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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
Molecular Weight:
143.14
MDL Number:
MFCD00047084
MOL File:
127-48-0.mol
Last updated:2024-12-18 14:08:52

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

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)
form Solid
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)
EWG's Food Scores 1
FDA UNII R7GV3H6FQ4
Proposition 65 List Trimethadione
ATC code N03AC02
EPA Substance Registry System Trimethadione (127-48-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H312+H332-H360
Precautionary statements  P201-P280-P302+P352+P312-P304+P340+P312-P308+P313
Hazard Codes  T
Risk Statements  61-20/21/22
Safety Statements  53-22-36/37/39-45
WGK Germany  3
RTECS  RQ2100000
NFPA 704
1
0 0

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T2100000 Trimethadione European Pharmacopoeia (EP) Reference Standard 127-48-0 t2100000 $150 2024-03-01 Buy
Sigma-Aldrich T0781 3,5,5,-Trimethyloxazolidine-2,4-dione analytical standard 127-48-0 1g $33.2 2022-05-15 Buy
Cayman Chemical 23893 Trimethadione ≥98% 127-48-0 50mg $32 2024-03-01 Buy
Cayman Chemical 23893 Trimethadione ≥98% 127-48-0 100mg $57 2024-03-01 Buy
Cayman Chemical 23893 Trimethadione ≥98% 127-48-0 250mg $122 2024-03-01 Buy
Product number Packaging Price Buy
T2100000 t2100000 $150 Buy
T0781 1g $33.2 Buy
23893 50mg $32 Buy
23893 100mg $57 Buy
23893 250mg $122 Buy

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Chemical Properties,Uses,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

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

Uses

antifungal

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].

Synthesis_127-48-0

6453-39-0
127-48-0
Synthesis of 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE from 5,5-Dimethyl-2-thioxooxazolidin-4-one

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

Global( 98)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32161 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6312 58
Dideu Industries Group Limited
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Nantong HI-FUTURE Biology Co., Ltd.
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TargetMol Chemicals Inc.
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Aladdin Scientific
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TargetMol Chemicals Inc.
+8613564774135 zijue.cai@tsbiochem.com United States 19885 58
Mainchem Co., Ltd. +86-0592-6210733 sale@mainchem.com China 32343 55
Meryer (Shanghai) Chemical Technology Co., Ltd. 021-61259108 18621169109 market03@meryer.com China 40228 62
Alfa Aesar 400-6106006 saleschina@alfa-asia.com China 30123 84

View Lastest Price from 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Trimethadione pictures 2024-11-19 Trimethadione
127-48-0
US $56.00 / mg 100% 10g TargetMol Chemicals Inc.
Trimethadione pictures 2024-11-19 Trimethadione
127-48-0
US $56.00 / mg 100% 10g TargetMol Chemicals Inc.
3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE USP/EP/BP pictures 2021-07-23 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE USP/EP/BP
127-48-0
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
TRIMETHADIONE 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE 3,5,5-TRIMETHYLOXOZOLIDINE-2,4-DIONE 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 3,5,5-Trimethyl-2,4-dioxooxazolidine -Trimethyloxazolidine-2 Trimethadione CRS 3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE USP/EP/BP Trimethadione[Tridione Trimethadione (1690000)