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72345

Sigma-Aldrich

Nicotinamide

≥98.5% (HPLC)

Sinônimo(s):

Niacinamide, Nicotinic acid amide, Pyridine-3-carboxylic acid amide, Vitamin B3, Vitamin PP

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About This Item

Fórmula empírica (Notação de Hill):
C6H6N2O
Número CAS:
98-92-0
Peso molecular:
122.12
Beilstein:
383619
Número CE:
202-713-4
Número MDL:
MFCD00006395
Código UNSPSC:
12352200
ID de substância PubChem:
329764008
NACRES:
NA.77

fonte biológica

synthetic

Nível de qualidade

200

Ensaio

≥98.5% (HPLC)

forma

powder

cor

colorless to white

pf

128-131 °C (lit.)
128-131 °C

cadeia de caracteres SMILES

NC(=O)c1cccnc1

InChI

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

chave InChI

DFPAKSUCGFBDDF-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H319

Classificações de perigo

Eye Irrit. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

302.0 °F - closed cup

Ponto de fulgor (°C)

150 °C - closed cup

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificados de análise (COA)

Lot/Batch Number
BCCM2517
BCCL9151
BCCJ5590
BCCJ0769
BCCF7122

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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
PTEN alpha regulates mitophagy and maintains mitochondrial quality control
Li G, et al.
Autophagy, 14(10), 1742-1760 (2018)
Deacetylation of serine hydroxymethyl-transferase 2 by SIRT3 promotes colorectal carcinogenesis
Wei Z, et al.
Nature Communications, 9(1), 4468-4468 (2018)
Nicotinamide adenine dinucleotide is transported into mammalian mitochondria
Davila A, et al.
eLife, 7(9), e33246-e33246 (2018)
William J Quinn et al.
Cell reports, 33(11), 108500-108500 (2020-12-17)
Immune cell function is influenced by metabolic conditions. Low-glucose, high-lactate environments, such as the placenta, gastrointestinal tract, and the tumor microenvironment, are immunosuppressive, especially for glycolysis-dependent effector T cells. We report that nicotinamide adenine dinucleotide (NAD+), which is reduced to NADH
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