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Encyclopedia > Niacin
Systematic name 3-Pyridinecarboxylic acid
Other names Niacin
Pyridine-β-carboxylic acid
Vitamin B3
Chemical formula C6H5NO2
Molecular mass 123.11 g/mol
Melting point 236.6 °C
Boiling point decomposes
CAS number [59-67-6]
SMILES OC(=O)c1cccnc1
Disclaimer and references

Niacin, also known as nicotinic acid or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair.[2] The designation vitamin B3 also includes the corresponding amide nicotinamide, or niacinamide, whose chemical formula is C6H6N2O. Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article does not cite its references or sources. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Retinol (Vitamin A) For the record label, see Vitamin Records Vitamins are nutrients required in tiny amounts for essential metabolic reactions in the body. ... Space-filling model of NADH Nicotinamide adenine dinucleotide (NAD+) is an important coenzymes found in cells. ... Cells in culture, stained for keratin (red) and DNA (green) The cell is the structural and functional unit of all living organisms, and are sometimes called the building blocks of life. ... DNA damage resulting in multiple broken chromosomes DNA repair refers to a collection of processes by which a cell identifies and corrects damage to the DNA molecules that encode its genome. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Nicotinamide, also known as niacinamide, is the amide of niacin (vitamin B3) which has the chemical formula C6H6N2O. Niacinamide is a derivative of vitamin B-3 can be used for the treatment of arthritis by aiding the body in its production of cartilage. ...


Deficiency and overdose

Chemical structure of nicotinamide.
Chemical structure of nicotinamide.

Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Pellagra is a vitamin deficiency disease caused by dietary lack of niacin (vitamin B3) and protein, especially proteins containing the essential amino acid tryptophan. ... A few of the metabolic pathways in a cell. ... Fig. ...

Niacin can have life-threatening acute toxic reactions[3]. One patient suffered vomiting after taking eleven 500-milligram niacin tablets over 36 hours, and another was unresponsive for several minutes after taking five 500-milligram tablets over two days.[4][5] Extremely high doses of niacin can cause niacin maculopathy, a thickening of the macula and retina which leads to blurred vision and blindness.[6] Human eye cross-sectional view. ... Human eye cross-sectional view. ...

The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women.[7]

Over 20 mg per day may cause flushing of the skin, lasting for about 15-30 minutes, sometimes accompanied by prickly or itching sensation. It may cause headache or nausea. This reaction is common[citation needed] in first-time users and is caused by the cells of the body releasing histamine, which results in vasodilation.[citation needed] When the body becomes used to the larger dose (usually over a period of days), these side effects may diminish or cease. Taking aspirin half an hour before the niacin will generally lessen the adverse effects.[citation needed] Slow or "sustained" release niacin supplement tablets are said to lessen side effects. Taking high doses of niacin may cause liver damage, particularly with slow-release formulations. High-dose niacin may also elevate blood sugar, thereby worsening diabetes mellitus. Hyperuricemia is another side effect of taking high-dose niacin; as such, it may worsen gout[citation needed]. This article or section does not cite any references or sources. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ... Aspirin or acetylsalicylic acid (acetosal) is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. ... Hepatotoxicity (from hepatic toxicity) is chemical-driven liver damage. ... In medicine, blood sugar is a term used to refer to levels of glucose in the blood. ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ... Hyperuricemia is the presence of high levels of uric acid in the blood. ...

Niacin is sometimes used by people using marijuana to try and pass theyre drug tests. The speculation is that it breaks down fat cells, witch THC binds to. There is no evidence to support this


Nicotinic acid was first discovered from the oxidation of nicotine. When the properties of nicotinic acid were discovered, it was thought prudent to choose a name to dissociate it from nicotine, done to avoid the perception that vitamins or niacin-rich food contain nicotine. The resulting name 'niacin' was derived from nicotinic acid + vitamin. Vitamin B3 is also referred to as "vitamin PP", a name derived from the obsolete term "pellagra-preventing factor." Distinguish from Niacin, which is the nicotinic acid, and has a very different biological effect. ...


The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely inefficient; 60 mg of tryptophan are required to make one milligram of niacin.[8] Dietary niacin deficiency tends to occur only in areas where people eat corn, the only grain low in niacin, as a staple food, and that don't use lime during maize (corn) meal/flour production. Alkali lime releases the tryptophan from the corn so that it can be absorbed in the intestine, and converted to niacin.[9] The liver is an organ present in vertebrates and some other animals. ... Phenylalanine is one of the standard amino acids. ... Tryptophan is an amino acid and essential in human nutrition. ... “Corn” redirects here. ... This article or section does not cite any references or sources. ... In chemistry, an alkali (from Arabic: al-qalyالقلوي, القالي ) is a basic, ionic salt of an alkali metal or alkali earth metal element. ... Tryptophan is an amino acid and essential in human nutrition. ...


The 5-membered aromatic heterocycle of the essential amino acid, tryptophan, is cleaved and rearranged with the alpha amino group of tryptophan into the 6-membered aromatic heterocycle of niacin by the following reaction: In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Pyridine a simple heterocyclic compound Heterocyclic compounds are organic compounds which contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. ... An essential amino acid or indispensable amino acid, is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... Tryptophan is an amino acid and essential in human nutrition. ... Phenylalanine is one of the standard amino acids. ...

Biosynthesis: Tryptophan → kynurenine → niacin
Biosynthesis: Tryptophankynurenine → niacin

Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Tryptophan is an amino acid and essential in human nutrition. ... Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. ...

Food sources

Animal products: Fruits and vegetables: Seeds: Fungi: Drinks:

Animalia redirects here. ... Popular Japanese fashion magazine throughout the 1990s; the photography of which has recently been reissued in two collections from Phaidon press. ... Vegetables on a market Vegetable is a nutritional and culinary term denoting any part of a plant that is commonly consumed by humans as food, but is not regarded as a culinary fruit, nut, herb, spice, or grain. ... This writeup is about biological seeds; for other meanings see Seed (disambiguation). ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ... The word drink is primarily a verb, meaning to ingest liquids, see Drinking. ... The liver is an organ present in vertebrates and some other animals. ... The heart and lungs, from an older edition of Grays Anatomy. ... It has been suggested that Renal anomalies and Renal plasma threshold be merged into this article or section. ... This article or section does not adequately cite its references or sources. ... For other uses, see Beef (disambiguation). ... A giant grouper at the Georgia Aquarium Fish are aquatic vertebrates that are typically cold-blooded; covered with scales, and equipped with two sets of paired fins and several unpaired fins. ... A shoal of skipjack tuna Tuna are several species of ocean-dwelling fish in the family Scombridae, mostly in the genus Thunnus. ... Illustration of a male Coho Salmon The Chinook or King Salmon is the largest salmon in North America and can grow to 1. ... A glass of cows milk. ... An egg is a body consisting of an ovum surrounded by layers of membranes and an outer casing of some type, which purpose is to nourishe and protect a developing embryo. ... Fresh Swiss chard Fresh water spinach Creamed spinach Steamed kale Leaf vegetables, also called potherbs, greens, or leafy greens, are plant leaves eaten as a vegetable, sometimes accompanied by tender petioles and shoots. ... Broccoli is a plant of the Cabbage family, Brassicaceae (formerly Cruciferae). ... Binomial name Solanum lycopersicum L. Percentages are relative to US recommendations for adults. ... Binomial name Daucus carota L. Percentages are relative to US recommendations for adults. ... Binomial name Phoenix dactylifera L. The Date Palm Phoenix dactylifera is a palm, extensively cultivated for its edible fruit. ... Binomial name Ipomoea batatas Linnaeus, The sweet potato (Ipomoea batatas) is a crop plant whose large, starchy, sweet-tasting tuberous roots are an important root vegetable. ... Binomial name Asparagus officinalis L. Asparagus officinalis is a plant species in the family Asparagaceae from which the popular vegetable known as asparagus is obtained. ... Binomial name Persea americana Mill. ... Hazelnuts from the Common Hazel Chestnut A nut can be either a seed or a fruit. ... This article or section does not cite its references or sources. ... Varieties of soybean seeds, a popular legume Pea pods A legume is a plant in the family Fabaceae (or Leguminosae), or a fruit of these plants. ... Species About 100-200 species, including: Atriplex alaskensis (Alaska Orach) Atriplex californica Atriplex calotheca Atriplex canescens Atriplex confertifolia Atriplex coronata (Crownscale Saltbush) Atriplex glabriuscula Atriplex hortensis (Garden or Red Orache) Atriplex halimus Atriplex heterosperma Atriplex hymenelytra Atriplex laciniata (Frosted Orache) Atriplex lentiformis Atriplex littoralis (Grass-leaved Orache) Atriplex longipes ( Orache... This article does not cite its references or sources. ... Brewers yeast (also known as brewers yeast or brewing yeast) can mean any live yeast used in brewing. ... Diet Coke Plus Diet Coke Plus is a new formulation of Diet Coke that Coca-Cola has announced they will be distributing beginning in the second quarter of 2007. ... A 250ml can of Red Bull A Thai Krating Daeng bottle Red Bull is the brand name of an Austrian carbonated soft drink. ...

Other uses

Niacin plays an important role in the production of several sex and stress-related hormones, particularly those made by the adrenal gland. It also plays a role in removing toxic chemicals from the body.[9]

Niacin, when taken in large doses, increases the level of high density lipoprotein (HDL) or "good" cholesterol in blood, and is sometimes prescribed for patients with low HDL, and at high risk of heart attack.[10] An extended release formulation of niacin for this indication is marketed by Abbott Laboratories under the trade name Niaspan. Niacin (but not niacinamide) is also used in the treatment of hyperlipidemia because it reduces very low density lipoprotein (VLDL), a precursor of low density lipoprotein (LDL) or "bad" cholesterol, secretion from the liver, and inhibits cholesterol synthesis.[11] The main problem with the clinical use of niacin for dyslipidemia is the occurrence of skin flushing, even with moderate doses.[12] There are current attempts to create a prolonged-release formulation of the substance, to allow it to be used more often and more comfortably.[13] High-density lipoproteins (HDL) form a class of lipoproteins, varying somewhat in their size (8–11 nm in diameter), that carry cholesterol from the bodys tissues to the liver. ... Sustained-release (SR), extended-release (ER, XR, or XL), time-release or timed-release, controlled-release (CR), or continuous-release (CR or Contin) tablets are pills formulated to dissolve slowly and release a drug over time. ... Abbott Laboratories (NYSE: ABT) is a diversified pharmaceuticals and health care company. ... Hypercholesterolemia (literally: high blood cholesterol) is the presence of high levels of cholesterol in the blood. ... Very Low Density Lipoprotein (VLDL) is a lipoprotein subclass. ... Low-density lipoprotein (LDL) is a class of lipoprotein particles that varies in size (18-25 nm in diameter) and contents (while carrying fatty acid molecules in blood and around the body). ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ...


  1. ^ Merck Index, 11th Edition, 6435.
  2. ^ Northwestern University Nutrition
  3. ^ [1]Toxicity From the Use of Niacin to Beat Urine Drug Screening, Presented at the 8th Annual Clinical Pathological Case Presentation Competition, 2006 North American Congress of Clinical Toxicology (NACCT) meeting, October 2006, San Francisco, CA, Manoj K. Mittal, et al. published online 6 April 2007. doi:10.1016/j.annemergmed.2007.01.014
  4. ^ [2]Hazards: Niacin to Pass a Drug Test Can Have Dangerous Results, By ERIC NAGOURNEY, New York Times, April 17, 2007
  5. ^ Mittal MK, Florin T, Perrone J, Delgado JH, Osterhoudt KC. Toxicity From the Use of Niacin to Beat Urine Drug Screening. Ann Emerg Med. 2007 Apr 4. PubMed
  6. ^ JD Gass, Nictonic Acid Maculopathy, Am. J. Opthamology, 1973;76:500-10
  7. ^ Jane Higdon, "Niacin", Micronutrient Information Center, Linus Pauling Institute
  8. ^ Oxidization Reactions of Niacin from the Linus Pauling Institute at Oregon State University Linus Pauling Institute.
  9. ^ a b Vitamin B3 University of Maryland Medical Center.
  10. ^ Postgraduate Medicine
  11. ^ Katzung and Trevors Pharmacology Examination and Board Review 7th edition, Authors: Trevor, Anthony J. Katzung, Bertram G. and Masters, Susan B., Lange Medical Books/ McGraw-Hill 2005
  12. ^ NIH Medline Plus: Niacin. http://www.nlm.nih.gov/medlineplus/ency/article/002409.htm.
  13. ^ Options for therapeutic intervention: how effective are the different agents? European Heart Journal Supplements Vol 8 Suppl F Pp. F47-F53 http://eurheartjsupp.oxfordjournals.org/cgi/content/abstract/8/suppl_F/F47

The Linus Pauling Institute was established at Oregon State University in August 1996 under an agreement reached between OSU and the Linus Pauling Institute of Science and Medicine (located in California from 1973 to 1996). ... Oregon State University (OSU) is a four-year research and degree-granting public university, located in Corvallis, Oregon in the United States. ... The University of Maryland, College Park (also known as UM, UMD, or UMCP) is a public university located in the city of College Park, in Prince Georges County, Maryland, just outside Washington, D.C., in the United States. ...

External links

  • Links to external chemical sources

  Results from FactBites:
Linus Pauling Institute at Oregon State University (3487 words)
Niacin deficiency was found to decrease bone marrow NAD and poly-ADP-ribose levels and increase the risk of chemically induced leukemia (12), and niacin supplementation decreased the risk of ultraviolet light-induced skin cancers in mice (13).
In the case of niacin, research on biochemical and cellular aspects of DNA repair have stimulated an interest in the relationship between niacin intake and cancer risk in human populations (16).
An increase in niacin intake of 6.2 mg was associated with about a 40% decrease in cases of cancers of the mouth and throat, while a 5.2 mg increase in niacin intake was associated with a similar decrease in cases of cancer of the esophagus.
Niacin - Wikipedia, the free encyclopedia (670 words)
Niacin, when taken in large doses, increases the level of High density lipoprotein (HDL)or "good" cholesterol in blood, and is sometimes prescribed for patients with low HDL, and at high risk of heart attack.
Niacin (but not niacinamide) is also used in the treatment of hyperlipidemia because it reduces Very low density lipoprotein (VLDL), a precursor of Low density lipoprotein (LDL) or "bad" cholesterol, secretion from the liver, and inhibits cholesterol synthesis.
Niacin in itself is not toxic, but the chemicals converted by niacin are toxic to the skin and liver in overdose, and high doses of niacin should only be reached with gradual increase.
  More results at FactBites »



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