Org 28312

Org 28312
Org 28312
Systematic (IUPAC) name
[1-(cyclohexylmethyl)-7-methoxyindol-3-yl]-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)methanone
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
ATC code  ?
PubChem CID 10069407
ChemSpider 24581999 YesY
Chemical data
Formula C24H35N3O2 
Mol. mass 397.552 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  28312 (verify)

Org 28312 is a drug developed by Organon International which acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors. It was developed with the aim of finding a water soluble cannabinoid agonist suitable for intravenous use as an analgesic, but did not proceed to human trials, with the related compound Org 28611 chosen instead due to its better penetration into the brain.[1] The structure-activity relationships of these compounds have subsequently been investigated further leading to the development of a number of more potent analogues, derived by cyclisation around the indole or piperazine rings.[2][3]

See also

References

  1. ^ Adam, J. M.; Cairns, J.; Caulfield, W.; Cowley, P.; Cumming, I.; Easson, M.; Edwards, D.; Ferguson, M. et al. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists". MedChemComm 1: 54. doi:10.1039/c0md00022a.  edit
  2. ^ Kiyoi T, York M, Francis S, Edwards D, Walker G, Houghton AK, Cottney JE, Baker J, Adam JM (August 2010). "Design, synthesis, and structure-activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists". Bioorganic & Medicinal Chemistry Letters 20 (16): 4918–21. doi:10.1016/j.bmcl.2010.06.067. PMID 20634067. 
  3. ^ Moir EM, Yoshiizumi K, Cairns J, Cowley P, Ferguson M, Jeremiah F, Kiyoi T, Morphy R, Tierney J, Wishart G, York M, Baker J, Cottney JE, Houghton AK, McPhail P, Osprey A, Walker G, Adam JM (December 2010). "Design, synthesis, and structure-activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists". Bioorganic & Medicinal Chemistry Letters 20 (24): 7327–30. doi:10.1016/j.bmcl.2010.10.061. PMID 21074434. 
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