N-(5-aminopentan-2-yl)-6-methoxy(2H5)quinolin-8-amine

• ChemBase ID: 176920
• Molecular Formular: C15H21N3O
• Molecular Mass: 259.34674
• Monoisotopic Mass: 259.16846231
• SMILES: c1c(cc2c(c1NC(CCCN)C)nccc2)OC
• Canonical SMILES: NCCCC(Nc1cc(OC)cc2c1nccc2)C
• InChI: InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
• InChIKey: INDBQLZJXZLFIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-aminopentan-2-yl)-6-methoxy(^2H₅)quinolin-8-amine
• IUPAC Traditional name: N-(5-aminopentan-2-yl)-6-methoxy(^2H₅)quinolin-8-amine
• Synonyms: N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine-d5 Phosphate; 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline-d5 Phosphate; (+/-)-Primaquine-d5 Phosphate; 6-Methoxy-8-[4-amino-1-methylbutylamino]quinoline-d5 Phosphate; NSC 27296-d5; Neo-Quipenyl-d5 Phosphate; Primachin-d5 Phosphate; Primaquin-d5 Phosphate; SN 13272-d5; WR 2975-d5; dl-Primaquine-d5 Phosphate; Primaquine-d5 Diphosphate

Database IDs

• PubChem SID: 164232830
• PubChem CID: 71751768

CALCULATED PROPERTIES

• Acid pKa: 17.10915
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3967301
• LogD (pH = 7.4): -0.96040577
• Log P: 1.642921
• Molar Refractivity: 78.5149 cm^3
• Polarizability: 31.407288 Å^3
• Polar Surface Area: 60.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P733502

Labelled Primaquine (P733500). Antimalarial.

REFERENCES

• Marrs, T., et al.: Toxicol Lett., 36, 281 (1987)
• Karbwang, J., et al.: Clin. Pharmacokinetic., 27, 104 (1987)
• Noedl, H., et al.: Antimicrob. Agents Chemother., 45, 2106 (2010)