2,4,5-Trimethylaniline

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 198(SRC), determined from a structure estimation method(2), indicates that 2,4,5-trimethylaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines (including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humate carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 5.09(4) suggests that 2,4,5-trimethylaniline will partially exist in the protonated form in moist soils and the protonated form of 2,4,5-trimethylaniline is expected to bind strongly to soil surfaces. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.48X10-6 atm-cu m/mole(4). 2,4,5-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.0X10-3 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 198(SRC), determined from an estimation method(2), indicates that 2,4,5-trimethylaniline is expected to adsorb very little to sediment and suspended solids in water(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon a Henry's Law constant of 2.48X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 12 and 129 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(4). Aromatic amines (including anilines) bind to humic material found in water in two phases(4). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humate carbonyls(4). Subsequently, there is a slow reaction that is not readily reversed(4). A pKa value of 5.09(5), suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of 2,4,5-trimethylaniline does not volatilize from water. According to a classification scheme(6), an estimated BCF of 11(SRC), from a log Kow of 2.27(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,5-trimethylaniline, which has a vapor pressure of 9.0X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4,5-trimethylaniline 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 2 hrs(SRC), from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=137-17-7]

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,4,5-trimethylaniline can be estimated to be 198(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4,5-trimethylaniline is expected to have moderate mobility in soil. However, aromatic amines(including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 5.09(4) suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in moist soils and the protonated form of 2,4,5-trimethylaniline is expected to bind strongly to soil surfaces(SRC).

SYMPTOMATOLOGY: 1. GRAYISH BLUE CYANOSIS, WITHOUT SIGNS OF CARDIAC OR PULMONARY INSUFFICIENCY. 2. SEVERE HEADACHE, NAUSEA, SOMETIMES VOMITING, DRYNESS OF THROAT. 3. CNS SYMPTOMS: CONFUSION, ATAXIA, VERTIGO, TINNITUS, WEAKNESS, DISORIENTATION, LETHARGY, DROWSINESS, & FINALLY COMA. CONVULSIONS...UNCOMMON. /ANILINE/

SYMPTOMATOLOGY: 4. CARDIAC EFFECTS: HEART BLOCKS, ARRHYTHMIAS, & SHOCK. 5. DEATH, ALTHOUGH UNCOMMON, IS USUALLY DUE TO CARDIOVASCULAR COLLAPSE & NOT RESPIRATORY PARALYSIS. 6. URINARY SIGNS & SYMPTOMS...PAINFUL MICTURITION, HEMATURIA, HEMOGLOBINURIA (& METHEMOGLOBINURIA), OLIGURIA, & RENAL INSUFFICIENCY... /ANILINE/

MODERATELY TOXIC.

2,4,5-Trimethylaniline

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

1987

1987

2,4,5-Trimethyl-aniline

An estimated BCF of 11 was calculated for 2,4,5-trimethylaniline(SRC), using a log Kow of 2.27(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Henry's Law constant for 2,4,5-trimethylaniline is 2.48X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that the neutral species of 2,4,5-trimethylaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 12 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 129 days(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(3). Aromatic amines (including anilines) bind to humic material found in water in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). 2,4,5-Trimethylanilne's Henry's Law constant(1) indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). A pKa value of 5.09(1), suggests that 2,4,5-trimethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of 2,4,5-trimethylaniline does not volatilize from water or moist soil surfaces(SRC). 2,4,5-Trimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.0X10-3 mm Hg(1).

PONCEAU 3R WAS REDUCED IN VITRO BY FUSOBACTERIUM TO 2,4,5-TRIMETHYLANILINE WHICH IS MUTAGENIC WHEN METABOLICALLY ACTIVATED BY LIVER S9 PREPN IN SALMONELLA/MAMMALIAN-MICROSOME MUTAGENICITY TEST.

LONG-TERM DIETARY ADMIN TO MALE RATS & MALE & FEMALE HAM/ICR MICE LED TO TUMORS IN NOT LESS THAN 1 TISSUE IN ALL 3 ANIMAL MODELS.

2,4,5-Trimethylaniline was found to be positive when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). 2,4,5-Trimethylaniline was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 1.000, 3.000, 10.000 33.000, 100.000, 333.000, and 1000.000 ug/plate. The compound was positive in strains TA100 and TA98 with activation. The lowest positive dose tested was 3.000 ug/plate in strain TA100 with 10% hamster liver S-9.

... It is concluded that under the conditions of this bioassay, 2,4,5-trimethylaniline was carcinogenic for male and female F344 rats and female B6C3F1 mice, inducing hepatocellular carcinomas or neoplastic nodules in the rats of each sex, alveolar/bronchiolar carcinomas in the female rats, and hepatocellular carcinomas in female mice. ... Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Equivocal; Female Mice: Positive.

The rate constant for the vapor-phase reaction of 2,4,5-trimethylaniline with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4,5-Trimethylaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). In general, anilines absorb light in the environmental UV spectrum(>290 nm)(3). Based on this, 2,4,5-trimethylaniline is expected to absorb light and may potentially undergo direct photolysis(SRC).