Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 444674170
| verifiedrevid = 444674170
| IUPAC_name = 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
| IUPAC_name = 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
| image = BML-190.png
| image = BML-190.svg


<!--Clinical data-->
<!--Clinical data-->
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2854-32-2
| CAS_number = 2854-32-2
| ATC_prefix =
| ATC_prefix =
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| 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 = 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 which acts as a selective [[cannabinoid receptor 2|CB<sub>2</sub>]] [[inverse agonist]].<ref>{{cite journal | last1 = New | first1 = DC | last2 = Wong | first2 = 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 | year = 2003 | pmid = 12586356 | doi=10.1016/S0014-5793(03)00048-6}}</ref> BML-190 is structurally derived from the [[NSAID]] [[indomethacin]] but has a quite different biological activity.<ref>{{cite journal | last1 = Klegeris | first1 = A | last2 = Bissonnette | first2 = CJ | last3 = McGeer | first3 = 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 | year = 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 | last1 = Melck | first1 = D | last2 = De Petrocellis | first2 = L | last3 = Orlando | first3 = P | last4 = Bisogno | first4 = T | last5 = Laezza | first5 = C | last6 = Bifulco | first6 = M | last7 = Di Marzo | first7 = 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 | year = 2000 | pmid = 10614630 | doi=10.1210/en.141.1.118}}</ref><ref>{{cite journal | last1 = Scutt | first1 = A | last2 = Williamson | first2 = EM | 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 | year = 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, more research is required to resolve this dispute.
'''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.


==References==
== References ==
{{Reflist}}
{{Reflist}}


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[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Morpholines]]
[[Category:4-Morpholinyl compounds]]
[[Category:Indoles]]
[[Category:Indole ethers at the benzene ring]]
[[Category:Amides]]
[[Category:Benzamides]]
[[Category:Organochlorides]]
[[Category:Chloroarenes]]
[[Category:Tryptamines]]




Latest revision as of 07:48, 25 March 2024

BML-190
Identifiers
  • 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H23ClN2O4
Molar mass426.90 g·mol−1
3D model (JSmol)
  • C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3
  • 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
 ☒NcheckY (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]

  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.


source: https://en.wikipedia.org/w/index.php?title=BML-190&diff=1215461303&oldid=455791641

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