Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
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| IUPAC_name = 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
| Watchedfields = changed
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| image = BML-190.png
| verifiedrevid = 444674170
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| CAS_number =
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| IUPAC_name = 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
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| ATC_prefix =
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| image = BML-190.svg
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| ATC_suffix =
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| PubChem = 2415
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| DrugBank =
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| chemical_formula = |C=23|H=23|Cl=1|N=2|O=4
| molecular_weight = 426.892
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| smiles = C4COCCN4C(=O)Cc(c(c1cc2)cc2OC)c(C)n1C(=O)c3ccc(Cl)cc3
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| pregnancy_category=
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| legal_status =
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| routes_of_administration =
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}}


<!--Clinical data-->
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'''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>New DC, Wong YH. BML-190 and AM251 act as inverse agonists at the human cannabinoid CB2 receptor: signalling via cAMP and inositol phosphates. ''FEBS Letters''. 2003 Feb 11;53(1-3):157-60. PMID 12586356</ref> BML-190 is structurally derived from the [[NSAID]] [[indomethacin]] but has a quite different biological activity.<ref>Klegeris A, Bissonnette CJ, McGeer PL. Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor. ''British Journal of Pharmacology''. 2003 Jun;139(4):775-86. PMID 12813001</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>Melck D, De Petrocellis L, Orlando P, Bisogno T, Laezza C, Bifulco M, Di Marzo V. Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation. ''Endocrinology''. 2000 Jan;141(1):118-26. PMID 10614630</ref><ref>Scutt A, Williamson EM. Cannabinoids stimulate fibroblastic colony formation by bone marrow cells indirectly via CB2 receptors. ''Calcified Tissue International''. 2007 Jan;80(1):50-9. PMID 17205329</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.
| tradename =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category =
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| legal_status =
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| routes_of_administration =


<!--Pharmacokinetic data-->
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==References==
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| bioavailability =
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{{Reflist}}
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =


<!--Identifiers-->
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{{pharma-stub}}
| CAS_number_Ref = {{cascite|correct|??}}
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| CAS_number = 2854-32-2
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| ATC_prefix =
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| ATC_suffix =
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| PubChem = 2415
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank =


<!--Chemical data-->
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| chemical_formula =
| C=23 | H=23 | Cl=1 | N=2 | O=4
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| 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
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}}

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'''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.

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== References ==
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{{Reflist}}


{{Cannabinoids}}
{{Cannabinoids}}


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


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{{cannabinoid-stub}}

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=210736728

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