WordNet

organic compound having powerful soporific effect; overdose can be fatal
street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

バルビツル酸塩(睡眠薬・鎮通剤用)
酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/09 01:10:40」(JST)

wiki en

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active.

Synthesis

The compound was discovered by the German chemist Adolf von Baeyer on December 4, 1864, the feast of Saint Barbara (who gave the compound its namesake), by combining urea and malonic acid in a condensation reaction.^[1] Malonic acid has since been replaced by diethyl malonate,^[2] as using the ester avoids the problem of having to deal with the acidity of the carboxylic acid and its unreactive carboxylate.

The synthesis of barbituric acid from malonic acid and urea

Properties

The α-carbon has a reactive hydrogen atom and is quite acidic (pKa = 4.01) even for a diketone species (cf. dimedone with pKa 5.23 and acetylacetone with pKa 8.95) because of the additional aromatic stabilization of the carbanion.

Uses

Using the Knoevenagel condensation reaction, barbituric acid can form a large variety of barbiturate drugs that behave as central nervous system depressants. As of 2007, more than 2550 barbiturates and related compounds have been synthesised, with 50 to 55 in clinical use around the world at present. The first to be used in medicine was barbital (Veronal) starting in 1903, and the second, phenobarbital was first marketed in 1912.

Barbituric acid is one of four ingredients used to make riboflavin (vitamin B₂).

Health and safety

Overdose of barbituric acid can cause respiratory problems and death.^{[citation needed]}

References

^ Baeyer, Adolf (1864). "Untersuchungen über die Harnsäuregruppe". Annalen der Chemie und Pharmacie 131 (3): 291. doi:10.1002/jlac.18641310306.
^ J. B. Dickey & A. R. Gray (1943). "Barbituric acid". Org. Synth. ; Coll. Vol. 2, p. 60

Mahmudov K.T., Kopylovich M.N., Maharramov A.M., Kurbanova M.M., Gurbanov A.V., Pombeiro A.J.L. Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds, Coordination Chemistry Reviews, 2014, 265, 1-37. DOI: 10.1016/j.ccr.2014.01.002 http://www.sciencedirect.com/science/article/pii/S0010854514000046

UpToDate Contents

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English Journal

Cyanogenic glycosides in plant-based foods available in New Zealand.

Cressey P, Saunders D, Goodman J.Sourcea Food Programme, Institute of Environmental Science and Research (ESR) , Christchurch Science Centre , Christchurch , New Zealand.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.Food Addit Contam Part A Chem Anal Control Expo Risk Assess.2013 Nov;30(11):1946-53. doi: 10.1080/19440049.2013.825819. Epub 2013 Aug 28.
Cyanogenic glycosides occur in a wide range of plant species. The potential toxicity of cyanogenic glycosides arises from enzymatic degradation to produce hydrogen cyanide, which may result in acute cyanide poisoning and has also been implicated in the aetiology of several chronic diseases. One hund
PMID 23984870

Efficient one-pot synthesis of novel and diverse furo[2,3-[Formula: see text]]pyrimidinediones and thioxofuro[2,3-[Formula: see text]]pyrimidineones by the rhodium (II) pivalate-catalyzed reactions of cyclic diazo compounds.

Somai Magar KB, Lee YR, Kim SH.SourceSchool of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea.
Molecular diversity.Mol Divers.2013 Nov;17(4):679-91. doi: 10.1007/s11030-013-9463-9. Epub 2013 Aug 2.
The rhodium(II)-catalyzed reactions of cyclic diazo compounds derived from barbituric acid or thiobarbituric acid with arylacetylenes and styrenes were examined. These reactions provide a rapid synthetic route to the preparation of a variety of novel and diverse furo[2,3-[Formula: see text]]pyrimidi
PMID 23907391

Bactericidal evaluation of N-halamine-functionalized silica nanoparticles based on barbituric acid.

Dong A, Xue M, Lan S, Wang Q, Zhao Y, Wang Y, Zhang Y, Gao G, Liu F, Harnoode C.SourceCollege of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, People's Republic of China. Electronic address: dongali@imu.edu.cn.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2013 Oct 3;113C:450-457. doi: 10.1016/j.colsurfb.2013.09.048. [Epub ahead of print]
Novel N-halamine-functionalized silica nanoparticles (NHFS NPs) were facilely fabricated from the 5-allylbarbituric acid (ABBA) by a seeded copolymerization using colloidal silica nanoparticles as support and ABBA-based N-halamine copolymers as shell. The NHFS NPs with spherical morphology and legib
PMID 24144511

Japanese Journal

バルビツル酸誘導体のラジカル重合開始機構

浜野寿久,中垣憲和,三輪實,武野明義,長坂信司
日本歯科理工学会誌 30(6), 400-409, 2011-11-25
1-シクロヘキシル-5-エチルバルビツル酸(CEBA),ジラウリルジメチル塩化アンモニウム,ビス(アセチルアセトナト)銅(II)からなる3元系のラジカル重合開始機構を解明するために,ESRスピントラッピング剤に,5,5-ジメチル-1-ピロリン-N-オキシド(DMPO)を用いて,ベンゼン溶液中で反応させて,ESRスペクトルを測定した.スペクトルには,12本線が観測され,超微細結合定数を算出すると,1 …
NAID 110008896688

ラジカル重合におけるバルビツール酸誘導体の触媒作用に関する研究

渕上清実,平田俊輔,澤田悠希,藤村英史,花崎知則
高分子論文集 68(7), 509-516, 2011-07-25
NAID 10029259804

「バルビツール酸」

Barbituric acid
Names
	IUPAC name pyrimidine-2,4,6(1H,3H,5H)-trione
	Other names 2,4,6(1H,3H,5H)-pyrimidinetrione; 2,4,6-trioxohexahydropyrimidine; 2,4,6-trihydroxypyrimidine; 2,4,6-trioxypyrimidine; 2,4,6-pyrimidinetriol; 2,4,6-pyrimidinetrione; pyrimidinetriol; 2,4,6-trihydroxy-1,3-diazine; N,N-malonylurea; malonylurea; 6-hydroxyuracil; 6-hydroxy-hydrouracil; N,N-(1,3-dioxo-1,3-propanediyl)urea;
Identifiers
CAS Registry Number	67-52-7
ChEBI	CHEBI:16294
ChEMBL	ChEMBL574699
ChemSpider	5976
EC number	200-658-0
	InChI InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9) ; Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N ; InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9); Key: HNYOPLTXPVRDBG-UHFFFAOYAE ;
Jmol-3D images	Image
KEGG	C00813
PubChem	6211
	SMILES O=C1NC(=O)NC(=O)C1 ;
UNII	WQ92Y2793G
Properties
Chemical formula	C4H4N2O3
Molar mass	128.09 g·mol−1
Appearance	White crystals
Melting point	245 °C (473 °F; 518 K)
Boiling point	260 °C (500 °F; 533 K)
Solubility in water	142 g/l (20 °C)
Hazards
Safety data sheet	External MSDS
R-phrases	R36/38, R43
S-phrases	S22, S26, S28
NFPA 704	1 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: barbiturate barbituric acid
同: バルビツレート
関: バルビツール酸系

GABA_A受容体に作用

イオンチャネル型。5量体。開口によりCl-が流入→電位依存性Ca2+の開口抑制など

ベンゾジアゼピン系薬物、バルビツール酸系薬物、エタノールが作用

「ethylphenylbarbituric acid」

　　[★] フェノバルビタール、エチルフェニルバルビツール酸

「thiobarbituric acid」

　　[★]

チオバルビツール酸

関: TBA、thiobarbiturate

「thiobarbituric acid reactive substance」

　　[★]

チオバルビツール酸反応性物質

関: TBARS

[1] Baeyer, Adolf (1864). "Untersuchungen über die Harnsäuregruppe". Annalen der Chemie und Pharmacie 131 (3): 291. doi:10.1002/jlac.18641310306.

[2] J. B. Dickey & A. R. Gray (1943). "Barbituric acid". Org. Synth. ; Coll. Vol. 2, p. 60

リンク元	「バルビツール酸」
拡張検索	「ethylphenylbarbituric acid」「thiobarbituric acid」「thiobarbituric acid reactive substance」

匿名

検索

案内

案内

barbituric acid