Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

Org 27569
  • 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)ethyl]amide
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Molar mass409.96 g·mol−1
3D model (JSmol)
  • CCc1c2cc(Cl)ccc2[nH]c1C(=O)NCCc3ccc(cc3)N4CCCCC4
  • InChI=1S/C24H28ClN3O/c1-2-20-21-16-18(25)8-11-22(21)27-23(20)24(29)26-13-12-17-6-9-19(10-7-17)28-14-4-3-5-15-28/h6-11,16,27H,2-5,12-15H2,1H3,(H,26,29)

Org 27569 is a drug which acts as a potent and selective negative allosteric modulator of the cannabinoid CB1 receptor. Studies in vitro suggest that it binds to a regulatory site on the CB1 receptor target, causing a conformational change that increases the binding affinity of CB1 agonists such as CP 55,940, while decreasing the binding affinity of CB1 antagonists or inverse agonists such as rimonabant. However while Org 27569 increases the ability of CB1 agonists to bind to the receptor, it decreases their efficacy at stimulating second messenger signalling once bound, and so in practice behaves as an insurmountable antagonist of CB1 receptor function.[1]

See also


  1. ^ Price MR, Baillie GL, Thomas A, Stevenson LA, Easson M, Goodwin R, McLean A, McIntosh L, Goodwin G, Walker G, Westwood P, Marrs J, Thomson F, Cowley P, Christopoulos A, Pertwee RG, Ross RA (November 2005). "Allosteric modulation of the cannabinoid CB1 receptor". Molecular Pharmacology. 68 (5): 1484–95. doi:10.1124/mol.105.016162. PMID 16113085. S2CID 17648541.