(1S,2R)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-N-ethyl-1-phenylcyclopropane-1-carboxamide

• ChemBase ID: 166232
• Molecular Formular: C21H20N2O3
• Molecular Mass: 348.3951
• Monoisotopic Mass: 348.14739251
• SMILES: c1c(cccc1)[C@@]1(C[C@H]1CN1C(=O)c2ccccc2C1=O)C(=O)NCC
• Canonical SMILES: CCNC(=O)[C@]1(C[C@H]1CN1C(=O)c2c(C1=O)cccc2)c1ccccc1
• InChI: InChI=1S/C21H20N2O3/c1-2-22-20(26)21(14-8-4-3-5-9-14)12-15(21)13-23-18(24)16-10-6-7-11-17(16)19(23)25/h3-11,15H,2,12-13H2,1H3,(H,22,26)/t15-,21+/m0/s1
• InChIKey: KXPNXMHTVGJNIW-YCRPNKLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-N-ethyl-1-phenylcyclopropane-1-carboxamide
• IUPAC Traditional name: (1S,2R)-2-[(1,3-dioxoisoindol-2-yl)methyl]-N-ethyl-1-phenylcyclopropane-1-carboxamide
• Synonyms: cis-2-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N-ethyl-1-phenylcyclopropanecarboxamide; rac-N-Desethyl-N'-phthalimido Milnacipran

Database IDs

• CAS Number: 105310-73-4
• PubChem SID: 162260365
• PubChem CID: 71315638

CALCULATED PROPERTIES

• Acid pKa: 15.153519
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3837805
• LogD (pH = 7.4): 2.3837805
• Log P: 2.3837805
• Molar Refractivity: 98.4569 cm^3
• Polarizability: 37.092804 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289410

N-Desethyl-N’-phthalimido Milnacipran is an impurity of Milnacipran (M344600) as potential antidepressant.

REFERENCES

• Bonnaud, B., et al.: J. Med. Chem., 30, 318 (1987)