Metharbital

Metharbital

Clinical data
AHFS/Drugs.com	Monograph
ATC code	N03AA30 (WHO)
Identifiers
IUPAC name 5,5-diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
CAS Number	50-11-3 Y
PubChem CID	4099
DrugBank	DB00463 Y
ChemSpider	3957 Y
UNII	02OS7K758T
KEGG	D01382 Y
ChEMBL	ChEMBL450 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C9H14N2O3
Molar mass	198.219 g/mol
3D model (JSmol)	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) Y Key:FWJKNZONDWOGMI-UHFFFAOYSA-N Y
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Metharbital was patented in 1905 by Emil Fischer working for Merck. It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy. It has similar properties to phenobarbital.

History

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

Synthesis

700px U.S. Patent 782,742

In an interesting variation on this theme (cf hexobarbital), the bis acid chloride of diethylmalonate (1) is condensed with the O-methyl ether of urea (2, Methyl carbamimidate) to afford the imino ether of the barbituric acid (3). Heating this ether at 200°C results in O to N migration of the methyl group and formation of metharbital 4.

References

• 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
• The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
• The Comparative Toxicogenomics Database: Metharbital