Salvinorin A

Salvinorin A
Clinical data
Routes of; administration	Buccal/Sublingual, Smoked
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 a dissociative hallucinogen.^[3]^[4]

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.^[3] It also differs in subjective experience, compared to other hallucinogens, and has been described as dissociative.^[4]

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.^[5]

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.^[5]

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ salvinorin A, PubChem, retrieved 2012-11-23
^ ^a ^b Butelman ER, Kreek MJ (2015). "Salvinorin A, a kappa-opioid receptor agonist hallucinogen: pharmacology and potential template for novel pharmacotherapeutic agents in neuropsychiatric disorders". Frontiers in Pharmacology. 6: 190. doi:10.3389/fphar.2015.00190. PMC 4561799. PMID 26441647.
^ ^a ^b MacLean KA, Johnson MW, Reissig CJ, Prisinzano TE, Griffiths RR (March 2013). "Dose-related effects of salvinorin A in humans: dissociative, hallucinogenic, and memory effects". Psychopharmacology. 226 (2): 381–392. doi:10.1007/s00213-012-2912-9. PMC 3581702. PMID 23135605.
^ ^a ^b Cite error: The named reference Roth2002 was invoked but never defined (see the help page).

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] salvinorin A, PubChem, retrieved 2012-11-23

[fp-3] Butelman ER, Kreek MJ (2015). "Salvinorin A, a kappa-opioid receptor agonist hallucinogen: pharmacology and potential template for novel pharmacotherapeutic agents in neuropsychiatric disorders". Frontiers in Pharmacology. 6: 190. doi:10.3389/fphar.2015.00190. PMC 4561799. PMID 26441647.

[NCBI-4] MacLean KA, Johnson MW, Reissig CJ, Prisinzano TE, Griffiths RR (March 2013). "Dose-related effects of salvinorin A in humans: dissociative, hallucinogenic, and memory effects". Psychopharmacology. 226 (2): 381–392. doi:10.1007/s00213-012-2912-9. PMC 3581702. PMID 23135605.

[Roth2002-5] Cite error: The named reference Roth2002 was invoked but never defined (see the help page).

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Clinical data


Routes of administration	Buccal/Sublingual, Smoked
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] 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)^[2]
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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