Name: ETHOSUXIMIDE
SKU: 77-67-8

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Basic Information

Molecular Structure:
CAS No.:	77-67-8
Name:	ETHOSUXIMIDE

Formula:	C7H11 N O2
Molecular Weight:	141.17
Synonyms:	Succinimide,2-ethyl-2-methyl- (6CI,7CI,8CI); (?à)-Ethosuximide; 2-Ethyl-2-methylsuccinimide; 2-Methyl-2-ethylsuccinimide;3-Ethyl-3-methylpyrrolidine-2,5-dione; 3-Ethyl-3-methylsuccinimide;3-Methyl-3-ethylpyrrolidine-2,5-dione; 3-Methyl-3-ethylsuccinimide; Atysmal;C.I. 366; CN 10395; Capitus; Emeside; Epileo Petitmal; Ethosuxide;Ethosuximide; Ethymal; Etosuximid; H 940; Mesentol; NSC 64013; PM 671; Pemal;Peptinimid; Petinimid; Petnidan; Piknolepsin; Pyknolepsinum; Ronton; Simatin;Succimal; Succimitin; Suxilep; Suximal; Suxinutin; Zarodan; Zarondan;Zarondan-Saft; Zarontin; a-Ethyl-a-methylsuccinimide;a-Methyl-a-ethylsuccinimide
EINECS:	201-048-7
Density:	1.1522 (rough estimate)
Melting Point:	51 °C
Boiling Point:	265.3 °C at 760 mmHg
Flash Point:	123.8 °C
Solubility:	ethanol: 100 mg/mL
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	36
PSA:	46.17000
LogP:	0.77800

Synthetic route

: C14H17NO3

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
Stage #1: C14H17NO3 With palladium on activated charcoal; hydrogen Stage #2: With triethylamine; α-bromoacetophenone	83%

: 166324-36-3
4-ethyl-1-(4-methoxybenzyl)-4-methylpyrrolidine-2,5-dione

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile for 1h; Ambient temperature;	47%

: 631-31-2
2-ethyl-2-methylsuccinic acid

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
With ammonia
With ammonium hydroxide at 200℃;
With ammonium hydroxide In water at 190℃; for 1.5h;

ammonium salt of/the/ α-methyl-α-ethyl-succinic acid: ammonium salt of/the/ α-methyl-α-ethyl-succinic acid

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
durch Destillation;

: 96-17-3, 57456-98-1
2-Methylbutyraldehyde

Ag2O: Ag2O

: 77-67-8
ethosuximide

Conditions

Yield

Multi-step reaction with 6 steps
1: 1.) MgSO4, 2.) N,N-diethylaniline / 1.) Et2O, 2 h, RT, 2.) toluene, -78 deg C to RT, 24 h
2: N-chlorosuccinimide / 40 deg C, 2 h; 80 deg C, 1 h
3: SiO2, H2O / 1.) 35 deg C, overnight then 60 deg C, 30 min, 2.) benzene, 1 h
4: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating
5: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
6: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme

: 166324-35-2
4-ethyl-5-hydroxy-1-(4-methoxybenzyl)-4-methylpyrrolidin-2-one

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: 166324-34-1
4-ethyl-5-hydroxy-1-(4-methoxybenzyl)-4-methyl-3-(methylthio)pyrrolidin-2-one

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating 2: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: N-(2-methylbut-1-enyl)-N-(4-methoxybenzyl)-α-(methylthio)acetamide

: 77-67-8
ethosuximide

Conditions

Yield

Multi-step reaction with 5 steps
1: N-chlorosuccinimide / 40 deg C, 2 h; 80 deg C, 1 h
2: SiO2, H2O / 1.) 35 deg C, overnight then 60 deg C, 30 min, 2.) benzene, 1 h
3: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating
4: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
5: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme

: 1027595-29-4
2-Chloro-N-(4-methoxy-benzyl)-N-((E)-2-methyl-but-1-enyl)-2-methylsulfanyl-acetamide

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: SiO2, H2O / 1.) 35 deg C, overnight then 60 deg C, 30 min, 2.) benzene, 1 h 2: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating 3: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: C15H21NO2

: 77-67-8
ethosuximide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper (I) acetate; Bathocuproine; oxygen / toluene / 80 °C / 760.05 Torr 2: hydrogen; palladium on activated charcoal View Scheme

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Chemistry

Molecular Structure of Ethosuximide (CAS NO.77-67-8):

EINECS: 201-048-7
IUPAC Name: 3-Ethyl-3-methylpyrrolidine-2,5-dione
Molecular Formula: C₇H₁₁NO₂
Molecular Weight: 141.167740 g/mol
XLogP3: 0.4
H-Bond Donor: 1
H-Bond Acceptor: 2
Canonical SMILES: CCC1(CC(=O)NC1=O)C
InChI: InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)
InChIKey: HAPOVYFOVVWLRS-UHFFFAOYSA-N
Index of Refraction: 1.608
Molar Refractivity: 35.06 cm³
Molar Volume: 101.3 cm³
Surface Tension: 56.1 dyne/cm
Density: 1.274 g/cm³
Flash Point: 77.9 °C
Melting Point: 51 °C
Enthalpy of Vaporization: 44.14 kJ/mol
Boiling Point: 205.2 °C at 760 mmHg
Vapour Pressure: 0.254 mmHg at 25 °C
Water Solubility: 5.51e+004 mg/L at 25 °C
BRN: 0117054

Toxicity Data With Reference

1.	cyt-hmn:lyms 30 mg/L	MUREAV Mutation Research. 204 (1988),623.
2.	orl-rat TDLo:66,600 µg/kg (6-14D preg):REP	40YJAX Evaluation of Embryotoxicity, Mutagenicity and Carcinogenicity Risks In New Drugs Benesova, O., et al., eds.,Prague, Czechoslovakia.: Univerzita Karlova,1970,59.
3.	orl-mus LD50:1530 mg/kg	EPILAK Epilepsia. 4 (4)(1963),66.
4.	ipr-mus LD50:1752 mg/kg	EPILAK Epilepsia. 29 (1988),198.
5.	scu-mus LD50:1810 mg/kg	NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),117.
6.	ivn-mus LD50:780 mg/kg	NEPHBW Neuropharmacology. 24 (1985),427.

Safety Profile

Safety Information of Ethosuximide (CAS NO.77-67-8):
Hazard Codes: Xn Harmful
Risk Statements: 22
R22:Harmful if swallowed
Safety Statements: 36
S36:Wear suitable protective clothing
WGK Germany: 3
RTECS: WN2800000
Moderately toxic by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. An anticonvulsant. When heated to decomposition it emits toxic fumes of NO_x.

Specification

Ethosuximide with CAS registry number of 77-67-8 is also known as Ethosuximide [USAN:INN:BAN:JAN] ; (+-)-2-Ethyl-2-methylsuccinimide ; 2,5-Pyrrolidinedione, 3-ethyl-3-methyl- ; 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-, (+-)- ; 2-Ethyl-2-methylsuccinimide ; 2-Methyl-2-ethylsuccinimide ; 3-Ethyl-3-methylpyrrolidine-2,5-dione ; 3-Ethyl-3-methylsuccinimide ; 3-Methyl-3-ethylpyrrolidine-2,5-dione ; 3-Methyl-3-ethylsuccinimide ; 5-21-09-00595 (Beilstein Handbook Reference) ; Aethosuccimidum ; Aethosuximide ; Aethosuximide [German] ; Asamid ; Atysmal ; C.I. 366 ; CI 366 ; CN-10,395 ; Capitus ; Emeside ; Epileo Petit MAL ; Ethosuccimide ; Ethosuccinimide ; Ethosuxide ; Ethosuximide ; Ethosuximidum ; Ethosuximidum [INN-Latin] ; Ethymal ; Etomal ; Etosuccimide ; Etosuccimide [DCIT] ; Etosuximid ; Etosuximida ; Etosuximida [INN-Spanish] ; Etosuximide ; H 940 ; H-490 ; HSDB 1119 ; Mesentol ; N-Ethyl methylsuccinimide ; NSC 64013 ; PM 671 ; Pemal ; Pemalin ; Pentinimid ; Peptinimid ; Petinimid ; Petnidan ; Piknolepsin ; Pyknolepsinum ; Ronton ; Simatin ; Simatin(E) ; Succimal ; Succimitin ; Succinimide, 2-ethyl-2-methyl- ; Suxilep ; Suximal ; Suxin ; Suxinutin ; Thetamid ; Thilopemal ; UNII-5SEH9X1D1D ; Zaraondan ; Zarodan ; Zarondan ; Zarondan-saft ; Zarontin ; Zartalin ; alpha-Ethyl-alpha-methylsuccinimide ; alpha-Methyl-alpha-ethylsuccinimide ; gamma-Methyl-gamma-ethyl-succinimide . It is a drug for treating absence seizures under the trade names Emeside and Zarontin due to the mechanism of action which is ethosuximide is a T-type calcium channel blocker with an IC₅₀ of 12 ± 2 mmol/L. Emeside capsules were discontinued by their manufacturer, Laboratories for Applied Biology, in 2005. Zarontin capsules were discontinued by Pfizer in 2007. Syrup preparations of both brands are still available.

77-67-8

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Chemistry

Toxicity Data With Reference

Safety Profile

Specification