Nicotinic acid

"Niacin" redirects here. For the vitamin group, see Vitamin B3. For other uses, see Niacin (disambiguation).

Nicotinic acid
Names
Pronunciation /ˈnaɪəsɪn/
Preferred IUPAC name
Pyridine-3-carboxylic acid[2]
Other names
  • Niacin (USAN US)[1]
  • Bionic
  • Vitamin B3
  • Vitamin PP
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 109591
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.401
EC Number
  • 200-441-0
Gmelin Reference
 3340
KEGG
MeSH Niacin
PubChem CID
RTECS number
  • QT0525000
UNII
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
 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
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 (ΔfH⦵298)
 −344.9 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −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:
Pictograms
Signal word
 Warning
Hazard statements
 H319
Precautionary statements
 P264, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)
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 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
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,[a] or niacin,[b] is an organic compound and a vitamer of vitamin B3, an essential human nutrient.[4][5] It is produced by plants and animals from the amino acid tryptophan.[6]

Nicotinic acid is also a prescription medication.[7] 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.[7] 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.[8] A 2010 review had concluded that nicotinic acid was effective as a mono-therapy,[9] 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.[10] Prescription nicotinic acid was shown to cause hepatotoxicity[11] and increase risk of type 2 diabetes.[12][13] Nicotinic acid prescriptions in the U.S. had peaked in 2009 at 9.4 million, declining to 800 thousand by 2020.[14]

Nicotinic acid has the formula C
6H
5NO
2 and belongs to the group of the pyridinecarboxylic acids.[5] As the precursor for nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate, it is involved in DNA repair.[15]

Extra-terrestrial nicotinic acid has been found in carbonaceous chondrite meteorites[16] and in sample-returns from the asteroids 162173 Ryugu[17] and 101955 Bennu.[18]

  1. ^ Sweetman SC (2011). Martindale: the complete drug reference (37 ed.). London: Pharmaceutical press. p. 2117. ISBN 978-0-85369-933-0. OCLC 1256529676.
  2. ^ "Chapter P-6. Applications to Specific Classes of Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. pp. 648–1047. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  3. ^ "Niacin Use During Pregnancy". Drugs.com. 29 July 2019. Archived from the original on 5 August 2020. Retrieved 4 May 2020.
  4. ^ "Niacin Fact Sheet for Health Professionals". Office of Dietary Supplements, US National Institutes of Health. 18 November 2022. Retrieved 12 December 2024.
  5. ^ a b "Niacin". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR. 8 October 2018. Archived from the original on 12 September 2019. Retrieved 16 September 2019.
  6. ^ Institute of Medicine (1998). "Niacin". Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. Washington, DC: The National Academies Press. pp. 123–149. ISBN 978-0-309-06554-2. Archived from the original on 1 September 2018. Retrieved 29 August 2018.
  7. ^ a b "Niacin". Drugs.com. 16 March 2019. Archived from the original on 9 June 2020. Retrieved 27 April 2020.
  8. ^ Cite error: The named reference Kee2014 was invoked but never defined (see the help page).
  9. ^ Bruckert E, Labreuche J, Amarenco P (June 2010). "Meta-analysis of the effect of nicotinic acid alone or in combination on cardiovascular events and atherosclerosis". Atherosclerosis. 210 (2): 353–61. doi:10.1016/j.atherosclerosis.2009.12.023. PMID 20079494.
  10. ^ Cite error: The named reference Schand2017 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference LiverTox2014 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Ong2014 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Goldie2016 was invoked but never defined (see the help page).
  14. ^ "Niacin - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 7 October 2022.
  15. ^ Kennedy DO (January 2016). "B Vitamins and the Brain: Mechanisms, Dose and Efficacy—A Review". Nutrients. 8 (2): 68. doi:10.3390/nu8020068. PMC 4772032. PMID 26828517.
  16. ^ Oba Y, Takano Y, Furukawa Y, Koga T, Glavin DP, Dworkin JP, et al. (April 2022). "Identifying the wide diversity of extraterrestrial purine and pyrimidine nucleobases in carbonaceous meteorites". Nature Communications. 13 (1) 2008. Bibcode:2022NatCo..13.2008O. doi:10.1038/s41467-022-29612-x. PMC 9042847. PMID 35473908.
  17. ^ Oba Y, Koga T, Takano Y, Ogawa NO, Ohkouchi N, Sasaki K, et al. (21 March 2023). "Uracil in the carbonaceous asteroid (162173) Ryugu". Nature Communications. 14 (1) 1292. Bibcode:2023NatCo..14.1292O. doi:10.1038/s41467-023-36904-3. ISSN 2041-1723. PMC 10030641. PMID 36944653. S2CID 257641373.
  18. ^ Glavin DP, Dworkin JP, Alexander CM, Aponte JC, Baczynski AA, Barnes JJ, et al. (2025). "Abundant ammonia and nitrogen-rich soluble organic matter in samples from asteroid (101955) Bennu". Nature Astronomy. 9 (2): 199–210. Bibcode:2025NatAs...9..199G. doi:10.1038/s41550-024-02472-9. PMC 11842271. PMID 39990238.


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