3-methyl-3-phenylpyrrolidine-2,5-dione

• ChemBase ID: 138098
• Molecular Formular: C11H11NO2
• Molecular Mass: 189.21054
• Monoisotopic Mass: 189.0789786
• SMILES: CC1(CC(=O)NC1=O)c1ccccc1
• Canonical SMILES: O=C1NC(=O)CC1(C)c1ccccc1
• InChI: InChI=1S/C11H11NO2/c1-11(7-9(13)12-10(11)14)8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H,12,13,14)
• InChIKey: UDESUGJZUFALAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-3-phenylpyrrolidine-2,5-dione
• IUPAC Traditional name: 3-methyl-3-phenylpyrrolidine-2,5-dione
• Synonyms: 3-Methyl-3-phenyl-2,5-pyrrolidinedione; 2-Methyl-2-phenylsuccinimide; (+/-)-α-Methyl-α-phenylsuccinimide; N-Demethylmethsuximide; N-Desmethylmethsuximide; N-Normethsuximide; α-Methyl-α-phenylsuccinimide; Normesuximide; 3-methyl-3-phenylpyrrolidine-2,5-dione; α-Methyl-α-phenylsuccinimide; 2-Methyl-2-phenylsuccinimide; α-甲基-α-苯基琥珀酰亚胺; 2-甲基-2-苯基琥珀酰亚胺

Database IDs

• CAS Number: 1497-17-2
• EC Number: 216-091-7
• MDL Number: MFCD00005496
• PubChem SID: 162232356; 24888515
• PubChem CID: 92154

CALCULATED PROPERTIES

• Acid pKa: 10.076927
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2393216
• LogD (pH = 7.4): 1.2384306
• Log P: 1.239333
• Molar Refractivity: 51.4519 cm^3
• Polarizability: 20.086967 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 74-78°C; 79 - 81°C; 83-85 °C(lit.)
• Hydrophobicity(logP): 0.905

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95%; 99%
• Empirical Formula (Hill Notation): C11H11NO2

DETAILS

Sigma Aldrich - 860581

Packaging
1 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - N720500

A metabolite of calcium channel succinimide antiepileptic drug Methsuximide. Anticonvulsant.

REFERENCES

• Herrington, J., et al.: J. Neurophysiol., 68, 213 (1992)
• Steriade, M., et al.: Science, 262, 679 (1992)
• Zhang, Y., et al.: Epilepsy Res., 23, 15 (1992)
• Lee, J., et al.: Biophys. J., 77, 3034 (1992)
• Todorovic, S., et al.: Mol.Pharmacol., 58, 98 (2000)