Butyramide is the
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
of
butyric acid
Butyric acid (; from grc, βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unple ...
. It has the molecular formula C
3H
7CONH
2. It is a white solid that is freely soluble in water and
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
, but slightly soluble in
diethyl ether
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
. At room temperature, butyramide is a crystalline solid and in contrast to
butyric acid
Butyric acid (; from grc, βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unple ...
, it is devoid of an unpleasant, rancid smell.
Synthesis
Butyramide can be synthesized by:
* catalytic hydration of
butyronitrile
Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.
Uses
Butyronitrile is mainly used as a precursor to the poultry drug amprolium.Peter Po ...
;
* reaction of
butyryl chloride
Butyryl chloride is an organic compound with the chemical formula CH3CH2CH2C(O)Cl. It is a colorless liquid with a pungent odor. Butyryl chloride is soluble in aprotic organic solvents, but it reacts readily with water and alcohols. It is usual ...
with
ammonium
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...
salts;
*
reduction of butyraldoxime.
Derivatives
Some of its derivatives have shown preliminary strong
anticonvulsive
Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of b ...
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. They act as spools around which DNA winds to create structural units called nucleosomes. Nucleosomes in turn are wr ...
deacetylases, which are crucial enzymes controlling the proliferative or differentiation status of most cells.
See also
*
Isobutyramide
Isobutyramide in chemistry is an amide with the molecular formula C4H9NO.
Isobutyramide can also refer to the functional group with the following chemical formula: R-NH-CO-CH(CH3)2.
:
See also
* Butyramide
Butyramide is the amide of butyric ...
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.