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 U.S. had peaked in 2009 at 9.4 million, declining to 800 thousand by 2020.

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.