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Metharbital

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Metharbital
Clinical data
Other namesEndiemal, metharbitone, methobarbitone[1]
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
Identifiers
  • 5,5-Diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.011 Edit this at Wikidata
Chemical and physical data
FormulaC9H14N2O3
Molar mass198.222 g·mol−1
3D model (JSmol)
  • O=C1N(C(=O)NC(=O)C1(CC)CC)C
  • 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) checkY
  • Key:FWJKNZONDWOGMI-UHFFFAOYSA-N checkY
  (verify)

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