A CB1 receptor antagonist
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AM251

Item No. 71670

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide
CAS Number
183232-66-8
Molecular Formula
C22H21Cl2IN4O
Formula Weight
555.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:3): 500 µg/mlEthanol: 14 mg/ml
SMILES
Ic1ccc(cc1)c1c(C)c(nn1c1ccc(Cl)cc1Cl)C(=O)NN1CCCCC1
InChi Code
InChI=1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
InChi Key
BUZAJRPLUGXRAB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $61

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    10 mg

    $109

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    50 mg

    $363

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    100 mg

    $666

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    Cayman Chemical
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    Product Description

    AM251 is a cannabinoid 1 (CB1) receptor 1 antagonist.1 It binds to CB1 receptors in rat forebrain membrane preparations (Ki = 7.5 nM) and is selective over CB2 receptors in mouse spleen preparations (Ki = 2,290 nM) in radioligand binding assays. AM251 inhibits GTPγS binding induced by the CB receptor agonist CP 55,940 in HEK293 cells expressing human CB1 receptors (EC50 = 8 nM).2 AM251 (10 mg/kg) decreases immobility time in the forced swim test in wild-type but not CB1 receptor-deficient mice.3 It reduces fasting-induced food intake and body weight gain in mice when administered at a dose of 30 mg/kg. AM251 also induces GTPγS binding in HEK293 cells expressing the orphan receptor GPR55 (EC50 = 39 nM) and potentiates GABA-induced GABAA receptor currents (EC50 = 0.4 µM).2,4 It prevents TGF-β1-induced epithelial-to-mesenchymal transition (EMT), inhibits SMAD2/3 and p38 MAPK activation, and reduces the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells.5 AM251 induces cell cycle arrest at the G2/M phase and apoptosis in A375 human melanoma cells.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Selinsky, B.S., Gupta, K., Sharkey, C.T., et al. Structural analysis of NSAID binding by prostaglandin H2 synthase: Time-dependent and time-independent inhibitors elicit identical enzyme conformations. Biochemistry 40(17), 5172-5180 (2001).

    2. Ryberg, E., Larsson, N., Sjögren, S., et al. The orphan receptor GPR55 is a novel cannabinoid receptor. Br. J. Pharmacol. 152(7), 1092-1101 (2007).

    3. Shearman, L.P., Rosko, K.M., Fleischer, R., et al. Antidepressant-like and anorectic effects of the cannabinoid CB1 receptor inverse agonist AM251 in mice. Behav. Pharmacol. 14(8), 573-582 (2003).

    4. Baur, R., Gertsch, J., and Sigel, E. The cannabinoid CB1 receptor antagonists rimonabant (SR141716) and AM251 directly potentiate GABAA receptors. Br. J. Pharmacol. 165(8), 2479-2484 (2012).

    5. Yoshinaga, T., Uwabe, K., Naito, S., et al. AM251 suppresses epithelial-mesenchymal transition of renal tubular epithelial cells. PloS One 11(12), e0167848 (2016).

    6. Carpi, S., Fogli, S., Romanini, A., et al. AM251 induces apoptosis and G2/M cell cycle arrest in A375 human melanoma cells. Anticancer Drugs 26(7), 754-762 (2015).

    Product Citations

    Bishay, P., Schmidt, H., Marian, C., et al. R-Flurbiprofen reduces neuropathic pain in rodents by restoring endogenous cannabinoids. PLoS One 5(5), e10628 (2010).