SALVINORIN A

Investigational

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12192085 | https://www.ncbi.nlm.nih.gov/pubmed/28190678 | http://pci.upenn.edu/wp-content/uploads/2016/03/Neurokappa-Company-Summary-March-2016.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
Kappa-type opioid receptor 60 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12192085	Agonist 2678		16.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cerebral vasospasm 9 Sources: http://pci.upenn.edu/wp-content/uploads/2016/03/Neurokappa-Company-Summary-March-2016.pdf	Primary		Phase I 428	Unknown Approved Use Unknown

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.	2002 Sep 3	12192085
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	14718611

Patents

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 GMT 2023` Edited by `admin` on `Sat Dec 16 04:41:00 GMT 2023`
Record UNII	T56W91NG6J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SALVINORIN A

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