2-[2-amino(2H4)ethyl]-3-(4-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one hydrochloride

• ChemBase ID: 160112
• Molecular Formular: C16H16Cl2N2O2
• Molecular Mass: 339.21644
• Monoisotopic Mass: 338.05888312
• SMILES: c1ccc2c(c1)C(=O)N(C2(c1ccc(cc1)Cl)O)CCN.Cl
• Canonical SMILES: NCCN1C(=O)c2c(C1(O)c1ccc(cc1)Cl)cccc2.Cl
• InChI: InChI=1S/C16H15ClN2O2.ClH/c17-12-7-5-11(6-8-12)16(21)14-4-2-1-3-13(14)15(20)19(16)10-9-18;/h1-8,21H,9-10,18H2;1H
• InChIKey: DJJFCISYZNGZCM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-amino(^2H₄)ethyl]-3-(4-chlorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one hydrochloride
• IUPAC Traditional name: 2-[2-amino(^2H₄)ethyl]-3-(4-chlorophenyl)-3-hydroxyisoindol-1-one hydrochloride
• Synonyms: 2-(2-Aminoethyl-d4)-3-(4-chlorophenyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one Hydrochloride; 2-(2-Aminoethyl)-3-(4-chlorophenyl)-3-hydroxyphthalimidine-d4 Hydrochloride (Mazindol Metabolite)

Database IDs

• CAS Number: 1276611-52-9
• PubChem SID: 162254247
• PubChem CID: 71313235

CALCULATED PROPERTIES

• Acid pKa: 11.523202
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.43867865
• LogD (pH = 7.4): 0.9691746
• Log P: 2.4240825
• Molar Refractivity: 81.9891 cm^3
• Polarizability: 31.546041 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 236-239°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A608912

A labelled metabolite of Mazindol. An imidazolinylphenyl ketone derivatives as antidepressants and diuretics.

REFERENCES

• Guengerich, F., et al.: Chem. Res. Toxicol., 14, 611 (2001)
• Murray, S., et al.: Xenobiotica, 31, 135 (2001)
• Lewis, D., et al.: Drug Metab. Rev., 34, 55 (2001)
• de Graaf, C., et al.: J. Med. Chem., 48, 2725 (2001)