Methsuximide

Base Information

• Chemical Name: Methsuximide
• CAS No.: 77-41-8
• Molecular Formula: C12H13 N O2
• Molecular Weight: 203.241
• Hs Code.: 2925190100
• European Community (EC) Number: 201-026-7
• NSC Number: 760075
• UNII: 0G76K8X6C0
• DSSTox Substance ID: DTXSID5023293
• Nikkaji Number: J4.203J
• Wikipedia: Mesuximide
• Wikidata: Q906414
• NCI Thesaurus Code: C47613
• RXCUI: 47858
• Pharos Ligand ID: DGZBPJC4XW7Y
• Metabolomics Workbench ID: 43651
• ChEMBL ID: CHEMBL697
• Mol file: 77-41-8.mol

Synonyms:Celontin;mesuximid;mesuximide;methsuximide;methsuximide, (+)-isomer;methsuximide, (+-)-isomer;methsuximide, (-)-isomer;N,2-dimethyl-2-phenylsuccinimide;Petinutin

Chemical Property of Methsuximide

Chemical Property:

• Vapor Pressure: 1.27E-11mmHg at 25°C
• Melting Point: 52-53°
• Refractive Index: 1.5440 (estimate)
• Boiling Point: 489.2°C at 760 mmHg
• Flash Point: 191.7°C
• PSA: 37.38000
• Density: 1.59g/cm³
• LogP: 1.27090
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 2.8g/L(25 oC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 294

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methsuximide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: CC1(CC(=O)N(C1=O)C)C2=CC=CC=C2
• Recent ClinicalTrials: Population Pharmacokinetics of Antiepileptic in Pediatrics
• Description: Methsuximide is a succinimide that is converted to N-desmethylmethosuximide, a channel blocker that targets low threshold calcium currents. Methsuximide is a substrate of cytochrome P450 (CYP) isoform 2C19 that, in turn, inhibits CYP2C19-mediated metabolism of biguanides. Methsuximide has been shown to have anticonvulsant properties in clinical trials.
• Uses: A calcium channel succinimide antiepileptic drug. Anticonvulsant.
• Therapeutic Function: Anticonvulsant
• Clinical Use: Although methsuximide is less commonly used, it may be indicated for the control of absence seizures refractory to other drugs. Although it does not precipitate tonic-clonic convulsions, it often is combined with phenytoin or phenobarbital when absence seizures coexist with tonic-clonic symptoms. Much of the efficacy of methsuximide is attributed to its desmethyl metabolite. The half-life of methsuximide is between 2.6 and 4.0 hours, but the half-life for N-desmethylsuximide is 25 hours, causing it to accumulate substantially. Concentrations of greater than 40 g/mL may be associated with toxicity. Methsuximide is considered to be more toxic than ethosuximide.

Technology Process of Methsuximide

There total 4 articles about Methsuximide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

3-methyl-3-phenyl-pyrrolidine-2,5-dione (1497-17-2) + methyl iodide (74-88-4) → methsuximide (77-41-8)

Guidance literature:

With potassium carbonate; In acetone;

DOI:10.1039/c9sc03175h

Reference yield:

(+/-)-2-Methyl-2-phenylbutanedioic acid (14231-67-5,40508-13-2,57572-94-8,34862-03-8) + methylamine (74-89-5) → methsuximide (77-41-8)

Guidance literature:

With water;

DOI:10.1021/ja01154a126

Reference yield:

C19H21NO2 → methsuximide (77-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: copper (I) acetate; Bathocuproine; oxygen / toluene / 80 °C / 760.05 Torr

2: hydrogen; palladium on activated charcoal

3: potassium carbonate / acetone

With palladium on activated charcoal; Bathocuproine; hydrogen; oxygen; copper (I) acetate; potassium carbonate; In acetone; toluene;

DOI:10.1039/c9sc03175h

upstream raw materials:

(+/-)-2-Methyl-2-phenylbutanedioic acid

methylamine

3-methyl-3-phenyl-pyrrolidine-2,5-dione

methyl iodide

Downstream raw materials:

(S)-Mesuximid

Refernces

• 1、 Knabe,Koch. "Synthesis of the enantiomers of some disubstituted succinic imides". . p. 757 - 765. Retrieved 2007/10/07.