Barbituric acid or
malonylurea or
6-hydroxyuracil is an
organic compoundAn organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered inorganic...
based on a
pyrimidinePyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring...
heterocyclic skeleton. It is an odorless powder soluble in hot water. Barbituric acid is the parent compound of
barbiturateBarbiturates are drugs that act as central nervous system depressants, and, by virtue of this, they produce a wide spectrum of effects, from mild sedation to total anesthesia. They are also effective as anxiolytics, hypnotics and as anticonvulsants. They have addiction potential, both physical and...
drugs, although barbituric acid itself is not pharmacologically active. The compound was discovered by the German chemist
Adolf von BaeyerJohann Friedrich Wilhelm Adolf von Baeyer was a German chemist who synthesized indigo, and was the 1905 recipient of the Nobel Prize in Chemistry. Born in Berlin, he initially studied mathematics and physics at Berlin University before moving to Heidelberg to study chemistry with Robert Bunsen...
on 4. December 1864—the feast of St Barbara and therefore the name given to the compound—by combining
ureaUrea or carbamide is an organic compound with the chemical formula
2CO. The molecule has two amine residues joined by a carbonyl functional group....
and
malonic acidMalonic acid is a dicarboxylic acid with structure CH
22. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester...
in a
condensation reactionA condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...
.
Barbituric acid or
malonylurea or
6-hydroxyuracil is an
organic compoundAn organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered inorganic...
based on a
pyrimidinePyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring...
heterocyclic skeleton. It is an odorless powder soluble in hot water. Barbituric acid is the parent compound of
barbiturateBarbiturates are drugs that act as central nervous system depressants, and, by virtue of this, they produce a wide spectrum of effects, from mild sedation to total anesthesia. They are also effective as anxiolytics, hypnotics and as anticonvulsants. They have addiction potential, both physical and...
drugs, although barbituric acid itself is not pharmacologically active. The compound was discovered by the German chemist
Adolf von BaeyerJohann Friedrich Wilhelm Adolf von Baeyer was a German chemist who synthesized indigo, and was the 1905 recipient of the Nobel Prize in Chemistry. Born in Berlin, he initially studied mathematics and physics at Berlin University before moving to Heidelberg to study chemistry with Robert Bunsen...
on 4. December 1864—the feast of St Barbara and therefore the name given to the compound—by combining
ureaUrea or carbamide is an organic compound with the chemical formula
2CO. The molecule has two amine residues joined by a carbonyl functional group....
and
malonic acidMalonic acid is a dicarboxylic acid with structure CH
22. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester...
in a
condensation reactionA condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...
. Malonic acid has since been replaced by
diethyl malonateDiethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes...
.
The α-carbon has a reactive hydrogen atom. Using the Knoevenagel condensation reaction, barbituric acid can form a large variety of
barbiturateBarbiturates are drugs that act as central nervous system depressants, and, by virtue of this, they produce a wide spectrum of effects, from mild sedation to total anesthesia. They are also effective as anxiolytics, hypnotics and as anticonvulsants. They have addiction potential, both physical and...
drugs that behave as central nervous system depressants.
Barbituric acid is used in synthesis of
riboflavinRiboflavin , also known as vitamin B
2, is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B
2 is required...
.
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
barbitalBarbital , also called barbitone, was the first commercially marketed barbiturate. It was used as a sleeping aid from 1903 until the mid-1950s. The chemical names for barbital are diethylmalonyl urea or diethylbarbituric acid...
(Veronal) starting in 1903, and the second, phenobarbitone a.k.a.
phenobarbitalPhenobarbital or phenobarbitone is a barbiturate, first marketed as Luminal by Friedr. Bayer et comp. It is the most widely used anticonvulsant worldwide...
was first marketed in 1912.
External links