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PHENSUXIMIDE

CAS No.
86-34-0
Chemical Name:
PHENSUXIMIDE
Synonyms
pm334;Lifen;Epimid;Lifene;PM 334;Epimal;Mirotin;Milontin;Milonton;Mirontin
CBNumber:
CB3480203
Molecular Formula:
C11H11NO2
Molecular Weight:
189.21
MDL Number:
MFCD00072136
MOL File:
86-34-0.mol
MSDS File:
SDS
Last updated:2023-06-08 09:02:58

PHENSUXIMIDE 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)
EWG's Food Scores 1
FDA UNII 6WVL9C355G
ATC code N03AD02

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
HS Code  2925190100
Toxicity LD50 orally in mice: 960 mg/kg (Chen, Ensor)
NFPA 704
0
1 0

PHENSUXIMIDE price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 27601 Phensuximide 86-34-0 10mg $65 2024-03-01 Buy
Cayman Chemical 27601 Phensuximide 86-34-0 25mg $142 2024-03-01 Buy
Cayman Chemical 27601 Phensuximide 86-34-0 5mg $37 2024-03-01 Buy
TRC P318900 Phensuximide 86-34-0 50mg $220 2021-12-16 Buy
American Custom Chemicals Corporation API0009009 Phensuximide 95.00% 86-34-0 10MG $255.15 2021-12-16 Buy
Product number Packaging Price Buy
27601 10mg $65 Buy
27601 25mg $142 Buy
27601 5mg $37 Buy
P318900 50mg $220 Buy
API0009009 10MG $255.15 Buy

PHENSUXIMIDE Chemical Properties,Uses,Production

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.

Originator

Milontin, Parke Davis, US ,1953

Uses

Phensuximide, like ethosuximide, is an anticonvulsant drug used in minor forms of epilepsy.

Uses

Phensuximide is an anticonvulsant drug, used in the treatment of neurological disorders stemming from the brain. Antiepileptic.

Definition

ChEBI: Phensuximide is a member of pyrrolidines.

Manufacturing Process

10 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 name

Milontin (Parke-Davis).

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.

Synthesis

Phensuximide, 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 Methods

Crystallise 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.]

930-88-1
98-80-6
86-34-0
Synthesis of PHENSUXIMIDE from N-Methylmaleimide and Phenylboronic acid
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(.+/-.)-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 2,5-Pyrrolidinedione, 1-methyl-3-phenyl- Epimid Fenosuccimide Lifene Methylphenylsuccinimide Milontin Milonton Mirontin Mirotin n-methyl-2-phenyl-succinimid N-Methyl-2-phenylsuccinimide n-methyl-2-phenyl-succinimide N-Methyl-alpha-phenolsuccinimide N-Methyl-alpha-phenylsuccinimide Phenosuccimide Phensuximid Phenylsuximide PM 334 pm334 Succinimide, N-methyl-2-phenyl- Succitimal PHENSUXIMIDE Epimal Lifen Succitmal 5-(Diallylaminomethyl)-3-[(5-nitrofurfurylidene)amino]-2-oxazolidinone 1-methyl-3-phenyl-pyrrolidine-2,5-dione 1-methyl-3-phenylpyrrolidine-2,5-dione PHENSUXIMIDE USP/EP/BP Phensuximide (1528002) AI3 20372 AI320372 AI3-20372 RSYY PHENSUXIMIDE 86-34-0 MILONTIN