Niacin
Organic compound and a form of vitamin B3 / From Wikipedia, the free encyclopedia
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Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient.[3] It is produced by plants and animals from the amino acid tryptophan.[4] Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds.[3][5] Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness.[6] Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.[3][7]
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Names | |||
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Pronunciation | /ˈnaɪəsɪn/ | ||
Preferred IUPAC name
Pyridine-3-carboxylic acid[1] | |||
Other names
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Identifiers | |||
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3D model (JSmol) |
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3DMet | |||
109591 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.000.401 | ||
EC Number |
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3340 | |||
KEGG | |||
MeSH | Niacin | ||
PubChem CID |
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RTECS number |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C6H5NO2 | |||
Molar mass | 123.111 g·mol−1 | ||
Appearance | White, translucent crystals | ||
Density | 1.473 g cm−3 | ||
Melting point | 237 °C; 458 °F; 510 K | ||
18 g L−1 | |||
log P | 0.219 | ||
Acidity (pKa) | 2.0, 4.85 | ||
Isoelectric point | 4.75 | ||
Refractive index (nD) |
1.4936 | ||
0.1271305813 D[citation needed] | |||
Thermochemistry | |||
Std enthalpy of formation (ΔfH⦵298) |
−344.9 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) |
−2.73083 MJ mol−1 | ||
Pharmacology | |||
C04AC01 (WHO) C10BA01 (WHO) C10AD02 (WHO) C10AD52 (WHO) | |||
License data |
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Intramuscular, by mouth | |||
Pharmacokinetics: | |||
20–45 min | |||
Hazards | |||
GHS labelling: | |||
Warning | |||
H319 | |||
P264, P280, P305+P351+P338, P337+P313, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 193 °C (379 °F; 466 K) | ||
365 °C (689 °F; 638 K) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Clinical data | |
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Trade names | Niacor, Niaspan, others |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682518 |
License data |
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Pregnancy category |
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Routes of administration | Intramuscular, by mouth |
Legal status | |
Legal status |
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Identifiers | |
PDB ligand | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.401 |
The amide derivative nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+). Although niacin and nicotinamide are identical in their vitamin activity, nicotinamide does not have the same pharmacological, lipid-modifying effects or side effects as niacin, i.e., when niacin takes on the -amide group, it does not reduce cholesterol nor cause flushing.[8][9] Nicotinamide is recommended as a treatment for niacin deficiency because it can be administered in remedial amounts without causing the flushing, considered an adverse effect.[10]
Niacin is also a prescription medication.[11] Amounts far in excess of the recommended dietary intake for vitamin functions will lower blood triglycerides and low density lipoprotein cholesterol (LDL-C), and raise blood high density lipoprotein cholesterol (HDL-C, often referred to as "good" cholesterol). There are two forms: immediate-release and sustained-release niacin. Initial prescription amounts are 500 mg/day, increased over time until a therapeutic effect is achieved. Immediate-release doses can be as high as 3,000 mg/day; sustained-release as high as 2,000 mg/day.[11] Despite the proven lipid changes, niacin has not been found useful for decreasing the risk of cardiovascular disease in those already on a statin.[12] A 2010 review had concluded that niacin was effective as a mono-therapy,[13] but a 2017 review incorporating twice as many trials concluded that prescription niacin, while affecting lipid levels, did not reduce all-cause mortality, cardiovascular mortality, myocardial infarctions, nor fatal or non-fatal strokes.[14] Prescription niacin was shown to cause hepatotoxicity[15] and increase risk of type 2 diabetes.[16][17] Niacin prescriptions in the U.S. had peaked in 2009, at 9.4 million,[citation needed] declining to 800 thousand by 2020.[18]
Niacin has the formula C
6H
5NO
2 and belongs to the group of the pyridinecarboxylic acids.[3] As the precursor for nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate, niacin is involved in DNA repair.[19]