Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424782539
| verifiedrevid = 424782539
| IUPAC_name = 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
| IUPAC_name = 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1''H''-indole
| image = GW-405,833-2D-skeletal.svg
| image = GW-405,833-2D-skeletal.svg
| width = 240px
| width = 240px

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| index_label =
| index2_label =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 180002-83-9
| CAS_number = 180002-83-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 85K154W99L
| PubChem = 9911463
| PubChem = 9911463
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 73711
| ChEMBL = 73711
| ChemSpiderID = 8087114
| ChemSpiderID = 8087114
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| 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

⚫
| smiles2 = C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl
| 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| StdInChIKey = FSFZRNZSZYDVLI-UHFFFAOYSA-N
<!--Chemical data-->
<!--Chemical data-->
| C=23 | H=24 | Cl=2 | N=2 | O=3
| C=23 | H=24 | Cl=2 | N=2 | O=3
| molecular_weight = 447.353 g/mol
⚫
| smiles = C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl
| ChemSpiderID = 8087114
| 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
| InChIKey = FSFZRNZSZYDVLI-UHFFFAOYAZ
⚫
| 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
}}
}}


'''GW-405,833''' ('''L-768,242''') is a drug that acts as a potent and selective [[partial agonist]] for the [[cannabinoid receptor]] subtype [[Cannabinoid receptor type 2|CB<sub>2</sub>]], with an [[EC50|EC<sub>50</sub>]] of 0.65nM and selectivity of around 1200x for CB<sub>2</sub> over [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptors.<ref>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</ref><ref>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</ref> Animal studies have shown it to possess [[antiinflammatory]] and anti-[[hyperalgesia|hyperalgesic]] effects at low doses, followed by [[ataxia]] and [[analgesic]] effects when the dose is increased.<ref>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</ref><ref>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</ref> Selective CB<sub>2</sub> 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.<ref>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</ref><ref>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</ref>
'''GW-405,833''' ('''L-768,242''') is a drug that acts as a potent and selective [[partial agonist]] for the [[cannabinoid receptor]] subtype [[Cannabinoid receptor type 2|CB<sub>2</sub>]], with an [[EC50|EC<sub>50</sub>]] of 0.65&nbsp;nM and selectivity of around 1200x for CB<sub>2</sub> over [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptors.<ref>{{cite journal | vauthors = Huffman JW | title = The search for selective ligands for the CB2 receptor | journal = Current Pharmaceutical Design | volume = 6 | issue = 13 | pages = 1323–37 | date = September 2000 | pmid = 10903395 | doi = 10.2174/1381612003399347 }}</ref><ref>{{cite journal | vauthors = Marriott KS, Huffman JW | title = Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor | journal = Current Topics in Medicinal Chemistry | year = 2008 | volume = 8 | issue = 3 | pages = 187–204 | pmid = 18289088 | doi = 10.2174/156802608783498014 }}</ref> Animal studies have shown it to possess [[antiinflammatory]] and anti-[[hyperalgesia|hyperalgesic]] effects at low doses, followed by [[ataxia]] and [[analgesic]] effects when the dose is increased.<ref>{{cite journal | vauthors = Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT | title = CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain | journal = Pain | volume = 96 | issue = 3 | pages = 253–60 | date = April 2002 | pmid = 11972997 | doi = 10.1016/s0304-3959(01)00454-7 | s2cid = 24816928 }}</ref><ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy | journal = Neuropharmacology | volume = 48 | issue = 5 | pages = 658–72 | date = April 2005 | pmid = 15814101 | doi = 10.1016/j.neuropharm.2004.12.008 | s2cid = 10121434 }}</ref> Selective CB<sub>2</sub> 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.<ref>{{cite journal | vauthors = Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A | title = CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms | journal = The European Journal of Neuroscience | volume = 23 | issue = 6 | pages = 1530–8 | date = March 2006 | pmid = 16553616 | doi = 10.1111/j.1460-9568.2006.04684.x | s2cid = 19266396 }}</ref><ref>{{cite journal | vauthors = Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H | title = Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 379 | issue = 6 | pages = 627–36 | date = June 2009 | pmid = 19152053 | doi = 10.1007/s00210-008-0386-4 | s2cid = 25085194 }}</ref>


==References==
== References ==
{{reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}
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[[Category:Aminoalkylindoles]]
[[Category:Aminoalkylindoles]]
[[Category:Benzoylindoles]]
[[Category:Benzoylindoles]]
[[Category:Morpholines]]
[[Category:4-Morpholinyl compounds]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
[[Category:Organochlorides]]
[[Category:Chlorobenzene derivatives]]
[[Category:CB2 receptor agonists]]
[[Category:CB2 receptor agonists]]

Latest revision as of 22:12, 3 February 2024

GW-405,833
Identifiers
  • 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.162.054 Edit this at Wikidata
Chemical and physical data
FormulaC23H24Cl2N2O3
Molar mass447.36 g·mol−1
3D model (JSmol)
  • CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4

  • C4COCCN4CCc1c(C)n(c(ccc3OC)c1c3)C(=O)c2cccc(Cl)c2Cl
  • 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 0.65 nM 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[edit]

  1. ^ Huffman JW (September 2000). "The search for selective ligands for the CB2 receptor". Current Pharmaceutical Design. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.
  2. ^ Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
  3. ^ Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT (April 2002). "CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain". Pain. 96 (3): 253–60. doi:10.1016/s0304-3959(01)00454-7. PMID 11972997. S2CID 24816928.
  4. ^ Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, et al. (April 2005). "Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy". Neuropharmacology. 48 (5): 658–72. doi:10.1016/j.neuropharm.2004.12.008. PMID 15814101. S2CID 10121434.
  5. ^ Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A (March 2006). "CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms". The European Journal of Neuroscience. 23 (6): 1530–8. doi:10.1111/j.1460-9568.2006.04684.x. PMID 16553616. S2CID 19266396.
  6. ^ Leichsenring A, Andriske M, Bäcker I, Stichel CC, Lübbert H (June 2009). "Analgesic and antiinflammatory effects of cannabinoid receptor agonists in a rat model of neuropathic pain". Naunyn-Schmiedeberg's Archives of Pharmacology. 379 (6): 627–36. doi:10.1007/s00210-008-0386-4. PMID 19152053. S2CID 25085194.
source: https://en.wikipedia.org/w/index.php?title=GW-405,833&diff=1202951881&oldid=638529528

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