isonicotinamine

Isonicotinamide, also known as pyridine-4-carboxamide, is an organic compound belonging to the class of pyridine derivatives. It is a white crystalline solid with a molecular formula of C6H6N2O and a molar mass of approximately 122.13 g/mol. The compound is characterized by a pyridine ring substituted with a carboxamide group at the 4-position.

Isonicotinamide is primarily recognized for its role as a precursor in the synthesis of various pharmaceuticals, particularly those used in the treatment of tuberculosis. One of its most notable derivatives is isoniazid (isonicotinic acid hydrazide), an essential first-line antituberculosis drug. The structural similarity between isonicotinamide and isoniazid allows for its use in synthetic pathways to produce the active compound.

In addition to its pharmaceutical applications, isonicotinamide has been studied for its potential biological activities. Research suggests it may exhibit antimicrobial, antiviral, and anticancer properties, though its direct therapeutic use remains limited compared to its derivatives. The compound is also used in organic synthesis as a building block for the preparation of more complex nitrogen-containing heterocycles.

Isonicotinamide is typically prepared through the hydrolysis of isonicotinic acid nitrile or by the reaction of 4-cyanopyridine with aqueous ammonia. It is soluble in water and polar organic solvents but sparingly soluble in nonpolar solvents. The compound is relatively stable under normal conditions but can decompose under harsh thermal or acidic conditions.

Due to its importance in medicinal chemistry, isonicotinamide is commercially available and often utilized in laboratory settings for synthetic and research purposes. Safety precautions should be observed when handling it, as with any chemical, to avoid potential skin or respiratory irritation.