Butyramide is the
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
of
butyric acid
Butyric acid (; from , meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula . It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-met ...
. It has the molecular formula C
3H
7CONH
2. It is a white solid that is freely soluble in water and
ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
, but slightly soluble in
diethyl ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
. At room temperature, butyramide is a crystalline solid and in contrast to
butyric acid
Butyric acid (; from , meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula . It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-met ...
, it is devoid of an unpleasant, rancid smell.
Synthesis
Butyramide can be synthesized by:
* catalytic hydration of
butyronitrile;
* reaction of
butyryl chloride with
ammonium
Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) polyatomic ion, molecular ion with the chemical formula or . It is formed by the protonation, addition of a proton (a hydrogen nucleu ...
salts;
*
reduction of butyraldoxime.
Derivatives
Some of its derivatives have shown preliminary strong
anticonvulsive
Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epilepsy, epileptic seizures. Anticonvulsants are also used in the ...
activity and inhibitory action on
histone
In biology, histones are highly basic proteins abundant in lysine and arginine residues that are found in eukaryotic cell nuclei and in most Archaeal phyla. They act as spools around which DNA winds to create structural units called nucleosomes ...
deacetylases, which are crucial enzymes controlling the proliferative or differentiation status of most cells.
See also
*
Isobutyramide
References
{{morefootnotes, date=November 2015
* Jiang J et al. PLos One 2012; 7(3): e34283
* Liu WH et al. Yao Xue Xue Bao 2012 Feb; 47(2): 194-99.
* Vitorivic-Todorovic MD et al. Bioorg Med Chem 2010 Feb; 18(3): 1181-93.