Nicotinic acid
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| Names | |||
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| Pronunciation | /ˈnaɪəsɪn/ | ||
| Preferred IUPAC name
Pyridine-3-carboxylic acid | |||
Other names
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| Identifiers | |||
3D model (JSmol) |
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| 109591 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| 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 | |||
| 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).
Infobox references | |||
| 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 |
Nicotinic acid, or niacin, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan.
Nicotinic acid is also a prescription medication. 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 nicotinic acid. 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. Despite the proven lipid changes, nicotinic acid has not been found useful for decreasing the risk of cardiovascular disease in those already prescribed a statin drug. A 2010 review had concluded that nicotinic acid was effective as a mono-therapy, but a 2017 review incorporating twice as many trials concluded that prescription nicotinic acid, while affecting lipid levels, did not reduce all-cause mortality, cardiovascular mortality, myocardial infarctions, nor fatal or non-fatal strokes. Prescription nicotinic acid was shown to cause hepatotoxicity and increase risk of type 2 diabetes. Nicotinic acid prescriptions in the U.S. had peaked in 2009 at 9.4 million, declining to 800 thousand by 2020.
Nicotinic acid has the formula C
6H
5NO
2 and belongs to the group of the pyridinecarboxylic acids. As the precursor for nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate, it is involved in DNA repair.
Extra-terrestrial nicotinic acid has been found in carbonaceous chondrite meteorites and in sample-returns from the asteroids 162173 Ryugu and 101955 Bennu.