72345

Nicotinamide

≥98.5% (HPLC)

• Synonym(s): Niacinamide, Nicotinic acid amide, Pyridine-3-carboxylic acid amide, Vitamin B₃, Vitamin PP
• Empirical Formula (Hill Notation): C₆H₆N₂O
• CAS Number: 98-92-0
• Molecular Weight: 122.12
• Beilstein: 383619
• EC Number: 202-713-4
• MDL number: MFCD00006395
• UNSPSC Code: 12352200
• PubChem Substance ID: 329764008
• NACRES: NA.77

Properties

• biological source: synthetic
• Quality Level: 200
• 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

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319
• Precautionary Statements: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): 302.0 °F - closed cup
• Flash Point(C): 150 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves