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Merck

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

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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

Product Name

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

SMILES string

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

InChI key

FSGCSTPOPBJYSX-VEIFNGETSA-N

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

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

Quality Level

100

Gene Information

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

Related Categories

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.

General description

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

Legal Information

Sold with the permission of Sterling-Winthrop, Inc.

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.

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
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)
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
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
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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