N-NITROSOPYRROLIDINE

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.

The Uses of N-NITROSOPYRROLIDINE

One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated.

The Uses of N-NITROSOPYRROLIDINE

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.

Fire Hazard

Combustible.

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 atmm³ 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.