U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O8
Molecular Weight 432.4636
Optical Activity ( - )
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALVINORIN A

SMILES

[H][C@]1(C[C@@]2(C)[C@@]([H])(CC[C@@]3(C)[C@@H](C[C@H](OC(C)=O)C(=O)[C@]23[H])C(=O)OC)C(=O)O1)C4=COC=C4

InChI

InChIKey=OBSYBRPAKCASQB-AGQYDFLVSA-N
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

HIDE SMILES / InChI
Molecular Formula C23H28O8
Molecular Weight 432.4636
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Salvinorin A has been reported to be the most potent naturally occurring hallucinogen, with an effective dose in humans in the 200- to the 1,000-μg range when smoked; it has been reported to induce an intense hallucinatory experience in humans, with a typical duration of action being several minutes to an hour or so. Salvinorin A is a highly selective agonist of the kappa-opioid receptor (KOR) with few off-target effects. It is a potent and selective dilator of the cerebral vasculature, exhibits rapid penetration through the blood-brain barrier, has potent anti-inflammatory properties, and has the ability to preserve neurovascular unit integrity. As such, salvinorin A is an ideal compound for the prevention and treatment of cerebral vasospasm following subarachnoid hemorrhage.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Kappa-type opioid receptor
60
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Agonist
2678
 16.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
31.25 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26874330
1 mg single, respiratory
dose: 1 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
SALVINORIN A plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
371.14 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26874330
1 mg single, respiratory
dose: 1 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
SALVINORIN A plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
49.21 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26874330
1 mg single, respiratory
dose: 1 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
SALVINORIN A plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
ApexBio Technology
B5260
https://www.apexbt.com/catalogsearch/result/?q=B5260
BioSynth
W-204249
https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-204249
Cayman Chemical
11487
http://www.caymanchem.com/app/template/Product.vm/catalog/11487
Compound Cloud
128563
Fluorochem
47235
http://www.fluorochem.co.uk/Products/Product?code=047235
Fluorochem
216162
http://www.fluorochem.co.uk/Products/Product?code=216162
Sigma Aldrich
S-012
http://www.sigmaaldrich.com/catalog/search?term=S-012&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
Tocris
2134
https://www.tocris.com/search.php?Type=QuickSearch&Value=2134
Toronto Research Chemicals
S100900
https://www.trc-canada.com/product-detail/?CatNum=S100900
mcule
MCULE-5490099839
https://mcule.com/MCULE-5490099839/
PubMed

PubMed

TitleDatePubMed
Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.
2002 Sep 3
Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations.
2004 Mar
Salvinorin A: a novel and highly selective kappa-opioid receptor agonist.
2004 Oct 15
Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2).
2005 Jun 2
Salvinorin A: allosteric interactions at the mu-opioid receptor.
2007 Feb
Effect of kappa-opioid receptor agonists U69593, U50488H, spiradoline and salvinorin A on cocaine-induced drug-seeking in rats.
2009 Dec
Learning and memory impairment induced by salvinorin A, the principal ingredient of Salvia divinorum, in wistar rats.
2011 Dec
Patents

Patents

US20070213394
1
WO2006031782A2
2

Sample Use Guides

In Vivo Use Guide
Low dose: Active Salvinorin A (SA) 250 μg; medium dose: active SA 500 μg; high dose: active SA 750 μg
Route of Administration: Oral
In Vitro Use Guide
To identify Salvinorin A's molecular target, it was screened Salvinorin A (10 μM) at a large panel of mainly cloned human G protein-coupled receptors (GPCRs), transporters, and ligand-gated ion channels by using the resources of the NIMH-PDSP. For comparison, it was screened the same molecular targets with the prototypic hallucinogen LSD, also at 10 μM. Salvinorin A inhibited only [3H]-bremazocine-labeled κ opioid receptor (KOR) KORs and did not significantly inhibit binding to cloned human μ (MOR) or δ opioid (DOR) receptors or any of the 48 other molecular targets screened. Ki determinations showed that Salvinorin A was a potent agonist of KOR and guinea pig (gp)KOR.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:41:00 UTC 2023
Edited
by admin
on Sat Dec 16 04:41:00 UTC 2023
Record UNII
T56W91NG6J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SALVINORIN A
HSDB   MI  
Common Name English
2H-NAPHTHO(2,1-C)PYRAN-7-CARBOXYLIC ACID, 9-(ACETYLOXY)-2-(3-FURANYL)DODECAHYDRO-6A,10B-DIMETHYL-4,10-DIOXO-, METHYL ESTER, (2S,4AR,6AR,7R,9S,10AS,10BR)-
Common Name English
SALVINORIN A [MI]
Common Name English
SALVINORIN A [HSDB]
Common Name English
DIVINORIN A
Common Name English
SALVINORIN
Common Name English
(-)-SALVINORIN A
Common Name English
Code System Code Type Description
MESH
C090499
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
MERCK INDEX
m9751
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID80232584
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
PUBCHEM
128563
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
FDA UNII
T56W91NG6J
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
WIKIPEDIA
SALVINORIN A
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
HSDB
7640
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
CAS
83729-01-5
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
DRUG BANK
DB12327
Created by admin on Sat Dec 16 04:41:00 UTC 2023 , Edited by admin on Sat Dec 16 04:41:00 UTC 2023
PRIMARY
Related Record Type Details
D(2) DOPAMINE RECEPTOR
TARGET->PARTIAL AGONIST
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Ki
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
EC50
Related Record Type Details
Structure of SALVINORIN A
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966