Chemical Properties
Off-White Crystals
Uses
This compound was present in the highest concentrations in smokeless tobacco out of the nitrosamines identified. Readily produces cancer in rats and hamsters
Definition
ChEBI: 4-(N-nitrosomethylamino)-1-(3-pyridyl)butan-1-one is a nitrosamine and a member of pyridines.
Production Methods
NNK is not produced commercially. NNK is formed by
oxidation and nitrosation of nicotine and is produced during
the curing, aging, processing, and smoking of tobacco. NNK
has been found in tobacco at levels up to 35 mg/kg, in snuff up
to 8.3 mg/kg, and in cigarette smoke up to 0.5 mg per cigarette
(179, 193). Common cigarette filters considerably
reduce the amount of NNK that reaches the smoker. NNK
is extracted from snuff by the saliva of users, and as much as
0.2 μg/g of saliva has been measured. Potential exposure
to NNK is widespread also among those exposed to
sidestream smoke and has been detected at 0.2–15.7 μg/
cigarette. Evidence from one comparative study of
tobacco-specific nitrosamines in cigarettes suggests that
levels of NNK (measured as a sum of all tobacco-specific
nitrosamines) are higher in non-Moldovan cigarette tobacco
and Moldovan blended cigarettes, suggesting that current
tobacco production and manufacturing technologies may
create conditions that favor N-nitrosation of alkaloids and
other tobacco constituents.
General Description
Pale yellow crystalline solid.
Air & Water Reactions
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE may be sensitive to prolonged exposure to air and light.
Reactivity Profile
A nitrated amine and ketone. 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. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Fire Hazard
Flash point data for 4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE are not available; however, 4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. An experimental
teratogen. Mutation data reported. A
flammable liquid. When heated to
decomposition it emits toxic fumes of NOx.
Carcinogenicity
4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
