Back Niasien Afrikaans نياسين Arabic Nikotin turşusu Azerbaijani Нікацінавая кіслата Byelorussian Nicotinsäure German Niacino Esperanto نیاسین Persian Nikotiinihappo Finnish Aigéad nicitíneach Irish नाइयासिन Hindi

Niacin

Niacin
Kekulé, skeletal formula of niacin
Kekulé, skeletal formula of niacin
Ball and stick model of niacin
Ball and stick model of niacin
Names
Pronunciation /ˈnaɪəsɪn/
Preferred IUPAC name
Pyridine-3-carboxylic acid[1]
Other names
  • Nicotinic acid (INN)
  • Bionic
  • Vitamin B3
  • Vitamin PP
Identifiers
3D model (JSmol)
3DMet
109591
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.401 Edit this at Wikidata
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) checkY
    Key: PVNIIMVLHYAWGP-UHFFFAOYSA-N checkY
  • 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[citation needed]
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:
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)
Niacin
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 Edit this at Wikidata
Space-filling model of niacin

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient.[3] It is produced by plants and animals from the amino acid tryptophan.[4] Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds.[3][5] Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness.[6] Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.[3][7]

The amide derivative nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+). Although niacin and nicotinamide are identical in their vitamin activity, nicotinamide does not have the same pharmacological, lipid-modifying effects or side effects as niacin, i.e., when niacin takes on the -amide group, it does not reduce cholesterol nor cause flushing.[8][9] Nicotinamide is recommended as a treatment for niacin deficiency because it can be administered in remedial amounts without causing the flushing, considered an adverse effect.[10]

Niacin is also a prescription medication.[11] 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 niacin. 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.[11] Despite the proven lipid changes, niacin has not been found useful for decreasing the risk of cardiovascular disease in those already on a statin.[12] A 2010 review had concluded that niacin was effective as a mono-therapy,[13] but a 2017 review incorporating twice as many trials concluded that prescription niacin, while affecting lipid levels, did not reduce all-cause mortality, cardiovascular mortality, myocardial infarctions, nor fatal or non-fatal strokes.[14] Prescription niacin was shown to cause hepatotoxicity[15] and increase risk of type 2 diabetes.[16][17] Niacin prescriptions in the U.S. had peaked in 2009, at 9.4 million,[citation needed] declining to 800 thousand by 2020.[18]

Niacin has the formula C
6H
5NO
2 and belongs to the group of the pyridinecarboxylic acids.[3] As the precursor for nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate, niacin is involved in DNA repair.[19]

  1. ^ "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.
  2. ^ "Niacin Use During Pregnancy". Drugs.com. 29 July 2019. Archived from the original on 5 August 2020. Retrieved 4 May 2020.
  3. ^ a b c d "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.
  4. ^ Cite error: The named reference DRItext was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference NIH Fact Sheet was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Hegyi2004 was invoked but never defined (see the help page).
  7. ^ "Why fortify?". Food Fortification Initiative. 2017. Archived from the original on 4 April 2017. Retrieved 4 April 2017.
  8. ^ Jaconello P (October 1992). "Niacin versus niacinamide". CMAJ. 147 (7): 990. PMC 1336277. PMID 1393911.
  9. ^ Kirkland JB (May 2012). "Niacin requirements for genomic stability". Mutation Research. 733 (1–2): 14–20. doi:10.1016/j.mrfmmm.2011.11.008. PMID 22138132. Archived from the original on 4 August 2020. Retrieved 3 July 2019.
  10. ^ Cite error: The named reference Pellagra And Its Prevention was invoked but never defined (see the help page).
  11. ^ a b "Niacin". Drugs.com. 16 March 2019. Archived from the original on 9 June 2020. Retrieved 27 April 2020.
  12. ^ Cite error: The named reference Kee2014 was invoked but never defined (see the help page).
  13. ^ 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.
  14. ^ Cite error: The named reference Schand2017 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference LiverTox2014 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Ong2014 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference Goldie2016 was invoked but never defined (see the help page).
  18. ^ "Niacin - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 7 October 2022.
  19. ^ 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.

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