(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone

(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
Systematic (IUPAC) name
(1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Pregnancy cat.  ?
Legal status uncontrolled
Identifiers
ATC code  ?
PubChem CID 44626619
Chemical data
Formula C21H29NO 
Mol. mass 311.461 g/mol
SMILES eMolecules & PubChem

(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone is a drug invented by Abbott Laboratories,[1] that acts as a selective full agonist of the peripheral cannabinoid receptor CB2, but with much lower affinity for the psychoactive CB1 receptor. It has high affinity for the CB2 receptor with a Ki of 1.8nM but 83x lower affinity for the CB1 receptor with a Ki of 150nM.[2] Chemically it is closely related to other 2,2,3,3-tetramethylcyclopropyl synthetic cannabinoids like A-796,260 and A-834,735 but with a different substitution on the 1-position of indole core, its 1-pentyl group replaced with alkylheterocycles like 1-(2-morpholinoethyl) and 1-(tetrahydropyran-4-ylmethyl).

See also

References

  1. ^ WO application 2006069196, Pace JM, Tietje K, Dart MJ, Meyer MD, "3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands", published 2006-06-29, assigned to Abbott Laboratories 
  2. ^ Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". J. Med. Chem. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781. 

Further reading