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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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