A CB1 receptor antagonist/inverse agonist
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AM281

Item No. 10006972

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-4-morpholinyl-1H-pyrazole-3-carboxamide
CAS Number
202463-68-1
Molecular Formula
C21H19Cl2IN4O2
Formula Weight
557.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMF:PBS (pH 7.2) (1:5): 0.2 mg/mlDMSO: 1 mg/ml
λmax
249 nm
SMILES
ClC1=CC(Cl)=CC=C1N2C(C3=CC=C(I)C=C3)=C(C)C(C(NN4CCOCC4)=O)=N2
InChi Code
InChI=1S/C21H19Cl2IN4O2/c1-13-19(21(29)26-27-8-10-30-11-9-27)25-28(18-7-4-15(22)12-17(18)23)20(13)14-2-5-16(24)6-3-14/h2-7,12H,8-11H2,1H3,(H,26,29)
InChi Key
AJFFBPZYXRNAIC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    AM281 is a potent and selective central cannabinoid (CB1) receptor antagonist/inverse agonist (Kis = 12 nM and 4,200 nM for CB1 and CB2, respectively).1,2 Structurally, it is an analog of the CB1 inverse agonist rimonabant (Item No. 9000484).2 It has no effect on the vanilloid TRPV1 receptor.3 AM281 has been used to evaluate the potential effects of compounds at CB1.4,5 It has also been used to study the membrane localization and cycling of CB1.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lan, R., Lu, Q., Fan, P., et al. Design and synthesis of the CB1 selective cannabinoid antagonist AM281: A potential human SPECT ligand. AAPS Pharmsci. 1(3), 1-7 (1999).

    2. Gatley, S.J., Lan, R., Pyatt, B., et al. Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors. Life Sci. 61(14), PL-191-PL-197 (1997).

    3. Jerman, J.C., Gray, J., Brough, S.J., et al. Comparison of effects of anandamide at recombinant and endogenous rat vanilloid receptors. Br. J. Anaesth. 89(6), 882-887 (2002).

    4. Baker, C.L., and McDougall, J.J. The cannabinomimetic arachidonyl-2-chloroethylamide (ACEA) acts on capsaicin-sensitive TRPV1 receptors but not cannabinoid receptors in rat joints. Br. J. Pharmacol. 142(8), 1361-1367 (2004).

    5. Brown, I., Cascio, M.G., Wahle, K.W.J., et al. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 31(9), 1584-1591 (2010).

    6. Leterrier, C., Bonnard, D., Carrel, D., et al. Constitutive endocytic cycle of the CB1 cannabinoid receptor. The Journal of Biological Chemisty 279(34), 36013-36021 (2004).