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 formula	C₂₃H₂₈O₈
Molecular mass	432.46 g/mol
Melting point	238 - 240 °C
CAS number	X1017952-1
SMILES	(see below)

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, similar in potency to LSD. 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.

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.

Salvinorins A - F

Salvinorin A is one of several structurally related salvinorins. While its des-acetylated analog salvinorin B is devoid of human activity, the related salvinorin C might be even more potent.

**Salvinorins A - F: General formulas**
Structure 1: Salvinorin A and B	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	probably very active
Salvinorin D	-OH	-OCOCH₃	2	unknown
Salvinorin E	-OCOCH₃	-OH	2	unknown
Salvinorin F	-H	-OH	2	unknown

Chemistry

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

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

External links

Categorization

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{DXM} {Ketamine} {Nitrous oxide} {PCP} {Salvinorin A}

pl:salvinorin A de:Salvinorin