Content deleted Content added
Importing Wikidata short description: "Chemical compound" (Shortdesc helper) |
auto mw |
||
(3 intermediate revisions by 3 users not shown) | |||
Line 38: | Line 38: | ||
| chemical_formula = |
| chemical_formula = |
||
| C=23 | H=23 | Cl=1 | N=2 | O=4 |
| C=23 | H=23 | Cl=1 | N=2 | O=4 |
||
| molecular_weight = 426.892 |
|||
| smiles = C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3 |
| smiles = C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3 |
||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
||
Line 48: | Line 47: | ||
}} |
}} |
||
'''BML-190''' ('''Indomethacin morpholinylamide''') is a drug used in scientific research that acts as a selective [[cannabinoid receptor 2|CB<sub>2</sub>]] [[inverse agonist]].<ref>{{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 }}</ref> BML-190 is structurally derived from the [[NSAID]] [[indomethacin]] but has a quite different biological activity.<ref>{{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 }}</ref> The activity produced by this compound is disputed, with some sources referring to it as a CB<sub>2</sub> [[agonist]] rather than an inverse agonist;<ref>{{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/ |
'''BML-190''' ('''Indomethacin morpholinylamide''') is a drug used in scientific research that acts as a selective [[cannabinoid receptor 2|CB<sub>2</sub>]] [[inverse agonist]].<ref>{{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 }}</ref> BML-190 is structurally derived from the [[NSAID]] [[indomethacin]] but has a quite different biological activity.<ref>{{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 }}</ref> The activity produced by this compound is disputed, with some sources referring to it as a CB<sub>2</sub> [[agonist]] rather than an inverse agonist;<ref>{{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 }}</ref><ref>{{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 }}</ref> 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. |
||
[[Lead optimization]] of the parent structure resulted in [[L-768,242]] & [[L-759,787]]. |
|||
== References == |
== References == |
||
{{Reflist}} |
{{Reflist}} |
||
Line 57: | Line 55: | ||
[[Category:Cannabinoids]] |
[[Category:Cannabinoids]] |
||
[[Category: |
[[Category:4-Morpholinyl compounds]] |
||
[[Category:Indole ethers at the benzene ring]] |
[[Category:Indole ethers at the benzene ring]] |
||
[[Category:Benzamides]] |
[[Category:Benzamides]] |
Latest revision as of 07:48, 25 March 2024
Identifiers | |
---|---|
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C23H23ClN2O4 |
Molar mass | 426.90 g·mol−1 |
3D model (JSmol) | |
| |
| |
(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[edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.