Mephenytoin

Base Information

• Chemical Name: Mephenytoin
• CAS No.: 50-12-4
• Molecular Formula: C12H14 N2 O2
• Molecular Weight: 218.255
• Hs Code.: 2933210000
• European Community (EC) Number: 200-012-8
• NSC Number: 34652
• UNII: R420KW629U
• DSSTox Substance ID: DTXSID9023257
• Nikkaji Number: J4.097E,J66.257G
• Wikipedia: Mephenytoin
• Wikidata: Q1175385
• NCI Thesaurus Code: C66091
• Pharos Ligand ID: 5ATU6LZWZF3S
• Metabolomics Workbench ID: 42871
• ChEMBL ID: CHEMBL861
• Mol file: 50-12-4.mol

Synonyms:5 Ethyl 3 Methyl 5 Phenylhydantoin;5-Ethyl-3-Methyl-5-Phenylhydantoin;Mefenetoin;Mephenytoin;Mesantoin;Methoin;Methyl Phenetoin;Phenantoin;Phenetoin, Methyl

Chemical Property of Mephenytoin

Chemical Property:

• Melting Point: 135-138 °C
• Refractive Index: 1.6660 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: pKa 8.1 (Uncertain)
• Flash Point: °C
• PSA: 49.41000
• Density: 1.154g/cm³
• LogP: 1.74020
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 310

Purity/Quality:

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

Mephenytoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
• Recent ClinicalTrials: Metabolic Capacity of Israeli Populations
• Description: Mephenytoin is N-methylated at position 3 with an ethyl group replacing one of the phenyl substituents at position 5. It is indicated for focal and jacksonian seizures in patients refractory to less toxic AEDs. Mephenytoin produces more sedation than phenytoin and should be used only when safer drugs have failed, because it is associated with an increased incidence of serious toxicities, such as severe rash, agranulocytosis, and hepatitis. Its N-desmethyl metabolite, 5-phenyl- 5-ethylhydantoin, contributes to both efficacy and toxicity for mephenytoin. The drug is no longer commercially available inside but is still available outside the United States.
• Uses: Anticonvulsant. rac-Mephenytoin is an anticonvulsant agent.
• Therapeutic Function: Anticonvulsant, Antiepileptic

Technology Process of Mephenytoin

There total 19 articles about Mephenytoin 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: 96.0%

5-ethyl-1-[(4-methoxyphenyl)methyl]-3-methyl-5-phenylimidazolidine-2,4-dione (1462367-31-2) → mephenytoin (50-12-4)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c3cc46193a

Reference yield: 85.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 5-ethyl-5-phenyl-imidazolidine-2,4-dione (2216-93-5) → mephenytoin (50-12-4)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1002/bscb.19850940611

Reference yield: 68.0%

2-(3-methyl-3-phenylureido)butanoic acid → mephenytoin (50-12-4)

Guidance literature:

With n-butyllithium; diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 17h;

DOI:10.1002/anie.201502569

upstream raw materials:

5-ethyl-5-phenyl-imidazolidine-2,4-dione

2-Ethyl-5-methyl-2-phenylhydantoinsaeure

mephobarbital

1-(1-Cyano-1-phenyl-propyl)-3-methyl-urea

Downstream raw materials:

(-)-Mephenytoin

2-Ethyl-5-methyl-2-phenylhydantoinsaeure

Refernces

• 1、 Atkinson, Rachel C.,Fernández-Nieto, Fernando,Mas Rosell?, Josep,Clayden, Jonathan. "Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives". supporting information. p. 8961 - 8965. Retrieved 2015/08/03.
• 2、 Poupaert,Smeyers,Bottcher. "A high-yield selective N(3)-alkylation process of hydantoins using dimethylformamide dialkyl acetals". . p. 431 - 434. Retrieved 2007/10/02.