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72340

Sigma-Aldrich

Nicotinamide

≥99.5% (HPLC)

Synonym(s):
Niacinamide, Vitamin PP, Nicotinic acid amide, Vitamin B3, Pyridine-3-carboxylic acid amide
Empirical Formula (Hill Notation):
C6H6N2O
CAS Number:
Molecular Weight:
122.12
Beilstein:
383619
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

assay

≥99.5% (HPLC)

form

powder or crystals

application(s)

cell analysis: suitable

ign. residue

≤0.2%

loss

≤0.2% loss on drying, 20 °C (HV)

color

colorless to white

mp

128-131 °C (lit.)
128-131 °C

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤150 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

NC(=O)c1cccnc1

InChI

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

InChI key

DFPAKSUCGFBDDF-UHFFFAOYSA-N

Gene Information

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Application

Nicotinamide has been used:
  • to study its effect on the expression of sirtuin 1
  • in nicotinamide adenine dinucleotide/nicotinamide adenine dinucleotide phopshate (NAD+/NADH) cycling assay
  • in cell lysis buffer, to serve as a sirtuin 1 inhibitor in order to study its role in resveratrol (RSV)-stimulated hepatitis B virus replication

Biochem/physiol Actions

Nicotinamide is an amide derivative of vitamin B3 and a PARP inhibitor
The coenzymes NAD and NADP take part in energy yielding metabolism and mediate several oxidation-reduction reactions. NAD hydrolyses to form nicotinamide, which is then transported to other tissues. Hydrolysis of nicotinamide yields nicotinic acid through salvage pathway.
Nicotinamide (Niacinamide) (Nam) is a building block (active component) of coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phopshate (NADP). Nicotinamide may be used as a substrate of nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12), the rate-limiting enzyme for NAD(+) biosynthesis and an important signaling molecule.

Other Notes

Coenzymes and Cofactors, vol. 2: Pyridine Nucleotide Coenzymes

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

359.6 °F

Flash Point(C)

182 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

D.Dolphin, R.Poulson, O.Avramovic, eds.
Chemical, Biochemical and Medical Aspects, 759-759 (1987)
Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease
Lin Su-Ju and Guarente Leonard
Current Opinion in Cell Biology, 15(2), 241-246 (2003)
Control of mitochondrial pH by uncoupling protein 4 in astrocytes promotes neuronal survival
Lambert HP, et al.
The Journal of biological chemistry, jbc-M114 (2014)
Nicotinamide N-methyltransferase enhances the progression of prostate cancer by stabilizing sirtuin 1
You Z, et al.
Oncology Letters, 15(6), 9195-9201 (2018)
Resveratrol enhances HBV replication through activating Sirt1-PGC-1alpha-PPARalpha pathway
Shi Y, et al.
Scientific Reports, 6, 24744-24744 (2016)

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