Chemistry:Metharbital

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Short description: Barbiturate anticonvulsant medication
Metharbital
Metharbital.svg
Metharbital ball-and-stick.png
Clinical data
Other namesEndiemal, metharbitone, methobarbitone[1]
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC9H14N2O3
Molar mass198.222 g·mol−1
3D model (JSmol)
  (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. http://ctdbase.org/detail.go?type=chem&acc=C084822. 
  2. 2.0 2.1 Fischer E, "Trisubstituted barbituric acids and process of making them.", US patent 782742, issued 14 February 1905, assigned to E. Merck
  3. The Treatment of Epilepsy (2nd ed.). Blackwell. 2004. ISBN 0-632-06046-8. 
  4. The Medical Treatment of Epilepsy. Marcel Dekker. 1991. ISBN 0-8247-8549-5. 
  5. "The characterization of the trialkylbarbiturates". Journal of the American Pharmaceutical Association 38 (6): 352–5. June 1949. doi:10.1002/jps.3030380619. PMID 18151714. 
  6. "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. 1953. doi:10.1021/ja01104a030.