Salvinorin-A
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| Salvinorin A | |
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| Chemical name |
(2S,4aR,6aR,7R,9S,10aS,10bR)-methyl |
| Chemical formula | C23H28O8 |
| Molecular mass | 432.46 g/mol |
| Melting point | 238 - 240 °C |
| CAS number | X1017952-1 |
| SMILES | O=C1[C@@]2([H])[C@](CC[C@]3([H])[C@] 2(C)C[C@](C4=COC=C4)([H])OC3=O)(C) [C@H]([C@](OC)=O)C[C@@H]1OC(C)=O |
| Missing image Salvinorin-A_structure.png Chemical structure of salvinorin A | |
Salvinorin A is the main active psychotropic constituent of the plant Salvia divinorum (diviner's sage, Mexican mint). It is an entheogenic dissociative hallucinogenic compound that is active at the extremely low doses of 0.2 - 0.5 mg, second only to LSD in quantitative potency, making it the most potent naturally occurring drug known to date. Salvinorin A is found together with several other structurally related salvinorins, some of which might be even more potent. Salvinorin is a diterpene of the neoclerodane family. 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.
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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.
Missing image Salvinorins-AB.png Structure 1: Salvinorin A and B |
Missing image Salvinorins-D-F.png Structure 2: Salvinorin D - F |
| 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.
External links
- Erowid Salvia divinorum vault (http://www.erowid.org/plants/salvia/salvia.shtml)
- Lycaeum Salvinorin A (http://leda.lycaeum.org/?ID=156)
- The Salvia divinorum Research and Information Center (Daniel Siebert) (http://www.sagewisdom.org/)
- Salvinorin A: A potent naturally occurring nonnitrogenous kappa opioid selective agonist (http://www.pnas.org/cgi/content/full/99/18/11934). Proc. Natl. Acad. Sci. U.S.A. 99(18):11934-11939 (2002) PMID 12192085
References
- Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist. J. Med. Chem. 48(2):345-348(2005) PMID 15658846
Categorization
Template:Dissociative hallucinogensde:Salvinorin fr:Salvinorine A pl:salvinorin A