Nicotinate

Niacin

Names
Preferred IUPAC name Pyridine-3-carboxylic acid
Other names Nicotinic acid (INN) Bionic Vitamin B3 Vitamin PP
Identifiers
CAS Number	59-67-6 Y
3D model (Jmol)	Interactive image
3DMet	B00073
Beilstein Reference	109591
ChEBI	CHEBI:15940 Y
ChemSpider	913 Y
DrugBank	DB00627 Y
ECHA InfoCard	100.000.401
EC Number	200-441-0
Gmelin Reference	3340
IUPHAR/BPS	1588
KEGG	D00049 Y
MeSH	Niacin
PubChem CID	938
RTECS number	QT0525000
UNII	2679MF687A Y
InChI 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
SMILES OC(=O)c1cccnc1
Properties
Chemical formula	C 6NH 5O 2
Molar mass	123.1094 g mol−1
Appearance	White, translucent crystals
Density	1.473 g cm−3
Melting point	237 °C; 458 °F; 510 K
Solubility in water	18 g L−1
log P	0.219
Acidity (pKa)	2.0,4.85
Isoelectric point	4.75
Refractive index (nD)	1.4936
Dipole moment	0.1271305813 D
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−344.9 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.73083 MJ mol−1
Pharmacology
ATC code	C04AC01 (WHO) C10AD02 (WHO)
Routes of administration	Intramuscular, Oral
Pharmacokinetics:
Biological half-life	20–45 min
Hazards
EU classification (DSD) (outdated)	Xi
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26, S36
NFPA 704	1 1 0
Flash point	193 °C (379 °F; 466 K)
Autoignition temperature	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  (what is YN ?)
Infobox references

Niacin, also known as nicotinic acid, is an organic compound with the formula C
6H
5NO
2 and, depending on the definition used, one of the 20 to 80 essential human nutrients. Together with nicotinamide it makes up the group known as vitamin B₃ complex.

Medication and supplemental niacin are primarily used to treat high blood cholesterol and pellagra (niacin deficiency). Insufficient niacin in the diet can cause nausea, skin and mouth lesions, anemia, headaches, and tiredness. The lack of niacin may also be observed in pandemic deficiency disease, which is caused by a lack of five crucial vitamins (niacin, vitamin C, thiamin, vitamin D, and vitamin A) and is usually found in areas of widespread poverty and malnutrition. Niacin is provided in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods and meat from various animal sources. Some countries require its addition to grains.

This colorless, water-soluble solid is a derivative of pyridine, with a carboxyl group (COOH) at the 3-position. Other forms of vitamin B₃ include the corresponding amide nicotinamide ("niacinamide"), where the carboxyl group has been replaced by a carboxamide group (CONH
2), as well as more complex amides and a variety of esters. Nicotinic acid and niacinamide are convertible to each other with steady world demand rising from 8,500 tonnes per year in the 1980s to 40,000 in recent years.