PHENSUXIMIDE

PHENSUXIMIDE Basic information
Product Name:PHENSUXIMIDE
Synonyms:(.+/-.)-N-Methyl-2-phenylsuccinimide;1-Methyl-3-phenyl-2,5-pyrrolidinedione;1-methyl-3-phenyl-5-pyrrolidinedione;1-Methyl-3-phenylpyrrolidin-2,5-dione;1-methyl-3-phenyl-pyrrolidine-2,5-quinone;Phensuximide (500 mg);PHENSUCCIMIDE;1-Methyl-3-Phenylsuccinimide
CAS:86-34-0
MF:C11H11NO2
MW:189.21
EINECS:201-664-6
Product Categories:MILONTIN
Mol File:86-34-0.mol
PHENSUXIMIDE Structure
PHENSUXIMIDE Chemical Properties
Melting point 71-73°
Boiling point 324.47°C (rough estimate)
density 1.1596 (rough estimate)
refractive index 1.5012 (estimate)
storage temp. Refrigerator
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Solid
pka-1.86±0.40(Predicted)
color White to Off-White
Water Solubility 4.2g/L(25 ºC)
Safety Information
HS Code 2925190100
ToxicityLD50 orally in mice: 960 mg/kg (Chen, Ensor)
MSDS Information
PHENSUXIMIDE Usage And Synthesis
DescriptionPhensuximide 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.
OriginatorMilontin, Parke Davis, US ,1953
UsesPhensuximide is an anticonvulsant drug, used in the treatment of neurological disorders stemming from the brain. Antiepileptic.
UsesPhensuximide, like ethosuximide, is an anticonvulsant drug used in minor forms of epilepsy.
DefinitionChEBI: Phensuximide is a member of pyrrolidines.
Manufacturing Process10 grams of phenylsuccinic anhydride is dissolved in 250 ml of absolute ether and the solution is treated with dry methylamine until a precipitate ceases to form. After standing for ? hour the ether is decanted off and the residue iswashed with 40 ml of water by decantation. The mixture is filtered and the precipitate washed with 10 ml of water. By acidification of the filtrate, a white precipitate is obtained. After drying it weighs 8 grams and melts at 136°140°C. The two precipitates are combined and recrystallized from aqueous alcohol to give β-N-methylphenylsuccinamic acid which melts at 158°-160°C.
9 grams of β-N-methylphenylsuccinamic acid and 200 ml of acetyl chloride are heated together on a steam bath for ? hour. The excess acetyl chloride is removed by distillation and 50 ml of water are added to the thick residue. After allowing for hydrolysis of the excess acetyl chloride the water is decanted and the yellow residue dissolved in 75 ml of ether. The resulting solution is treated with charcoal twice and dried over anhydrous magnesium sulfate. On partial evaporation of the ether a white solid precipitates. There is obtained 4 grams of N-methyl-α-phenylsuccinimide which melts at 71°-73°C.
Brand nameMilontin (Parke-Davis).
Therapeutic FunctionAnticonvulsant
Clinical UsePhensuximide 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.
SynthesisPhensuximide, 1-methyl-3-phenylpyrrolidine-2,5-dione (9.3.5) is synthesized by the reaction of phenylsuccinic acid or its anhydride with methylamine [10,11].

Synthesis_86-34-0

Purification MethodsCrystallise phensuximide from hot 95% EtOH (m 72-73o). At 25o 1g of the imide dissolves in 1g of *C6H6, 18g of Et2O, 9.5g of EtOH, 5.1g of MeOH and 235g of H2O. [Beilstein 21 II 300, 21 III/IV 5465.]
2,5-Pyrrolidinedione, 1-(5-(diethylamino)pentyl)-3-phenyl-, monohydroc hloride (9CI) Benzenesulfonamide, 3-(2,5-dioxo-3-methyl-3-phenyl-1-pyrrolidinyl)- Morsuximide 3-(3-Chlorophenyl)-1-(4-methyl-2-pyridinyl)-2,5-pyrrolidinedione Benzenesulfonamide, 4-(2,5-dioxo-3-(4-chlorophenyl)-3-methyl-1-pyrroli dinyl)- PB 601 METHSUXIMIDE 2,5-Pyrrolidinedione, 1-cyclohexyl-3-phenyl- 4-(2,5-Dioxo-3-phenyl-1-pyrrolidinyl)-3-fluorobenzenesulfonamide PHENSUXIMIDE 1,2-NAPHTHALENEDICARBOXIMIDE, 1,2,3,4-TETRAHYDRO-N-METHYL- 3,5-dibromophenylsuccinic acid N-methylimide 2,5-Pyrrolidinedione, 1-(3-(diethylamino)propyl)-3-phenyl-, monohydroc hloride (9CI) 2,5-Pyrrolidinedione, 1-(2-(dimethylamino)ethyl)-3-phenyl-, monohydroc hloride (9CI) 2,5-Pyrrolidinedione, 3-(4-chlorophenyl)-1-(3-methyl-2-pyridinyl)- 2-Chloro-4-(2,5-dioxo-3-phenyl-1-pyrrolidinyl)benzenesulfonamide 3-(3-Chlorophenyl)-1-(3-methyl-2-pyridinyl)-2,5-pyrrolidinedione suclofenide

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