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Org 28312

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Org 28312
Identifiers
  • [1-(cyclohexylmethyl)-7-methoxyindol-3-yl]-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)methanone
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H35N3O2
Molar mass397.563 g·mol−1
3D model (JSmol)
  • COc2cccc1c2n(CC4CCCCC4)cc1C(=O)N(CC3C)CC(C)N3C
  • InChI=1S/C24H35N3O2/c1-17-13-27(14-18(2)25(17)3)24(28)21-16-26(15-19-9-6-5-7-10-19)23-20(21)11-8-12-22(23)29-4/h8,11-12,16-19H,5-7,9-10,13-15H2,1-4H3/t17-,18+ checkY
  • Key:DMYGECJTVMCGEP-HDICACEKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Org 28312 is a drug developed byOrganon International which acts as a potentcannabinoidreceptorfull agonist at both theCB1 andCB2 receptors. It was developed with the aim of finding awater-soluble cannabinoid agonist suitable forintravenous use as ananalgesic, but did not proceed to human trials, with the related compoundOrg 28611 chosen instead due to its better penetration into the brain.[1] Thestructure-activity relationships of these compounds have subsequently been investigated further leading to the development of a number of more potent analogues, derived bycyclisation around theindole orpiperazine rings.[2][3]

See also

[edit]

References

[edit]
  1. ^Adam, J. M.; et al. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists".MedChemComm.1.Royal Society of Chemistry: 54.doi:10.1039/c0md00022a.
  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.
Phytocannabinoids
(comparison)
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AllostericCBRTooltip Cannabinoid receptorligands
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