1497-17-2

Basic information

• Product Name: ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE
• Synonyms: 2,5-Pyrrolidinedione, 3-methyl-3-phenyl-;3-Methyl-3-phenyl-2,5-pyrrolidinedione;Mesuximide, M(nor-);N-Demethylmethsuximide;n-desmethylmethsuximide;ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE;2-methyl-2-phenylsuccinimide;A-METHYL-A-PHENYLSUCCINIMIDE
• CAS NO: 1497-17-2
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• EINECS: 216-091-7
• Product Categories: Carbonyl Compounds;Cyclic Imides;Organic Building Blocks;Heterocycles;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Metabolites & Impurities;Pharmaceuticals
• Mol File: 1497-17-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 371.1°Cat760mmHg
• Flash Point: 165.3°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE(1497-17-2)
• EPA Substance Registry System: ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE(1497-17-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1497-17-2(Hazardous Substances Data)

Usage

Description

ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE, also known as Methsuximide metabolite, is an organic compound derived from the calcium channel succinimide antiepileptic drug Methsuximide. It is characterized by its off-white solid appearance and exhibits anticonvulsant properties, making it a valuable compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE is used as an active pharmaceutical ingredient for its anticonvulsant properties, specifically in the treatment of epilepsy. It helps to control seizures and prevent their recurrence, providing relief to patients suffering from this neurological disorder.
Used in Metabolite Research:
ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE is used as a labelled metabolite in research studies, particularly in the field of drug metabolism and pharmacokinetics. Its role as a metabolite of Methsuximide allows researchers to better understand the metabolic pathways and the effects of the parent drug on the body.
Used in Drug Development:
As a metabolite of a calcium channel succinimide antiepileptic drug, ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE can be utilized in the development of new anticonvulsant medications. Its study can lead to the discovery of novel compounds with improved efficacy, safety, and reduced side effects for the treatment of epilepsy and other related conditions.

InChI:InChI=1/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)

Upstream product

• 14231-67-5 (+/-)-2-Methyl-2-phenylbutanedioic acid 

Downstream Products

• 91091-20-2 3-(4-nitrophenyl)-3-methylpyrrolidine-2,5-dione 
• 98832-24-7 (3RS)-3-Methyl-3-phenyl-1-(trimethylsilyl)-2,5-pyrrolidindion 
• 28172-29-4 3-methyl-3,5-diphenyl-1,3-dihydropyrrol-2-one 
• 98832-26-9 (3RS)-3-Methyl-3-phenyl-1-(β-D-ribofuranosyl)-2,5-pyrrolidindion 
• 98832-25-8 (3RS)-3-Methyl-3-phenyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,5-pyrrolidindion 
• 1402546-99-9 C₂₀H₂₃N₅O₂ 
• 1402547-01-6 C₂₂H₃₁N₃O₂ 
• 1402547-03-8 C₂₄H₂₈N₂O₂ 
• 3780-72-1 Morfolep 

Relevant articles and documents

Cu-catalyzed oxygenation of alkene-tethered amides with O2: Via unactivated CC bond cleavage: A direct approach to cyclic imides

The transformations of unactivated alkenes through CC bond double cleavage are always attractive but very challenging. We report herein a chemoselective approach to valuable cyclic imides by a novel Cu-catalyzed geminal amino-oxygenation of unactivated CC bonds. O2 was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via CC bond cleavage for the efficient preparation of succinimide or glutarimide derivatives. Moreover, the present strategy under simple conditions can be used in the late-stage modification of biologically active compounds and the synthesis of pharmaceuticals, which demonstrated the potential application.

Synthesis and anticonvulsant properties of new mannich bases derived from 3,3-disubstituted pyrrolidine-2,5-diones. Part IV

A library of 21 new N-Mannich bases of 3,3-diphenyl- (5a-g), 3-methyl-3-phenyl- (6a-g), and 3-ethyl-3-methylpyrrolidine-2,5-diones (7a-g) were synthesized and evaluated for their anticonvulsant activity in the maximum electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests after intraperitoneal injection into mice. The acute neurological toxicity was determined applying the rotarod screen. The results in mice showed that 13 compounds were effective in the MES or/and scPTZ screen. From these, seven molecules were tested in the MES seizures after oral administration in rats. The quantitative studies showed that N-[{4-(2-hydroxyethyl)-piperazin-1-yl}-methyl] -3-methyl-3-phenylpyrrolidine-2,5-dione (6c) and N-[(4-benzylpiperidin-1-yl)- methyl]-3-methyl-3-phenylpyrrolidine-2,5-dione (6f) revealed higher protection in the MES and scPTZ tests than valproic acid or ethosuximide which were used as reference antiepileptic drugs. Four compounds (5c, 6c, 6e, 6f) showed high effectiveness in the 6-Hz psychomotor seizure model of partial and therapy resistant epilepsy.