| Identification | More | [Name]
6-Aminopyridine-3-carboxamide | [CAS]
329-89-5 | [Synonyms]
2-AMINOPYRIDINE-5-CARBOXAMIDE
6-AMINO-3-PYRIDINECARBOXAMIDE
6-AMINONICOTINAMIDE
6-AMINOPYRIDINE-3-CARBOXAMIDE
2-Amino-5-carbamoylpyridine
3-Pyridinecarboxamide, 6-amino-
6-amino-3-pyridinecarboxamid
6-amino-nicotinamid
6-Aminonicotinic acid amide
6-aminonicotinicacidamide
6-Amino-nicotinsaeureamid
6-Aminonikotinsaeureamid
6-AN
6-ANA
Aminonicotinamide
FDA 0121
fda0121
NSC 21206
nsc21206
U-8774 | [EINECS(EC#)]
206-349-7 | [Molecular Formula]
C6H7N3O | [MDL Number]
MFCD00006327 | [Molecular Weight]
137.14 | [MOL File]
329-89-5.mol |
| Chemical Properties | Back Directory | [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) | [NIST Chemistry Reference]
Nicotinamide, 6-amino-(329-89-5) | [EPA Substance Registry System]
6-Aminonicotinamide (329-89-5) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R61:May cause harm to the unborn child. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
1655 | [WGK Germany ]
3
| [RTECS ]
US4550000
| [Hazard Note ]
Toxic | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [General Description]
White crystalline solid. | [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). | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of NOx. | [Fire Hazard]
Flash point data for this chemical are not available; however, 6-AMINONICOTINAMIDE(329-89-5) is probably combustible. | [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. | [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). |
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