5-(4-chlorophenyl)(2,2,3,3-2H4)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol

• ChemBase ID: 172560
• Molecular Formular: C16H13ClN2O
• Molecular Mass: 284.74022
• Monoisotopic Mass: 284.07164073
• SMILES: c1ccc2c(c1)C(N1C2=NCC1)(c1ccc(cc1)Cl)O
• Canonical SMILES: Clc1ccc(cc1)C1(O)c2ccccc2C2=NCCN12
• InChI: InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2
• InChIKey: ZPXSCAKFGYXMGA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)(2,2,3,3-^2H₄)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol
• IUPAC Traditional name: 5-(4-chlorophenyl)(2,2,3,3-^2H₄)imidazo[2,1-a]isoindol-5-ol
• Synonyms: 5-(4-Chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol-d4; 5-(4-Chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]isoindole-d4; 5-Hydroxy-5-p-chlorophenyl-2,3-dihydro-5H-imidazo[2,1-a]isoindole-d4; AN 448-d4; Magrilon-d4; Mazanor-d4; Mazildene-d4; Mazindol-d4; SaH 42548-d4; Sanorex-d4; Terenac-d4; Teronac-d4; Mazindol-d4

Database IDs

• CAS Number: 1246815-50-8
• PubChem SID: 164228470
• PubChem CID: 71749912

CALCULATED PROPERTIES

• Acid pKa: 11.61332
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4254982
• LogD (pH = 7.4): 3.435128
• Log P: 3.435279
• Molar Refractivity: 79.4221 cm^3
• Polarizability: 30.1431 Å^3
• Polar Surface Area: 35.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 180-185°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - M198502

Labelled Mazindol (M198500). Clinical trials as appetite depressant. Anorexic; CNS stimulant. Controlled substance (stimulant).

REFERENCES

• Sirtori, C., et al.: Am. J. Med. Sci., 261, 341 (1971)
• Hadler, A.J., et al.: J. Clin. Pharmacol., 12, 453 (1971)
• Thompson, D.A., et al.: Metabolism., 30, 1015 (1971)