Metharbital

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.

Metharbital
Clinical data
Other namesEndiemal, metharbitone, methobarbitone[1]
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC9H14N2O3
Molar mass198.222 g·mol−1
3D model (JSmol)
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
  (verify)

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][2]

References
  1. "Metharbital". The Comparative Toxicogenomics Database.
  2. US 782742, Fischer E, "Trisubstituted barbituric acids and process of making them.", issued 14 February 1905, assigned to E. Merck
  3. Shorvon SR, Fish DR, Perucca E, Dodson WE, eds. (2004). The Treatment of Epilepsy (2nd ed.). Blackwell. ISBN 0-632-06046-8.
  4. Resor SR (1991). The Medical Treatment of Epilepsy. Marcel Dekker. ISBN 0-8247-8549-5.
  5. Halpern A, Jones JW (June 1949). "The characterization of the trialkylbarbiturates". Journal of the American Pharmaceutical Association. 38 (6): 352–5. doi:10.1002/jps.3030380619. PMID 18151714.
  6. Snyder JA, Link KP (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.


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