Salvinorin A

Salvinorin A
Clinical data
Routes of; administration	Inhalation, sublingual, buccal
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule IV; UK: Under Psychoactive Substances Act; 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 ;
PubChem CID	128563;
IUPHAR/BPS	1666;
ChemSpider	113947 ;
UNII	T56W91NG6J;
KEGG	C20196 ;
ChEBI	CHEBI:67900 ;
ChEMBL	ChEMBL445332 ;
CompTox Dashboard (EPA)	DTXSID80232584 ;
ECHA InfoCard	100.215.796
Chemical and physical data
Formula	C23H28O8
Molar mass	432.469 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	[α]D = -45.3° at 22 °C/ (c = 8.530 CHCl3); [α]D = -41° at 25 °C (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 ; Key:OBSYBRPAKCASQB-AGQYDFLVSA-N ;
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Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered an atypical dissociative hallucinogen.

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 rather is a terpenoid. It also differs in subjective experience, compared to other hallucinogens, and has been described as having strong dissociative effects.

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.

Clinical data


Routes of administration	Inhalation, sublingual, buccal
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics) CA: Schedule IV UK: Under Psychoactive Substances Act 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
CompTox Dashboard (EPA)	DTXSID80232584
ECHA InfoCard	100.215.796
Chemical and physical data
Formula	C₂₃H₂₈O₈
Molar mass	432.469 g·mol⁻¹
3D model (JSmol)	Interactive image
Specific rotation	[α]_D = -45.3° at 22 °C/ (c = 8.530 CHCl₃); [α]_D = -41° at 25 °C (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
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