Benz(c)acridine

Very slightly soluble in water

Very soluble in benzene, ether and ethanol

Soluble in acetone

Benz[c]acridine is a solid.

Yellow solid; [HSDB]

Warning

H400 (92.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 13 reports by companies from 2 notifications to the ECHA C&L Inventory.

USEPA; Health Assessment Document: Polycyclic Organic Matter (1979) EPA-600/9-79-008

Dangerous Prop Ind Mater Rep 5 (1): 31-2 (1985). A review of safety toxicology, health hazards, and safety of benzacridine

IARC Monogr Eval Carcinog Risk Chem Hum 32: 129-34 (1983)

U016; As stipulated in 40 CFR 261.33, when benz[c]acridine, 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).

BENZ[C]ACRIDINE 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.

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. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

One third of the total polycyclic aromatic hydrocarbons (PAH) is bound to larger suspended particles, one third is bound to finely dispersed particles, and the other third is present in dissolved form. The particle-bound portion of PAH can be removed by sedimentation, flocculation, and filtration processes. The remaining one-third dissolved PAH usually requires oxidation for partial removal/transformation. /Polynuclear aromatic hydrocarbons/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. Also, 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.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Respiratory protection for coal tar pitch volatiles is as follows: Particulate concentration of 2 mg/cu m or less: A chemical cartridge respirator with an organic vapor cartridge(s) and with a fume or high efficiency, or any supplied-air respirator, or any self-contained breathing apparatus. 10 mg/cu m or less: A chemical cartridge respirator with a full facepiece and an organic vapor cartridge(s) and with a fume or high-efficiency filter, or gas mask with a chin-style or a front- or back-mounted organic vapor canister and with a full facepiece and a fume or high-efficiency filter, or any supplied-air respirator with a full facepiece, helmet, or hood, or any self-contained breathing apparatus with a full facepiece. 200 mg/cu m or less: A type C supplied-air respirator operated in pressure-demand or other positive pressure or continuous-flow mode, a powered air-purifying respirator with an organic vapor cartridge and a high-efficiency particulate filter. 400 mg/cu m or less: A type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure mode or with a full facepiece, helmet, or hood operated in continuous-flow mode. Greater than 400 mg/cu m or entry and escape from unknown concentrations: A combination respirator which includes a type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure mode; Escape. Any gas mask providing protection against organic vapors and particulates, including pesticide respirators which meet the requirements of this class, any escape self-contained breathing apparatus. /Coal tar pitch volatiles/

Employees should be provided with and required to use impervious clothing, gloves, face-shields (eight-inch minimum), and other appropriate protective clothing necessary to prevent any possibility of skin contact with coal tar pitch volatiles. Employees should be provided with and required to use splash-proof goggles where there is any possibility of liquid coal tar volatiles contacting the eyes. /Coal tar pitch volatiles/

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats has been studied by gas chromatography/mass spectrometry. Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-oxidation is likely to occur in the case of benz(c)acridine. However, no unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides). K-region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites incr after BkF treatment in the case of benz(c)acridine.

LC50; Species: Chironomus riparius (Midge) organisms at different lifestages, newly hatch, 1st instar larvae; Conditions: freshwater, static, 20 °C; Concentration: 6.9 ug/L for 96 hr (95% confidence interval: 6.7-7.2 ug/L) />99% purity/

LC50; Species: Daphnia pulex; Concentration: 0.45 mg/L for 24 hr /Conditions of bioassay not specified in source examined/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.8X10+5(SRC), determined from a structure estimation method(2), indicates that benz(c)acridine is expected to be immobile in soil(SRC). Volatilization of benz(c)acridine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Benz(c)acridine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.8X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Benz(c)acridine strongly absorbs at wavelengths >290 nm(3) and has been shown to photodegrade readily in aqueous solutions exposed to sunlight(4); therefore, exposure to sunlight on soil surfaces may be an important fate process(SRC). Biodegradation data in soil specific to benz(c)acridine were not available(SRC, 2013).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.8X10+5(SRC), determined from a structure estimation method(2), indicates that benz(c)acridine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.7X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 420(SRC), from an estimated log Kow of 4.49(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Polyaromatic hydrocarbons (PAH) are not likely to appreciably bioconcentrate in organisms which have microsomal oxidase, such as fish, as this enzyme allows the organism to metabolize PAH's(5). Benz(c)acridine strongly absorbs at wavelengths >290 nm(6) and has been shown to photodegrade readily in aqueous solutions exposed to sunlight(7); therefore, exposure to sunlight in water may be an important fate process(SRC). Benz(c)acridine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data in water specific to benz(c)acridine were not available(SRC, 2013).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benz(c)acridine, which has an estimated vapor pressure of 9.8X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Monitoring data suggest it will exist primarily in the particulate phase(3,4). Vapor-phase benz(c)acridine 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 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase benz(c)acridine may be removed from the air by wet and dry deposition(SRC). Benz(c)acridine strongly absorbs at wavelengths >290 nm(5) and has been shown to photodegrade readily in aqueous solutions exposed to sunlight(6); therefore, photodegradation may be an important fate process(SRC).

Benz(c)acridine particulate concentrations of 15 mg/1000 cu m gas were detected in domestic coal combustion stack effluents and concentrations of 18.0 and 60.0 mg/1000 cu m gas were detected in petroleum refinery incinerator effluents(1). Particulate concentrations of 0.200 mg/1000 cu m gas were detected in the motor exhaust of a gasoline powered 1956 model truck(2); this concentration was low compared to other polycyclic aromatic hydrocarbons(2). Benz(c)acridine has also been identified in coke oven emissions(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of benz(c)acridine can be estimated to be 1.8X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that benz(c)acridine is expected to be immobile in soil. The pKa of benz(c)acridine is 4.70(3), indicating that this compound is a weak base and will exist primarily in the undissociated form in the environment with a small fraction in cation form. Cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

URBAN/SUBURBAN: Benz(c)acridine particulate concentrations ranging from below the detection limit to 1.5 ng/cu m were found in airborne samples from 50 cities in the USA in 1966, with an average concentration of 0.43 ng/cu m(1). An average atmospheric level of 0.6 ng/cu m was reported for the average urban atmosphere in the USA in 1963(2). Air polluted from coal-tar pitch was found to contain 0.12 ng/cu m(3). Atmospheric particulate samples collected in the city of Lanzhou China in March 2003 contained benz(c)acridine concentration of 52.3 ng/cu m(4). Benz(c)acridine particulate concentrations of 0.09-0.17 ng/cu m were detected in residential and busy street ambient samples collected in Copenhagen Denmark in Feb 1976-1982(5).

URBAN/SUBURBAN: Benz(c)acridine concentration in atmosphere of 2 cities in North-Rhine-Westphalia (West Germany) is much higher than the average concentration in USA cities. Proportion of benz(c)acridine to benz(a)pyrene is 0.1-0.3 (relatively high). Main source of these is coal processing and combustion.

URBAN/SUBURBAN: Benz(c)acridine particulate concentrations ranging from below the detection limit to 1.5 ng/cu m were found in airborne samples from 50 cities in the USA in 1966 with an average concentration of 0.43 ng/cu m(1). An average atmospheric level of 0.6 ng/cu m was reported for the average urban atmosphere in the USA in 1963(2). Air polluted from coal-tar pitch was found to contain 0.12 ng/cu m(3). Atmospheric particulate samples collected in the city of Lanzhou China in March 2003 contained benz(c)acridine concentration of 52.3 ng/cu m(4). Benz(c)acridine particulate concentrations of 0.09-0.17 ng/cu m were detected in residential and busy street ambient samples collected in Copenhagen Denmark in Feb 1976-1982(5).

Benz(c)acridine is not produced or used as a commercial product(1) with the exception as a research chemical. Benz(c)acridine is released in stack effluents from residential coal-burning furnaces and in incineration effluents from oil refineries(2). It can be released in exhaust generated by gasoline engines(3). It occurs in emissions associated with coal-tar, coke ovens, creosote and in combustion products from fossil fuels that have a high nitrogen content(1,2,4). Benz(c)acridine is a component of cigarette smoke and condensate(1).

Benz(c)acridine was quantitatively identified in samples of bottom sediments in China(1). Soils samples collected from a wood-processing plant and military area in northern Germany contained benz(c)acridine concentrations of 7.3 and 13.3 mg/kg respectively(2).

Benz[c]acridine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 32: (1983) Polynuclear Aromatic Compounds, Part 1: Chemical, Environmental and Experimental Data

2013

2011

An estimated BCF of 420 was calculated in fish for benz(c)acridine(SRC), using an estimated log Kow of 4.49(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). Polyaromatic hydrocarbons (PAH) are not likely to appreciably bioconcentrate in organisms which have microsomal oxidase, such as fish, as this enzyme allows the organism to metabolize PAH's(3).

U016; As stipulated in 40 CFR 261.33, when benz[c]acridine, 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. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

The bay-region diol epoxides and tetrahydro epoxides of benz(c)acridine were from 1-4 orders of magnitude more mutagenic to bacterial (Salmonella typhimurium) and mammalian cells (Chinese hamster V-79 cells) than were their non-bay-region counterparts. In all the mutagenic test systems studied, the bay-region diol epoxides and tetrahydro epoxides of B(c)AC were substantially more active than the analogs and derivatives of B(a)AC, indicating the importance of the position of N-heteroatom on the biological activity. Metabolic activation studies with hepatic microsomes from Aroclor 1254-treated rats indicated that B(c)Ac 3,4-dihydrodiol was metabolized to mutagenic products to a greater extent than B(a)AC 3,4-dihydrodiol. The 1,2-, 5,6-, 8,9-, and 10,11-dihydrodiol of B(c)AC were not metabolically activated to mutagenic metabolites.

The 5,6-dihydrodiol of benz(c)acridine has been detected as a metabolite together with other, unidentified dihydrodiols & monohydroxyderivatives in studies in which benz(c)acridine was incubated with rat liver and lung microsomal preparations.

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats was studied by gas chromatography/mass spectrometry (GC/MS). Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-Oxidation is likely to occur in the case of benz(c)acridine. No unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides) in case of both benz(a)- and benz(c)acridine. K-Region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites increased after BkF treatment in the case of benz(c)acridine.

The main pathway of the metabolic activation of benz(a)- and benz(c)acridine in rat lung and liver microsomes was oxidation to phenols and dihydrodiols. Oxidation at the K-region predominated in both acridines with microsomes of untreated rats and was stimulated by phenobarbital pretreatment. The benz(c)acridine metabolism with lung and liver microsomes showed a similar behavior. Even induction by phenobarbital and benzo(K)fluoranthene did not influence the ratio between K-region and non-K region oxidation.

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats has been studied by gas chromatography/mass spectrometry. Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-oxidation is likely to occur in the case of benz(c)acridine. However, no unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides). K-region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites incr after BkF treatment in the case of benz(c)acridine.

The mechanism of transport by polynuclear aromatic hydrocarbons (PAH) into cells & between intracellular membranes is discussed. From the partitioning parameters, the rate limiting step involves solvation of transfer species in the interfacial water at phospholipid surface. Transfer of pyrene out of the phosphatidylcholine vesicles was examined. /Polynuclear aromatic hydrocarbons/

Polynuclear aromatic hydrocarbons are highly soluble in adipose tissue and lipids. /Polynuclear aromatic hydrocarbons/

Used as a research chemical; Not commercially used or produced; [HSDB]

There is no commercial production and no known use ... found in coal-tar-based therapeutic agents, coke oven emissions, cigarette smoke and condensate, air pollutant source effluents, synthetic coal fuels, creosote mixtures, and contaminated water.

RESEARCH CHEMICAL

(1978) No Data

(1982) No Data

(1987) No Data

(1978) No Data

(1982) No Data

(1987) No Data

(1978) NOT PRODUCED COMMERCIALLY IN USA

(1982) NOT PRODUCED COMMERCIALLY IN USA

(1983) Not produced commercially in USA