Nicotinate

HCID 937

Basic information

Standard SMILES
O=C([O-])c1cccnc1
InChIKey
PVNIIMVLHYAWGP-UHFFFAOYSA-M
Molecular formula
C6H4NO2-
Average molar mass
122.1 g/mol
Monoisotopic mass
122.02420337

Names & identifiers

Preferred name
Nicotinate
IUPAC
pyridine-3-carboxylate

Names & synonyms

nicotinate3-pyridinecarboxylateCHEBI:32544RefChem:927733pyridine-3-carboxylatenico-400-PVNIIMVLHYAWGP-UHFFFAOYSA-MAC-907/25004509AE-848/01496050Q27104221

Database identifiers

PubChem CID
937
ChEBI
CHEBI:32544
Nikkaji
J239.335B

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
53 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

Collision Cross Section · 2 items

121 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];124 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

124 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Safety & regulation

Toxicology

TreatmentSupportive measures should be undertaken in the event of an overdose. (L1712)
Health Effects · 1 item

Niacin at extremely high doses can have life-threatening acute toxic reactions. Extremely high doses of niacin can also cause niacin maculopathy, a thickening of the macula and retina which leads to blurred vision and blindness. This maculopathy is reversible after stopping niacin intake. Side effects of hyperglycemia, cardiac arrhythmias and birth defects have also been reported. (A729)

Exposure RoutesOral (L1436) ; Intramuscular (L1436). Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
Toxicity Summary · 1 item

Niacin binds to Nicotinate D-ribonucleotide phyrophsopate phosphoribosyltransferase, Nicotinic acid phosphoribosyltransferase, Nicotinate N-methyltransferase and the Niacin receptor. Niacin is the precursor to nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), which are vital cofactors for dozens of enzymes. The mechanism by which niacin exerts its lipid lowering effects is not entirely understood, but may involve several actions, including a decrease in esterification of hepatic triglycerides. Niacin treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions.

Signs and Symptoms · 1 item

Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Niacin is rapidly metabolized and undergoes extensive first-pass metabolism in the liver. The drug is converted to several metabolites, including nicotinuric acid (NUA), nicotinamide, and nicotinamide adenine dinucleotide (NAD). At doses used to treat hyperlipoproteinemia, the principal metabolic pathways appear to be saturable, and niacin is thought to exhibit nonlinear, dose-dependent pharmacokinetics. (L1323) Half Life: 20-45 minutes.

MeSH Pharmacological Classification · 3 items

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.

Drugs used to cause dilation of the blood vessels.

A group of water-soluble vitamins, some of which are COENZYMES.

Uses & manufacturing

Uses · 1 item

For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy. It can be found in various foods, such as liver, chicken, beef, fish, cereal, peanuts and legumes. Niacin is also used as a pharmaceutical to reverse atherosclerosis. (A729)

Related reactions

13 records

Linked notes

Loading…