Cannabis Ruderalis

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Updating {{drugbox}} (changes to verified fields - updated 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report errors or bugs)
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| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 73711
| ChEMBL = 73711
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8087114
| ChemSpiderID = 8087114
| SMILES = CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4
| SMILES = CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4


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| molecular_weight = 447.353 g/mol
| molecular_weight = 447.353 g/mol
| smiles = C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl
| smiles = C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8087114
| ChemSpiderID = 8087114
| SMILES = CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4
| SMILES = CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4
| InChI = 1/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3
| InChI = 1/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3
| InChIKey = FSFZRNZSZYDVLI-UHFFFAOYAZ
| InChIKey = FSFZRNZSZYDVLI-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3
| StdInChI = 1S/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3
⚫
| StdInChIKey = FSFZRNZSZYDVLI-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| StdInChIKey = FSFZRNZSZYDVLI-UHFFFAOYSA-N
}}
}}


Revision as of 18:47, 17 December 2014

GW-405,833
Identifiers
  • 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.162.054 Edit this at Wikidata
Chemical and physical data
FormulaC23H24Cl2N2O3
Molar mass447.353 g/mol g·mol−1
3D model (JSmol)
  • CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4
  • InChI=1S/C23H24Cl2N2O3/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25/h3-7,14H,8-13H2,1-2H3 ☒N
  • Key:FSFZRNZSZYDVLI-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

GW-405,833 (L-768,242) is a drug that acts as a potent and selective partial agonist for the cannabinoid receptor subtype CB2, with an EC50 of 0.65nM and selectivity of around 1200x for CB2 over CB1 receptors.[1][2] Animal studies have shown it to possess antiinflammatory and anti-hyperalgesic effects at low doses, followed by ataxia and analgesic effects when the dose is increased.[3][4] Selective CB2 agonist drugs such as GW-405,833 are hoped to be particularly useful in the treatment of allodynia and neuropathic pain for which current treatment options are often inadequate.[5][6]

References

  1. ^ Huffman JW. The search for selective ligands for the CB2 receptor. Current Pharmaceutical Design. 2000 Sep;6(13):1323-37. doi:10.2174/1381612003399347 PMID 10903395
  2. ^ Marriott KS, Huffman JW. Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor. Current Topics in Medicinal Chemistry. 2008;8(3):187-204. doi:10.2174/156802608783498014 PMID 18289088
  3. ^ Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT. CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain. Pain. 2002 Apr;96(3):253-60. PMID 11972997
  4. ^ Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, Mark L, Pearson MS, Miller W, Shan S, Rabadi L, Rotshteyn Y, Chaffer SM, Turchin PI, Elsemore DA, Toth M, Koetzner L, Whiteside GT. Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy. Neuropharmacology. 2005 Apr;48(5):658-72. PMID 15814101
  5. ^ Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A. CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms. European Journal of Neuroscience. 2006 Mar;23(6):1530-8. doi:10.1111/j.1460-9568.2006.04684.x PMID 16553616
  6. ^ Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H. Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain. Naunyn Schmiedebergs Archives of Pharmacology. 2009 Jan 18. PMID 19152053
source: https://en.wikipedia.org/w/index.php?title=GW-405,833&diff=prev&oldid=638531025

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