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S8071

Sigma-Aldrich

Salvinorin A

≥98% (HPLC), solid

Synonym(s):

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(3-furanyl)dodechydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C23H28O8
CAS Number:
83729-01-5
Molecular Weight:
432.46
MDL number:
MFCD05664742
UNSPSC Code:
12352200
PubChem Substance ID:
24899776
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

protect from light

color

white

solubility

DMSO: ≥10 mg/mL
ethanol: ~3 mg/mL

storage temp.

−20°C

SMILES string

[H][C@@]12CC[C@@]3(C)[C@@H](C[C@H](OC(C)=O)C(=O)[C@]3([H])[C@@]1(C)C[C@H](OC2=O)c4ccoc4)C(=O)OC

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

InChI key

OBSYBRPAKCASQB-AGQYDFLVSA-N

Gene Information

human ... OPRD1(4985) , OPRK1(4986) , OPRM1(4988)
rat ... Oprk1(29335)

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Application

Salvinorin A was administered to rats to study effects on lactic acid-stimulated stretching.1

Biochem/physiol Actions

Salvinorin A is a potent, non-nitrogenous κ opioid selective receptor agonist. Salvinorin A is isolated from Salvia divinorum. Salvinorin A displays high affinity at both native (Ki=4.3 nm) and cloned (Ki=16 nm) κ -opioid receptors. Preliminary studies suggest that Salvanorin A is chemically unique among the psychtropic drugs and does not bind to any known receptor.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fang Ji et al.
Brain research, 1490, 95-100 (2012-10-30)
Since herkinorin is the first non-opioid mu agonist derived from salvinorin A that has the ability to induce cerebral vascular dilatation, we hypothesized that herkinorin could have similar vascular dilatation effect via the mu and kappa opioid receptors and the
Aashish S Morani et al.
Behavioural pharmacology, 23(2), 162-170 (2012-02-02)
Kappa opioid receptor (KOPr) activation antagonizes many cocaine-related behaviors but adverse side-effects such as sedation, dysphoria, and depression limit their therapeutic use. Recently, salvinorin A (Sal A), a naturally occurring KOPr agonist, has been shown to attenuate cocaine-induced drug seeking
Francesca Guida et al.
Molecular pain, 8, 60-60 (2012-08-24)
Salvinorin A (SA), the main active component of Salvia Divinorum, is a non-nitrogenous kappa opioid receptor (KOR) agonist. It has been shown to reduce acute pain and to exert potent antinflammatory effects. This study assesses the effects and the mode
John Stogner et al.
The International journal on drug policy, 23(6), 512-521 (2012-04-17)
A plant with dissociative and psychoactive properties began to attract the attention of the media and United States policymakers following a well-publicized suicide in 2006 and reports that the plant served as a 'legal high' and substitute for cannabis. As
Justyna Piekielna et al.
Postepy biochemii, 58(4), 485-491 (2012-01-01)
Salvinorin A (SA) is the main active ingredient of Salvia divinorum, a naturally occurring hallucinogen plant from Mexico. Traditionally, herbal preparations obtained from Salvia were used by the Mazatec Indians for their divination rites and the treatment of gastrointestinal disorders.
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