W102

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

≥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
• Linear Formula: C₂₇H₂₆N₂O₃ · CH₃SO₃H
• CAS Number: 131543-23-2
• Molecular Weight: 522.61
• MDL number: MFCD00153882
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278779
• NACRES: NA.77

Properties

• 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)

Description

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.

Safety Information

• 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