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Merck
CN

I17451

Sigma-Aldrich

Isonicotinamide

ReagentPlus®, 99%

Synonym(s):

Pyridine-4-carboxylic acid amide

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About This Item

Empirical Formula (Hill Notation):
C6H6N2O
CAS Number:
Molecular Weight:
122.12
Beilstein:
2173
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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product line

ReagentPlus®

Assay

99%

mp

155-157 °C (lit.)

SMILES string

NC(=O)c1ccncc1

InChI

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

InChI key

VFQXVTODMYMSMJ-UHFFFAOYSA-N

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Application

Isonicotinamide (pyridine-4-carboxamide) can be used as a heterocyclic building block to synthesize:
  • 4-oxo-1,3-thiazinan-3-yl isonicotinamide derivatives as potential anti-tubercular agents.
  • Organotin(IV) complexes of isonicotinamide via synthesis of phosphoramidate ligands for various biological activity studies.
  • Bis-pyridinium isonicotinamide derivatives of 2-(hydroxyimino)-N-(pyridin-3-yl)acetamide as potent reactivators sarin.

It can also be used as a co-former with active pharmaceutical ingredients (APIs) to prepare co-crystals.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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New organotin (IV) complexes of nicotinamide, isonicotinamide and some of their novel phosphoric triamide derivatives: Syntheses, spectroscopic study and crystal structures
Gholivand K, et al.
Journal of Organometallic Chemistry, 695(9), 1383-1391 (2010)
QSAR, docking studies of 1, 3-thiazinan-3-yl isonicotinamide derivatives for antitubercular activity
Chitre TS, et al.
Computational Biology and Chemistry, 68, 211-218 (2017)
Joseph A Baur
Biochimica et biophysica acta, 1804(8), 1626-1634 (2009-11-10)
SIRT1 is the closest mammalian homologue of enzymes that extend life in lower organisms. Its role in mammals is incompletely understood, but includes modulation of at least 34 distinct targets through its nicotinamide adenine dinucleotide (NAD(+))-dependent deacetylase activity. Recent experiments
Jianqi Yang et al.
The Journal of biological chemistry, 284(40), 27042-27053 (2009-08-05)
The SIRT1 activators isonicotinamide (IsoNAM), resveratrol, fisetin, and butein repressed transcription of the gene for the cytosolic form of phosphoenolpyruvate carboxykinase (GTP) (PEPCK-C). An evolutionarily conserved binding site for hepatic nuclear factor (HNF) 4alpha (-272/-252) was identified, which was required
Srinu Tothadi et al.
Philosophical transactions. Series A, Mathematical, physical, and engineering sciences, 370(1969), 2900-2915 (2012-05-23)
The idea of a structural landscape is based on the fact that a large number of crystal structures can be associated with a particular organic molecule. Taken together, all these structures constitute the landscape. The landscape includes polymorphs, pseudopolymorphs and

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