Nicotinamide 21968 214490813 2008-05-23T20:14:56Z ImperfectlyInformed 5106682 m {{Chembox new | ImageFile = Nicotinamide structure.svg | ImageSize = | IUPACName = pyridine-3-carboxamide | OtherNames = 3-pyridinecarboxamide<br/>niacinamide<br />nicotinamide<br/>nicotinic acid amide<br />Vitamin PP | Section1 = {{Chembox Identifiers | PubChem = 7847104 | CASNo = 98-92-0 | InChI = 1/C6H6N2O/c7-6(9)5-2-1-3-8- 4-5/h1-4H,(H2,7,9)/f/h7H2 | EINECS = 202-713-4 | SMILES = NC(=O)c1cccnc1}} | Section2 = {{Chembox Properties | MolarMass = 122.12 | Formula = C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O | Appearance = | Density = | MeltingPt = | BoilingPt = }} | Section3 = {{Chembox Hazards | Solubility = | MainHazards = | FlashPt = | Autoignition = }} }} '''Nicotinamide''', also known as '''niacinamide''' and '''nicotinic acid amide''', is the [[amide]] of [[nicotinic acid]] (vitamin B<sub>3</sub>). Nicotinamide is a water-soluble [[vitamin]] and is part of the [[B vitamins|vitamin B]] group. Nicotinic acid, also known as niacin, is converted to niacinamide ''in vivo'', and though the two are identical in their vitamin functions, niacinamide does not have the same pharmacologic and toxic effects of niacin, which occur incidental to niacin's conversion. Thus niacinamide does not reduce cholesterol or cause flushing,<ref>Jacenollo, P. (1992). [http://www.pubmedcentral.nih.gov/pagerender.fcgi?artid=1336277&pageindex=1 Niacin versus niacinamide]</ref> although nicotinamide may be toxic to the liver at doses exceeding 3 g/day for adults.<ref>{{cite journal |author=Knip M, Douek IF, Moore WP, ''et al'' |title=Safety of high-dose nicotinamide: a review |journal=Diabetologia |volume=43 |issue=11 |pages=1337–45 |year=2000 |pmid=11126400 | doi = 10.1007/s001250051536</ref> 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 [[coenzyme]]s in a wide variety of enzymatic [[redox|oxidation-reduction]] reactions.<ref name=Belenky>{{cite journal | author = Belenky P | coauthors = Bogan KL, Brenner C | title = NAD+ metabolism in health and disease | journal = Trends Biochem. Sci. | volume = 32 | issue = 1 | pages = 12&ndash;9 | year = 2007 | pmid = 17161604 | url = http://www.dartmouth.edu/~brenner/belenky07a.pdf | accessdate = 2007-12-23 | doi = 10.1016/j.tibs.2006.11.006}}</ref> ==Use in medicine== Nicotinamide has demonstrated anti-inflammatory actions which may be of benefit in patients with inflammatory skin conditions.<ref>{{cite journal |author=Niren NM |title=Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review |journal=Cutis |volume=77 |issue=1 Suppl |pages=11–6 |year=2006 |pmid=16871774}}</ref> 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]].<ref>{{cite journal |author=Tallman JF, Paul SM, Skolnick P, Gallager DW |title=Receptors for the age of anxiety: pharmacology of the benzodiazepines |journal=Science |volume=207 |issue=4428 |pages=274–81 |year=1980 |pmid=6101294 | doi = 10.1126/science.6101294 <!--Retrieved from CrossRef by DOI bot-->}}</ref> [[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.<ref>{{cite journal |author=Knip M, Douek IF, Moore WP, ''et al'' |title=Safety of high-dose nicotinamide: a review |journal=Diabetologia |volume=43 |issue=11 |pages=1337–45 |year=2000 |pmid=11126400 | doi = 10.1007/s001250051536 <!--Retrieved from CrossRef by DOI bot-->}}</ref> In overall, it rarely causes side effects, and is considered generally safe as a food additive, component in cosmetics and medication.<ref>{{cite journal |author= |title=Final report of the safety assessment of niacinamide and niacin |journal=Int. J. Toxicol. |volume=24 Suppl 5 |issue= |pages=1–31 |year=2005 |pmid=16596767}}</ref> Nicotinamide is produced by the aqueous ammonolysis of 3-cyanopyridine (nicotinonitrile) and subsequent crystallisation. ==References== {{reflist|2}} ==See also== * [[Nicotinamide adenine dinucleotide]] * [[Isonicotinamide]] ==External links== * {{ATC|A11|HA01}} {{Vitamin}} [[Category:Amides]] [[Category:Pyridines]] [[Category:Vitamins]] {{heterocyclic-stub}} [[de:Nicotinamid]] [[it:Nicotinamide]] [[tr:Niyasinamit]]