All Photos(2)

72345

Sigma-Aldrich

Nicotinamide

≥98.5% (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.77

Quality Level

biological source

synthetic

assay

≥98.5% (HPLC)

form

powder

color

colorless to white

mp

128-131 °C (lit.)
128-131 °C

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

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General description

Nicotinamide is synthesized in the liver from nicotinic acid. It is also produced as a result of nicotinamide adenine dinucleotide (NAD+) hydrolysis.

Application

Nicotinamide has been used:
  • as a precursor to study its effect on nicotinamide adenine dinucleotide (NAD) concentration in NAD-deficient mammalian mitochondria
  • as an inhibitor of sirtuin (SIRT) family of deacetylases in in vitro serine hydroxymethyltransferase 2 (SHMT2) deacetylation assay
  • to study its effect on ischemia-reperfusion (I-R) injury-induced cell death in ptenαm/m mice

Biochem/physiol Actions

Nicotinamide is an amide derivative of vitamin B3 and a PARP inhibitor
Nicotinamide serves as a precursor for β-nicotinamide adenine dinucleotide (NAD+) coenzyme production. It is involved in the synthesis of NAD+ phosphate (NADP+). It also regulates the mechanism of cell survival and cell death. Fatigue, skin pigmentation, decreased appetite and mouth ulcers are indications of nicotinamide deficiency. Its chronic deficiency can lead to pellagra. Nicotinamide is known to show protective effects on oxidative stress.

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

Nicotinamide adenine dinucleotide is transported into mammalian mitochondria
Davila A, et al.
eLife, 7(9), e33246-e33246 (2018)
Deacetylation of serine hydroxymethyl-transferase 2 by SIRT3 promotes colorectal carcinogenesis
Wei Z, et al.
Nature Communications, 9(1), 4468-4468 (2018)
PTEN alpha regulates mitophagy and maintains mitochondrial quality control
Li G, et al.
Autophagy, 14(10), 1742-1760 (2018)
Robert J Motzer et al.
The Lancet. Oncology, 14(6), 552-562 (2013-04-20)
In a phase 3 trial comparing the efficacy and safety of axitinib versus sorafenib as second-line treatment for metastatic renal cell carcinoma, patients given axitinib had a longer progression-free survival (PFS). Here, we report overall survival and updated efficacy, quality...
Thomas J Herzog et al.
Gynecologic oncology, 130(1), 25-30 (2013-04-18)
Sorafenib, an oral multikinase inhibitor of the VEGFR/PDGFR/Raf/MEK/ERK pathway, has shown potential activity in patients with recurrent ovarian cancer (OC). One strategy to prolong disease control and survival in patients with OC is maintenance therapy after achieving a complete response....

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