Salvinorin A

From Wikipedia, the free encyclopedia

You have new messages (last change).
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[f]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[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
Chemical structure of salvinorin A

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 200–1000 μg, near the levels of LSD in quantitative potency, making it the most potent naturally occurring psychoactive drug known to date.[1] 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.

Contents

[edit] 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.

[edit] 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.

Salvinorins A - F: General formulas
Structure 1:Salvinorin A and B
Structure 1:
Salvinorin A and B
Structure 2:Salvinorin D - F
Structure 2:
Salvinorin D - F
Salvinorins A - 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

[edit] Chemistry

Salvinorin A can be synthesized from the inactive Salvinorin B by acetylation.

[edit] 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.[2]

[edit] See also

[edit] External links


[edit] References

  1. ^ 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
  2. ^ ibid.
  • 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


Dissociative hallucinogens edit

DXM, Ketamine, Nitrous oxide, PCP, Salvinorin-A, Tiletamine
Retrieved from "http://en.wikipedia.org../../../s/a/l/Salvinorin_A_fd75.html"