ContaminantDB: Niacinamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:48:50 UTC

Update Date

2026-04-17 19:49:51 UTC

Accession Number

CHEM003128

Identification

Common Name

Niacinamide

Class

Small Molecule

Description

Nicotinamide is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Niacinamide or vitamin B3 is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. Niacinamide is used to increase the effect of radiation therapy on tumor cells. Niacin (nicotinic acid) and niacinamide, while both labeled as vitamin B3 also have different applications. Niacinamide is useful in arthritis and early-onset type I diabetes while niacin is an effective reducer of high cholesterol levels.

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Ester
Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Pyridinecarboxamide	ChEBI
beta-Pyridinecarboxamide	ChEBI
Niacin	ChEBI
Nicotinamid	ChEBI
Nicotinic acid amide	ChEBI
Nicotinsaeureamid	ChEBI
Nikotinamid	ChEBI
Nikotinsaeureamid	ChEBI
Vitamin b3	ChEBI
Vitamin PP	ChEBI
Nicotinamide	Kegg
b-Pyridinecarboxamide	Generator
Β-pyridinecarboxamide	Generator
Nicotinate amide	Generator
3-Carbamoylpyridine	HMDB
3-Pyridinecarboxylic acid amide	HMDB
Acid amide	HMDB
Amid kyseliny nikotinove	HMDB
Amide PP	HMDB
Aminicotin	HMDB
Amixicotyn	HMDB
Amnicotin	HMDB
Austrovit PP	HMDB
Benicot	HMDB
Delonin amide	HMDB
Dipegyl	HMDB
Dipigyl	HMDB
Endobion	HMDB
Factor PP	HMDB
Hansamid	HMDB
Inovitan PP	HMDB
m-(Aminocarbonyl)pyridine	HMDB
Mediatric	HMDB
NAM	HMDB
Nandervit-N	HMDB
Niacevit	HMDB
Niamide	HMDB
Niavit PP	HMDB
Nicamide	HMDB
Nicamina	HMDB
Nicamindon	HMDB
Nicasir	HMDB
Nicobion	HMDB
Nicofort	HMDB
Nicogen	HMDB
Nicomidol	HMDB
Nicosan 2	HMDB
Nicosylamide	HMDB
Nicota	HMDB
Nicotamide	HMDB
Nicotilamide	HMDB
Nicotililamido	HMDB
Nicotinamida	HMDB
Nicotinamidum	HMDB
Nicotine acid amide	HMDB
Nicotine amide	HMDB
Nicotinic amide	HMDB
Nicotinsaureamid	HMDB
Nicotol	HMDB
Nicotylamide	HMDB
Nicotylamidum	HMDB
Nicovel	HMDB
Nicovit	HMDB
Nicovitina	HMDB
Nicovitol	HMDB
Nicozymin	HMDB
Nictoamide	HMDB
Niko-tamin	HMDB
Niocinamide	HMDB
Niozymin	HMDB
Papulex	HMDB
Pelmin	HMDB
Pelmine	HMDB
Pelonin amide	HMDB
PP-Faktor	HMDB
Propamine a	HMDB
Pyridine-3-carboxylic acid amide	HMDB
Savacotyl	HMDB
Vi-nicotyl	HMDB
Vi-noctyl	HMDB
Witamina PP	HMDB
3 Pyridinecarboxamide	HMDB
Astra brand OF niacinamide	HMDB
b 3, Vitamin	HMDB
Niacinamide merck brand	HMDB
Pharmagenix brand OF niacinamide	HMDB
b3, Vitamin	HMDB
Enduramide	HMDB
Jenapharm, nicotinsäureamid	HMDB
Niacinamide jenapharm brand	HMDB
Niacinamide pharmagenix brand	HMDB
Jenapharm brand OF niacinamide	HMDB
Nicotinsäureamid jenapharm	HMDB
Vitamin b 3	HMDB
Merck brand OF niacinamide	HMDB
Niacinamide astra brand	HMDB
Niacinamide	ChEBI

Chemical Formula

C₆H₆N₂O

Average Molecular Mass

122.125 g/mol

Monoisotopic Mass

122.048 g/mol

CAS Registry Number

98-92-0

IUPAC Name

pyridine-3-carboxamide

Traditional Name

nicotinamide

SMILES

NC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

InChI Key

DFPAKSUCGFBDDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

Alternative Parents

Substituents

Nicotinamide
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine alkaloid (CHEBI:17154 )
pyridinecarboxamide (CHEBI:17154 )
Water-soluble vitamins (C00153 )
Pyridine alkaloids (C00153 )
a vitamin (NIACINAMIDE )
an aliphatic amide (NIACINAMIDE )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Bladder
Fibroblasts
Neuron
Pancreas
Placenta
Prostate
Skin
Spleen
Stratum Corneum

Pathways

Name	SMPDB Link	KEGG Link
Nicotinate and Nicotinamide Metabolism	SMP00048	map00760

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	130°C
Boiling Point	334°C
Solubility	500 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	50.1 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.39	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	3.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.98 m³·mol⁻¹	ChemAxon
Polarizability	11.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-0900000000-acb6a21304b0c09c8472	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004r-0900000000-ce86dcff0153b66dd538	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9500000000-790385e574240b8d39de	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-2910000000-d760b65bb76d6464038e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-4900000000-47c6f72d1bb5465c1376	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-1809e537780b814af0c9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-c4a5ff5285417499eff8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-0e84a60cc2a2d44704f4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-acb6a21304b0c09c8472	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004r-0900000000-ce86dcff0153b66dd538	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9500000000-790385e574240b8d39de	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-2910000000-d760b65bb76d6464038e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-4900000000-47c6f72d1bb5465c1376	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-23a567506bfbc259e77c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-8900000000-931c139355be3ef594f2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-2900000000-72a7c92eb2667f5b6c3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kor-9800000000-89d56b6cb7e033699d24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-eed71abbb10ba926c13d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9100000000-4357a8833611d1756c59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-c9685717817d0081fe6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f6d71a6c467f84ddd6ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-62c4bd312efbfa37d1a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-05714b528dc84942b9db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-edb6a77c0dfdcbdacc5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-eed71abbb10ba926c13d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-4357a8833611d1756c59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-c9685717817d0081fe6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0900000000-960acce7ead55399b5db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c7ec333d35eb740520a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-9600000000-466f98885e2efba73575	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-f38177aa475e58941088	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9800000000-6a883d82fcd7c450f6ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-882d0c59d946a5087b9f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-9600000000-2b1c5667d92bc1b80b36	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as nicotinamide are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (3). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (4).

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

DB02701

HMDB ID

HMDB0001406

FooDB ID

FDB012485

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Helmut Beschke, Heinz Friedrich, Klaus-Peter Muller, Gerd Schreyer, “Process for the production of nicotinamide.” U.S. Patent US4314064, issued May, 1949.

MSDS

Link

General References

1. Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.

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. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.

4. Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6.

5. 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

6. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

7. Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/

8. Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.

9. Draelos ZD, Ertel K, Berge C: Niacinamide-containing facial moisturizer improves skin barrier and benefits subjects with rosacea. Cutis. 2005 Aug;76(2):135-41.