4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE Chemical Properties

Melting point:

63-65°C

Boiling point:

346.25°C (rough estimate)

Density 

1.1933 (rough estimate)

refractive index 

1.4830 (estimate)

Flash point:

9℃

storage temp. 

Amber Vial, -20°C Freezer

solubility 

DMF: 30 mg/ml, DMSO: 25 mg/ml, Ethanol: 25 mg/ml,

pka

3.19±0.10(Predicted)

form 

Solid

color 

White to light yellow

BRN 

3548355

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

InChIKey

FLAQQSHRLBFIEZ-UHFFFAOYSA-N

SMILES

C(C1=CC=CN=C1)(=O)CCCN(C)N=O

CAS DataBase Reference

64091-91-4

IARC

1 (Vol. Sup 7, 89, 100E) 2012

EPA Substance Registry System

4-(Nitrosomethylamino)-1-(3-pyridyl)-1-butanone (64091-91-4)

Safety Information

Hazard Codes 

Xn,T,F

Risk Statements 

26/27/28-45-43-40-22-39/23/24/25-23/24/25-11

Safety Statements 

45-53-36/37-16

RIDADR 

2811

WGK Germany 

3

RTECS 

OB6465000

HazardClass 

6.1

PackingGroup 

II

HS Code 

38220090

Hazardous Substances Data

64091-91-4(Hazardous Substances Data)

Toxicity

LD50 intraperitoneal in mouse: 1gm/kg

MSDS

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4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE Usage And Synthesis

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

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.

Definition

ChEBI: 4-(N-nitrosomethylamino)-1-(3-pyridyl)butan-1-one is a nitrosamine and a member of pyridines.

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.

4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE(64091-91-4)Related Product Information

• 4-(N-METHYL-N-NITROSOAMINO)-1-(3-PYRIDYL-D4)-1-BUTANONE
• 4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone
• 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone N-b-D-Glucuronide
• 4-(Acetoxymethyl)nitrosamino]-1-(3-pyridyl)-1-butanone
• 4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanone
• 4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE
• NNK-d3, 4-(Methyl-d3-nitrosoamino)-1-(3-pyridinyl)-1-butanone
• 2-HYDROXYIMINO-4-METHYLNITROSAMINO-1-(3-PYRIDYL)-1-BUTANONE
• (RS)-4-(N-METHYL-N-NITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE, [PYRIDYL-5-3H]-