Metharbital

Metharbital
Clinical data
Other namesEndiemal, metharbitone, methobarbitone[1]
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
  • CA: Schedule IV
  • US: Schedule III
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) 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][2]

References

  1. ^ "Metharbital". The Comparative Toxicogenomics Database.
  2. ^ a b 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): 1881–1883. doi:10.1021/ja01104a030.


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