Metharbital

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Metharbital

Systematic (IUPAC) name
5,5-diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	50-11-3^Y
ATC code	N03AA30
PubChem	CID 4099
DrugBank	APRD00757
ChemSpider	3957^Y
UNII	02OS7K758T^Y
KEGG	D01382^Y
ChEMBL	CHEMBL450^Y
Chemical data
Formula	C₉H₁₄N₂O₃
Mol. mass	198.219 g/mol
SMILES	eMolecules & PubChem
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)^Y Key:FWJKNZONDWOGMI-UHFFFAOYSA-N^Y
N(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.

[edit] History

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

[edit] Chemistry

Metharbital (5,5-diethyl-1-methylbarbituric acid) is synthesized by condensation of diethylmalonic ester with methylurea.

A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).
Snyder, J. A.; Link, K. P. (1953). Journal of the American Chemical Society 75 (8): 1881. doi:10.1021/ja01104a030. edit

[edit] References

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

^ US Patent 782742

v d e GABA_A receptor PAMs

Barbiturates	Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Bucolome Butabarbital Butalbital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopal Difebarbamate Enallylpropymal Ethallobarbital Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenobarbital Phetharbital Primidone Prazitone Probarbital Propallylonal Proxibarbal Proxibarbital Reposal Secbutabarbital Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Valofane Vinbarbital Vinylbital

Benzodiazepines	Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Chlordiazepoxide Ciclotizolam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Diazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Girisopam Halazepam Haloxazolam Iclazepam Imidazenil Ketazolam Lofendazam Lopirazepam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Nerisopam Nimetazepam Nitrazepam Nitrazepate Nordazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tofisopam Triazolam Triflubazam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates	Carisbamate Carisoprodol Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Methocarbamol Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Ganaxolone Hydroxydione Minaxolone Org 20599 THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem Necopidem Saripidem Zolpidem; Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon; Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 ELB-139 GBLD-345 L-838,417 NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Y-23684

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone

Volatiles/gases	2-Methyl-2-butanol Acetone Acetophenone Acetylglycinamide chloral hydrate Benzene Butane Butanol Butylene Centalun Chloral Chloral hydrate Chlorobutanol Chloroform Cyclopropane Desflurane Dichloromethane Diethyl ether Enflurane Ethanol (Alcohol) Ethyl chloride Ethylene Gasoline Halothane Isoflurane Kerosine Menthol Methanol Methoxyflurane Methoxypropane Methylbutanol Nitric oxide Nitrogen Nitrous oxide Paraldehyde Pentanol Propane Propanol Propylene Sevoflurane Toluene Trichloroethanol Trichloroethylene Vinyl ether Xenon

Others	Bromide (Lithium bromide Potassium bromide Sodium bromide) Chloralodol Chloralose Chlormezanone Clomethiazole DEABL Etazepine Ethchlorvynol Etifoxine Etomidate GABA Kavalactones (Kava) Loreclezole Methylpentynol Metomidate Org 25,435 Petrichloral Propanidid Skullcap Stiripentol Sulfonmethane Tetronal Triclofos Trional Valeric acid Valerenic acid (Valerian)