Salvinorin A

Salvinorin A

Clinical data
Routes of administration	Buccal/Sublingual, Smoked
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule IV Uncontrolled (though Salvia divinorum is controlled in some parts of the world, such as in certain states in the US)
Identifiers
IUPAC name methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate
CAS Number	83729-01-5 N
PubChem CID	128563
IUPHAR/BPS	1666
ChemSpider	113947 Y
UNII	T56W91NG6J
KEGG	C20196 N
ChEBI	CHEBI:67900 N
ChEMBL	CHEMBL445332 Y
ECHA InfoCard	100.215.796
Chemical and physical data
Formula	C23H28O8
Molar mass	432.46362 g/mol
3D model (Jmol)	Interactive image
Specific rotation	-45.3 °C at 22 deg C/D (c = 8.530 CHCl3); -41 °C at 25°C/D (c = 1 in CHCl3)
Melting point	238 to 240 °C (460 to 464 °F) (also reported 242–244 °C)
Boiling point	760.2 °C (1,400.4 °F)
Solubility in water	25.07 mg/L at 25 °C (water, est) mg/mL (20 °C)
SMILES O=C(OC)[C@H]2[C@@]3(CC[C@H]4C(=O)O[C@H](c1ccoc1)C[C@@]4([C@H]3C(=O)[C@@H](OC(=O)C)C2)C)C
InChI InChI=1S/C23H28O8/c1-12(24)30-16-9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(22)18(16)25/h6,8,11,14-17,19H,5,7,9-10H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1 Y Key:OBSYBRPAKCASQB-AGQYDFLVSA-N Y
NY (what is this?)

Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans. Salvinorin A is considered a dissociative.

It is structurally distinct from other naturally occurring hallucinogens (such as DMT, psilocybin, and mescaline) because it contains no nitrogen atoms; hence, it is not an alkaloid (and cannot be rendered as a salt) but a terpenoid. It also differs in subjective experience, compared to other hallucinogens, and has been described as dissociative.

Salvinorin A can produce psychoactive experiences in humans with a typical duration of action being several minutes to an hour or so, depending on the method of ingestion.

Salvinorin A is found 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.

Salvinorin A was first described and named in 1982 by Alfredo Ortega and colleagues in Mexico. They used a combination of spectroscopy and x-ray crystallography to determine the chemical structure of the compound, which was shown to have a bicyclic diterpene structure. Around the same time, Leander Julián Valdés III independently isolated the molecule as part of his PhD research, published in 1983. Valdés named the chemical divinorum, and also isolated an analog that he named divinorum B. The naming was subsequently corrected to salvinorin A and B after the work was published in 1984. Valdés later isolated salvinorin C.