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Nicotinamide

Nicotinamide
IUPAC name pyridine-3-carboxamide
Other names 3-pyridinecarboxamide
niacinamide
nicotinamide
nicotinic acid amide
Vitamin PP
Identifiers
CAS number [98-92-0]
PubChem 7847104
EINECS number 202-713-4
SMILES NC(=O)c1cccnc1
InChI 1/C6H6N2O/c7-6(9)5-2-1-3-8- 4-5/h1-4H,(H2,7,9)/f/h7H2
Properties
Molecular formula C6H6N2O
Molar mass 122.12
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Nicotinamide, also known as niacinamide and nicotinic acid amide, is the amide of nicotinic acid (vitamin B(3)). Nicotinamide is a water-soluble vitamin and is part of the vitamin B group. Collectively, nicotinic acid and nicotinamide are called niacin.[1] In cells, niacin is incorporated into nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), although the pathways for nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction reactions.[2]

Contents

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 Use in medicine

Nicotinamide has demonstrated anti-inflammatory actions which may be of benefit in patients with inflammatory skin conditions.[3] These conditions include acne vulgaris, and the compound can suppress antigen induced-lymphocytic transformation and inhibit of 3'-5' cyclic AMP phosphodiesterase. Nicotinamide has demonstrated the ability to block the inflammatory actions of iodides known to precipitate or exacerbate inflammatory acne. Animal studies show that nicotinamide has anti-anxiety (anxiolytic) properties. It may work in a way similar to benzodiazepines.[4] Nicomide (take note the naming similarity), is an acne medication, and in its vitamin supplement form, the most predominant ingredient is 750 mg of nicotinamide, based on this area of research.

Nicotinamide lacks the vasodilator, gastrointestinal, hepatic, and hypolipemic actions of nicotinic acid. As such nicotinamide has not been shown to produce the flushing, itching and burning sensations of the skin as is commonly seen when large doses of nicotinic acid are administered orally. However, nicotinamide can produce liver toxicity at high doses.[5] In overall, it rarely causes side effects, and is considered generally safe as a food additive, component in cosmetics and medication.[6]

Nicotinamide is produced by the aqueous ammonolysis of 3-cyanopyridine (nicotinonitrile) and subsequent crystallisation.

 References

  1. ^ Henderson LM (1983). "Niacin". Annu. Rev. Nutr. 3: 289–307. PMID 6357238. 
  2. ^ Belenky P; Bogan KL, Brenner C (2007). "NAD+ metabolism in health and disease". Trends Biochem. Sci. 32 (1): 12–9. PMID 17161604. Retrieved on 2007-12-23. 
  3. ^ Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis 77 (1 Suppl): 11–6. PMID 16871774. 
  4. ^ Tallman JF, Paul SM, Skolnick P, Gallager DW (1980). "Receptors for the age of anxiety: pharmacology of the benzodiazepines". Science 207 (4428): 274–81. PMID 6101294. 
  5. ^ Knip M, Douek IF, Moore WP, et al (2000). "Safety of high-dose nicotinamide: a review". Diabetologia 43 (11): 1337–45. PMID 11126400. 
  6. ^ "Final report of the safety assessment of niacinamide and niacin" (2005). Int. J. Toxicol. 24 Suppl 5: 1–31. PMID 16596767. 

 See also

 External links


 

The content of this section is licensed under the GNU Free Documentation License (local copy). It uses material from the Wikipedia article "Nicotinamide" modified December 22, 2007 with previous authors listed in its history.

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