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Chemical compound
Org 28611
Legal status
[1-(cyclohexylmethyl)-7-methoxyindol-3-yl]-[(3S)-3,4-dimethylpiperazin-1-yl]methanone
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
Formula C 23 H 33 N 3 O 2
Molar mass 383.536 g·mol−1 3D model (
JSmol )
COc3cccc(c13)c(C(=O)N(CC2C)CCN2C)cn1CC4CCCCC4
InChI=1S/C23H33N3O2/c1-17-14-25(13-12-24(17)2)23(27)20-16-26(15-18-8-5-4-6-9-18)22-19(20)10-7-11-21(22)28-3/h7,10-11,16-18H,4-6,8-9,12-15H2,1-3H3/t17-/m0/s1
Y Key:ONXJNAIZJKLJGA-KRWDZBQOSA-N
Y
N Y
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Org 28611 (SCH-900,111 ) 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 ,
[1] and while it achieved this aim and has progressed as far as Phase II
clinical trials in humans as both a
sedative and an
analgesic , results against the comparison drugs (
midazolam and
morphine respectively) were not particularly favourable in initial testing.
[2]
[3]
See also
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 .
^ Zuurman L, Passier PC, de Kam M, Kleijn HJ, Cohen AF, van Gerven JM (August 2009). "Pharmacodynamic and pharmacokinetic effects of the intravenously administered CB1 receptor agonist Org 28611 in healthy male volunteers". Journal of Psychopharmacology . 23 (6): 633–44.
doi :
10.1177/0269881108091551 .
PMID
18635703 .
S2CID
43609218 .
^
A Comparison of Analgesic Efficacy Between a Single Dose of ORG 28611, Morphine, and Placebo After Dental Impaction Surgery
Phytocannabinoids (
comparison )
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Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
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Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
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Anticannabinoids (antagonists/inverse agonists/antibodies)