Metharbital

Metharbital: 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.

History

1952 Gemonil was introduced by Abbott Laboratories.

1990 Abbott stopped marketing.

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

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 · eGABA_A receptor PAMs

Barbiturates
Allobarbital • Alphenal • Amobarbital • Aprobarbital • Barbexaclone • Barbital • Benzobarbital • Benzylbutylbarbiturate • Brallobarbital • Brophebarbital • Bucolome • Butabarbital • Butalbital • Butobarbital • Butallylonal • Carbubarb • Crotylbarbital • Cyclobarbital • Cyclopal • Enallylpropymal • Ethallobarbital • Febarbamate • Heptabarbital • Hexethal • Hexobarbital • Mephobarbital • Metharbital • Methohexital • Methylphenobarbital • Narcobarbital • Nealbarbital • Pentobarbital • Phenobarbital • Phetharbital • Primidone • Prazitone • Probarbital • Propallylonal • Proxibarbal • Proxibarbital • Reposal • Secbutabarbital • Secobarbital • Sigmodal • Spirobarbital • Talbutal • 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 • Emylcamate • Ethinamate • Febarbamate • Felbamate • Hexapropymate • Mebutamate • Meprobamate • Methocarbamol • Phenprobamate • Procymate • Styramate • 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 • Ethchlorvynol • Etifoxine • Etomidate • GABA • Kavalactones (Kava) • Loreclezole • Methylpentynol • Metomidate • Petrichloral • Propanidid • Skullcap • Stiripentol • Sulfonmethane • Tetronal • Triclofos • Trional • Valeric acid, Valerenic acid (Valerian)

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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
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)

Academic Dictionaries and Encyclopedias

Wikipedia

Metharbital

History

Chemistry

References

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