ContaminantDB: Salvinorin A

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:59:08 UTC

Update Date

2026-04-03 04:00:31 UTC

Accession Number

CHEM002530

Identification

Common Name

Salvinorin A

Class

Small Molecule

Description

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 a hallucinogenic compound with dissociative effects (7).

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₈

Average Molecular Mass

432.464 g/mol

Monoisotopic Mass

432.178 g/mol

CAS Registry Number

83729-01-5

IUPAC Name

methyl 9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl 9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

SMILES

COC(=O)C1CC(OC(C)=O)C(=O)C2C1(C)CCC1C(=O)OC(CC21C)C1=COC=C1

InChI Identifier

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

InChI Key

OBSYBRPAKCASQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Alpha-acyloxy ketone
Pyran
Oxane
Methyl ester
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless crystals from methanol (3).

Experimental Properties

Property	Value
Melting Point	238-244°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.39	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106 m³·mol⁻¹	ChemAxon
Polarizability	44.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-5079300000-0c3d81b169f1ec02eb08	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1008900000-3dde4855bc69f27483e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gi3-1019500000-0d06ceb5fd22972dfc1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gxw-3249100000-797004a599225d2018a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-3009600000-a9c68bc515eddd483f7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a5i-3009200000-0bf80f4121126284c9d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9006000000-f6147bd53d5e352b972c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009200000-3c86e6f8f5d793dd7a0b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0019100000-511b0cc4a7bbe7ac17a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9057100000-1307ddb5b9baf63a568b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000200000-4490b6cd9718932fc15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9002000000-18739f0784b8f7ec39da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6v-9036300000-46b86aa451b8356c46c8	Spectrum

Toxicity Profile

Route of Exposure

Ingestion (8) ; dermal (8)

Mechanism of Toxicity

Salvinorin A, the active component of the hallucinogenic sage Salvia divinorum, is an apparently selective and highly potent kappa-opioid receptor (KOR) agonist. Salvinorin A is unique among ligands for peptidergic G protein-coupled receptors in being nonnitrogenous and lipid-like in character (4).

Metabolism

Salvinorin A’s chemical structure suggests that it may be a substrate of CYP450 (oxidative metabolism), UGT (hydrolysis) or carboxylesterases (ChEs) (hydrolysis). In addition, as observed for CYP1A1, CPY2C18 and CYP2E1, Salvinorin A metabolism via UGTB27 appears to be saturable at higher concentrations.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (6)

Uses/Sources

Traditional medicine used by the Mazatec people of Oaxaca, Mexico (3).

Minimum Risk Level

Not Available

Health Effects

Psychedelic-like changes in visual perception, mood, and body sensations (2).

Symptoms

Hallucinations or delusional episodes that mimic psychosis. ; emotional swings; feelings of detachment; and importantly, a highly modified perception of external reality and the self, which leads to a decreased ability to interact with one's surroundings (2).

Treatment

Treatment for salvinorin A overdose would be similar to the treatments for hallucinogen intoxication. (5)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0257471

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Salvinorin A

Chemspider ID

3189819

ChEBI ID

Not Available

PubChem Compound ID

3969708

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Salvinorin A (CHEM002530)

Structure for CHEM002530: Salvinorin A