | Carboxylate esters | Furans | Lactones | Heterocyclic compounds | Dissociatives
Salvinorin | Salvinorina | Salvinorine A | Salvinorin A | Salvinorin A
"Salvinorin A"