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

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O8
Molecular Weight 432.4645
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALVINORIN A

SMILES

CC(=O)O[C@@]1([H])C[C@@]([H])(C(=O)OC)[C@]2(C)CC[C@@]3([H])C(=O)O[C@@]([H])(C[C@]3(C)[C@@]2([H])C1=O)c4ccoc4

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 432.4645
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
16.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
31.25 ng/mL
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
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
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
PubMed

PubMed

TitleDatePubMed
Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.
2002 Sep 3
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

Sample Use Guides

Low dose: Active Salvinorin A (SA) 250 μg; medium dose: active SA 500 μg; high dose: active SA 750 μg
Route of Administration: Oral
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 Jun 26 06:53:53 UTC 2021
Edited
by admin
on Sat Jun 26 06:53:53 UTC 2021
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 Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
MERCK INDEX
M9751
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY Merck Index
EPA CompTox
83729-01-5
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
PUBCHEM
128563
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
FDA UNII
T56W91NG6J
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
WIKIPEDIA
SALVINORIN A
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
HSDB
7640
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
CAS
83729-01-5
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
DRUG BANK
DB12327
Created by admin on Sat Jun 26 06:53:53 UTC 2021 , Edited by admin on Sat Jun 26 06:53:53 UTC 2021
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST