BML-190

BML-190

Identifiers
IUPAC name 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
CAS Number	2854-32-2  Y
PubChem CID	2415
ChemSpider	2321  N
CompTox Dashboard (EPA)	DTXSID50951230
Chemical and physical data
Formula	C23H23ClN2O4
Molar mass	426.90 g·mol−1
3D model (JSmol)	Interactive image
SMILES C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3
InChI 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 N Key:BJSDNVVWJYDOLK-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

BML-190 (Indomethacin morpholinylamide) is a drug used in scientific research that acts as a selective CB₂ inverse agonist. ^[1] BML-190 is structurally derived from the NSAID indomethacin but has a quite different biological activity. ^[2] The activity produced by this compound is disputed, with some sources referring to it as a CB₂ agonist rather than an inverse agonist; ^{[3] [4]} this may reflect an error in classification, or alternatively it may produce different effects in different tissues, and more research is required to resolve this dispute.

References

1. New DC, Wong YH (February 2003). "BML-190 and AM251 act as inverse agonists at the human cannabinoid CB2 receptor: signalling via cAMP and inositol phosphates". FEBS Letters. 536 (1–3): 157–60. doi: 10.1016/S0014-5793(03)00048-6 . PMID   12586356. S2CID   38569901.
2. Klegeris A, Bissonnette CJ, McGeer PL (June 2003). "Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor". British Journal of Pharmacology. 139 (4): 775–86. doi:10.1038/sj.bjp.0705304. PMC   1573900 . PMID   12813001.
3. Melck D, De Petrocellis L, Orlando P, Bisogno T, Laezza C, Bifulco M, Di Marzo V (January 2000). "Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation". Endocrinology. 141 (1): 118–26. doi: 10.1210/endo.141.1.7239 . PMID   10614630.
4. Scutt A, Williamson EM (January 2007). "Cannabinoids stimulate fibroblastic colony formation by bone marrow cells indirectly via CB2 receptors". Calcified Tissue International. 80 (1): 50–9. doi:10.1007/s00223-006-0171-7. PMID   17205329. S2CID   23624771.