関: veronal

WordNet

a barbiturate used as a hypnotic (同)veronal, barbitone, diethylbarbituric acid, diethylmalonylurea

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バルビタール(催眠剤に用いられる)
ベロナール(睡眠薬の商標名)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/04 06:53:21」(JST)

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Barbital (as known in the United States) or barbitone (as known elsewhere), marketed under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbitone are diethylmalonyl urea or diethylbarbituric acid; hence, the sodium salt (known as medinal, a genericised trademark in the United Kingdom) is known also as sodium diethylbarbiturate.

Synthesis

Barbitone was first synthesized in 1902 by German chemists Emil Fischer and Joseph von Mering, who published their discovery in 1903.^[1] Barbitone was prepared by condensing diethylmalonic ester with urea in the presence of sodium ethoxide, and then by adding at least two molar equivalents of ethyl iodide to the silver salt of malonylurea or possibly to a basic solution of the acid. The result was an odorless, slightly bitter, white crystalline powder.

Barbitone can also be synthesized in a condensation reaction from urea and diethyl-2,2-diethylmalonate, a diethyl malonate derivative:

Marketing

Barbitone was marketed in 1904 by the Bayer company as “Veronal”. A soluble salt of barbitone was marketed by the Schering company as “Medinal.” It was dispensed for “insomnia induced by nervous excitability”.^[2]^{[unreliable source?]} It was provided in either capsules or cachets. The therapeutic dose was ten to fifteen grains (0.65-0.97 grams). 3.5 to 4.4 grams is the deadly dose but sleep has also been prolonged up to ten days with recovery.

Pharmacology

Barbitone was considered to be a great improvement over the existing hypnotics. Its taste was slightly bitter, but better than the strong, unpleasant taste of the commonly used bromides. It had few side effects, and its therapeutic dose was far below the toxic dose. However, prolonged usage resulted in tolerance to the drug, requiring higher doses to reach the desired effect. Fatal overdoses of this slow-acting hypnotic were not uncommon. Pioneering aviator Arthur Whitten Brown (of "Alcock and Brown" fame) died of an accidental overdose.^[3]

pH Buffer

Solutions of sodium barbital have also been used as pH buffers for biological research, e.g., in immunoelectrophoresis or in fixative solutions.^[4]^[5] As barbital is a controlled substance, barbital-based buffers have largely been replaced by other substances.^[6]

References

^ Fischer, Emil; von Mering, Joseph (1903). "Ueber eine neue Klasse von Schlafmitteln". Therapie der Gegenwart 44: 97–101.
^ Finley, Ellingwood (1919). "Veronal". The American Materia Medica, Therapeutics and Pharmacognosy. p. 115. Retrieved 25 July 2015.
^ "Arthur Whitten Brown (1886–1948) – Find A Grave Memorial". Findagrave.com. Retrieved 19 April 2014.
^ "Wolf D. Kuhlmann, "Buffer Solutions"" (PDF). 10 September 2006. Retrieved 28 July 2014.
^ Steven E. Ruzin (1999). Plant Microtechnique and Microscopy. Oxford University Press. Retrieved 28 July 2014.
^ Monthony, JF; Wallace, EG; Allen, DM (Oct 1978). "A non-barbital buffer for immunoelectrophoresis and zone electrophoresis in agarose gels". Clinical Chemistry 24 (10): 1825–7. PMID 568042.

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English Journal

A study on quality components and sleep-promoting effects of GABA black tea.

Zhao W1, Li Y, Ma W, Ge Y, Huang Y.
Food & function.Food Funct.2015 Oct 7;6(10):3393-8. doi: 10.1039/c5fo00265f.
The aims of this study were to analyze the changes in quality components of gamma (γ)-aminobutyric acid (GABA) black tea during processing, and to investigate the effect of three dosages of GABA black tea on sleep improvement. The results showed that the GABA content was increased significantly up
PMID 26290415

Calculated and experimental studies on the performances of barbital-imprinted systems.

Liu JB1, Wang Y1, Su TT1, Li B2, Tang SS1, Jin RF3.
Journal of separation science.J Sep Sci.2015 Sep 30. doi: 10.1002/jssc.201500891. [Epub ahead of print]
By using density functional theory, we studied the interaction process between barbital and 2-vinyl-4,6-diamino-1,3,5-triazine in acetonitrile at 333 K. Barbital and 2-vinyl-4,6-diamino-1,3,5-triazine were used as the template and functional monomer, respectively. The molecularly imprinted polymers
PMID 26420630

Resolving Transferrin Isoforms via Agarose Gel Electrophoresis.

Anani WQ1, Ojerholm E2, Shurin MR2.
Laboratory medicine.Lab Med.2015 Winter;46(1):26-33. doi: 10.1309/LMVS2JB8JZN8MDVM.
OBJECTIVE: Cerebrospinal fluid (CSF) leaks may present as rhinorrhea or otorrhea and can lead to life-threatening complications if not detected. The usefulness of the morpholinopropanesulfonic acid (MOPS)-histidine buffer in detecting β2-transferrin, which is only found in the cerebrospinal fluid,
PMID 25617389

Japanese Journal

Surface-Assisted Laser Desorption Ionization Mass Spectrometry (SALDI-MS) of Low-Molecular-Weight Medicines and Toxic Materials Using Commercial TiO₂ Nanoparticles

Bulletin of the Chemical Society of Japan 89(3), 346-353, 2016
NAID 130005137573

Surface Assisted Laser Desorption Ionization Mass Spectrometry (SALDI-MS) of Low-molecular-weight Medicines and Toxic Materials Using Commercial TiO<sub>2</sub> Nanoparticles

Bulletin of the Chemical Society of Japan advpub(0), 2016
NAID 130005112199

ドッキング計算によるバルビツル対掌体のアセチルコリン受容体への結合様式　麻酔作用機構への示唆

Chem-Bio Informatics Journal 12(0), 14-24, 2012
NAID 130004138124

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★リンクテーブル★

リンク元	「バルビタール」「veronal」
拡張検索	「methylphenobarbital」「narcobarbital」「pentobarbitalum」

「バルビタール」

Barbital
Systematic (IUPAC) name
	5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682221
Routes of; administration	Oral
Legal status	DE: Anlage III; US: Schedule IV;
Pharmacokinetic data
Biological half-life	30.3 (± 3.2) hours
Identifiers
CAS Number	57-44-3
ATC code	N05CA04
PubChem	CID 2294
DrugBank	DB01483
ChemSpider	2206
UNII	5WZ53ENE2P
KEGG	D01740
ChEBI	CHEBI:31252
ChEMBL	CHEMBL444
Chemical data
Formula	C8H12N2O3
Molar mass	184.193 g/mol
	SMILES O=C1NC(=O)NC(=O)C1(CC)CC ;
	InChI InChI=1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13) ; Key:FTOAOBMCPZCFFF-UHFFFAOYSA-N ;
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