2465-27-2CN(C)c1ccc(C(=N)c2ccc(N(C)C)cc2)cc1JPIYZTWMUGTEHX-UHFFFAOYSA-NAuramine can cause cancer according to an independent committee of scientific and health experts.
2465-27-2、492-80-8DTXSID7043821CHEMBL1626329CHEBI:51874Dyes -> Di- and Triaryl Dyes
Carcinogens
SOL IN ETHYL ETHER, VERY SOL IN ETHANOL.
Sol in alcohol
136 °C
267 °C
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Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Chemical: Benzenamine, 4,4'-carbonimidoylbis[N,N-dimethyl-
Hazard Traits - Carcinogenicity
Regulation (EC) No 178/2002 (amended)
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
May cause eye injury; Causes tumors in high-dose feeding studies of laboratory animals; [HSDB] Danger of cutaneous absorption; [MAK] See Auramine Production.
The major hazards encountered in the use and handling of auramine stem from its toxicologic properties. Exposure to this yellow or colorless crystalline substance may occur from its manufacture and use as a yellow dye for paper, textiles, leather, oils, waxes, lacquers, pen inks, and typewriter ribbons; and as an antiseptic for use in nose and ear surgery, and the treatment of gonorrhea. Effects from exposure may include injury to the eyes. Also, the International Agency for Research on Cancer (IARC) has designated auramine as a Group 2B carcinogen, meaning, "The agent is possibly carcinogenic to humans". Mechanical exhaust ventilation equipped with a high-efficiency particulate arrestor (HEPA) should be used to minimize airborne levels of auramine. In activities and situations where over-exposure may occur, wear protective clothing and a carefully fitted respirator. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed and discarded or cleaned before reuse. Smoking, drinking, and eating should be prohibited in auramine work areas. Auramine should be stored in a securely sealed, watertight container, which should be enclosed in a second, unbreakable, leakproof container.
ALTHOUGH THE REQUIREMENT FOR METABOLIC ACTIVATION REGARDING AURAMINE IS UNRESOLVED, IT IS CONSIDERED TO BE A PRO-CARCINOGEN. IT POSSESSES METHYLATED AMINO GROUPS. IT WILL UNDERGO RESONANCE CONJUGATION RENDERING THE AMINO N ATOM POSITIVELY CHARGED & THUS MORE PRONE TO HYDROXYLATION. THE DIRECT ACTIVITY OF AURAMINE VARIOUSLY REPORTED MAY BE DUE TO WEAK ELECTROPHILICITY AT THE UNSUBSTITUTED POSITIVELY CHARGED CENTRAL N ATOM IN THE OTHER EXTREME RESONANCE FORM.
Used to dye food, smoke, paper, cardboard, textiles, leather, oils, waxes, alcoholic solvents, lacquers, pen inks, carbon papers, and typewriter ribbons; Also used as an antiseptic, fungicide, and to prepare solvent yellow 34; [HSDB]
Pulp and Paper Processing [Category: Industry]
USED TO PREPARE SOLVENT YELLOW 34, A SOLVENT-SOLUBLE YELLOW DYE; FOOD DYE IN SOME COUNTRIES; SMOKE DYE.
DYE FOR PAPER, CARDBOARD, TEXTILES, LEATHER, OILS, WAXES, ALCOHOLIC SOLVENTS, LACQUERS, PEN INKS, CARBON PAPERS, & TYPEWRITER RIBBONS. /FORMER USE/
MEDICATION
Antiseptic; fungicide
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS
(1978) Greater than 4.54X10+6 g
Benzenamine, 4,4'-carbonimidoylbis[N,N-dimethyl-: ACTIVE
In the United States ... virtually all the dye companies /have/ discontinued use of the compound.
Auramine and its hydrochloride salt have been used in large amounts as a yellow dye for the coloring of paper and color board, and to a lesser extent for certain textiles and leather.
Wird geladen…
C.i. solvent yellow 34 appears as yellow crystalline powder or yellow needles.
Colorless or yellow solid; [HSDB]
DACRE JC ET AL; PROBLEM DEFINITION STUDIES ON POTENTIAL ENVIRONMENTAL POLLUTANTS. V. PHYSICAL, CHEMICAL, TOXICOLOGICAL, & BIOLOGICAL PROPERTIES OF 7 CHEMICALS USED IN PYROTECHNIC COMPOSITIONS; REPORT; USAMBRDL-TR-7704; DTIC NUMBER AD-A090631, 101, (1979). A DATA BASE & SUMMARY REGARDING AURAMINE.
COMBES RD, HAVELAND-SMITH RB; A REVIEW OF THE GENOTOXICITY OF FOOD, DRUG AND COSMETIC COLORS AND OTHER AZO, TRIPHENYLMETHANE AND XANTHENE DYES; MUTAT RES 98 102 (1982). AURAMINE IS CONSIDERED TO BE A PRO-CARCINOGEN DESPITE EVIDENCE SHOWING IT TO BE INACTIVE USING IN VITRO CELL TRANSFORMATION.
U014; As stipulated in 40 CFR 261.33, when auramine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
C.I. SOLVENT YELLOW 34 neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U014, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
For more Disposal Methods (Complete) data for AURAMINE (7 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
For more Preventive Measures (Complete) data for AURAMINE (10 total), please visit the HSDB record page.
0.81 [mg/m3]
8.9 [mg/m3]
53 [mg/m3]
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
TERRESTRIAL FATE: If auramine is released to soil, it will be expected to have low mobility(1,SRC) based upon an estimated Koc of 2000 which was calculated(2,SRC) from an estimated log Kow of 3.5(3) and a suggested classification scheme(1). Auramine will not, therefore, be expected to leach in soil(1,SRC). It may be subject to slow hydrolysis based upon the slow measured rate of hydrolysis observed in aqueous media at pH 5-9 at 25 °C(4). Auramine may slowly biodegrade in soil based upon data from aqueous aerobic activated sludge screening tests(4). Volatilization should not be an important removal process from moist near surface soil(SRC) based upon an estimated Henry's Law constant of 8.05X10-8 atm-cu m/mole which was calculated(6,SRC) from an estimated water solubility(5,SRC) and an estimated vapor pressure(6,SRC). Based upon its estimated vapor pressure(1), volatilization of auramine from surfaces and dry near surface soil will probably not be significant processes(SRC).
AQUATIC FATE: If auramine is released to water, it may be subject to direct photolysis based upon its strong absorption of light at wavelengths >290 nm(1,SRC). It will be subject to very slow hydrolysis based upon measured neutral and acid catalyzed hydrolysis rate constants of 3.9X10-4 h-1 and 5.5 M-1 h-1 at 25 °C, respectively(1,SRC), which correspond to half-lives of 65 days at pH 5 and 74 days at pH 5-9(8,SRC). It may be subject to photooxidation by various oxidants present in natural waters including hydroxyl and peroxyl radicals and singlet oxygen based upon estimated and measured rate data for aromatic amines as a class(2,3,SRC). Auramine may slowly biodegrade in natural water based upon data from aerobic activated sludge screening tests(4). Volatilization should not be an important removal process from water based upon an estimated Henry's Law constant of 8.05X10-8 atm-cu m/mole which was calculated(5,SRC) from an estimated water solubility(6,SRC) and an estimated vapor pressure(6,SRC). Auramine will not be expected to bioconcentrate in aquatic organisms based upon an estimated BCF of 288 which was calculated(5,SRC) from an estimated log Kow of 3.5(7). It will be expected to adsorb to sediment and particulate matter based upon an estimated Koc of 2000 which was calculated(5,SRC) from an estimated log Kow of 3.5(7).
ATMOSPHERIC FATE: If auramine is released to the atmosphere, it is expected to exist in both the vapor and particulate phases(1), based upon an estimated vapor pressure of 2.5X10-6 mm Hg at 25 °C(2). Auramine may be susceptible to direct photolysis in the atmosphere based upon its strong absorption of light at wavelengths >290 nm(3,SRC). The rate constant for the vapor phase reaction of auramine with photochemically produced hydroxyl radicals has been estimated to be 2.05X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of 1.9 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm (4,SRC).
PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/
An estimated Koc of 2030 can be calculated(1,SRC) from an estimated log Kow of 3.5(2). This estimated Koc indicates that auramine will be expected to adsorb to soils, sediment, and suspended particulate matter(3,SRC) and that the compound will be expected to be slightly mobile in soil(3,SRC).
INJURIOUS TO ... HUMAN EYES.
THE MFR OF AURAMINE LED TO BLADDER CANCER IN /MALE EMPLOYEES/.
No data were available on the genetic and related effects of auramine in humans.
ONE EPIDEMIOLOGICAL STUDY INDICATES THAT THE OPEN MFR OF AURAMINE PRESENTS AN OCCUPATIONAL BLADDER CANCER RISK.
Auramine may be subject to slow biodegradation in the environment based upon a theoretical BOD of 1.5% observed in aerobic aqueous screening tests utilizing municipal waste activated sludge inoculums(1). No data were located concerning the biodegradation of auramine in natural systems(SRC).
Auramine
Group 2B: Possibly carcinogenic to humans
Volume 1: (1972) Some Inorganic Substances, Chlorinated Hydrocarbons, Aromatic Amines, N-Nitroso Compounds, and Natural Products
2012
2009
Based upon an estimated water solubility of 11 mg/l(1) and an estimated vapor pressure of 2.5X10-6 mm Hg at 25 °C(1), the Henry's Law constant for auramine has been calculated to be 8.05X10-8 atm-cu m/mole(2,SRC). This value for the Henry's Law constant indicates that volatilization of auramine from surface waters and near surface moist soil should not be important processes(2,SRC). Based upon its estimated vapor pressure(1), volatilization of auramine from surfaces and near surface dry soil will probably not be significant processes(SRC).
THIRTY MICE ... GIVEN A DIET CONTAINING 0.1% COMMERCIAL AURAMINE FOR 52 WK (TOTAL DOSE: 728 MG PER ANIMAL). THE ANIMALS WERE KEPT FOR THEIR LIFE SPAN. SEVEN HEPATOMAS & 11 LYMPHOMAS WERE FOUND AS COMPARED WITH 0 & 5, RESPECTIVELY, IN 60 CONTROL ANIMALS.
THIRTY STOCK MICE AND 27 CBA MICE OF BOTH SEXES WERE GIVEN ... /FOR/ 52 WK 0.1% & 0.2%, RESPECTIVELY, OF AURAMINE DISSOLVED IN ACETONE IN THEIR DIET (APPROX TOTAL DOSE: 1820 MG & 3650 MG PER MOUSE, RESPECTIVELY). IN STOCK MICE, 57% OF MALES & 30% OF THE FEMALES THAT SURVIVED TO TUMOR BEARING AGE SHOWED HEPATOMAS. NO CHOLANGIOMAS WERE OBSERVED AND THE DEGREE OF CIRRHOSIS WAS MINIMAL. NO HEPATOMAS WERE SEEN IN CONTROL ANIMALS. IN CBA MICE, THE FREQUENCY OF HEPATOMAS WAS OVER 50% IN THE TREATED GROUP AND ONLY 7/90 IN THE CONTROL GROUP.
TWELVE MALE WISTAR RATS WERE GIVEN, DURING 87 WK, A DIET CONTAINING 0.1% OF COMMERCIAL AURAMINE (EST TOTAL DOSE: 10 G PER RAT). NINETY-TWO PERCENT OF THE ANIMALS (11/12) DEVELOPED HEPATOMAS BETWEEN THE 91ST AND THE 122ND WK FOLLOWING START OF TREATMENT. ... TWELVE CONTROL RATS WERE TUMOR-FREE AT DEATH BETWEEN 90 AND 120 WK.
... 9 RABBITS WERE GIVEN AURAMINE (PURITY NOT STATED) ORALLY TO THE LIMIT OF TOLERANCE, AND THE TREATMENT WAS CONTINUED UNTIL THE ONSET OF THE FINAL ILLNESS. SIX ANIMALS WERE SACRIFICED IN THE FIRST 2 YR AND 3 BETWEEN 3 AND 4 YR. METAPLASIA OF THE URINARY TRACT EPITHELIUM, SUGGESTIVE OF PRECANCEROUS CHANGE, WAS SEEN IN 2 OUT OF 5 RABBITS EXAMINED.
For more Non-Human Toxicity Excerpts (Complete) data for AURAMINE (11 total), please visit the HSDB record page.
The Human Health Assessment Group in EPA's Office of Health and Environmental Assessment has evaluated auramine for carcinogenicity. According to their analysis, the weight-of-evidence for auramine is group B2, which is based on inadequate evidence in humans and sufficient evidence in animals. As a group B2 chemical, auramine is considered probably carcinogenic to humans.
Auramine, technical grade - Inadequate evidence of carcinogenicity in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans. Auramine, manufacture of - Sufficient evidence of carcinogenicity in humans. No data on the carcinogenicity in animals. OVERALL EVALUATION: Group 1: The process is carcinogenic to humans.
U014; As stipulated in 40 CFR 261.33, when auramine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
AURAMINE HAS BEEN INCORPORATED IN DRUGS, HAS MISCELLANEOUS LABORATORY APPLICATIONS & HAS BEEN USED AS AN ANTI-TUMOR AGENT IN VIEW OF ITS CYTOTOXIC EFFECTS.
VerwendenYellow dye for paper, textiles, leather; antisep- tic; fungicide.
synthetische(a) will Sulphur dissolved in 4-(4-(Dimethylamino)benzyl)-N,N-dimethylbenzenaminemethane. Add in ammonia and sodium chloride, ammonia in 175 ℃ heat the mixture, with hot water extraction dye and salting out (GP53614); (b) Bis (4 – (dimethylamino) phenyl) methanone and ammonia and Zinc chloride in a total of 150 ~ 160 ℃ heat (GP 29060). Free base is to add the same amount of naoh aqueous solution hydrochloride, sodium carbonate and ammonia and have to.
DefinitionChEBI: A member of the class of imines that is benzophenone imine carrying two dimethylamino substituents at positions 4 and 4'. The hydrochloride salt is the biological stain 'auramine O'