The structure of<unk>  consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of<unk> otinic 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, :500px from<unk> otinonitrile 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.<unk> DH, contains the<unk>  moiety (highlighted in red) Industrial production The hydrolysis of<unk> otinonitrile is catalysed by the enzyme nitrile hydratase from Rhodococcus rhodochrous J1, producing 3500 tons per annum of<unk>  for use in animal feed. The enzyme allows for a more selective synthesis as further hydrolysis of the amide to<unk> otinic acid is avoided.<unk>  can also be made from<unk> otinic acid. According to Ullmann's Encyclopedia of Industrial Chemistry, worldwide 31,000 tons of<unk>  were sold in 2014. Biochemistry The active<unk>  group on the molecule<unk> D+ undergoes oxidation in many metabolic pathways.<unk> , as a part of the cofactor<unk>  adenine dinucleotide <unk> DH /<unk> D+) is crucial to life. In cells,<unk>  is incorporated into<unk> D+ and<unk>  adenine dinucleotide phosphate <unk> DP+).<unk> D+ and<unk> DP+ are cofactors in a wide variety of enzymatic oxidation-reduction reactions, most notably glycolysis, the citric acid cycle, and the electron transport chain. If humans ingest<unk> , it will likely undergo a series of reactions that transform it into<unk> D, which can then undergo a transformation to form<unk> DP+. This method of creation of<unk> D+ is called a salvage pathway. However, the human body can produce<unk> D+ from the amino acid tryptophan and niacin without our ingestion of<unk> .<unk> D+ acts as an electron carrier that helps with the interconversion of energy between nutrients and the cell's energy currency, adenosine triphosphate (ATP). In oxidation-reduction reactions, the active part of the cofactor is the<unk> . In<unk> D+, the nitrogen in the aromatic<unk>  ring is covalently bonded to adenine dinucleotide. The formal charge on the nitrogen is stabilized by the shared electrons of the other carbon atoms in the aromatic ring. When a hydride atom is added onto<unk> D+ to form<unk> DH, the molecule loses its aromaticity, and therefore a good amount of stability. This higher energy product later releases its energy with the release of a hydride, and in the case of the electron transport chain, it assists in forming adenosine triphosphate. When one mole of<unk> DH is oxidized, 158.2 kJ of energy will be released. Biological role<unk>  occurs as a component of a variety of biological systems, including within the vitamin B family and specifically the vitamin B3 complex. It is also a critically important part of the structures of<unk> DH and<unk> D+, where the N-substituted aromatic ring in the oxidised<unk> D+ form undergoes reduction with hydride attack to form<unk> DH. The<unk> DPH/NADP+ structures have the same ring, and are involved in similar biochemical reactions.<unk>  can be methylated in the liver to biologically active 1-Methylnicotinamide when there's sufficient methyl donors.
Nicotinamide
Carnitine
Inositol
Choline
Cysteamine
Phenserine
Uridine triacetate
Creatine