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
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
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
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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.
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C090499
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m9751
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DTXSID80232584
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SALVINORIN A
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83729-01-5
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DB12327
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ACTIVE MOIETY
