Fluoren-2-ylamin

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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.

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

TERRESTRIAL FATE: Limited aqueous screening test data suggest the biodegradation of 2-aminofluorene in soil will be very slow(1,2). 2-Aminofluorene is not expected to undergo hydrolysis in soils. A calculated Koc range of 640 to 1100(3), indicates 2-aminofluorene is characterized by a low mobility in soil(4). An estimated Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C(5), suggests the volatilization of 2-aminofluorene from moist soils will not be important(3).

AQUATIC FATE: Limited aqueous screening test data suggest the biodegradation of 2-aminofluorene in aquatic systems will be very slow. 2-Aminofluorene is not expected to undergo hydrolysis in environmental waters. An estimated Koc ranging in the low mobility class for soil(1), indicates 2-aminofluorene will partition from the water column to organic matter contained in sediments and suspended solids. 2-Aminofluorene also has a low potential to bioconcentrate in aquatic systems. A Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C(2) suggests volatilization of 2-aminofluorene from environmental waters will not be important(3).

ATMOSPHERIC FATE: Based upon a calculated vapor pressure of 2.06X10-6 mm Hg at 25 °C(SRC), 2-aminofluorene is expected to exist in both the particulate and gaseous phases in ambient air(1). The vapor phase rection of 2-aminofluorene with photochemically produced hydroxyl radicals is likely to be an important fate process. The rate constant for the vapor-phase reaction of 2-aminofluorene with photochemically produced hydroxyl radicals has been estimated to be 2.21X(-10) cu cm/molecule-sec at 25 °C; which corresponds to an atmospheric half-life of about 2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2). Washout by precipitation and gravitational settling may be important atmospheric removal mechanisms for 2-aminofluorene in particulate matter(SRC).

Based on an estimated water solubility of 33 mg/L at 25 °C(1) and an estimated log Kow of 3.00(2), the Koc of 2-aminofluorene has been calculated to range from 650 to 1100 from various regression-derived equations(4,SRC). These Koc values indicate 2-aminofluorene is characterized by a low mobility class in soil(4). Furthermore, aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinonal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(5).

Levels of oxygen uptake for 500 mg/L of 2-aminofluorene oxidized in activated sewage sludge suspensions with suspended solid concn of 2,500 mg/L did not differ from the controls(1,2). After 144 hours, oxygen consumptions were about 1600, 1400 and 250 mg/L for Franklin, Nashville and Ashland sludge, respectively(1), whereas, corresponding controls accounted for losses of approximately 1650, 1500 and 450 mg of oxygen per liter(1).

Based on an estimated water solubility of 33 mg/L at 25 °C(1) and an estimated log Kow of 3.00(2), the log BCF of 2-aminofluorene has been calculated to range from 1.93 to 2.05 from various regression-derived equations(3,SRC). These log BCF values suggest 2-aminofluorene has a low potential to bioconcentrate in aquatic systems(SRC).

The Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C for 2-aminofluorene has been estimated using a bond contribution method(1). This Henry's Law constant suggests volatilization of 2-aminofluorene from environmental waters will not be important(2).

2-FLUORENAMINE GIVEN TO MICE & RATS BY VARIOUS ROUTES PRODUCED LIVER TUMORS IN MICE & LIVER, INTESTINE, EAR DUCT, BREAST, AND LUNG TUMORS IN RATS. /FROM TABLE/

2-AMINOFLUORENE ... & ITS ACETYL DERIVATIVE WERE DISCOVERED TO BE CARCINOGENIC IN MOST SPECIES /IN CHRONIC TOXICITY STUDIES/ EXCEPT THE GUINEA PIG & STEPPE LEMMING. TESTS IN RHESUS MONKEY ARE NEGATIVE SO FAR, EVEN THOUGH EXPOSURES HAVE BEEN UNDERWAY FOR MORE THAN 10 YEARS. THE 1 & 3 ISOMERS OF FLUOURENAMINE CMPD ARE WEAKLY CARCINOGENIC, IF AT ALL, & THE 4-ISOMER DOES NOT SEEM TO BE CARCINOGENIC TO RODENTS.

BECAUSE SHORT IN VITRO TREATMENTS OF CHINESE HAMSTER CELLS WITH 2-AMINOFLUORENE (2-AF) DID NOT INCREASE SISTER CHROMATID EXCHANGE (SCE) EVEN IN THE PRESENCE OF A METABOLIC ACTIVATION SYSTEM, EXPT WERE CARRIED OUT WITH RABBITS TO SEE WHETHER IN VIVO ACTIVATION OCCURRED. RABBITS INJECTED WITH 2-AMINOFLUORENE COULD ACTIVATE THE CMPD & A TRANSIENT DOSE DEPENDENT INCREASE IN SCE WAS FOUND IN PERIPHERAL LYMPHOCYTES CULTURED AT VARIOUS TIMES AFTER THE INJECTION. THE ADDITION OF PHYTOHEMAGGLUTININ /TO THE PERIPHERAL LYMPHOCYTES/ & THE CONSEQUENT METABOLIC STIMULATION AFFECTS THE INDUCTION OF ENZYMES INVOLVED IN THE ACTIVATION OF 2-AMINOFLUORENE.

CARCINOGENS WHICH CAUSE STRAIN TA1538 TO REVERT TO HISTIDINE INDEPENDENCE IN THE IN VITRO ASSAYS DEVELOPED BY AMES WILL, WHEN INGESTED, CAUSE AN INCREASED CONCN OF HISTIDINE INDEPENDENT REVERTANTS TO APPEAR IN THE FECES. THIS HOST MEDIATED ASSAY OFFERS A POSSIBLE MEANS OF STUDYING THE RELATIONSHIP OF THE BACTERIAL FLORA TO THE FORMATION OF REACTIVE INTERMEDIATES THAT MAY BE RELATED TO GI CARCINOGENESIS. GNOTOBIOTIC SPRAGUE DAWLEY RATS, ASSOC WITH SALMONELLA TYPHIMURIUM TA1538, MAY ALSO BE ASSOC WITH LACTOBACILLUS PLANTARUM OR BACTERIODES VULGATUS AS WELL AS WITH BOTH OF THESE STRAINS. AFTER THE INGESTION OF 2-NITROFLUORENE (3.4 MG), FECAL CONCENTRATION OF HIS+ REVERTANTS WAS GREATLY INCREASED IN ALL GROUPS OF RATS EXCEPT THOSE ASSOCIATED WITH STRAIN TA1538 AND BACTERIODES VULGATUS. THE CONCN OF THE VARIOUS BACTERIA WERE MEASURED AT 8 SITES IN THE GI TRACT. BACTERIODES VULGATUS ACHIEVED HIGH CONCN IN THE STOMACH WHEN IT WAS ASSOC WITH STRAIN TA1538, BUT ITS CONCN WAS NOT AS HIGH WHEN IT WAS ASSOC WITH LACTOBACILLUS PLANTARUM TOGETHER WITH STRAIN TA1538. BACTERIODES VULGATUS READILY REDUCES 2-NITROFLUORENE TO 2-AMINOFLUORENE, A REACTION WHICH IS NEGLIGIBLE IN CULTURES OF LACTOBACILLUS PLANTARUM & STRAIN TA1538. SINCE 2-AMINOFLUORENE IS LESS MUTAGENIC THAN 2-NITROFLUORENE, BACTERIODES VULGATUS APPEARS TO DIMINISH THE REVERTANT RESPONSE BY REMOVING THE MORE POTENT MUTAGEN FROM WITHIN THE GI TRACT.

Aromatic-amines are generally resistant to hydrolysis(1). Therefore, 2-aminofluorene probably will not undergo hydrolysis in the environment. Vapor phase reactions with photochemically produced hydroxyl radicals may be important in ambient air. The rate constant for the vapor-phase reaction of 2-aminofluorene with photochemically produced hydroxyl radicals has been estimated to be 221X10-12 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2).

Information regarding the production of 2-aminofluorene was not available. 2-Aminofluorene is expected to biodegrade very slowly and is not expected to hydrolyze in the environment. A calculated Koc range of 640 to 1100, indicates 2-aminofluorene is characterized by a low mobility class in soil. In aquatic systems, 2-aminofluorene may partition from the water column to organic matter contained in sediments and suspended solids. 2-Aminofluorene also has a low potential to bioconcentrate in aquatic systems. A Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C, suggests volatilization of 2-aminofluorene from environmental waters will not be important. 2-Aminofluorene is expected to exist in both the particulate and vapor phases in ambient air. For vapor phase 2-aminofluorene in the atmosphere, the vapor phase reaction with photochemically produced hydroxyl radicals (half-life of 2 hr) is likely to be an important fate process. Otherwise, washout by precipitation and gravitational settling may be an important removal mechanism for 2-aminofluorene in atmospheric particulate matter. (SRC)

Used as an experimental carcinogen for research; [HSDB]

CHEMICAL RESEARCH

/SRP/: EXPERIMENTAL CARCINOGEN

... N-2-fluorenylacetamide was discovered to be a powerful carcinogen prior to the possible use of the parent 2-fluorenamine as an insecticide. ... in 1938 before DDT was known & when insect pests were controlled with difficulty, 2-fluorenamine was a potent & promising insecticide.