64091-91-4 Usage
Uses
Used in Toxicological Research:
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE is used as a research compound for studying the carcinogenic effects of nitrosamines in smokeless tobacco. Its presence in high concentrations in smokeless tobacco makes it a valuable tool for understanding the mechanisms of cancer development and progression in rats and hamsters.
Used in Public Health and Regulatory Efforts:
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE is used as a reference compound in public health and regulatory efforts to assess the safety of smokeless tobacco products. Its carcinogenic properties highlight the need for stringent regulations and consumer awareness about the potential health risks associated with the use of smokeless tobacco.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 64091-91-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,0,9 and 1 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 64091-91:
(7*6)+(6*4)+(5*0)+(4*9)+(3*1)+(2*9)+(1*1)=124
124 % 10 = 4
So 64091-91-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H13N3O2/c14-10(4-2-6-12-8-13-15)9-3-1-5-11-7-9/h1,3,5,7,12H,2,4,6,8H2
64091-91-4Relevant academic research and scientific papers
Methyl DNA Phosphate Adduct Formation in Rats Treated Chronically with 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone and Enantiomers of Its Metabolite 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
Ma, Bin,Zarth, Adam T.,Carlson, Erik S.,Villalta, Peter W.,Upadhyaya, Pramod,Stepanov, Irina,Hecht, Stephen S.
, p. 48 - 57 (2018/05/04)
The tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a powerful lung carcinogen in animal models and is considered a causative factor for lung cancer in tobacco users. NNK is stereoselectively and reversibly metabolized
Synthesis of [4-2H2]-, (4R)[4-2H1]-and (4S)[4-2H1]- 4-(methylnitrosamino)-1 -(3′-pyridyl)-1-butanone, c-4 deuteriated isotopomers of the procarcinogen nnk
Pathak, Tanmaya,Thomas, Noel F.,Akhtar, Mahmoud,Gani, David
, p. 1733 - 1744 (2007/10/02)
The synthesis of C-4 dideuteriated and both C-4 monodeuteriated enantiomers of NNK, the metabolic precursor to a variety of potential carcinogens, starting from (2S)-glutamic acid and nicotinic acid is described. The route is suitable for the synthesis of NNK isotopomers labelled in each of the putative sites for metabolic activation.
