Nicotinamide
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| Nicotinamide | |
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| IUPAC name | pyridine-3-carboxamide |
| Other names | 3-pyridinecarboxamide niacinamide nicotinamide nicotinic acid amide Vitamin PP |
| Identifiers | |
| CAS number | [98-92-0] |
| PubChem | |
| EINECS number | |
| 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 |
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Nicotinamide, also known as niacinamide and nicotinic acid amide, is the amide of nicotinic acid (vitamin B3). Nicotinamide is a water-soluble vitamin and is part of the 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,[1] although nicotinamide may be toxic to the liver at doses exceeding 3 g/day for adults.[2] 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.[3]
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[edit] Use in medicine
Nicotinamide has demonstrated anti-inflammatory actions which may be of benefit in patients with inflammatory skin conditions.[4] 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.[5]
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.[6] In overall, it rarely causes side effects, and is considered generally safe as a food additive, component in cosmetics and medication.[7]
Nicotinamide is produced by the aqueous ammonolysis of 3-cyanopyridine (nicotinonitrile) and subsequent crystallisation.
[edit] References
- ^ Jacenollo, P. (1992). Niacin versus niacinamide
- ^ {{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
- ^ Belenky P; Bogan KL, Brenner C (2007). "NAD+ metabolism in health and disease". Trends Biochem. Sci. 32 (1): 12–9. doi:. PMID 17161604.
- ^ Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis 77 (1 Suppl): 11–6. PMID 16871774.
- ^ Tallman JF, Paul SM, Skolnick P, Gallager DW (1980). "Receptors for the age of anxiety: pharmacology of the benzodiazepines". Science 207 (4428): 274–81. doi:. PMID 6101294.
- ^ Knip M, Douek IF, Moore WP, et al (2000). "Safety of high-dose nicotinamide: a review". Diabetologia 43 (11): 1337–45. doi:. PMID 11126400.
- ^ "Final report of the safety assessment of niacinamide and niacin" (2005). Int. J. Toxicol. 24 Suppl 5: 1–31. PMID 16596767.
[edit] See also
[edit] External links
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