Description
N-Nitrosopyrrolidine (NPYR) is a nitrosamine compound that
is used primarily as a research chemical and is not produced
commercially. There is the possibility of generating NPYR after
frying in dry-cured bacon. The major amine precursors to NPYR
in cooked bacon are free proline in the adipose tissue and to
a lesser extent, collagenous connective tissues. When proline
peptides were heated with nitrite at pH 3.4, small amounts of
NPYR were formed from all tested peptides. There are several
potential sources of exposure of man to this group of potent
carcinogens. Certain foods were thought to be derived from the
interaction of nitrite with secondary amines in the food, either
spontaneously or by the agency of bacteria. Recently the
possibility that nitrosamines may be formed from secondary
amines and nitrite in the gastrointestinal tract has been
explored. The acid conditions that prevail in the human
stomach favor the nitrosation of dimethylamine. In addition,
at neutral pH, many secondary amines can be nitrosated by
nitrite or nitrate in the presence of intestinal bacteria, or the
cecal contents of the rat, and soluble enzymes which catalyze
the N-nitrosation of several secondary amines have been
extracted from two microorganisms. The rate of nitrosamine
formation depends greatly on the basicity of the amine; the less
basic amines such as diphenylamine and pyrrolidine are
nitrosated far more readily than the strongly basic dimethylamine
and diethylamine.
Chemical Properties
Light-Yellow Oil
Chemical Properties
N-Nitrosopyrrolidine is a yellow liquid.
Uses
One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated.
Uses
1-Nitrosopyrrolidine is one of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis (1,2,3) but the toxicological mechanisms involved have not been elucidated. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
Definition
ChEBI: N-Nitrosopyrrolidine is a member of pyrrolidines.
General Description
Yellow liquid found in certain food products and tobacco smoke. Probably a carcinogen.
Air & Water Reactions
Soluble in water.
Reactivity Profile
A cyclic nitrosamine. Nitrated organics, such as N-NITROSOPYRROLIDINE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction.
Health Hazard
ACUTE/CHRONIC HAZARDS: Flammable.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by ingestion and subcutaneous routes.
Human mutation data reported. When
heated to decomposition it emits toxic
fumes of NOx. See also N-NITROSO
COMPOUNDS.
Potential Exposure
N-Nitrosopyrrolidine is a cyclic
nitrosamine and a research chemical. Not commercially
produced in the U.S.
Carcinogenicity
N-Nitrosopyrrolidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
It is a yellow liquid at room temperature. It is totally soluble in
water with solubility of 1.00×10+6 mg l
-1 and also is soluble
in organic liquids and lipids. Log Pow is -0.19 that expected to
move readily from water to soil, sediment, or biota. According
to Henry’s law constant 4.89×10
-8 atmm
3 mol
-1 and vapor
pressure 0.06 mmHg in 20 ℃, volatilization from water and
solid surface is expected to be rapid and an important fate
process.
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name
Required. UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required
Toxicity evaluation
2-OHTHF and several other reactive electrophilic intermediates
can bind with proteins and form DNA adducts mainly with
guanines.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides.
Waste Disposal
Under 40 CFR 261.5 small
quantity generators of this waste may qualify for partial
exclusion from hazardous waste regulations. Consult with
environmental regulatory agencies for guidance on
acceptable disposal practices. Generators of waste containing
this contaminant (≥100 kg/mo) must conform with
EPA regulations governing storage, transportation, treatment,
and waste disposal.
