6-chloro-5-methyl-N-(quinolin-4-yl)-2,3-dihydro-1H-indole-1-carboxamide

• ChemBase ID: 129393
• Molecular Formular: C19H16ClN3O
• Molecular Mass: 337.80284
• Monoisotopic Mass: 337.09818983
• SMILES: Cc1c(cc2c(c1)CCN2C(=O)Nc1ccnc2ccccc12)Cl
• Canonical SMILES: O=C(N1CCc2c1cc(Cl)c(c2)C)Nc1ccnc2c1cccc2
• InChI: InChI=1S/C19H16ClN3O/c1-12-10-13-7-9-23(18(13)11-15(12)20)19(24)22-17-6-8-21-16-5-3-2-4-14(16)17/h2-6,8,10-11H,7,9H2,1H3,(H,21,22,24)
• InChIKey: BPVGSWDWIRIUME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-5-methyl-N-(quinolin-4-yl)-2,3-dihydro-1H-indole-1-carboxamide
• IUPAC Traditional name: 6-chloro-5-methyl-N-(quinolin-4-yl)-2,3-dihydroindole-1-carboxamide
• Synonyms: SB-215,505; SB-215505; 6-Chloro-5-methyl-1-5-quinolycarbamoyl-indoline

Database IDs

• CAS Number: 162100-15-4
• MDL Number: MFCD05664741
• PubChem SID: 162223687; 24278573
• PubChem CID: 6603999
• CHEMBL: 525998
• Wikipedia Title: SB-215,505

CALCULATED PROPERTIES

• Acid pKa: 11.10219
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.205912
• LogD (pH = 7.4): 4.2963486
• Log P: 4.2977304
• Molar Refractivity: 96.2456 cm^3
• Polarizability: 37.27873 Å^3
• Polar Surface Area: 45.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ~11 mg/mL at 60 °C; H2O: insoluble
• Apperance: off-white solid

Safety Information

• 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

• Gene Information: human ... HTR2B(3357)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C19H16N3OCl

DETAILS

Sigma Aldrich - S1068

Biochem/physiol Actions
Selective 5-HT2B serotonin receptor antagonist; 100-fold higher affinity at 2B versus 2C.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline