A competitive neutral antagonist of CB2
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(−)-WIN 55,212-3 (mesylate)

Item No. 12022

Restricted Product (Schedule I)
Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[(3S)-2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenyl-methanone, methanesulfonate
CAS Number
131543-25-4
Molecular Formula
C27H26N2O3 • CH3SO3H
Formula Weight
522.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.25 mg/mlEthanol: 5 mg/ml
λmax
219, 246, 330 nm
SMILES
CC1=C(C(C2=CC=CC3=C2C=CC=C3)=O)C4=CC=CC(OC5)=C4N1[C@H]5CN6CCOCC6.CS(=O)(O)=O
InChi Code
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-;/m0./s1
InChi Key
FSGCSTPOPBJYSX-BDQAORGHSA-N
Regulatory Information
DEA Schedule
I
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (−)-WIN 55,212-3 is an aminoalkylindole derivative which acts as a competitive neutral antagonist of the human cannabinoid CB2 receptor, blocking both the stimulating action of CP 55,940 (pA2 = 6.1) and the inverse agonism of SR 144528 (Item No. 9000491) (pEC50 = 5.3).1 (−)-WIN 55,212-3 neither antagonizes nor mimics the effects of Δ9-THC on rat cerebellar membranes, which presumably express the CB1 receptor.2,3 (−)-WIN 55,212-3 also weakly antagonizes the melatonin MT1 and muscarinic M4 receptors but has no effect on several other G protein-coupled receptors.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Savinainen, J.R., Kokkola, T., Salo, O.M.H., et al. Identification of WIN55212-3 as a competitive neutral antagonist of the human cannabinoid CB2 receptor. Br. J. Pharmacol. 145(5), 636-645 (2005).

    2. Pacheco, M., Childers, S.R., Arnold, R., et al. Aminoalkylindoles: Actions on specific G-protein-linked receptors. J. Pharmacol. Exp. Ther. 257(1), 170-183 (1991).

    3. Compton, D.R., Gold, L.H., Ward, S.J., et al. Aminoalkylindole analogs: Cannabimimetic activity of a class of compounds structurally distinct from Δ9-tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 263(3), 1118-1126 (1992).