Nicotinic acid

Nicotinic acid
Names
Pronunciation /ˈnəsɪn/
Preferred IUPAC name
Pyridine-3-carboxylic acid
Other names
  • Niacin (USAN US)
  • Bionic
  • Vitamin B3
  • Vitamin PP
Identifiers
3D model (JSmol)
109591
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.401
EC Number
  • 200-441-0
3340
KEGG
MeSH Niacin
RTECS number
  • QT0525000
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9) Y
    Key: PVNIIMVLHYAWGP-UHFFFAOYSA-N Y
  • InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
    Key: PVNIIMVLHYAWGP-UHFFFAOYAA
  • OC(=O)c1cccnc1
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
1.4936
0.1271305813 D
Thermochemistry
−344.9 kJ mol−1
−2.73083 MJ mol−1
Pharmacology
C04AC01 (WHO) C10BA01 (WHO) C10AD02 (WHO) C10AD52 (WHO)
License data
Intramuscular, by mouth
Pharmacokinetics:
20–45 min
Hazards
GHS labelling:
Warning
H319
P264, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)
1
1
0
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).
Y verify (what is YN ?)
Infobox references
Nicotinic acid
INN: Nicotinic acid
Clinical data
Trade namesNiacor, Niaspan, others
AHFS/Drugs.comMonograph
MedlinePlusa682518
License data
Pregnancy
category
  • AU: Exempt
Routes of
administration
Intramuscular, by mouth
Legal status
Legal status
  • US: OTC / Rx-only
Identifiers
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.401

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 United States had peaked in 2009 at 9.4 million, declining to 800 thousand by 2020. In 2023, it was the 288th most commonly prescribed medication in the US, with more than 500,000 prescriptions.

Nicotinic acid has the formula C
6
H
5
NO
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.