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6-Aminopyridine-3-carboxamide

CAS No.329-89-5
Chemical Name:6-Aminopyridine-3-carboxamide
CBNumber:CB9224555
Molecular Formula:C6H7N3O
Formula Weight:137.14
MOL File:329-89-5.mol

6-Aminopyridine-3-carboxamide Property

Melting point 245-248 °C (lit.)
Boiling point 251.97°C (rough estimate)
Density 1.2620 (rough estimate)
refractive index 1.6910 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility insoluble in H2O; insoluble in EtOH; ≥13.7 mg/mL in DMSO
form powder to crystal
pka 15.66±0.50(Predicted)
color White to Light yellow
Water Solubility Soluble in Dimethyl sulfoxide (DMSO). Insoluble in water.
BRN 116042
CAS DataBase Reference 329-89-5(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII D6FNW67F2B
NIST Chemistry Reference Nicotinamide, 6-amino-(329-89-5)
EPA Substance Registry System 6-Aminonicotinamide (329-89-5)
UNSPSC Code 12352100
NACRES NA.22

Safety

Hazard Codes :T
Risk Statements :61
Safety Statements :53-45
RIDADR :1655
WGK Germany :3
RTECS :US4550000
Hazard Note :Toxic
HazardClass :6.1
PackingGroup :II
HS Code :29333990

NFPA 704:

	1
3		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H360FD
Precautionary statements P201-P308+P313

6-Aminopyridine-3-carboxamide Price More Price(6)

Brand: Sigma-Aldrich(India)
Product number: A68203
Product name : 6-Aminonicotinamide
Purity: 99%
Packaging: 1G
Price: ₹4178.45
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: A68203
Product name : 6-Aminonicotinamide
Purity: 99%
Packaging: 5G
Price: ₹34802.38
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Brand: TCI Chemicals (India)
Product number: A0986
Product name : 6-Aminonicotinamide
Purity:
Packaging: 1G
Price: ₹6700
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Brand: TCI Chemicals (India)
Product number: A0986
Product name : 6-Aminonicotinamide
Purity:
Packaging: 5G
Price: ₹27400
Updated: 2022/05/26
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Brand: ottokemi
Product number: A 8996
Product name : 6-Aminonicotinamide, 99%
Purity:
Packaging: 1gm
Price: ₹9603
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6-Aminopyridine-3-carboxamide Chemical Properties,Usage,Production

Uses 6-Aminonicotinamide induces apoptosis in tumor cells. It is clinically used in disseminated neoplastic disease. It also acts as 6-phosphogluconate dehydrogenase inhibitor. It aids in the treatment of psoriasis. It is used as cancer chemotherapeutic drug in animals.
Uses antineoplastic, apoptosis inducer
Definition ChEBI: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 6-aminonicotinic acid with ammonia. An inhibitor of the NADP+-dependent enzyme, 6-phosphogluconate dehydrogenase, it interferes with glycolysis resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as cisplatin, in killing cancer cells.
General Description White crystalline solid.
Air & Water Reactions Insoluble in water.
Reactivity Profile An amine and amide. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard ACUTE/CHRONIC HAZARDS: When heated to decomposition 6-Aminopyridine-3-carboxamide emits toxic fumes of NOx.
Fire Hazard Flash point data for 6-Aminopyridine-3-carboxamide are not available; however, 6-Aminopyridine-3-carboxamide is probably combustible.
Biological Activity ki: 0.46 μm6-aminonicotinamide is a 6-phosphogluconate dehydrogenase inhibitor.6-phosphogluconate dehydrogenase, an enzyme in the pentose phosphate pathway, can produce ribulose 5-phosphate from 6-phosphogluconate. 6-phosphogluconate dehydrogenase is also an oxidative carboxylase catalyzing the decarboxylating reduction of 6-phosphogluconate into ribulose 5-phosphate in the presence of nadp.
in vitro 6-aminonicotinamide could be metabolized to 6-amino-nad(p+), a competitive inhibitor of nad(p+)-requiring processes, especially the pentose phosphate pathway enzyme, 6-phosphogluconate dehydrogenase. moreove, 6-aminonicotinamide as a single agent could cause a significant inhibition of glycolytic flux but had no effect on the pentose phosphate pathway. 31p-nmr studies of perifused rif-1 cells indicated that 4 h of exposure to 6-aminonicotinamide was enough to cause significant accumulation of 6-phosphogluconate, the substrate for this enzyme [1].
in vivo the influence of 6-aminonicotinamide on the g-6-p-dh- and 6-pg-dh-levels of the pentose phosphate pathway in the kidney was investigated. following i.p. administration of 6-aminonicotinamide at 6 mg/kg, the 6-pg-level rose from a value less than 10 nmoles/g to 1000 nmoles/g fresh weight within 24 h. in addition, at the end of the assay, after 7 days, a 6-pg-concentration of about 150 nmoles/g fresh weight was still seen. moreove, the g-6-p level simultaneously rose with the 6-pg-level to about 150% of the control level and returned to normal on the 5th day [2].
References [1] street, j. c.,alfieri, a.a. and koutcher, j.a. quantitation of metabolic and radiobiological effects of 6-aminonicotinamide in rif-1 tumor cells in vitro. cancer research 57, 3956-3962 (1997).
[2] lange, k. and proft, e.r. inhibition of the 6-phosphogluconate dehydrogenase in the rat kidney by 6-aminonicotinamide. naunyn-schmiedeberg's archives of pharmacology 267, 177-180 (1970).