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72345

Sigma-Aldrich

Nicotinamide

≥98.5% (HPLC)

Synonyme(s) :

Acide nicotinique amide, Acide pyridine-3-carboxylique amide, Vitamine PP, Vitamine B3

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About This Item

Formule empirique (notation de Hill):
C6H6N2O
Numéro CAS:
98-92-0
Poids moléculaire :
122.12
Numéro Beilstein :
383619
Numéro CE :
202-713-4
Numéro MDL:
MFCD00006395
Code UNSPSC :
12352200
ID de substance PubChem :
329764008
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Niveau de qualité

200

Pureté

≥98.5% (HPLC)

Forme

powder

Couleur

colorless to white

Pf

128-131 °C (lit.)
128-131 °C

Chaîne SMILES 

NC(=O)c1cccnc1

InChI

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

Clé InChI

DFPAKSUCGFBDDF-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

302.0 °F - closed cup

Point d'éclair (°C)

150 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCF7122
BCCC7997
BCBZ9782
BCBX5160
BCBV4980

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Consulter la Bibliothèque de documents

Rūta Barisevičiūtė et al.
PloS one, 15(8), e0237605-e0237605 (2020-08-18)
The vertical distribution of radiocarbon (14C) was examined in the bottom sediment core, taken from Lake Drūkšiai, which has served as a cooling pond since 1983 for the 26 years of the Ignalina Nuclear Power Plant (INPP) operation using two
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)
Nicotinamide adenine dinucleotide is transported into mammalian mitochondria
Davila A, et al.
eLife, 7(9), e33246-e33246 (2018)
Andrew Philp et al.
American journal of physiology. Cell physiology, 299(2), C240-C250 (2010-04-23)
Sodium pyruvate can increase mitochondrial biogenesis in C2C12 myoblasts in a peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC1alpha)-independent manner. The present study examined the effect of 72-h treatment with sodium pyruvate (5-50 mM) or sodium chloride (50 mM) as an osmotic control
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