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Merck

W102

Sigma-Aldrich

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

≥98% (HPLC), powder, CB2 agonist

Sinónimos:

WIN552122 mesylate

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About This Item

Fórmula lineal:
C27H26N2O3 · CH3SO3H
Número de CAS:
Peso molecular:
522.61
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

product name

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

Nivel de calidad

Análisis

≥98% (HPLC)

formulario

powder

control farmacológico

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to beige

solubilidad

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

cadena SMILES

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

Clave InChI

FSGCSTPOPBJYSX-VEIFNGETSA-N

Información sobre el gen

Descripción general

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

Aplicación

(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.

Acciones bioquímicas o fisiológicas

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

Características y beneficios

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.

Información legal

Sold with the permission of Sterling-Winthrop, Inc.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)
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)
Autophagy activation by novel inducers prevents BECN2-mediated drug tolerance to cannabinoids
Kuramoto K, et al.
Autophagy, 12(9), 1460-1471 (2016)
A Richter et al.
European journal of pharmacology, 264(3), 371-377 (1994-11-03)
The effects of the novel high affinity cannabinoid receptor agonist (+)-WIN 55,212-2 ((R)-4,5-dihydro-2-methyl-4(4-morphoinylmethyl)-1-(1-naphthalen ylcarbonyl)-6H-pyrrolo[3,2,1-ij]quinolin-6-one) on severity of dystonia were investigated in mutant Syrian hamsters with primary generalized dystonia. Following injections of (+)-WIN 55,212-2 (1.0-5.0 mg/kg i.p.) a dose-dependent reduction of
X Pan et al.
Molecular pharmacology, 49(4), 707-714 (1996-04-01)
Modulation of neuronal ion channels by the cloned rat brain CB1 cannabinoid receptor was investigated with the use of a heterologous neuronal expression system. Transient expression of the rat brain CB1 cannabinoid receptor was accomplished through microinjection of in vitro

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