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14-September-2008 10:43:23 - Niacin This article is about the organic compound and vitamin. For the band, see Niacin band. Niacin IUPAC name nicotinic acid Other names pyridine-3-carboxylic acid, nicotinic acid, vitamin B3 Identifiers CAS number 59-67-6 PubChem 938 MeSH Niacin SMILES C1=CC=CN=C1C=OO ChemSpider ID 913 Properties Molecular formula C6H5NO2 Molar mass 123.11 Melting point 236.6 °C Boiling point decomposes Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Niacin, also known as vitamin B3, is a water-soluble vitamin which prevents the deficiency disease pellagra. It is an organic compound with the molecular formula C6H5NO2. It is a derivative of pyridine, with a carboxyl group COOH at the 3-position. Other forms of vitamin B3 include the corresponding amide, nicotinamide niacinamide, where the carboxyl group has been replaced by an amide group CONH2, as well as more complex amides and a variety of esters. The terms niacin, nicotinamide, and vitamin B3 are often used interchangeably to refer to any one of this family of molecules, since they have a common biochemical activity. Depending on the definition used, niacin is one of between 40 and 80 essential human nutrients. It is one of only four essential nutrients associated with a pandemic deficiency disease, namely Niacin pellagra, vitamin C scurvy, thiamin beriberi, and vitamin D rickets. Niacin is converted to nicotinamide and then to NAD and NADP in vivo. Although the two are identical in their vitamin activity, nicotinamide does not have the same pharmacological effects of niacin, which occur as side-effects of niacin's conversion. Thus nicotinamide 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 Niacin is a precursor to NADH, NAD, NAD+, NADP and NADPH, which play essential metabolic roles in living cells.3 DNA repair, and the production of steroid hormones in the adrenal gland. Contents 1 History 2 Dietary needs 3 Pharmacological uses 3.1 Lipid modifying effects 3.2 Topical use 3.3 Niacin and drug screening tests 4 Toxicity 5 Inositol hexanicotinate 6 Biosynthesis 7 Receptor 8 Food sources 9 References 10 External links History Niacin was first described by Hugo Weidel in 1873 in his studies of nicotine.4 The original preparation remains useful: the oxidation of nicotine using nitric acid.5 Niacin was extracted from livers by Conrad Elvehjem who later identified the active ingredient, then referred to as the pellagra-preventing factor and the anti-blacktongue factor.6 When the biological significance of nicotinic acid was realized, it was thought appropriate to choose a name to dissociate it from nicotine, in order to avoid the perception that vitamins or niacin-rich food contains nicotine. The resulting name 'niacin' was derived from nicotinic acid + vitamin. Carpenter found in 1951 that niacin in corn is biologically unavailable and can only be released in very alkali lime water of pH 11.7 This process is known as nixtamalization.8 Niacin is referred to as Vitamin B3 because it was the third of the B vitamins to be discovered. It has historically been referred to as vitamin PP. Dietary needs Severe deficiency of niacin in the diet causes the disease pellagra, whereas mild deficiency slows the metabolism, causing decreased tolerance to cold. Dietary niacin deficiency tends to occur only in areas where people eat corn maize, the only grain low in niacin as a staple food, and that do not use lime during meal/flour production. The recommended daily allowance of niacin is 2-12 mg/day for children, 14 mg/day for women, 16 mg/day for men, and 18 mg/day for pregnant or breast-feeding women.9 Note: Niacin synthesis is deficient in carcinoid syndrome because of metabolic diversion of its precursor, tryptophan, to form serotonin. Pharmacological uses The recommended daily allowance RDA for niacin is 20 mg/day. The argument that niacin does not provide any benefits at doses above the RDA has been decisively disproven. There are two decisively proven uses of pharmacological doses of niacin. These are for heart disease and skin conditions. Extensive evidence combining known biochemical functions of vitamin B3, controlled trials, and clinical observations indicate that doses of niacin above the RDA speed wound healing and help the immune system fight off viral infections. The available evidence supports the hypothesis that response is proportional to dose well past the side effect threshold. The side effect threshold for niacin varies dramatically from person to person, ranging from between 30 and 300 mg for the majority of the population. Lipid modifying effects Niacin, prescribed in doses between 1000 and 3000 mg/day, blocks the breakdown of fats in adipose tissue, a very-low-density lipoprotein VLDL, a precursor of low-density lipoprotein LDL or bad cholesterol. Because niacin blocks breakdown of fats, it causes a decrease in free fatty acids in the blood and, as a consequence, decreased secretion of VLDL and cholesterol by the liver.10 By lowering VLDL levels, niacin also increases the level of high-density lipoprotein HDL or good cholesterol in blood, and therefore it is sometimes prescribed for patients with low HDL, who are also at high risk of a heart attack.1112 As of August 2008update, a combination of niacin with laropiprant is tested in a clinical trial. Laropiprant reduces facial flushes induced by niacin. Topical use A fat-soluble derivative of niacin has been developed that efficiently penetrates the skin. This form of niacin has been shown to improve a variety of skin conditions in a number of controlled clinical trials. Niacin and drug screening tests Niacin is sometimes consumed in large quantities by people who wish to fool drug screening tests, particularly for lipid soluble drugs such as marijuana.13 It is believed to promote metabolism of the drug and cause it to be flushed out. Scientific studies have shown it does not affect drug screenings, but can pose a risk of overdose, causing arrhythmias, metabolic acidosis, hyperglycemia, and other serious problems.14 Toxicity People taking pharmacological doses of niacin 1.5 - 6 g per day often experience a side-effects that can include dermatological complaints such as facial flushing and itching, dry skin, skin rashes including acanthosis nigricans. Gastrointestinal complaints, such as dyspepsia indigestion and liver toxicity fulminant hepatic failure have also been reported. Also reported include hyperglycemia, cardiac arrhythmias, birth defects, and orthostasis.15 Facial flushing is the most commonly reported side effect.16 It lasts for about 15 to 30 minutes, and is sometimes accompanied by a prickly or itching sensation, particularly in areas covered by clothing. This effect is mediated by prostaglandin and can be blocked by taking 300 mg of aspirin half an hour before taking niacin, or by taking one tablet of ibuprofen per day. Taking the niacin with meals also helps reduce this side effect. After 1 to 2 weeks of a stable dose, most patients no longer flush.citation needed Slow- or sustained-release forms of niacin have been developed to lessen these side-effects.1017 One study showed the incidence of flushing was significantly lower with a sustained release formulation18 though doses above 2 g per day have been associated with liver damage, particularly with slow-release formulations.15 High-dose niacin may also elevate blood sugar, thereby worsening diabetes mellitus.15 Hyperuricemia is another side-effect of taking high-dose niacin, and may exacerbate gout.19 Niacin at doses used in lowering cholesterol has been associated with birth defects in laboratory animals, with possible consequences for infant development in pregnant women.15 Niacin at extremely high doses can have life-threatening acute toxic reactions.20 Extremely high doses of niacin can also cause niacin maculopathy, a thickening of the macula and retina which leads to blurred vision and blindness. This maculopathy is reversible after stopping niacin intake.21 Inositol hexanicotinate One popular form of dietary supplement is inositol hexanicotinate, usually sold as flush-free or no-flush niacin although those terms are also used for regular sustained-release. While this form of niacin does not cause the flushing associated with the nicotinic acid form, it is not clear whether it is pharmacologically equivalent in its positive effect.22 Biosynthesis Biosynthesis: Tryptophan → kynurenine → niacin Biosynthesis: Tryptophan → kynurenine → niacin Biosynthesis Biosynthesis The liver can synthesize niacin from the essential amino acid tryptophan, requiring 60 mg of tryptophan to make one mg of niacin.23 The 5-membered aromatic heterocycle of tryptophan is cleaved and rearranged with the alpha amino group of tryptophan into the 6-membered aromatic heterocycle of niacin. Receptor The receptor for niacin is a G protein-coupled receptor called HM74A.24 It couples to Gi alpha subunit.25 Food sources Animal products: Fruits and vegetables: Seeds: Fungi: liver, heart and kidney chicken beef fish: tuna, salmon milk eggs leaf vegetables broccoli tomatoes carrots dates sweet potatoes asparagus avocados nuts whole grain products legumes saltbush seeds mushrooms brewer's yeast References ^ Jaconello P October 1992. Niacin versus niacinamide. CMAJ 147 7: 990. PMID 1393911. ^ Knip M, Douek IF, Moore WP, et al 2000. Safety of high-dose nicotinamide: a review. Diabetologia 43 11: 1337-45. doi:10.1007/s001250051536. PMID 11126400. ^ Cox, Michael; Lehninger, Albert L; Nelson, David R. 2000. Lehninger principles of biochemistry. New York: Worth Publishers. ISBN 1-57259-153-6. ^ Weidel, H 1873. Zur Kenntniss des Nicotins. Justus Liebig's Annalen der Chemie und Pharmacie 165: 330-349. doi:10.1002/jlac.18731650212. ^ Samuel M. McElvain 1941. Nicotinic Acid. Org. Synth.; Coll. Vol. 1: 385. ^ Elvehjem, C.A.; Madden, R.J.; Strongandd, F.M.. W. WOOLLEY 1938 The isolation and identification of the anti-blacktongue factor J. J. Biol. Chem 123: 137. ^ LAGUNA J, CARPENTER KJ September 1951. Raw versus processed corn in niacin-deficient diets. J. Nutr. 45 1: 21-8. PMID 14880960. ^ Vitamin B3. University of Maryland Medical Center 2002-01-04. Retrieved on 2008-03-31. ^ Jane Higdon, Niacin, Micronutrient Information Center, Linus Pauling Institute ^ a b Katzung, Bertram G. 2006. Basic and clinical pharmacology. New York: McGraw-Hill Medical Publishing Division. ISBN 0071451536. ^ McGovern ME 2005. Taking aim at HDL-C. Raising levels to reduce cardiovascular risk. Postgrad Med 117 4: 29-30, 33-5, 39 passim. PMID 15842130. ^ Canner PL, Berge KG, Wenger NK, et al 1986. Fifteen year mortality in Coronary Drug Project patients: long-term benefit with niacin. J. Am. Coll. Cardiol. 8 6: 1245-55. PMID 3782631. ^ Niacin abuse in the attempt to alter urine drug tests 2007. Pharmacy Technician's Letter 23 6. Retrieved on 2008-03-31. . ^ Phend, C 2007-04-12. Psychiatric Times - Overdoing Niacin Can't Thwart Drug Abuse Tests and Is Risky. Retrieved on 2008-03-31. ^ a b c d Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred 2006. Goodman Gilman's the pharmacological basis of therapeutics. New York: McGraw-Hill. ISBN 0071422803. ^ McGee, W 2007-02-01. Medical Encyclopedia: Niacin. MedlinePlus. Retrieved on 2008-03-31. ^ Barter, P 2006. Options for therapeutic intervention: How effective are the different agents?. European Heart Journal Supplements 8 F: F47-F53. doi:10.1093/eurheartj/sul041. Retrieved on 2008-03-31. ^ Chapman MJ, Assmann G, Fruchart JC, Shepherd J, Sirtori C 2004. Raising high-density lipoprotein cholesterol with reduction of cardiovascular risk: the role of nicotinic acid--a position paper developed by the European Consensus Panel on HDL-C. Curr Med Res Opin 20 8: 1253-68. doi:10.1185/030079904125004402. PMID 15324528. ^ Capuzzi DM, Morgan JM, Brusco OA, Intenzo CM 2000. Niacin dosing: relationship to benefits and adverse effects. Curr Atheroscler Rep 2 1: 64-71. doi:10.1007/s11883-000-0096-y. PMID 11122726. ^ Mittal MK, Florin T, Perrone J, Delgado JH, Osterhoudt KC 2007. Toxicity from the use of niacin to beat urine drug screening. Ann Emerg Med 50 5: 587-90. doi:10.1016/j.annemergmed.2007.01.014. PMID 17418450. ^ Gass JD 2003. Nicotinic acid maculopathy. 1973. Retina Philadelphia, Pa. 23 6 Suppl: 500-10. PMID 15035390. ^ Kittams, B 2003-01-15. No-Flush Niacin for the Treatment of Hyperlipidemia. Medscape. Retrieved on 2008-03-31. ^ Jacobson, EL 2007. Niacin. Linus Pauling Institute. Retrieved on 2008-03-31. ^ Zhang Y, Schmidt RJ, Foxworthy P, et al 2005. Niacin mediates lipolysis in adipose tissue through its G-protein coupled receptor HM74A. Biochem. Biophys. Res. Commun. 334 2: 729-32. doi:10.1016/j.bbrc.2005.06.141. PMID 16018973. ^ Zellner C, Pullinger CR, Aouizerat BE, et al 2005. Variations in human HM74 GPR109B and HM74A GPR109A niacin receptors. Hum. Mutat. 25 1: 18-21. doi:10.1002/humu.20121. PMID 15580557. External links v d e Vitamins A11 Fat soluble A: Retinol - Beta-carotene - Tretinoin - Alpha-carotene D3: 7-Dehydrocholesterol → Previtamin D3 → Cholecalciferol D3 → Calcidiol → Calcitriol active form → Calcitroic acid D2: Ergosterol → Ergocalciferol D2 D analogues: Dihydrotachysterol - Calcipotriol - Tacalcitol D4: Dihydroergocalciferol E: Tocopherol - Tocotrienol K: Naphthoquinone - Phylloquinone/K1 - Menatetrenone/K2 Water soluble: B vitamins B1 Thiamine - B2 Riboflavin - B3 Niacin, Nicotinamide - B5 Pantothenic acid, Dexpanthenol, Pantethine - B6 Pyridoxine, Pyridoxal phosphate, Pyridoxamine - B7 Biotin - B9 Folic acid, Folinic acid - B12 Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide Water soluble: other C Ascorbic acid - Choline see also enzyme cofactors v d e Peripheral vasodilators C04 Imidazoline derivatives Phentolamine - Tolazoline Niacin and derivatives Niacin Purine derivatives Pentoxifylline Ergot alkaloids Ergoloid- Nicergoline Other peripheral vasodilators Phenoxybenzamine - Vincamine - Naftidrofuryl v d e Lipid modifying agents C10 Statins HMG-CoA reductase Atorvastatin Cerivastatin‡ Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin Fibrates PPAR Clofibrate‡ Bezafibrate Aluminium clofibrate Gemfibrozil Fenofibrate Simfibrate Ronifibrate Ciprofibrate Etofibrate Clofibride Clinofibrate Bile acid sequestrants Colestyramine Colestipol Colestilan Colextran Colesevelam Niacin and derivatives Niceritrol Niacin Nicofuranose Aluminium nicotinate Nicotinyl alcohol Acipimox CETP inhibitors Anacetrapib†Torcetrapib§ Combinations Niacin/lovastatin Niacin/simvastatin Ezetimibe/simvastatin Other Dextrothyroxine Probucol Tiadenol Benfluorex Meglutol Omega-3-triglycerides Magnesium pyridoxal 5-phosphate glutamate Policosanol Ezetimibe Lapaquistat§ †Undergoing clinical trials. ‡Withdrawn from market. §Development terminated. Retrieved from http://en..org/wiki/Niacin Categories: Hypolipidemic agents | B vitamins | Pyridines | Carboxylic acidsHidden categories: Articles containing potentially dated statements from August 2008 | All articles containing potentially dated statements | All articles with statements | Articles with statements since April 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Bosanski ÄŒesky Dansk Deutsch Eesti Español Français Galego í•œêµì–´ Hrvatski Italiano עברית ქáƒ?რთული Lëtzebuergesch Lietuvių Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Occitan Polski Português Română РуÑ?Ñ?кий Simple English SlovenÄ?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Suomi Svenska ไทย Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 12 September 2008, at 20:32
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