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W102

Sigma-Aldrich

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

≥98% (HPLC), powder, CB2 agonist

Synonyme(s) :

WIN552122 mesylate

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About This Item

Formule linéaire :
C27H26N2O3 · CH3SO3H
Numéro CAS:
131543-23-2
Poids moléculaire :
522.61
Numéro MDL:
MFCD00153882
Code UNSPSC :
12352200
ID de substance PubChem :
24278779
Nomenclature NACRES :
NA.77

product name

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

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Couleur

white to beige

Solubilité

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

Chaîne 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

Clé InChI

FSGCSTPOPBJYSX-VEIFNGETSA-N

Informations sur le gène

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

Description générale

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.

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Notes préparatoires

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.

Informations légales

Sold with the permission of Sterling-Winthrop, Inc.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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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