Metharbital: Difference between revisions

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Metharbital
Clinical data
AHFS/Drugs.com	Monograph
ATC code	N03AA30 (WHO) ;
Identifiers
	IUPAC name 5,5-diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione;
CAS Number	50-11-3 ;
PubChem CID	4099;
DrugBank	DB00463 ;
ChemSpider	3957 ;
UNII	02OS7K758T;
KEGG	D01382 ;
ChEMBL	ChEMBL450 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C9H14N2O3
Molar mass	198.219 g/mol
3D model (JSmol)	Interactive image;
	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) ; Key:FWJKNZONDWOGMI-UHFFFAOYSA-N ;
(verify)

VisualWikitext

Latest revision as of 13:14, 14 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

700px[2][3] U.S. Patent 782,742 — 700px^[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

↑ US Patent 782742
↑ A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).
↑ Template:Cite doi
↑ http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966

The Treatment of Epilepsy 2nd Ed by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
The Comparative Toxicogenomics Database: Metharbital

Template:GABAAR PAMs

This anticonvulsant-related article is a stub. You can help Wikipedia by expanding it.

[1] US Patent 782742

[2] A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).

[3] Template:Cite doi

[4] ttp://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966

[1]

[2]

[3]

[4]

@@ Line 2: / Line 2: @@
 | verifiedrevid = 459493742
 | IUPAC_name = 5,5-diethyl-1-methylpyrimidine-2,4,6(1''H'',3''H'',5''H'')-trione
-| image = Metharbital syn.png
+| image = Metharbital Wiki Str.png
 | width = 141
@@ Line 61: / Line 61: @@
 * '''1990''' Abbott stopped marketing.
 ==Synthesis==
-[[File:Metharbital Wiki Str.png|center|700px<ref>A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).</ref><ref>{{Cite doi|10.1021/ja01104a030}}</ref> {{US patent|782742}}]]
+[[File:Metharbital syn.png|center|700px<ref>A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).</ref><ref>{{Cite doi|10.1021/ja01104a030}}</ref> {{US patent|782742}}]]
 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<ref>http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966</ref>) 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==