2-Aminopyridine 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 H₂NC₅H₄N. It is one of three

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 ...

ic aminopyridines. It is a colourless solid that is used in the production of the drugs

piroxicam Piroxicam is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful inflammatory conditions like arthritis. Piroxicam works by preventing the production of endogenous prostaglandins which are inv ...

, sulfapyridine, tenoxicam, and tripelennamine. It is produced by the reaction of

sodium amide Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is whit ...

with

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 ...

, the Chichibabin reaction.

Reactions

Although 2-hydroxypyridine converts significantly to the pyridone

tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...

, the related imine tautomer (HNC₅H₄NH) is less important for 2-aminopyridine. 2-Aminopyridine catalyzes the conversion of

maleic anhydride Maleic anhydride is an organic compound with the formula . It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers. Str ...

to 2,3-dimethylmaleic anhydride.

Toxicity

The acute toxicity is indicated by the

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

= 200 mg/kg (rat, oral).

References

External links

MSDS

{{DEFAULTSORT:Aminopyridine, 2- 2-Pyridyl compounds 2-Aminopyridines