Org 28312

Org 28312
Identifiers
	IUPAC name [1-(cyclohexylmethyl)-7-methoxyindol-3-yl]-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)methanone;
CAS Number	1244028-73-6 ;
PubChem CID	10069407;
ChemSpider	24581999 ;
ChEMBL	ChEMBL1209708 ;
Chemical and physical data
Formula	C24H35N3O2
Molar mass	397.563 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc2cccc1c2n(CC4CCCCC4)cc1C(=O)N(CC3C)CC(C)N3C;
	InChI 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+ ; Key:DMYGECJTVMCGEP-HDICACEKSA-N ;
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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]

References

^ 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.
^ 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.
^ 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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Identifiers

IUPAC name [1-(cyclohexylmethyl)-7-methoxyindol-3-yl]-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)methanone
CAS Number	1244028-73-6^N
PubChem CID	10069407
ChemSpider	24581999^Y
ChEMBL	ChEMBL1209708^Y
Chemical and physical data
Formula	C₂₄H₃₅N₃O₂
Molar mass	397.563 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc2cccc1c2n(CC4CCCCC4)cc1C(=O)N(CC3C)CC(C)N3C
InChI 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+^Y Key:DMYGECJTVMCGEP-HDICACEKSA-N^Y
^NY (what is this?) (verify)