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W109

Sigma-Aldrich

S(–)-WIN 55,212-3 mesylate salt

solid

Synonym(s):

S(–)-[2,3-Dihydro-5-methyl-3-[(4-morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone mesylate salt

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About This Item

Linear Formula:
C27H26N2O3 · CH3SO3H
CAS Number:
131543-25-4
Molecular Weight:
522.61
MDL number:
MFCD00467944
UNSPSC Code:
12352200
PubChem Substance ID:
24900777

form

solid

optical activity

[α]/D −48.0°, c = 0.246 in DMSO(lit.)

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

off-white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2.4 mg/mL
DMSO: soluble
methanol: soluble

SMILES string

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

Biochem/physiol Actions

Inactive enantiomer of WIN 55,212-2.

Caution

Hygroscopic

Legal Information

Manufactured and sold with the permission of Sterling Winthrop.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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