Metharbital

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Metharbital
Metharbital Wiki Str.png
Clinical data
AHFS/Drugs.comMonograph
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
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UNII
KEGG
ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC9H14N2O3
Molar mass198.219 g/mol
3D model (JSmol)
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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.[1] 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[2][3] 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[4]) 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

  1. US Patent 782742
  2. A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).
  3. Template:Cite doi
  4. http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966
  • 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


Template:GABAAR PAMs



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