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Metharbital

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Metharbital
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Systematic (IUPAC) name
5,5-diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
Clinical data
AHFS/Drugs.com monograph
Identifiers
50-11-3 7pxY
N03AA30
PubChem CID 4099
DrugBank DB00463 7pxY
ChemSpider 3957 7pxY
UNII 02OS7K758T 7pxY
KEGG D01382 7pxY
ChEMBL CHEMBL450 7pxY
Chemical data
Formula C9H14N2O3
198.219 g/mol
 14pxY (what is this?)  (verify)

Metharbital was patented in 1905 by Emil Fischer working for Merck.[1] It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy. It has similar properties to phenobarbital.

History

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

Synthesis

In an interesting variation on this theme (cf hexobarbital), the bis acid chloride of diethylmalonate (1) is condensed with the O-methyl ether of urea (2, Methyl carbamimidate[4]) to afford the imino ether of the barbituric acid (3). Heating this ether at 200°C results in O to N migration of the methyl group and formation of metharbital 4.

References

  1. US Patent 782742
  2. A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).
  3. 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)-pyrimidinedione1". Journal of the American Chemical Society 75 (8): 1881. doi:10.1021/ja01104a030.  edit
  4. http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966



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