Metharbital

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Metharbital
Metharbital.png
Metharbital ball-and-stick.png
Systematic (IUPAC) name
5,5-Diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
Clinical data
AHFS/Drugs.com monograph
Identifiers
CAS Registry Number 50-11-3 YesY
ATC code N03AA30
PubChem CID: 4099
IUPHAR/BPS 7230
DrugBank DB00463 YesY
ChemSpider 3957 YesY
UNII 02OS7K758T YesY
KEGG D01382 YesY
ChEMBL CHEMBL450 YesY
Synonyms Endiemal, metharbitone, methobarbitone[1]
Chemical data
Formula C9H14N2O3
Molecular mass 198.219 g/mol
 YesY (what is this?)  (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[edit]

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

Synthesis[edit]

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

References[edit]

  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