BML-190
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444674170
| IUPAC_name = 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
| image = BML-190.svg
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2854-32-2
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| PubChem = 2415
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| chemical_formula =
| C=23 | H=23 | Cl=1 | N=2 | O=4
| smiles = C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2321
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BJSDNVVWJYDOLK-UHFFFAOYSA-N
}}
BML-190 (Indomethacin morpholinylamide) is a drug used in scientific research that acts as a selective CB2 inverse agonist.{{cite journal | vauthors = New DC, Wong YH | title = BML-190 and AM251 act as inverse agonists at the human cannabinoid CB2 receptor: signalling via cAMP and inositol phosphates | journal = FEBS Letters | volume = 536 | issue = 1–3 | pages = 157–60 | date = February 2003 | pmid = 12586356 | doi = 10.1016/S0014-5793(03)00048-6 | s2cid = 38569901 | doi-access = free }} BML-190 is structurally derived from the NSAID indomethacin but has a quite different biological activity.{{cite journal | vauthors = Klegeris A, Bissonnette CJ, McGeer PL | title = Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor | journal = British Journal of Pharmacology | volume = 139 | issue = 4 | pages = 775–86 | date = June 2003 | pmid = 12813001 | pmc = 1573900 | doi = 10.1038/sj.bjp.0705304 }} The activity produced by this compound is disputed, with some sources referring to it as a CB2 agonist rather than an inverse agonist;{{cite journal | vauthors = Melck D, De Petrocellis L, Orlando P, Bisogno T, Laezza C, Bifulco M, Di Marzo V | title = Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation | journal = Endocrinology | volume = 141 | issue = 1 | pages = 118–26 | date = January 2000 | pmid = 10614630 | doi = 10.1210/endo.141.1.7239 | doi-access = free }}{{cite journal | vauthors = Scutt A, Williamson EM | s2cid = 23624771 | title = Cannabinoids stimulate fibroblastic colony formation by bone marrow cells indirectly via CB2 receptors | journal = Calcified Tissue International | volume = 80 | issue = 1 | pages = 50–9 | date = January 2007 | pmid = 17205329 | doi = 10.1007/s00223-006-0171-7 }} 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.