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A68203

Sigma-Aldrich

6-Aminonicotinamide

99%

Synonym(s):

6AN, 6-Aminopyridine-3-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C6H7N3O
CAS Number:
329-89-5
Molecular Weight:
137.14
Beilstein:
116042
EC Number:
206-349-7
MDL number:
MFCD00006327
UNSPSC Code:
12352100
PubChem Substance ID:
24891142
NACRES:
NA.22

Assay

99%

form

powder

mp

245-248 °C (lit.)

SMILES string

NC(=O)c1ccc(N)nc1

InChI

1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)

InChI key

ZLWYEPMDOUQDBW-UHFFFAOYSA-N

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General description

6-Aminonicotinamide is an aminopyridine, which is a specific pentose inhibitor and thus inhibits the NADP production.

Application

6-Aminonicotinamide can be used as a reactant:
  • For the synthesis of 6-substituted imidazo[1,2-a]pyridines with potential application as chemotherapeutic drugs.
  • In the dehydrative N-monobenzylation.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water.
Hikawa H, et al.
Green Chemistry, 20(13), 3044-3049 (2018)
6-Substituted imidazo [1, 2-a] pyridines: Synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2.
Dahan-Farkas N, et al.
European Journal of Medicinal Chemistry, 46(9), 4573-4583 (2011)
Laurent M Paardekooper et al.
Frontiers in immunology, 10, 1216-1216 (2019-06-14)
Neutrophils kill ingested pathogens by the so-called oxidative burst, where reactive oxygen species (ROS) are produced in the lumen of phagosomes at very high rates (mM/s), although these rates can only be maintained for a short period (minutes). In contrast
Electrocatalytic synthesis of 6-aminonicotinic acid at silver cathodes under mild conditions.
Gennaro A, et al.
Electrochemical Communications, 6(7), 627-631 (2004)
Jorge Domínguez-Andrés et al.
PLoS pathogens, 13(9), e1006632-e1006632 (2017-09-19)
Monocytes are innate immune cells that play a pivotal role in antifungal immunity, but little is known regarding the cellular metabolic events that regulate their function during infection. Using complementary transcriptomic and immunological studies in human primary monocytes, we show
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