{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amine

• ChemBase ID: 166132
• Molecular Formular: C16H22ClN3
• Molecular Mass: 291.81898
• Monoisotopic Mass: 291.1502254
• SMILES: c1c(cc2c(c1)c(ccn2)NC(CCCNCC)C)Cl
• Canonical SMILES: CCNCCCC(Nc1ccnc2c1ccc(c2)Cl)C
• InChI: InChI=1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)
• InChIKey: MCYUUUTUAAGOOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amine
• IUPAC Traditional name: {4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amine
• Synonyms: N4-(7-Chloro-4-quinolinyl)-N1-ethyl-1,4-pentanediamine; Deethylchloroquine; Monodeethylchloroquine; NSC 13254; WR 29623; Desethyl Chloroquine

Database IDs

• CAS Number: 1476-52-4
• PubChem SID: 162260265
• PubChem CID: 95478

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.2576234
• LogD (pH = 7.4): 0.030893495
• Log P: 3.1940253
• Molar Refractivity: 86.3797 cm^3
• Polarizability: 34.38937 Å^3
• Polar Surface Area: 36.95 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Tan Solid
• Melting Point: 94-97°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288735

The major product of the stereoselective human metabolism of Chloroquine, used for the therapy and prevention of malaria.

REFERENCES

• Essien, E., et al.: J. Pharm. Pharmacol., 38, 543 (1986)
• Akintonwa, A., et al.: Ther. Drug Monit., 10, 147 (1986)
• Boelaert, J., et al.: AIDS, 15, 2205 (1986)
• Basco, L., et al.: Antimicrob. Agents Chemother., 47, 1391 (1986)