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6-Aminonicotinamide

6-Aminonicotinamide structure

CAS No:
329-89-5
Formula:
C6H7N3O
Chemical Name:
6-Aminonicotinamide
Synonyms:
3-Pyridinecarboxamide,6-amino-;Nicotinamide,6-amino-;6-Amino-3-pyridinecarboxamide;6-Aminonicotinamide;2-Amino-5-carbamoylpyridine;SR 4388;NSC 21206;5-Aminocarbonyl-2-Aminopyridine;6 AN
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

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.

6-aminonicotinamide is a white crystalline solid. (NTP, 1992)

6-aminonicotinamide is a white crystalline solid. (NTP, 1992)|6-aminonicotinamide is 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. It has a role as a teratogenic agent, an antimetabolite and an EC 1.1.1.44 (NADP(+)-dependent decarboxylating phosphogluconate dehydrogenase) inhibitor. It is an aminopyridine, a primary amino compound and a monocarboxylic acid amide. It derives from a 6-aminonicotinic acid.|6-Aminonicotinamide is a synthetic analogue and nicotinamide antagonist with cytotoxic properties, 6-Aminonicotinamide forms an abnormal NAD (ubiquitous metabolic pathway coenzyme) analog that inhibits NAD-dependent enzyme activity associated with ATP production. 6-Aminonicotinamide impairs cartilage formation, may have teratogenic effects, and enhances the effect of radiation and cisplatin treatment (formation of platinum-DNA complexes). (NCI04)|A vitamin antagonist which has teratogenic effects.

6-Aminonicotinamide Basic Attributes

Molecular Weight：

137.14

Exact Mass：

137.14

BRN：

116042

EC Number：

206-349-7

UNII：

D6FNW67F2B

NSC Number：

21206

DSSTox ID：

DTXSID5051446

NCI Thesaurus Code：

C38127

HScode：

2933399090

Characteristics

PSA：

XLogP3：

0.7

Appearance：

6-aminonicotinamide is a white crystalline solid. (NTP, 1992)

Density：

1.3±0.1 g/cm3

Melting Point：

200 °C

Boiling Point：

381.6°C at 760 mmHg

Flash Point：

184.6±23.7 °C

Refractive Index：

1.644

Water Solubility：

soluble in Dimethyl sulfoxide (DMSO). Insoluble in water.

Toxicity：

Peritoneal-rat LD50: 11 mg/kg; oral-mouse LDL0: 320 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

Collision Cross Section：

125.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Air and Water Reactions：

Insoluble in water.

Reactive Group：

Amides and Imides

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).

Safety Information

Packing level：

Hazard category：

6.1

Transport codes：

1655

wgk germany：

hazard class code：

safety instructions：

53-45

RTECS Number：

US4550000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Hazard note：

Toxic

Precautionary statement(s)：

P201-P308 + P313

Hazard Statements：

H360

Fire Hazards：

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Fire Fighting：

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Nonfire Spill Response：

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in ambient temperatures. (NTP, 1992)

Personal Protective Equipment：

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)

Health Hazards：

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of NOx. (NTP, 1992)

First Aid：

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

MeSH Entry Terms：

6 Aminonicotinamide

6-Aminonicotinamide Use and Manufacturing

antineoplastic, apoptosis inducer

Computed Properties

Molecular Weight:137.14
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.058911855
Monoisotopic Mass:137.058911855
Topological Polar Surface Area:82
Heavy Atom Count:10
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 329-89-5

Grade: Industrial Grade

Content: 99%

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