Org 27569

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
UNII	7YW2S3Z2CB
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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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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.

See also

• GAT100
• PSNCBAM-1
• ZCZ-011