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Salvinorin-A

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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 formulaC23H28O8
Molecular mass432.46 g/mol
Melting point238 - 240 C
CAS numberX1017952-1
SMILESO=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.

Contents

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.


Salvinorins A - F: General formulas
Missing image
Salvinorins-AB.png
Structure 1:
Salvinorin A and B
Missing image
Salvinorins-D-F.png
Structure 2:
Salvinorin D - F


Salvinorins A - F
NameR1R2StructureActivity
Salvinorin A-OCOCH3-1active
Salvinorin B-OH-1inactive
Salvinorin C-OCOCH3-OCOCH32inactive
Salvinorin D-OH-OCOCH32inactive
Salvinorin E-OCOCH3-OH2inactive
Salvinorin F-H-OH2unknown

Chemistry

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

External links

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

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