A CB2 receptor inverse agonist
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IMMA

Item No. 70275

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-1-(4-morpholinyl)-ethanone
CAS Number
2854-32-2
Synonyms
  • BML-190
  • Indomethacin Morpholinylamide
  • LM-4131
Molecular Formula
C23H23ClN2O4
Formula Weight
426.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 12.75 mg/mlEthanol: 1.25 mg/mlPBS acidic: 50 µg/mlPBS basic: 50 µg/mlPBS pH 7.2: 50 µg/ml
SMILES
CC1=C(C(C=C(OC)C=C2)=C2N1C(C3=CC=C(Cl)C=C3)=O)CC(N4CCOCC4)=O
InChi Code
InChI=1S/C23H23ClN2O4/c1-15-19(14-22(27)25-9-11-30-12-10-25)20-13-18(29-2)7-8-21(20)26(15)23(28)16-3-5-17(24)6-4-16/h3-8,13H,9-12,14H2,1-2H3
InChi Key
BJSDNVVWJYDOLK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    IMMA is a cannabinoid (CB) receptor 2 inverse agonist (Ki = 435 nM for recombinant human CB2).1,2 It is selective for CB2 over CB1 receptors (Ki = >20 µM). IMMA (0.001-1 µM) reduces basal production of inositol phosphate and increases forskolin-induced accumulation of cAMP in HEK293 cells expressing human CB2 receptors.2 It inhibits LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2: Item No. 14010) production in J774 macrophages in a concentration-dependent manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gallant, M., Dufresne, C., Gareau, Y., et al. New class of potent ligands for the human peripheral cannabinoid receptor. Bioor. Med. Chem. Lett. 6(19), 2263-2268 (1996).

    2. New, D.C., and Wong, Y.H. BML-190 and AM251 act as inverse agonists at the human cannabinoid CB2 receptor: Signalling via cAMP and inositol phosphates. FEBS Lett. 536(1-3), 157-160 (2003).

    3. Chang, Y.-H., Lee, S.T., and Lin, W.-W. Effects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: Involvement of eicosanoids. J. Cell. Biochem. 81(4), 715-723 (2001).