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Merck
CN

S8071

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
NACRES:
NA.77
PubChem Substance ID:
24899776
UNSPSC Code:
12352200
MDL number:
MFCD05664742

Key Documents

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InChI key

OBSYBRPAKCASQB-AGQYDFLVSA-N

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

assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada; Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet

storage condition

protect from light

color

white

solubility

DMSO: ≥10 mg/mL, ethanol: ~3 mg/mL

storage temp.

−20°C

Quality Level

100

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

Salvanorin A is a non-nitrogenous κ opioid receptor agonist.
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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9510
MKCT3685
MKCP8805
MKCM8644
MKCL7574

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Zhenhong Wang et al.
PloS one, 7(7), e41724-e41724 (2012-08-23)
Cerebral hypoxia/ischemia (HI) is not uncommon during the perinatal period. If occurring, it can result in severe neurologic disabilities that persist throughout life. Salvinorin A, a non-opioid Kappa opioid receptors (KOR) selective agonist, has the potential to address this devastating
Eduardo R Butelman et al.
The Journal of pharmacology and experimental therapeutics, 341(3), 802-808 (2012-03-22)
Active blood-brain barrier mechanisms, such as the major efflux transporter P-glycoprotein (mdr1), modulate the in vivo/central nervous system (CNS) effects of many pharmacological agents, whether they are used for nonmedical reasons or in pharmacotherapy. The powerful, widely available hallucinogen salvinorin
Katherine A MacLean et al.
Psychopharmacology, 226(2), 381-392 (2012-11-09)
Salvinorin A is a kappa opioid agonist and the principal psychoactive constituent of the plant Salvia divinorum, which has increased in popularity as a recreational drug over the past decade. Few human studies have examined salvinorin A. This double-blind, placebo-controlled
Mitchell T Harden et al.
Behavioural pharmacology, 23(7), 710-715 (2012-08-29)
Salvinorin A (SalvA), the hallucinogenic derivative of the plant Salvia divinorum, is a selective κ-opioid receptor agonist that may also have antidepressant properties. Chronic mild stress (CMS) was applied to male and female Long-Evans rats to model anhedonia common in
Ivo Moreno et al.
Bioanalysis, 5(6), 661-668 (2013-03-15)
The aim of this work was to develop and validate a method for the determination of Salvinorin A in human urine using microextraction by packed sorbent (MEPS) and GC-MS/MS. The technique uses a sample volume as low as 0.2 ml
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