Org 27569

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]

Org 27569

Identifiers
IUPAC name 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)ethyl]amide
CAS Number	868273-06-7^Y
PubChem CID	44828492
IUPHAR/BPS	7851
ChemSpider	22369629^Y
CompTox Dashboard (EPA)	DTXSID00660764
Chemical and physical data
Formula	C24H28ClN3O
Molar mass	409.96 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCc1c2cc(Cl)ccc2[nH]c1C(=O)NCCc3ccc(cc3)N4CCCCC4
InChI 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) Key:AHFZDNYNXFMRFQ-UHFFFAOYSA-N^Y
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See also

• GAT100
• PSNCBAM-1
• ZCZ-011

References

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.