Isonicotinic acid or pyridine-4-carboxylic acid is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula C
5H
4N(CO
2H). It is a derivative of
pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...
with a
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
substituent at the 4-position. It is an
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
of
picolinic acid
Picolinic acid is an organic compound with the formula . It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. It is an isomer of nicotinic acid and isonicotinic acid, which have the carboxyl side chain at th ...
and
nicotinic acid
Nicotinic acid, or niacin, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan.
Nicotinic acid is also a prescription medication. Amounts f ...
, which have the
carboxyl
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl group (e.g. ...
group at the 2- and 3-position respectively compared to the 4-position for isonicotinic acid.
Production
On a commercial scale, isonicotinic acid, like other pyridine carboxylic acid is produced by
ammoxidation
In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrate ...
of 4-picoline (4-methylpyridine) followed by hydrolysis of the resulting nitrile:
:
:
It is also produced by oxidation of 4-picoline with nitric acid.
Derivatives
Isonicotinic acids is a term loosely used for
derivatives of isonicotinic acid.
Hydrazide
Hydrazides in organic chemistry are a class of organic compounds with the formula where R is acyl (), sulfonyl (), phosphoryl (), phosphonyl () and similar groups (chalcogen analogs are included, for example sulfur analogs called thiohydrazide ...
derivatives include
isoniazid
Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. F ...
,
iproniazid
Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible inhibition, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine (antidepressant), hydrazine class. It is a xenobiotic that was origi ...
, and
nialamide.
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 ...
and
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
derivatives include
ethionamide
Ethionamide is an antibiotic used to treat tuberculosis. Specifically it is used, along with other antituberculosis medications, to treat active multidrug-resistant tuberculosis. It is no longer recommended for leprosy. It is taken by mouth.
E ...
and
dexamethasone isonicotinate.
Its conjugate base forms
coordination polymer
Coordination may refer to:
* Coordination (linguistics), a compound grammatical construction
* Coordination complex, consisting of a central atom or ion and a surrounding array of bound molecules or ions
** A chemical reaction to form a coordinat ...
s and
MOFs by binding metal ions through both the N and carboxylate.
See also
*
Pyridinecarboxylic acids A pyridinecarboxylic acid is any member of a group of organic compounds which are monocarboxylic derivatives of pyridine. Pyridinecarboxylic acid comes in three isomers:
*Picolinic acid (2-pyridinecarboxylic acid)
*Nicotinic acid (3-pyridinecarbo ...
References
External links
* {{MeshName, Isonicotinic+Acids
Aromatic acids
4-Pyridyl compounds