W102

(R)-(+)-WIN 55,212-2 mesylate salt

Name: (<I>R</I>)-(+)-WIN 55,212-2 mesylate salt
Brand: SIGMA

≥98% (HPLC), powder, CB2 agonist

Synonyme(s) :

(R)-(+)-[2,3-Dihydro-5-methyl-3[(4-morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone mesylate salt, WIN 55212-2 methanesulfonate, WIN 552122 mesylate

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About This Item

Formule linéaire :

C₂₇H₂₆N₂O₃ · CH₃SO₃H

Numéro CAS:

131543-23-2

Poids moléculaire :

522.61

UNSPSC Code:

12352200

PubChem Substance ID:

24278779

NACRES:

NA.77

MDL number:

MFCD00153882

Nom du produit

(R)-(+)-WIN 55,212-2 mesylate salt, ≥98% (HPLC)

SMILES string

CS(O)(=O)=O.Cc1c(C(=O)c2cccc3ccccc23)c4cccc5OC[C@@H](CN6CCOCC6)n1c45

InChI key

FSGCSTPOPBJYSX-VEIFNGETSA-N

InChI

1S/C27H26N2O3.CH4O3S/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28;1-5(2,3)4/h2-11,20H,12-17H2,1H3;1H3,(H,2,3,4)/t20-;/m1./s1

assay

≥98% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to beige

solubility

0.1 M HCl: 0.25 mg/mL
DMSO: 12 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2.4 mg/mL
0.1 M NaOH: insoluble
H₂O: insoluble

Application

(R)-(+)-WIN 55,212-2 mesylate salt has been used as a high affinity cannabinoid agonist for intraperitoneal injection into rats to induce behavioural sensitization. It has also been used as a synthetic cannabinoid drug and cannabinoid receptor 1 (CNR1) agonist to treat Becn2+/− mice and wild-type (WT) littermate to analyze the levels of CNR1 in the brain.

Biochem/physiol Actions

It is known to decrease the lipopolysaccharide mediated release of tumor necrosis factor- α and interleukin-1 in mice.

Features and Benefits

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

General description

WIN 55,212-2 is a member of the aminoalkylindole class of compounds.

Legal Information

Sold with the permission of Sterling-Winthrop, Inc.

Preparation Note

The solubility of this chemical in DMF has not been determined. However, various sources state this chemical can be solubilized in about 30 mg/ml of DMF.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number

0000331176

0000336687

0000276026

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Rational design and synthesis of an orally active indolopyridone as a novel conformationally constrained cannabinoid ligand possessing antiinflammatory properties

Wrobleski ST, et al.

Journal of Medicinal Chemistry, 46(11), 2110-2116 (2003)

Dual Role of PPAR-c in Induction and Expression of Behavioral Sensitization to Cannabinoid Receptor Agonist WIN55,212-2

Enayatfard L, et al.

Neuromolecular Medicine, 15, 523-535 (2013)

The analgesic effects of R(+)-WIN 55,212-2 mesylate, a high affinity cannabinoid agonist, in a rat model of neuropathic pain.

U Herzberg et al.

Neuroscience letters, 221(2-3), 157-160 (1997-01-17)

The effects of a high affinity cannabinoid receptor agonist were evaluated in rats subjected to chronic constriction injury of the sciatic nerve (CCI) or a sham operation. Intraperitoneal (i.p.) injections of the active, but not the inactive enantiomer, alleviated the

Autophagy activation by novel inducers prevents BECN2-mediated drug tolerance to cannabinoids

Kuramoto K, et al.

Autophagy, 12(9), 1460-1471 (2016)

Sex-dependent pharmacological profiles of the synthetic cannabinoid MMB-Fubinaca.

José F Oliveira da Cruz et al.

Addiction biology, 26(3), e12940-e12940 (2020-08-04)

Synthetic cannabinoids have emerged as novel psychoactive substances with damaging consequences for public health. They exhibit high affinity at the cannabinoid type-1 (CB1 ) receptor and produce similar and often more potent effects as other CB1 receptor agonists. However, we

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