Niacinamide

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What is Niacinamide?  Nicotinamide (NAM), also known as niacinamide, is a form of vitamin B3 found in food and used as a dietary supplement and medication. Commercially, nicotinamide is made from either nicotinic acid or nicotinonitrile. In a number of countries grains have nicotinamide added to them.

Niacinamide Chemistry  The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Examples of these reactions reported in Organic Syntheses include the preparation of 2-chloronicotinonitrile by a two-step process via the N-oxide, from nicotinonitrile by reaction with phosphorus pentoxide, and from 3-aminopyridine by reaction with a solution of sodium hypobromite, prepared in situ from bromine and sodium hydroxide.

Production of Niacinamide  The hydrolysis of nicotinonitrile is catalysed by the enzyme nitrile hydratase from Rhodococcus rhodochrous J1, producing 3500 tons per annum of nicotinamide for use in animal feed. The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided. Nicotinamide can also be made from nicotinic acid. According to Ullmann’s Encyclopedia of Industrial Chemistry, worldwide 31,000 tons of nicotinamide were sold in 2014.

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