Nicotinic acid (CED0000905)

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 belongs to the pyridinecarboxylic acids and derivatives, a subclass of pyridines and derivatives within the organic compounds. This endogenous compound has the formula C6H5NO2 and an average molecular weight of 123.11 g/mol. At room temperature, it exists as a solid. It is detected in most tissues, including the liver, kidney, intestine, skin, stratum corneum, skeletal muscle, adipose tissue, and fibroblasts. Nicotinic acid functions as a B vitamin, metabolite, and antioxidant (PMC7690615). It is a precursor to nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), which serve as vital cofactors for dozens of enzymes. Its recorded protein targets include nicotinamide N-methyltransferase (NNMT), hydroxycarboxylic acid receptor 2 (HCAR2), hydroxycarboxylic acid receptor 3 (HCAR3), and nicotinate-nucleotide pyrophosphorylase [carboxylating] (QPRT), and it acts as an inhibitor of diacylglycerol O-acyltransferase 2 (DGAT2). It binds to the niacin receptor, nicotinic acid phosphoribosyltransferase, and nicotinate D-ribonucleotide phyrophsopate phosphoribosyltransferase. The compound is utilized as an antilipemic drug, vasodilator agent, antidote, and antimicrobial agent (PMC13208484), as well as a general drug (PMC8839250). Industrially, it is used as a humectant, anti-static agent, and as a nutrient and flavouring. It is used in the treatment of cancer (PMC2887708) and schizophrenia (PMC8839250), and has a therapeutic effect on schizophrenia (PMC9826852). Nicotinic acid is found in 45 recorded sources, including drinking water, medical devices, synthetic textiles, and food processing. Exposure routes include oral, intravenous, intramuscular, topical, inhalation, and touch.
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
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
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-053i-0900000000-5daf0093df6c21c7279fNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-053i-0900000000-f38b6609b45de8c74565Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0540-0900000000-4f55c81a6cd42f1b961dNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-057r-5900000000-00bf3662b5b9db533c0aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0569-2900000000-7820ea736b03b71d2cb8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0kmi-7900000000-9e4efda763cce5ddfe57Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-053i-0900000000-5daf0093df6c21c7279fNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-053i-0900000000-f38b6609b45de8c74565Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0540-0900000000-4f55c81a6cd42f1b961dNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-057r-5900000000-00bf3662b5b9db533c0aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0569-2900000000-7820ea736b03b71d2cb8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0540-0900000000-a701904fe6ded0abd98fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05i0-9700000000-d7620f1dc8f42d1498b9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-9600000000-c3303cf4e83870b3e656Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-27508608b33f1fb9f221Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003r-9100000000-a2037c9695659dceabd1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-9100000000-4a2649a83ad2a40e5194Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0kmi-7900000000-1bc47d1b1850f54fb7c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-a352c5ce16d4b682b052Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-ab23ecb032e387b40bd9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-02e37a1cfd3947037579Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-75d7e6658d2d6eca736eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9000000000-21a2d68d4f364c596f1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0900000000-a74db528f61c435876c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-6900000000-773c08ab92ace4d48a9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00aj-9100000000-07b12fbe942e6c7fb12dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-66e0a5ba2ca8dbba1ed5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-fbf8ba47b56d7cc7be81Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-eaf82f6ab0befde118e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-eaf82f6ab0befde118e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9300000000-b1a48f694fba565108a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-a352c5ce16d4b682b052Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-ab23ecb032e387b40bd9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-02e37a1cfd3947037579Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-75d7e6658d2d6eca736eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9000000000-21a2d68d4f364c596f1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9300000000-b1a48f694fba565108a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-affdac58f480428e02c6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-19b41866469269d2235bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-b84242a938bd40d61ff6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-1174a7f46485752c0daaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ea-9400000000-4539592b8e6a4564120cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-df6b83e44b493afab79bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-82b9c8aec085da3d0553Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0900000000-a74db528f61c435876c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-6900000000-773c08ab92ace4d48a9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00aj-9100000000-7dcd57505ae0cfbee247Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-66e0a5ba2ca8dbba1ed5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-fbf8ba47b56d7cc7be81Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-eaf82f6ab0befde118e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-eaf82f6ab0befde118e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4l-9600000000-fc78f932208250ddafafNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-cc3a4b4e586e5dbe55beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ea-9500000000-c7860d4a7f2b8173d151Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-5e9c380c3aa111dc9147Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-6e60417b2d19f20855bbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001j-9200000000-d2cb18d79c804b6ced81Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003r-9200000000-d19de4320e8cf9d5b008Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-110e054beddf929edb0eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-1319c6281cdf7179f309Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-4900000000-d6b0e25449750e713edeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-3b0c41e632044921a155Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-f54ce72d8181f1cce1e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-df6b83e44b493afab79bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ea-9400000000-4539592b8e6a4564120cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-b84242a938bd40d61ff6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-1174a7f46485752c0daaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-eaf82f6ab0befde118e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005a-9000000000-82b9c8aec085da3d0553Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-7900000000-3e1db0cc8f0981a00f77Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00gi-9500000000-24a3c13da3a0535754daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-9000000000-df50a7c817d1359aa1e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-5c5b5936fd9c6a321319Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-9000000000-ec0572fe8d949ccdecf1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ai-9300000000-90f5a4a774e9f18a9100Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-c7515c1d47eb2a660bb2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-8af25c32bafc55380bccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-377c83c865133833bd87Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-9591390ac2514b2be258Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-dbd22d956a31aa9c5650Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9100000000-cb8086acfa9c493820e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-9ce5da573bc4b03c726fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-490e62707ffeaedf7ab4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-1ebdcfc1bef88a3c4c22Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-97f9300106631a379052Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fr-5900000000-e6c2c56ed37b826f4973Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9100000000-fd35b54f34200171ad97Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-9000000000-8b94531f1e3f3f5df5f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-25068c42378f72756922Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-3900000000-6278a1e122005f48fcafNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-9000000000-e4e41ed9bef32955889eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-4900000000-85d44ecd8ad348eeacd1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9300000000-4911305982583ae20895Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-4dea4a2d4a55907605eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-3900000000-ae4e653ffcdf40e3aafeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-9300000000-9e9fb47c4d0c68cbfeddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fb9-9000000000-50321c932955cf15a2b6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-c2850ce6846335b0374dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-c2850ce6846335b0374dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-0fbcd8c99379587a3b19Not AvailableView Spectrum
MSMS Spectrumsplash10-0kor-8900000000-7d3f033a49f5fad75f33Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
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.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
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)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
7000.0mg/kgNot AvailableRatLD50OralexperimentalT14
730.0mg/kgNot AvailableRatLD50IntraperitonealexperimentalT14
3500.0mg/kgNot AvailableMouseLD50SubcutaneousexperimentalT14
2468.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
canceris_treatment_forNot AvailablePMC2887708
schizophreniahas_therapeutic_effect_onNot AvailablePMC9826852
schizophreniais_treatment_forNot AvailablePMC8839250
pellagrahas_therapeutic_effect_onNot AvailablePMC8839250
pellagraassociated_withNot AvailablePMC8839250
pellagrais_treatment_forNot AvailablePMC8839250
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
291Peripheral vasodilatorsHealthcare, pharmaceuticals & veterinary productsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
495CeilingsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Aquaporin-4 structureClick to view 3D structureAquaporin-4P55087HumansPredicted (SEA)0.233548
Click to view 3D structureD-aspartate oxidaseQ922Z0Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureD-aspartate oxidaseD3ZDM7Rattus norvegicusPredicted (SEA)0.0778492
Lysine-specific demethylase 4C structureClick to view 3D structureLysine-specific demethylase 4CQ9H3R0HumansPredicted (SEA)5.99439
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)0.233548
Click to view 3D structureAdvanced glycosylation end product-specific receptorQ63495Rattus norvegicusPredicted (SEA)0.467095
Lysine-specific demethylase 4D structureClick to view 3D structureLysine-specific demethylase 4DQ6B0I6HumansPredicted (SEA)2.64687
Lysine-specific demethylase 4E structureClick to view 3D structureLysine-specific demethylase 4EB2RXH2HumansPredicted (SEA)3.11397
Lysine-specific demethylase 4A structureClick to view 3D structureLysine-specific demethylase 4AO75164HumansPredicted (SEA)4.7488
Click to view 3D structureBeta-lactamaseQ44079Aeromonas hydrophilaPredicted (SEA)0.389246
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)164.573
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)112.57
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)265.232
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)22.4984
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)3.26967
Lysine-specific demethylase 6B structureClick to view 3D structureLysine-specific demethylase 6BO15054HumansPredicted (SEA)4.04816
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)2.95827
Click to view 3D structureLysine-specific demethylase 3AQ9Y4C1HumansPredicted (SEA)2.33548
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)86.5683
Prolyl 4-hydroxylase subunit alpha-1 structureClick to view 3D structureProlyl 4-hydroxylase subunit alpha-1P13674HumansPredicted (SEA)0.0778492
Cytochrome P450 11B1, mitochondrial structureClick to view 3D structureCytochrome P450 11B1, mitochondrialP15538HumansPredicted (SEA)11.6774
Cytochrome P450 11B2, mitochondrial structureClick to view 3D structureCytochrome P450 11B2, mitochondrialP19099HumansPredicted (SEA)9.49761
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)102.917
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)131.643
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)114.516
Hydroxycarboxylic acid receptor 2 structureClick to view 3D structureHydroxycarboxylic acid receptor 2Q8TDS4HumansKnownNiacin 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. (A1386, A1387, A1388, A1380, A1381)
Hydroxycarboxylic acid receptor 3 structureClick to view 3D structureHydroxycarboxylic acid receptor 3P49019HumansKnownNiacin 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. (A1378, A1379, A1380, A1381, A1382)
Nicotinate-nucleotide pyrophosphorylase [carboxylating] structureClick to view 3D structureNicotinate-nucleotide pyrophosphorylase [carboxylating]Q15274HumansKnownNiacin 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. (A1383, A1384, A1385)
Nicotinamide N-methyltransferase structureClick to view 3D structureNicotinamide N-methyltransferaseP40261HumansKnownNiacin 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. (A358, A359)
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.
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