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W102

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

≥98% (HPLC), powder, CB2 agonist

Sinónimos:

(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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Acerca de este artículo

Fórmula lineal:
C27H26N2O3 · CH3SO3H
Número CAS:
131543-23-2
Peso molecular:
522.61
UNSPSC Code:
12352200
PubChem Substance ID:
24278779
NACRES:
NA.77
MDL number:
MFCD00153882
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Servicio técnico
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Nombre del producto

(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)

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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000331176
0000331176
0000336687
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)
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)
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
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