868273-06-7

Basic information

• Product Name: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide
• Synonyms: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide;Org 27569;Org27569 5-Chloro-3-ethyl-N-[2-[4-(1-piperidinyl)phenyl]ethyl-1H -indole-2-carboxamide;5-Chloro-3-ethyl-N-[2-[4-(1-piperidinyl)phenyl]ethyl-1H-indole-2-carboxamide;1H-Indole-2-carboxamide,5-chloro-3-ethyl-N-[2-[4-(1-piperidinyl)phenyl]ethyl]-;5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide;N-(4-(piperidin-1-yl)phenethyl)-5-chloro-3-ethyl-1H-indole-2-carboxamide
• CAS NO: 868273-06-7
• Molecular Formula: C24H28ClN3O
• Molecular Weight: 409.95
• EINECS: 278-169-7
• Product Categories: Inhibitors
• Mol File: 868273-06-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 660.3 ºC at 760 mmHg
• Flash Point: 353.2 ºC
• Appearance: white/
• Density: 1.218
• Vapor Pressure: 2.61E-17mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: 2-8°C
• Solubility: H2O:
• PKA: 14.87±0.30(Predicted)
• CAS DataBase Reference: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide(868273-06-7)
• EPA Substance Registry System: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide(868273-06-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 868273-06-7(Hazardous Substances Data)

Usage

Uses

Org 27569 is a drug that is a used in biological studies for structure-activity relationships of indole-carboxamides as CB1 receptor allosteric modulators.

Biological Activity

Potent CB 1 receptor allosteric modulator (pEC 50 = 8.24). Significantly increases binding of the CB 1 agonist [ 3 H]CP 55.940 (pK b = 5.67) and decreases binding of the CB 1 inverse agonist [ 3 H]SR 141716A (pK b = 5.95). Inhibits CB 1 receptor antagonist efficacy in vitro (pK b = 7.57).

references

[1] price mr1, 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. allosteric modulation of the cannabinoid cb1 receptor. mol pharmacol. 2005 nov;68(5):1484-95. epub 2005 aug 19.[2] fay jf1, farrens dl. a key agonist-induced conformational change in the cannabinoid receptor cb1 is blocked by the allosteric ligand org 27569. j biol chem. 2012 sep 28;287(40):33873-82. epub 2012 jul 30.

InChI:InChI=1/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)

Upstream product

• 38589-09-2 2-[4-(piperidin-1-yl)phenyl]ethan-1-amine 
• 446830-67-7 5-chloro-3-ethyl-1H-indole-2-carboxylic acid 
• 1374964-61-0 ethyl 3-acetyl-5-chloro-1H-indole-2-carboxylate 
• 1377838-25-9 2-(4-(piperidin-1-yl)phenethyl)isoindoline-1,3-dione 
• 1377838-23-7 ethyl 5-chloro-3-ethyl-1H-indole-2-carboxylate 
• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 4654-39-1 4-bromophenethanol 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 124499-18-9 2-(2-(4-bromophenyl)ethyl)isoindolin-1,3-dione 
• 1540-28-9 ethyl 2-propylacetoacetate 
• 110-89-4 piperidine 
• 459-57-4 4-fluorobenzaldehyde 
• 10338-57-5 4-(piperidin-1-yl)benzaldehyde 
• 1446648-75-4 1-[4-((1E)-2-nitrovinyl)phenyl]piperidine 

Relevant articles and documents

Novel Electrophilic and Photoaffinity Covalent Probes for Mapping the Cannabinoid 1 Receptor Allosteric Site(s)

Undesirable side effects associated with orthosteric agonists/antagonists of cannabinoid 1 receptor (CB1R), a tractable target for treating several pathologies affecting humans, have greatly limited their translational potential. Recent discovery of CB1R negative allosteric modulators (NAMs) has renewed interest in CB1R by offering a potentially safer therapeutic avenue. To elucidate the CB1R allosteric binding motif and thereby facilitate rational drug discovery, we report the synthesis and biochemical characterization of first covalent ligands designed to bind irreversibly to the CB1R allosteric site. Either an electrophilic or a photoactivatable group was introduced at key positions of two classical CB1R NAMs: Org27569 (1) and PSNCBAM-1 (2). Among these, 20 (GAT100) emerged as the most potent NAM in functional assays, did not exhibit inverse agonism, and behaved as a robust positive allosteric modulator of binding of orthosteric agonist CP55,940. This novel covalent probe can serve as a useful tool for characterizing CB1R allosteric ligand-binding motifs.