Metharbital

Metharbital

Clinical data
Routes of administration	By mouth (tablets)
ATC code	N03AA30 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Identifiers
IUPAC name 5,5-Diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
Synonyms	Endiemal, metharbitone, methobarbitone[1]
CAS Number	50-11-3
PubChem (CID)	4099
IUPHAR/BPS	7230
DrugBank	DB00463
ChemSpider	3957
UNII	02OS7K758T
KEGG	D01382
ChEMBL	CHEMBL450
ECHA InfoCard	100.000.011
Chemical and physical data
Formula	C9H14N2O3
Molar mass	198.219 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1N(C(=O)NC(=O)C1(CC)CC)C
InChI InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14) Key:FWJKNZONDWOGMI-UHFFFAOYSA-N
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Metharbital was patented in 1905 by Emil Fischer working for Merck.^[2] It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy.^[3][4] It has similar properties to phenobarbital.

History

• 1952 Gemonil was introduced by Abbott Laboratories.
• 1990 Abbott stopped marketing.

Synthesis

Metharbital can be synthesized from 2,2-diethylmalonic acid and O-methylisourea.^[5][6][7]

References

1. The Comparative Toxicogenomics Database: Metharbital
2. US Patent 782742
3. The Treatment of Epilepsy 2nd Ed by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
4. The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5
5. A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949)
6. Snyder, J. A.; Link, K. P. (1953). "Preparation and Characterization by Alkaline Methanolysis of 5,5-Diethyl-4-(tetraacetyl-β-D-glucosyloxy)-2,6(1,5)-pyrimidinedione". Journal of the American Chemical Society. 75 (8): 1881. doi:10.1021/ja01104a030.
7. U.S. Patent 782,742