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T3D3532 - Salvinorin A

Record Information
Version 1.0
Creation Date 2009-07-30 17:59:08 UTC
Update Date 2013-04-25 08:47:51 UTC
Accession Number T3D3532
Identification
Common Name Salvinorin A
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 (S670).
Compound Type
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. Diviner's sage
  2. Divinorin a
  3. Herbal ecstasy
  4. Mexican mint
  5. Salvinorin
  6. Salvinorin a
  7. Ska maria pastora
Chemical Formula C23H28O8
Average Molecular Weight 432.4636
Monoisotopic Molecular Weight 432.178417872
Chemical IUPAC Name
methyl 9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1H-naphtho[2,1-c]pyran-7-carboxylate
CAS Registry Number 83729-01-5
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 InChIKey=OBSYBRPAKCASQB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Naphthopyrans
Sub Class Not Available
Direct Parent Naphthopyrans
Alternative Parents
  • Naphthalenes
  • Furanolactones
  • Pyran Carboxylic Acids and Derivatives
  • Dicarboxylic Acids and Derivatives
  • Oxanes
  • Furans
  • Ketones
  • Carboxylic Acid Esters
  • Lactones
  • Enolates
Molecular Framework Aromatic Heteropolycyclic Compounds
Substituents
  • naphthalene
  • oxane
  • dicarboxylic acid derivative
  • carboxylic acid ester
  • enolate
  • ketone
  • acene
  • lactone
  • furan
  • pyran
  • furanolactone
  • pyran carboxylic acid
  • delta_valerolactone
External Descriptors Not Available
DrugBank ID Not Available
PubChem Compound ID 128563 Link_out
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Salvinorin A Link_out
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Salvinorin Link_out
Physical Properties
Appearance Colorless crystals from methanol (S672).
Melting Point 238-244 C
Solubility Not Available
Predicted LogP 2.389013855999999
Toxicity Profile
Route of Exposure Ingestion (W468) ; dermal (W468)
Mechanism of Action 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 (S673).
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) Not listed.
Uses/Sources Traditional medicine used by the Mazatec people of Oaxaca, Mexico (S672).
Minimum Risk Level Not Available
Health Effects Psychedelic-like changes in visual perception, mood, and body sensations (S671).
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 (S671).
Treatment Treatment for salvinorin A overdose would be similar to the treatments for hallucinogen intoxication. (S676)
References
General References
  • S670 — Wikipedia. Salvinorin. Last Updated 8 August 2009. [Link]
  • S672 — O'Neil MJ (ed) (2006). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.
  • S673 — Vortherms TA et al; J Biol Chem 282 (5): 3146-56 (2007).
  • S671 — National Institute on Drug Abuse (NIDA) (2007). Infofacts: Salvia.
  • S676 — Biller J (2007). The Interface of Neurology & Internal Medicine. Philadelphia, PA: Wolters Kluwer Health, Lippincott/Williams and Wilkins.
  • S675 — Teksin ZS, Lee IJ, Nemieboka NN, Othman AA, Upreti VV, Hassan HE, Syed SS, Prisinzano TE, Eddington ND. Evaluation of the Transport, In Vitro Metabolism and Pharmacokinetics of Salvinorin A, a Potent Hallucinogen. Eur J Pharm Biopharm. 2009 Jan 19. [19602379 Link_out]
  • W468 — Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]

Targets

1. Kappa-type opioid receptor

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions.

Salvinorin A has been found to be a potent and selective kappa opioid receptor agonist in vitro and in vivo (S686).
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • S686 — Tidgewell K, Groer CE, Harding WW, Lozama A, Schmidt M, Marquam A, Hiemstra J, Partilla JS, Dersch CM, Rothman RB, Bohn LM, Prisinzano TE. Herkinorin analogues with differential beta-arrestin-2 interactions. J Med Chem. 2008 Apr 24;51(8):2421-31. Epub 2008 Apr 2. [18380425 Link_out]