Nicotinamide (INN, BAN [ While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing.]
Side effects are minimal.[ Normal amounts are safe for use during pregnancy.]
Nicotinamide was discovered between 1935 and 1937.[ It is on the World Health Organization's List of Essential Medicines.][ Commercially, nicotinamide is made from either nicotinic acid (niacin) or nicotinonitrile.]
Extra-terrestrial nicotinamide has been found in carbonaceous chondrite meteorites.
Medical uses
Niacin deficiency
Nicotinamide is the preferred treatment for pellagra, caused by niacin deficiency.
Acne
Nicotinamide cream is used as a treatment for acne.
Nicotinamide increases the biosynthesis of in human in vitro and improves the epidermal permeability barrier in vivo.
Skin cancer
Nicotinamide at doses of 500 to 1000mg a day decreases the risk of , other than melanoma, in those at high risk.
Side effects
Nicotinamide has minimal side effects.[ Normal doses are safe during pregnancy.]
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 . 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,
Industrial production
The hydrolysis of nicotinonitrile is catalysed by the enzyme nitrile hydratase from Rhodococcus rhodochrous J1,[
]
Biochemistry
Nicotinamide, as a part of the cofactor nicotinamide adenine dinucleotide (NADH / NAD+) is crucial to life. In cells, nicotinamide is incorporated into NAD+ and nicotinamide adenine dinucleotide phosphate (NADP+). NAD+ and NADP+ are cofactors in a wide variety of enzymatic redox reactions, most notably glycolysis, the citric acid cycle, and the electron transport chain.
NAD+ acts as an electron carrier that mediates 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 nicotinamide. In NAD+, the nitrogen in the aromatic nicotinamide 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 NAD+ to form NADH, 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 NADH is oxidized, 158.2kJ of energy will be released.
Biological role
Nicotinamide occurs as a component of a variety of biological systems, including within the vitamin B family and specifically the vitamin B3 complex.
Nicotinamide can be methylated in the liver to biologically active 1-Methylnicotinamide when there are sufficient methyl donors.
Food sources
Nicotinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables.
Compendial status
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British Pharmacopoeia
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Japanese Pharmacopoeia
Research
A 2015 trial found nicotinamide to reduce the rate of new nonmelanoma skin cancers and actinic keratoses in a group of people at high risk for the conditions.
Nicotinamide has been investigated for many additional disorders, including treatment of bullous pemphigoid and nonmelanoma skin cancers.
Nicotinamide may be beneficial in treating psoriasis.
There is tentative evidence for a potential role of nicotinamide in treating acne, rosacea, autoimmune blistering disorders, ageing skin, and atopic dermatitis.
Research has suggested nicotinamide may play a role in the treatment of HIV.
Extra-terrestrial occurrence
Extra-terrestrial nicotinamide has been found in carbonaceous chondrite meteorites.
| + Vitamin B3 vitamers from extra-terrestrial sources |
|
| 214 ppb |
| 65 ppb |
16 ppb |
| 5 ppb |
