Nicotinic acid (CHEM002233)

Record Information
Version1.0
Creation Date2009-07-21 20:27:16 UTC
Update Date2026-05-14 16:44:29 UTC
Accession NumberCHEM002233
Identification
Common NameNicotinic acid
ClassSmall Molecule
Description
Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antilipemic Agent
  • Cosmetic Toxin
  • Drug
  • Ester
  • Food Toxin
  • Household Toxin
  • Hypolipidemic Agent
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Vasodilator Agent
  • Vitamin B Complex
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-CarboxypyridineChEBI
3-Pyridinecarboxylic acidChEBI
3-Pyridylcarboxylic acidChEBI
Acide nicotiniqueChEBI
Acido nicotinicoChEBI
Acidum nicotinicumChEBI
Anti-pellagra vitaminChEBI
beta-Pyridinecarboxylic acidChEBI
m-Pyridinecarboxylic acidChEBI
NiacinChEBI
NikotinsaeureChEBI
P.P. factorChEBI
Pellagra preventive factorChEBI
PP FactorChEBI
Pyridine-beta-carboxylic acidChEBI
Vitamin b3ChEBI
NiacorKegg
NiaspanKegg
3-PyridinecarboxylateGenerator
3-PyridylcarboxylateGenerator
b-PyridinecarboxylateGenerator
b-Pyridinecarboxylic acidGenerator
beta-PyridinecarboxylateGenerator
Β-pyridinecarboxylateGenerator
Β-pyridinecarboxylic acidGenerator
m-PyridinecarboxylateGenerator
Pyridine-b-carboxylateGenerator
Pyridine-b-carboxylic acidGenerator
Pyridine-beta-carboxylateGenerator
Pyridine-β-carboxylateGenerator
Pyridine-β-carboxylic acidGenerator
NicotinateGenerator
3-CarboxylpyridineHMDB
AkotinHMDB
ApelagrinHMDB
DaskilHMDB
EfacinHMDB
EnduracinHMDB
LinicHMDB
NiacHMDB
NiacineHMDB
NicacidHMDB
NicaminHMDB
NicanginHMDB
Nico-spanHMDB
NicobidHMDB
NicocapHMDB
NicodelmineHMDB
NicolarHMDB
NiconacidHMDB
Nicosan 3HMDB
NicotinipcaHMDB
NicylHMDB
NyclinHMDB
PellagrinHMDB
PeloninHMDB
Slo-niacinHMDB
WampocapHMDB
Aluminum salt, niacinHMDB
InduracinHMDB
Niacin cobalt (2+) saltHMDB
Niacin iron (2+) saltHMDB
Niacin lithium saltHMDB
Niacin magnesium saltHMDB
Niacin sodium saltHMDB
Nico-400HMDB
Potassium salt, niacinHMDB
Sodium salt, niacinHMDB
Tosylate, niacinHMDB
Nicotinate, lithiumHMDB
Hydrochloride, niacinHMDB
Niacin aluminum saltHMDB
Niacin calcium saltHMDB
Niacin copper (2+) saltHMDB
Niacin hydrochlorideHMDB
Niacin lithium salt, hemihydrateHMDB
Nico400HMDB
Tartrate, niacinHMDB
3 Pyridinecarboxylic acidHMDB
Lithium nicotinateHMDB
Niacin ammonium saltHMDB
Niacin manganese (2+) saltHMDB
Niacin potassium saltHMDB
Niacin tartrateHMDB
Niacin tosylateHMDB
Niacin zinc saltHMDB
Nico 400HMDB
Chemical FormulaC6H5NO2
Average Molecular Mass123.109 g/mol
Monoisotopic Mass123.032 g/mol
CAS Registry Number59-67-6
IUPAC Namepyridine-3-carboxylic acid
Traditional Nameniacin
SMILESOC(=O)C1=CN=CC=C1
InChI IdentifierInChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Most Tissues
  • Skeletal Muscle
  • Skin
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point236.6°C
Boiling PointNot Available
Solubility1.8E+004 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility83.1 g/LALOGPS
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (32) ; Intramuscular (32). Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
Mechanism of ToxicityNiacin 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.
MetabolismNiacin 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. (31) Half Life: 20-45 minutes.
Toxicity ValuesLD50: 7000 mg/kg (Oral, Rat) (34) LD50: 730 mg/kg (Intraperitoneal, Rat) (34) LD50: 3500 mg/kg (Subcutaneous, Mouse) (34)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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. (3)
Minimum Risk LevelNot Available
Health EffectsNiacin 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. (3)
SymptomsNicotinic 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.
TreatmentSupportive measures should be undertaken in the event of an overdose. (33)
Concentrations
Not Available
External Links
DrugBank IDDB00627
HMDB IDHMDB0001488
FooDB IDFDB001014
Phenol Explorer IDNot Available
KNApSAcK IDC00000208
BiGG ID34401
BioCyc IDNIACINE
METLIN ID6272
PDB IDNot Available
Wikipedia LinkNiacin
Chemspider ID913
ChEBI ID15940
PubChem Compound ID938
Kegg Compound IDC00253
YMDB IDYMDB00224
ECMDB IDECMDB01488
References
Synthesis Reference

Joseph E. Toomey, Jr., “Electrochemical synthesis of niacin and other N-heterocyclic compounds.” U.S. Patent US5002641, issued 1914.

MSDSLink
General References
1. McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.
2. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.
3. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.
4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
5. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013
6. USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/
7. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
8. McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.
9. Salvi A, Carrupt PA, Mayer JM, Testa B: Esterase-like activity of human serum albumin toward prodrug esters of nicotinic acid. Drug Metab Dispos. 1997 Apr;25(4):395-8.
10. Hertle H, Kiese M, Renner G: Absorption in rats, dogs, pigs, and humans of nicotinic acid after oral administration of phosphatidyl inositol pentanicotinate hydrochloride (PIN). Arzneimittelforschung. 1979;29(1):114-6.
11. Zarzycki PK, Kowalski P, Nowakowska J, Lamparczyk H: High-performance liquid chromatographic and capillary electrophoretic determination of free nicotinic acid in human plasma and separation of its metabolites by capillary electrophoresis. J Chromatogr A. 1995 Aug 11;709(1):203-8.
12. Hengen N, Seiberth V, Hengen M: High-performance liquid-chromatographic determination of free nicotinic acid and its metabolite, nicotinuric acid, in plasma and urine. Clin Chem. 1978 Oct;24(10):1740-3.
13. Santos RD: [Pharmacology of niacin or nicotinic acid]. Arq Bras Cardiol. 2005 Oct;85 Suppl 5:17-9. Epub 2006 Jan 2.
14. Mrochek JE, Jolley RL, Young DS, Turner WJ: Metabolic response of humans to ingestion of nicotinic acid and nicotinamide. Clin Chem. 1976 Nov;22(11):1821-7.
15. Pike NB: Flushing out the role of GPR109A (HM74A) in the clinical efficacy of nicotinic acid. J Clin Invest. 2005 Dec;115(12):3400-3.
16. Kobayashi M, Shimizu S: [Nicotinic acid and nicotinamide]. Nihon Rinsho. 1999 Oct;57(10):2211-7.
17. Sutherland WH, Larking PW, Nye ER: Modification of nicotinic acid and prostaglandin E1 antilipolytic action in vitro. Atherosclerosis. 1976 Oct;25(1):45-53.
18. Stratford MR, Dennis MF, Hoskin P, Phillips H, Hodgkiss RJ, Rojas A: Nicotinamide pharmacokinetics in humans: effect of gastric acid inhibition, comparison of rectal vs oral administration and the use of saliva for drug monitoring. Br J Cancer. 1996 Jul;74(1):16-21.
19. Angelin B, Einarsson K, Leijd B: Biliary lipid composition during treatment with different hypolipidaemic drugs. Eur J Clin Invest. 1979 Jun;9(3):185-90.
20. Patterson MC, Di Bisceglie AM, Higgins JJ, Abel RB, Schiffmann R, Parker CC, Argoff CE, Grewal RP, Yu K, Pentchev PG, et al.: The effect of cholesterol-lowering agents on hepatic and plasma cholesterol in Niemann-Pick disease type C. Neurology. 1993 Jan;43(1):61-4.
21. Tunaru S, Kero J, Schaub A, Wufka C, Blaukat A, Pfeffer K, Offermanns S: PUMA-G and HM74 are receptors for nicotinic acid and mediate its anti-lipolytic effect. Nat Med. 2003 Mar;9(3):352-5. Epub 2003 Feb 3.
22. Muller B, Kasper M, Surber C, Imanidis G: Permeation, metabolism and site of action concentration of nicotinic acid derivatives in human skin. Correlation with topical pharmacological effect. Eur J Pharm Sci. 2003 Oct;20(2):181-95.
23. Chekalina SI, Guseva LI, Bardyechev MS: [Use of nicotinic acid and midocalm for correcting blood coagulation in patients with radiation edema of the extremities]. Med Radiol (Mosk). 1985 Aug;30(8):28-30.
24. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59.
25. Gopal E, Fei YJ, Miyauchi S, Zhuang L, Prasad PD, Ganapathy V: Sodium-coupled and electrogenic transport of B-complex vitamin nicotinic acid by slc5a8, a member of the Na/glucose co-transporter gene family. Biochem J. 2005 May 15;388(Pt 1):309-16.
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=12563315
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=12789870
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=15037193
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=15183629
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=15205990
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=15311728
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=15627518
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=16018787
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=16172771
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=16400392
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=16449845
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=16767301
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=16877271
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=16945375
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=18037924
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=18993152
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=18996527
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=19369827
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=19592242
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=19678716
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=19779335
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=20979384
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=21632263
49. https://www.ncbi.nlm.nih.gov/pubmed/?term=22116693
50. https://www.ncbi.nlm.nih.gov/pubmed/?term=22155410
51. https://www.ncbi.nlm.nih.gov/pubmed/?term=22229411
52. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366213
53. https://www.ncbi.nlm.nih.gov/pubmed/?term=22458880
54. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
55. https://www.ncbi.nlm.nih.gov/pubmed/?term=24568240
56. https://www.ncbi.nlm.nih.gov/pubmed/?term=24675661
57. https://www.ncbi.nlm.nih.gov/pubmed/?term=24848081
58. https://www.ncbi.nlm.nih.gov/pubmed/?term=24975217
59. https://www.ncbi.nlm.nih.gov/pubmed/?term=25040591
60. https://www.ncbi.nlm.nih.gov/pubmed/?term=25241762
61. https://www.ncbi.nlm.nih.gov/pubmed/?term=25429652
62. https://www.ncbi.nlm.nih.gov/pubmed/?term=4259917