5-chloro-3-ethyl-N-{2-[4-(piperidin-1-yl)phenyl]ethyl}-1H-indole-2-carboxamide

• ChemBase ID: 73142
• Molecular Formular: C24H28ClN3O
• Molecular Mass: 409.95162
• Monoisotopic Mass: 409.19209021
• SMILES: c1(ccc2c(c1)c(c([nH]2)C(=O)NCCc1ccc(cc1)N1CCCCC1)CC)Cl
• Canonical SMILES: CCc1c([nH]c2c1cc(Cl)cc2)C(=O)NCCc1ccc(cc1)N1CCCCC1
• 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)
• InChIKey: AHFZDNYNXFMRFQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-3-ethyl-N-{2-[4-(piperidin-1-yl)phenyl]ethyl}-1H-indole-2-carboxamide
• IUPAC Traditional name: 5-chloro-3-ethyl-N-{2-[4-(piperidin-1-yl)phenyl]ethyl}-1H-indole-2-carboxamide
• Synonyms: Org27569; Org 27569; 5-Chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-ylphenyl)ethyl]amide; Org 27569; 5-chloro-3-ethyl-1H-indole-2-carboxylic acid [2-(4-piperidin-1-yl-phenyl)-ethyl]-amide

Database IDs

• CAS Number: 868273-06-7
• EC Number: 278-169-7
• MDL Number: MFCD11045300
• PubChem SID: 162038062
• PubChem CID: 44828492
• Chemspider ID: 22369629
• Wikipedia Title: Org_27569

CALCULATED PROPERTIES

• Acid pKa: 13.328563
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.316665
• LogD (pH = 7.4): 5.5949
• Log P: 5.5999045
• Molar Refractivity: 121.3823 cm^3
• Polarizability: 46.747425 Å^3
• Polar Surface Area: 48.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL; H2O: <2 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: CB receptor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C24H28ClN3O

DETAILS

Selleck Chemicals - S1534

Research Area: Cancer
Biological Activity:
Org 27569 is an allosteric modulator of CB1 cannabinoid receptor. It significantly increases the binding of CB1 receptor agonist [3H]-CP 55,940 (pKB = 5.67) and causes a significant decrease in specific binding of CB1 receptor inverse agonist SR141716A (Rimonabant; pKB = 5.95); in the reporter gene assay behaves as insurmountable CP 55,940 antagonist; pKB = 7.57 at CB1 receptors in mouse vas deferens. [1][2]

Sigma Aldrich - O8014

Biochem/physiol Actions
Org 27569 is an allosteric modulator of CB1 cannabinoid receptor. It significantly increases the binding of CB1 receptor agonist [3H]-CP 55,940 (pKB = 5.67) and causes a significant decrease in specific binding of CB1 receptor inverse agonist SR141716A (Rimonabant; pKB = 5.95); in the reporter gene assay behaves as insurmountable CP 55,940 antagonist; pKB = 7.57 at CB1 receptors in mouse vas deferens

REFERENCES

• Ross RA. Trends Pharmacol Sci. 2007 Nov;28(11):567-72