3213. Dimethadione

Nomenclature

CAS number: 695-53-4
5,5-Dimethyl-2,4-oxazolidinedione; DMO; AC-1198; BAX-1400Z; NSC-30152; Eupractone (Baxter).
C5H7NO3; mol wt 129.11.
C 46.51%, H 5.46%, N 10.85%, O 37.18%.

Description and references

Active metabolite of trimethadione, q.v. Prepn: F. Urech, Ber. 13, 485 (1880); R. W. Stoughton, J. Am. Chem. Soc. 63, 2376 (1941). Anticonvulsant activity: C. D. Withrow et al., J. Pharmacol. Exp. Ther. 161, 335 (1968); in comparison with trimethadione: H. Ferngren, Acta Pharmacol. Toxicol. 26, 177 (1968). Use in measurement of intracellular pH and cellular pH gradients: S. Addanki et al., J. Biol. Chem. 243, 2337 (1968); V. Ehrhardt, Biochim. Biophys. Acta 775, 182 (1984); J. B. Arnold et al., J. Cereb. Blood Flow Metab. 5, 369 (1985). GLC determn: W. Gazdzik, W. Kmiotek, J. Chromatogr. 378, 482 (1986); LC determn in serum: E. Tanaka, S. Misawa, J. Chromatogr. 413, 376 (1987).

Chemical structure

Properties

Crystals, mp 76-77°. Weak organic acid, pKa (37°) 6.13. LD50 i.v. in mice: 450 mg/kg (Stoughton).

Use

In vivo measurement of intracellular pH.

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant