ChemicalBook > CAS DataBase List > 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE

Product Name
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE
CAS No.
127-48-0
Chemical Name
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE
Synonyms
a2297;Edion;A 2297;Epixal;Pitmal;Ptimal;Absetil;Epidone;Etydion;Petidon
CBNumber
CB3477704
Molecular Formula
C6H9NO3
Formula Weight
143.14
MOL File
127-48-0.mol
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3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Property

Melting point:
45-46°C
Boiling point:
78-80°C 5mm
Density 
1.3075 (rough estimate)
refractive index 
1.4290 (estimate)
Flash point:
78-80°C/5mm
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Soluble in water, very soluble in ethanol (96 per cent).
pka
-2.18±0.40(Predicted)
color 
White to Off-White
Water Solubility 
Soluble in water 50 g/L.
Merck 
14,9706
BRN 
121627
CAS DataBase Reference
127-48-0(CAS DataBase Reference)
EPA Substance Registry System
Trimethadione (127-48-0)
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Safety

Hazard Codes 
T
Risk Statements 
61-20/21/22
Safety Statements 
53-22-36/37/39-45
WGK Germany 
3
RTECS 
RQ2100000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T2100000
Product name
Trimethadione
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
t2100000
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
T0781
Product name
3,5,5,-Trimethyloxazolidine-2,4-dione
Purity
analytical standard
Packaging
1g
Price
$33.2
Updated
2022/05/15
Cayman Chemical
Product number
23893
Product name
Trimethadione
Purity
≥98%
Packaging
50mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
23893
Product name
Trimethadione
Purity
≥98%
Packaging
100mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
23893
Product name
Trimethadione
Purity
≥98%
Packaging
250mg
Price
$122
Updated
2024/03/01
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3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Chemical Properties,Usage,Production

Chemical Properties

White, granular, crystalline substance; camphor-like odor. Soluble in water; freely soluble in alcohol, chloroform, and ether; pH 6.0 (5% solution).

Originator

Tridione,Abbott,US,1946

Uses

antifungal

Uses

Trimethadione is used in minor forms of epilepsy that does not respond to treatment of other drugs.

Uses

3,5,5-Trimethyloxazolidine-2,4-dione is used in the control of absence (petit mal) seizures that are refractory to treatment with other medications. It is used in the treatment of epilepsy.

Definition

ChEBI: Trimethadione is an oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent. It has a role as a geroprotector and an anticonvulsant.

Manufacturing Process

To a cooled solution of 23 parts of sodium in 400 parts of dry ethanol are added 60 parts of dry urea and 132 parts of ethyl α-hydroxy-isobutyrate. The mixture is heated on a steam bath under reflux for about 16 hours and the liberated ammonia is removed from the solution by drawing a current of dry air through it at the boiling point. The solution of the sodium salt of 5,5- dimethyloxazolidine-2,4-dione so obtained is cooled and treated with 284 parts of methyl iodide. The mixture is allowed to stand at room temperature for 3 days, excess methyl iodide and ethanol are then removed by distillation under reduced pressure.
The residue is dissolved in ether and the solution is washed with sodium chloride solution and then with a little sodium thiosulfate solution. The ethereal solution is dried over sodium sulfate and ether removed by distillation. A yield of 108 parts of 3,5,5-trimethyloxazolidine-2,4-dione is obtained having a melting point of 45° to 46°C with slight softening at 43°C. This represents a 75% theory yield on the ethyl α-hydroxy-iso-butyrate taken. The product may be further purified by dissolving the minimum quantity of dry ether and cooling to -10°C. The product so obtained melts sharply at 45.5° to 46.5°C according to US Patent 2,559,011.

brand name

Absentol (Nourypharma), Epidione (Bellon), Ptimal (EGIS), Tridione/Trimedone (Abbott).

Therapeutic Function

Anticonvulsant

Synthesis Reference(s)

Tetrahedron, 51, p. 5891, 1995 DOI: 10.1016/0040-4020(95)00257-9

Hazard

May have adverse side effects; toxic in overdose.

Clinical Use

Trimethadione is indicated only for control of absence seizures refractory to treatment with other AEDs. It is ineffective against other seizure types. Trimethadione is a pro-drug and is metabolized by N-demethylation to dimethadione, which is effective in the pentylenetetrazole test, which acts by decreasing T-type calcium currents. Trimethadione is rapidly absorbed, is not protein bound, and has a half-life of 16 to 24 hours. The half-life of dimethadione, however, is substantially longer (i.e., 6–13 days), and dimethadione accumulates to concentrations greater than the parent drug. Because of its potentially fatal side effects. including aplastic anemia, nephrosis, idiosyncratic rashes, and exfoliative dermatitis, trimethadione rarely is used today.

Synthesis

Trimethadione, 3,5,5-trimethyloxazolidine-2,4-dione (9.8.2), is synthesized by methylating 5,5-trimethyloxazolidine-2,4-dione (9.8.1) with dimethylsulfate.Starting 5,5-trimethyloxazolidine-2,4-dione (9.8.1) is in turn synthesized by the cyclocondensation of the ester of 2-hydroxyisobutyric acid with urea [26¨C28].

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Preparation Products And Raw materials

Raw materials

Preparation Products

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3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Suppliers

Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
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China
ProdList
40241
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Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
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Energy Chemical
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021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
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China
ProdList
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LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
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Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
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sj_scrc@sinopharm.com
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China
ProdList
9823
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Beijing HuaMeiHuLiBiological Chemical
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010-56205725
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010-65763397
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waley188@sohu.com
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China
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Haoyuan Chemexpress Co., Ltd.
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021-58950125
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(86) 21-58955996
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info@chemexpress.com
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China
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Guangzhou Isun Pharmaceutical Co., Ltd
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020-39119399 18927568969
Fax
020-39119999
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isunpharm@qq.com
Country
China
ProdList
4428
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TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Fax
021-33632979
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marketing@targetmol.com
Country
China
ProdList
7934
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58
ChemStrong Scientific Co.,Ltd
Tel
0755-66853366 15920483169
Fax
0755-28363542
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sales@chem-strong.com
Country
China
ProdList
17944
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View Lastest Price from 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE manufacturers

Dideu Industries Group Limited
Product
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE 127-48-0
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-22

127-48-0, 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONERelated Search:


  • TRIMETHADIONE
  • 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE
  • 3,5,5-TRIMETHYLOXOZOLIDINE-2,4-DIONE
  • 3,5,5-Trimethyl-2,4-dioxooxazolidine
  • 2,4-Oxazolidinedione, 3,5,5-trimethyl-
  • 3,3,5-Trimethyl-2,4-diketooxazolidine
  • 3,5,5-Trimethyl-1,3-oxazolidine-2,4-dione
  • 3,5,5-Trimethyl-2,4-oxazolidinedione
  • 3,5,5-Trimethyl-2,4-oxazolidinedionenol
  • 3,5,5-trimethyl-4-oxazolidinedione
  • 3,5,5-Trojmetylooksazolidyno-2,4-dion
  • A 2297
  • a2297
  • Absentol
  • Absetil
  • Convenixa
  • Convexina
  • Edion
  • Epidione
  • Epidone
  • Epixal
  • Etydion
  • Minoaleuiatin
  • minoaleviatin
  • Mino-aleviatin
  • Neo-absentol
  • Petidion
  • Petidon
  • Petilep
  • Petimalin
  • Pitmal
  • Ptimal
  • Tioxanona
  • Tredione
  • Tricione
  • Tridilona
  • Tridion
  • Tridione
  • Tridone
  • Trilidona
  • Trimedal
  • Trimedone
  • Trimetadione
  • Trimethadion
  • Trimethdione
  • Trimethin
  • Trioxanona
  • Triozanona
  • Tromedone
  • Troxidone
  • 3,5,5-trimethyloxazolidine-2,4-quinone
  • Trimethadione (200 mg)
  • trimethadioine
  • -Trimethyloxazolidine-2
  • Trimethadione CRS
  • 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE USP/EP/BP
  • Trimethadione[Tridione
  • Trimethadione (1690000)