127-48-0 Usage
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
Different sources of media describe the Uses of 127-48-0 differently. You can refer to the following data:
1. antifungal
2. Trimethadione is used in minor forms of epilepsy that does not respond to treatment of
other drugs.
3. 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.
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
Tridione (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 [26–28].
Check Digit Verification of cas no
The CAS Registry Mumber 127-48-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 127-48:
(5*1)+(4*2)+(3*7)+(2*4)+(1*8)=50
50 % 10 = 0
So 127-48-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3
127-48-0Relevant articles and documents
NONAQUEOUS SECONDARY BATTERY AND FLAME RETARDANT FOR THE SAME
-
, (2012/06/01)
A nonaqueous secondary battery, comprising: a positive electrode; a negative electrode; and a nonaqueous electrolyte solution, the nonaqueous electrolyte solution containing at least a cyclic compound having, in the molecule, a functional group having an ester bond to which a nitrogen atom is attached, in which is the general formula (I).
