A CB2 receptor agonist
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GW 842166X

Item No. 10010372

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(trifluoromethyl)-5-pyrimidinecarboxamide
CAS Number
666260-75-9
Molecular Formula
C18H17Cl2F3N4O2
Formula Weight
449.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:3): 0.25 mg/mlDMSO: 10 mg/mlEthanol: 0.3 mg/ml
λmax
280 nm
SMILES
Clc1ccc(Nc2ncc(C(=O)NCC3CCOCC3)c(n2)C(F)(F)F)c(Cl)c1
InChi Code
InChI=1S/C18H17Cl2F3N4O2/c19-11-1-2-14(13(20)7-11)26-17-25-9-12(15(27-17)18(21,22)23)16(28)24-8-10-3-5-29-6-4-10/h1-2,7,9-10H,3-6,8H2,(H,24,28)(H,25,26,27)
InChi Key
TWQYWUXBZHPIIV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $25

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    5 mg

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    10 mg

    $185

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    25 mg

    $351

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    Product Description

    GW 842166X is a cannabinoid 2 (CB2) receptor agonist.1 It increases intracellular calcium mobilization induced by the CB receptor agonist CP 55,940 (Item No. 13241) in HEK cells co-expressing a chimeric Gαq/05 protein and the human CB2 receptor (EC50 = 7.78 µM).2 GW 842166X is selective for CB2 over the CB1 receptor (IC50s = 0.133 and >25 µM, respectively). It inhibits LPS-induced production of inducible nitric oxide synthase (iNOS), as well as reduces LPS-induced phosphorylation of ERK1/2 in BV-2 microglia cells when used at a concentration of 100 nM.3 GW 842166X inhibits hyperalgesia in a rat model of inflammatory pain induced by complete Freund’s adjuvant (ED50 = 0.1 mg/kg).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Giblin, G.M.P., O'Shaughnessy, C.T., Naylor, A., et al. Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(trifluoromethyl)-5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain. J. Med. Chem. 50(11), 2597-2600 (2007).

    2. Yao, B.B., Hsieh, G.C., Frost, J.M., et al. In vitro and in vivo characterization of A-796260: A selective cannabinoid CB2 receptor agonist exhibiting analgesic activity in rodent pain models. Br. J. Pharmacol. 153(2), 390-401 (2008).

    3. Ribeiro, R., Wen, J., Li, S., et al. Involvement of ERK1/2, cPLA2 and NF-κB in microglia suppression by cannabinoid receptor agonists and antagonists. Prostaglandins Other Lipid Mediat. 100-101, (2013).

    Product Citations

    Ribeiro, R., Wen, J., Li, S., et al. Involvement of ERK1/2, cPLA2 and NF-κB in microglia suppression by cannabinoid receptor agonists and antagonists. Prostaglandins Other Lipid Mediat. 100-101, (2013).