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
50-11-3 YesY
N03AA30
PubChem CID 4099
DrugBank DB00463 YesY
ChemSpider 3957 YesY
UNII 02OS7K758T YesY
KEGG D01382 YesY
ChEMBL CHEMBL450 YesY
Chemical data
Formula C9H14N2O3
198.219 g/mol
 YesY (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[edit]

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

Synthesis[edit]

Metharbital synthesis:[2][3] U.S. Patent 782,742

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[edit]

  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