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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

Synonym(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

Linear Formula:

C₂₇H₂₆N₂O₃ · CH₃SO₃H

CAS Number:

131543-23-2

Molecular Weight:

522.61

UNSPSC Code:

12352200

PubChem Substance ID:

24278779

NACRES:

NA.77

MDL number:

MFCD00153882

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

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

Quality Level

100

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

SMILES string

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

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

InChI key

FSGCSTPOPBJYSX-VEIFNGETSA-N

Gene Information

human ... CNR1(1268), CNR2(1269)

Related Categories

Bioactive Small Molecules

Bioactive Small Molecule Agonists

General description

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

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.

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.

Legal Information

Sold with the permission of Sterling-Winthrop, Inc.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number

0000331176

0000336687

0000276026

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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)

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)

A Cannabinoid Receptor Type 1 (CB1R) Agonist Enhances the Developmental Neurotoxicity of Acetaminophen (Paracetamol).

Gaëtan Philippot et al.

Toxicological sciences : an official journal of the Society of Toxicology, 166(1), 203-212 (2018-08-31)

Acetaminophen (AAP; also known as paracetamol) is the most used and only recommended analgesic and antipyretic among pregnant women and young children. However, recent findings in both humans and rodents suggest a link between developmental exposure to AAP and adverse

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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Global Trade Item Number

SKU	GTIN
W102-100MG	04061837488610
W102-25MG	04061837488627

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