N-Methyl-N-nitrosoaniline

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 154(SRC), determined from an estimated log Kow of 1.49(2,SRC) and a recommended regression-derived equation(3), N-methyl-N-nitrosobenzenamine is expected to have moderately high mobility in soil(SRC). Volatilization of N-methyl-N-nitrosobenzenamine from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). N-Methyl-N-nitrosobenzenamine is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.154 mm Hg(SRC), determined from a fragment constant method(5). Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 154(SRC), determined from an estimated log Kow of 1.49(2,SRC) and a recommended regression-derived equation(3), indicates that N-methyl-N-nitrosobenzenamine is not expected to adsorb to any significant extent to suspended solids and sediment in water(SRC). N-Methyl-N-nitrosobenzenamine may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 9 and 69, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 8(3,SRC), from an estimated log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine(SRC). N-Methyl-N-nitrosobenzenamine may undergo hydrolysis in the environment due to the presence of hydrolyzable functional groups(3,SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-methyl-N-nitrosobenzenamine, which has an estimated vapor pressure of 0.154 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-methyl-N-nitrosobenzenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 1.2 days(3,SRC). Any particulate-phase N-methyl-N-nitrosobenzenamine may be physically removed from the air by wet and dry deposition(SRC). The maximum adsorption of N-methyl-N-nitrosobenzenamine, dissolved in methanol, in the UV spectrum was determined to be 270 nm, with adsorption reported up to 350 nm(4), suggesting that N-methyl-N-nitrosobenzenamine may directly photolyze since it has some adsorption above 290 nm (sunlight)(SRC).

An N-methyl-N-nitrosobenzenamine concentration of 9 ng/ul in organic chemicals was identified in an industrial wastewater survey in which samples collected between November 1, 1979 to November 1, 1981 were analyzed for organic pollutants other than Priority Pollutants(1).

The Koc of N-methyl-N-nitrosobenzenamine is estimated as approximately 154(SRC), using an estimated log Kow of 1.49(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that N-methyl-N-nitrosobenzenamine is expected to have moderately high mobility in soil(SRC).

... FETAL TISSUES ARE ESP SUSCEPTIBLE TO TRANSPLACENTAL CARCINOGENESIS, & TO SOME CMPD ... SUCH AS METHYLNITROSOANILINE ... WHICH PRODUCE PROFOUND TERATOGENIC EFFECTS AT CRITICAL PERIODS IN EMBRYOGENESIS, BUT WHICH CAUSE CARCINOGENESIS WHEN ADMIN LATER IN GESTATION.

... Health hazards ... related to the consumption of water containing large concentrations of nitrate (or nitrite) ... /include/ potential formation of carcinogenic nitrosamines. /Nitrosamines/

An estimated BCF of 8 was calculated for N-methyl-N-nitrosobenzenamine(SRC), using an estimated log Kow of 1.49(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF suggests that bioconcentration in aquatic organisms is low.

The Henry's Law constant for n-methyl-N-nitrosobenzeneamine is estimated as 4.83X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that N-methyl-N-nitrosobenzenamine is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 9 days(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 69 days(2,SRC). N-Methyl-N-nitrosobenzenamine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). N-Methyl-N-nitrosobenzenamine is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.154 mm Hg(SRC), determined from a fragment constant method(3).

PRINCIPAL ORGANS AFFECTED BY CARCINOGENIC ACTIVITY OF N-NITROSO-N-METHYLANILINE IN RAT ARE ESOPHAGUS, PHARYNX & FORESTOMACH; & IN MOUSE, THE LUNGS. /FROM TABLE/

N-METHYL-N-NITROSOANILINE INCR PRECANCEROUS PROCESSES & APPEARANCE OF CANCEROUS FLAT CELLS IN ESOPHAGUS OF RATS EXPOSED TO IRRITANTS, SUCH AS TEA EXTRACTS, TOBACCO SMOKE OR ALCOHOL.

N-METHYL-N-NITROSANILINE INDUCED TUMORS IN RATS' ESOPHAGUS EPITHELIUM. AT LOW DOSES, ACANTHOSIS, HYPERKERATOSIS, PARAKERATOSIS, LEUKOPLAKIA, LEUKOKERATOSIS, PAPILLOMA, INTRAEPITHELIAL CANCER, & INVASIVE SPINAL CELLULAR CANCER WERE OBSERVED.

ACUTE & CHRONIC TOXICITIES OF N-NITROSO-N-METHYLANILINE & N-NITROSO-N-METHYLCYCLOHEXYLAMINE IN RATS OF BOTH SEXES SHOWED THAT NMA WAS A POWERFUL CONVULSANT IN RODENTS. CHRONIC ADMIN SHOWED BOTH TO BE CARCINOGENS ACTING MAINLY IN UPPER ALIMENTARY TRACT.

For more Non-Human Toxicity Excerpts (Complete) data for N-METHYL-N-NITROSOBENZENAMINE (12 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of N-methyl-N-nitrosobenzenamine with photochemically-produced hydroxyl radicals has been estimated as 1.36X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The maximum adsorption of N-methyl-N-nitrosobenzenamine, dissolved in methanol, in the UV spectrum was determined to be 270 nm, with adsorption reported up to 350 nm(2), suggesting that N-methyl-N-nitrosobenzenamine may directly photolyze since it has some adsorption above 290 nm (sunlight)(SRC). N-Methyl-N-nitrosobenzenamine may be expected to undergo hydrolysis in the environment due to hydrolyzable functional groups(3).

N-Methyl-N-nitrosobenzenamine's presence in organic chemical effluent has been reported. If released into the atmosphere, N-methyl-N-nitrosobenzenamine will exist predominantly in the vapor phase in the ambient atmosphere, based on an estimated vapor pressure of 0.154 mm Hg at 25 °C. Vapor phase N-methyl-N-nitrosobenzenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals with a half-life of about 1.2 days. An estimated Koc value of 154 suggests that N-methyl-N-nitrosobenzenamine will have moderately high mobility in soil. Volatilization from moist soil may occur based upon an estimated Henry's Law constant of 4.83X10-6 atm-cu m/mole. Volatilization from dry soil surfaces should not be important given the vapor pressure of this compound. Limited data are present in the scientific literature regarding the biodegradation of N-methyl-N-nitrosobenzenamine. In water, N-methyl-N-nitrosobenzenamine should not adsorb to sediment or particulate matter based on its Koc value. This compound may volatilize from water surfaces given its estimated Henry's Law constant. Bioconcentration in aquatic organisms should be low based upon an estimated BCF value of 8. Occupational exposure may occur through inhalation of dust particles and dermal contact with this compound at workplaces where N-methylaniline is produced or used. (SRC)

Toxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Nitrosamines/

The levels for nitrosamines through ingestion of contaminated water and contaminated aquatic organisms ... which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding criteria are 8.0 ng/l, 0.8 ng/l, and 0.08 ng/l, respectively. For consumption of aquatic organisms only, excluding consumption of water, the levels are 12,400 ng/l, 1,240 ng/l, and 124 ng/l, respectively. /Nitrosamines/

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1979) NOT PRODUCED COMMERCIALLY IN USA

Benzenamine, N-methyl-N-nitroso-: INACTIVE

A HIGH YIELD SYNTHESIS OF (14)C-RING-LABELED & (14)C-METHYL-LABELED N-METHYL-N-NITROSOANILINE IS DESCRIBED.