Phensuximide

Base Information

• Chemical Name: Phensuximide
• CAS No.: 86-34-0
• Molecular Formula: C11H11 N O2
• Molecular Weight: 189.214
• Hs Code.: 2925190100
• European Community (EC) Number: 201-664-6
• NSC Number: 760079
• UNII: 6WVL9C355G
• DSSTox Substance ID: DTXSID4023460
• Nikkaji Number: J4.938G
• Wikipedia: Phensuximide
• Wikidata: Q999805
• NCI Thesaurus Code: C66375
• Pharos Ligand ID: KBB3K8C4MP4Z
• Metabolomics Workbench ID: 43120
• ChEMBL ID: CHEMBL797
• Mol file: 86-34-0.mol

Synonyms:phensuccimide;phensuximide;phensuximide, (+-)-isomer

Chemical Property of Phensuximide

Chemical Property:

• Melting Point: 71-73°
• Refractive Index: 1.5012 (estimate)
• Boiling Point: 324.47°C (rough estimate)
• PKA: -1.86±0.40(Predicted)
• PSA: 37.38000
• Density: 1.1596 (rough estimate)
• LogP: 1.09680
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: 4.2g/L(25 oC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 256

Purity/Quality:

99.0% ^*data from raw suppliers

Phensuximide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CC(C1=O)C2=CC=CC=C2
• Description: Phensuximide is an anticonvulsant. It inhibits seizures induced by maximal electroshock (MES) and pentylenetetrazole in mice (ED50s = 112 and 50 mg/kg, respectively). Phensuximide (1.25 mmol/kg, i.p.) induces proteinuria and hematuria in rats. Formulations containing phensuximide have been used in the treatment of petit mal seizures.
• Uses: Phensuximide, like ethosuximide, is an anticonvulsant drug used in minor forms of epilepsy. Phensuximide is an anticonvulsant drug, used in the treatment of neurological disorders stemming from the brain. Antiepileptic.
• Therapeutic Function: Anticonvulsant
• Clinical Use: Phensuximide occasionally is used for the treatment of absence seizures refractory to other drugs, although it is considered to be less effective than ethosuximide. It is excreted in both urine and bile, and it may cause harmless pink to red discoloration of the urine. It should be used with caution in patients with acute intermittent porphyria.

Technology Process of Phensuximide

There total 20 articles about Phensuximide 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: 98.0%

1-methyl- 3-phenyl-1H-pyrrole-2,5-dione (54433-49-7) → (R)-1-methyl-3-phenylpyrrolidine-2,5-dione (86-34-0)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S,R)-ZhaoPhos; hydrogen; In 1,4-dioxane; at 25 ℃; for 12h; under 22502.3 Torr; enantioselective reaction;

DOI:10.1021/acscatal.6b01615

Reference yield: 94.0%

N-methylmaleimide (930-88-1) + phenylboronic acid (98-80-6) → (R)-1-methyl-3-phenylpyrrolidine-2,5-dione (86-34-0)

Guidance literature:

With [Rh(OH)(cod)]2; (R)-MeO-F₁₂-BIPHEP; In diethyl ether; dichloromethane; water; at -10 - 20 ℃; for 3.16667h; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere;

DOI:10.1021/jo4014707

Reference yield: 93.0%

1-methyl-3-methylsulfanyl-4-phenyl-pyrrole-2,5-dione (398130-26-2) → phensuximide (86-34-0)

Guidance literature:

With acetic acid; zinc; for 1h; Heating;

DOI:10.3987/COM-01-9336

upstream raw materials:

1-methyl- 3-phenyl-1H-pyrrole-2,5-dione

2-phenylsuccinic acid

methylamine

2-phenylsuccinic anhydride

Downstream raw materials:

1-methyl-3-phenyl-1H-pyrrole

1-methyl-3-phenylpyrrolidine

(S)-1-methyl-3-phenylpyrrolidine-2,5-dione

1-methyl- 3-phenyl-1H-pyrrole-2,5-dione

Refernces

• 1、 Bloom, Steven,Chilamari, Maheshwerreddy,Immel, Jacob R.. "General access to C-centered radicals: Combining a bioinspired photocatalyst with boronic acids in aqueous media". . p. 12727 - 12737. Retrieved 2020/11/18.
• 2、 Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.. "Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase". . p. 1067 - 1078. Retrieved 2018/08/01.