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DIBENZ(a,h)ACRIDINE

HCID 9183
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
226-36-8
Standard-SMILES
c1ccc2c(c1)ccc1nc3c(ccc4ccccc43)cc12
InChIKey
JNCSIWAONQTVCF-UHFFFAOYSA-N
Summenformel
C21H13N
Durchschnittliche Molmasse
279,3 g/mol
Monoisotopische Masse
279,10479942

Überblick

Dibenz[a,h]acridine can cause cancer according to an independent committee of scientific and health experts.

Namen und Bezeichner

Bevorzugter Name
DIBENZ(a,h)ACRIDINE
IUPAC
2-azapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaene
Englischer Name
Dibenz(a,h)acridine
Summenformel
C21H13N
Molmasse
279.33

Namen und Synonyme

Dibenz[a,h]acridine226-36-8DIBENZ(A,H)ACRIDINE1,2,5,6-Dibenzacridine7-Azadibenz(a,h)anthraceneDB(a,h)ACDibenz(a,d)acridine1,2,5,6-Dibenzoacridine1,2,5,6-DinaphthacridineI64KK77PZYDTXSID3059761RefChem:132788
Weitere Namen anzeigen
Brn 0209261DIBENZ[A,D]ACRIDINEDIBENZO(A,H)ACRIDINE1,Dibenz[a,d]acridine
DTXCID9036725Dibenzo[a,H]acridineDIBENZ (a,h) ACRIDINE (purity)2-azapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaeneCCRIS 206HSDB 4038UNII-I64KK77PZY1,2:5,6-Dibenzacridine

Datenbank-Bezeichner

CAS
226-36-8
PubChem CID
9183
DTXSID
DTXSID3059761
ChEBI
CHEBI:82310
UNII
I64KK77PZY
EC Number
680-472-8
Nikkaji
J2.977G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6
Polarare Oberfläche (TPSA)
12,9 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
22
Formalladung
0
Komplexität
405

Experimentelle und physikochemische Eigenschaften

Chemical ClassesCarcinogens
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
LogP · 2 Einträge

log Kow = 5.73

5.38

Color/FormYellow crystals
Solubility · 2 Einträge

In water, 0.159 mg/L at 25 °C

Sparingly soluble in ethanol; soluble in benzene, acetone, and cyclohexane

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point228 °C
Physical Description · 2 Einträge

Dibenz[a,h]acridine appears as yellow crystals. Insoluble in water.

Yellow solid; [HSDB] Crystalline solid; [Cerilliant MSDS]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 5.6% (3 of 54) of reports.

Danger

H301 (72.2%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P316, P305+P354+P338, P317, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 2 Einträge

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence

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.)

DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards Summary · 1 Eintrag

There is no data available on cancer in humans. There is sufficient evidence of carcinogenicity in experimental animals. Dibenz(a,h)acridine is possibly carcinogenic to humans (Group 2B). [IARC, Vol. 103, 2013] See POLYCYCLIC AROMATIC HYDROCARBONS.

Reactive GroupAmines, Phosphines, and Pyridines
Special Reports

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

... /The authors/ have investigated the biotransformation of dibenz(a,h)acridine (DB(a,h)ACR), an aza-PAH with two nonidentical bay regions, by recombinant human cytochromes P450 1A1, 1B1, and 3A4 and rat P450 1A1. Among the three P450s, 1A1 was the most effective in metabolizing DB(a,h)ACR followed by 1B1 and 3A4. The major DB(a,h)ACR metabolites produced by human P450 1A1 and 1B1 were the dihydrodiols with a bay region double bond, namely, DB(a,h)ACR-3,4-diol and DB(a,h)ACR-10,11-diol (putative proximate carcinogen). P450 1A1 produced a higher proportion of DB(a,h)ACR-10,11-diol (derived from the benzo ring adjacent to the nitrogen) (44.7%) than of DB(a,h)ACR-3,4-diol (derived from benzo ring away from the nitrogen) (23.8%). In contrast, 1B1 produced a much greater proportion of 3,4-diol (54.7%) than of 10,11-diol (6.4%). These data indicate that (i) human P450 1A1 and 1B1 differ dramatically with respect to the regiospecific metabolism of DB(a,h)ACR, (ii) human P450 1A1 is substantially more active than human P450 1B1 in the metabolic activation of the aza-PAH to its 10,11-diol, and (iii) the presence of nitrogen influences the relative extent to which the two benzo ring diols with a bay region double bond are formed by human P450s 1A1 and 1B1. In contrast to human P450s 1A1 and 1B1, rat P450 1A1 showed no regioselectivity in the metabolism of DB(a,h)ACR producing nearly equal proportions of 10,11-diol and 3,4-diol. Despite significant differences in their regioselectivity, human P450 1A1 and 1B1 and rat P450 1A1 showed similar stereoselectivity in the metabolism of DB(a,h)ACR to its diols having a bay region double bond, producing primarily the R,R enantiomers (>94%). The data of these studies indicate that human and rat P450 1A1 differ in their regioselectivity in the metabolism of DB(a,h)ACR to its two benzo ring diols with a bay region double bond and consequently in their ability to metabolically activate the parent aza-PAH. However, human and rat P450 1A1 do not differ with respect to their stereoselectivity in the metabolism of DB(a,h)ACR to the diols.

The carcinogen dibenz(a,h)acridine (DB(a,h)ACR is metabolized predominantly to trans-3,4-dihydroxy-3,4-dihydro-dibenz(a,h)acridine (DB(a,h)ACR-3,4-diol) and the proximate carcinogen trans-10,11-dihydroxy-10,11-dihydrodibenz(a,h)acridine (DB(a,h)ACR-10,11-diol). In the present investigation, the stereoselectivity of rat liver enzymes in metabolism of DB(a,h)ACR to its 3,4-diol and 10,11-diol and of DB(a,h)ACR-10,11-diol enantiomers to their bay-region diol epoxides has been examined with liver microsomes from control and 3-methylcholanthrene-treated rats. Both microsomal preparations produced the major metabolites DB(a,h)ACR-3,4-diol and DB(a,h)ACR-10,11-diol containing predominantly R,R-enantiomers with 38-54% optical purity. Metabolism of (-)-(10R,11R)- and (+)-(10S,11S)-enantiomers of DB(a,h)ACR-10,11-diol by liver microsomes from control rats produced predominantly bay-region diol epoxides (46-59% of total metabolites), whereas very little bay-region diol epoxides (14-17% of total metabolites) were produced by liver microsomes from 3-methylcholanthrene-treated rats. The bay-region diol epoxides produced in these studies consisted of predominantly DB(a,h)ACR-10,11-trans-diol epoxide diastereomer in which the benzylic hydroxyl group and epoxide oxygen are trans. However, (-)-DB(a,h)ACR-10R,11R-diol, a major metabolite of DB(a,h)ACR, was metabolized by liver microsomes from 3-methylcholanthrene-treated rats to (+)-(8R,9S,10S,11R)-DB(a,h)ACR-10,11-trans-diol epoxide ... in an amount which was 6.5-fold greater than that of the corresponding cis-diol epoxide diastereomer. The relative amounts of trans-diol epoxide versus cis-diol epoxide in the mixture of bay-region diol epoxides produced from DB(a,h)ACR-10R,11R-diol and DB(a,h)ACR-10S,11R-diol with liver microsomes from control rats and from DB(a,h)ACR-10S,11S-diol with liver microsomes from 3-methylcholanthrene-treated rats were 1.7, 2.1 and 2.3 respectively.

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Physikochemische Eigenschaften

Schmelzpunkt
223 · 223-224oC
Siedepunkt
412.11 °C · 412.11°C (rough estimate)
Dichte
1.0343 · 1.0343 (rough estimate)
Brechungsindex
1.824 · 1.8240 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Benzene (Slightly), Chloroform (Slightly)
pka
4.71 · 4.71±0.30(Predicted)
Farbe
Light Yellow to Yellow
BRN
209261 · 209261
Henry's Law Constant
5.2 · 5.2×103 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
InChI=1S/C21H13N/c1-3-7-17-14(5-1)11-12-20-19(17)13-16-10-9-15-6-2-4-8-18(15)21(16)22-20/h1-13H
InChIKey
JNCSIWAONQTVCF-UHFFFAOYSA-N
SMILES
C12=CC=CC=C1C=CC1C2=CC2C(=C3C=CC=CC3=CC=2)N=1
EPA chemische Informationen
Dibenz[a,h]acridine (226-36-8)
· 2 Einträge

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Dibenz(a,h)acridine (226-36-8) is listed as reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

WORLD HEALTH ORGANIZATION, IARC (INTERNATIONAL AGENCY FOR RESEARCH ON CANCER) MONOGRAPHS ON THE EVALUATION OF THE CARCINOGENIC RISK OF CHEMICALS TO MAN, VOL 3. CERTAIN POLYCYCLIC AROMATIC HYDROCARBONS & HETEROCYCLIC COMPOUNDS. IARC (INT AGENCY RES CANCER) MONOGR P271 (1972). REVIEW OF CARCINOGENIC POTENTIAL OF CERTAIN POLYCYCLIC AROMATIC AND HETEROCYCLIC COMPOUNDS.

Reactivity Profile · 1 Eintrag

DIBENZ[A,H]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.

Air and Water ReactionsDust/air mixtures may ignite and explode. Insoluble in water.
Hazard Classes and Categories · 3 Einträge

Acute Tox. 3 (72.2%)

Germ cell mutagenicity - Category 2

Carcinogens

Shipment Methods and Regulations · 2 Einträge

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Storage Conditions · 1 Eintrag

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/

Cleanup Methods · 1 Eintrag

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/

Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Disposal Methods · 5 Einträge

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.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

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.

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/

For more Disposal Methods (Complete) data for DIBENZ(A,H)ACRIDINE (8 total), please visit the HSDB record page.

Preventive Measures · 5 Einträge

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

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/

For more Preventive Measures (Complete) data for DIBENZ(A,H)ACRIDINE (10 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 2 Einträge

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

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/

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9.4X10+4(SRC), determined from a log Kow of 5.73(2) and a regression-derived equation(3), indicates that dibenz(a,h)acridine is expected to be immobile in soil(SRC). Volatilization of dibenz(a,h)acridine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Dibenz(a,h)acridine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Utilizing activated sludge from 3 municipal treatment plants, 0.3-9.3% of the theoretical oxygen demand was reached in 144 hours(6), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9.3X10+4(SRC), determined from a log Kow of 5.73(2) and a regression-derived equation(3), indicates that dibenz(a,h)acridine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), a BCF of 100 measured in fathead minnows (Pimephales promelas)(7), suggests bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Utilizing activated sludge from 3 municipal treatment plants, 0.3-9.3% of the theoretical oxygen demand was reached in 144 hours(8), suggesting that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenz(a,h)acridine, which has an estimated vapor pressure of 7.5X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dibenz(a,h)acridine may be removed from the air by wet or dry deposition(SRC). Dibenz(a,h)acridine absorbs light at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDibenz(a,h)acridine was detected in sausage and salmon at unreported concentrations(1).
Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Effluent Concentrations · 5 Einträge

Dibenz(a,h)acridine was detected in air from residential coal furnace stacks at a concentration of 17 mg/1000 cu m gas. It was detected in a catalyst regeneration flue gas of a gas-oil stock from an oil refinery at concentrations ranging from <0.12 to 0.7 mg/1000 cu m gas(1). Dibenz(a,h)acridine was detected in a coal tar pitch polluted air sample at a concentration of 0.01 mg/1000 cu m air(1). Dibenz(a,h)acridine was detected in automobile exhaust at levels lower than 0.3 ug/g benzene soluble fraction, in coal burning effluent at 160 ug/g benzene soluble fraction, and at 4.0 ug/g in incinerator effluent(2). The compound was detected in fly ash from a municipal waste incinerator(3). The average urban air contains 0.2 ng/cu m dibenz(a,h)acridine(4).

Exam of several air pollution source effluents reveals...levels of 17 mg/1000 cu m of gas in domestic coal combustion stack effluent, less than 0.12 and 0.7 mg/1000 cu m of gas in petroleum refinery incinerator effluents and 0.01 mg/1000 cu m in air polluted by coal-tar pitch...

Levels below 300 ug/kg of benzene sol fraction have been found in motor exhaust gas... db(a,h)ac occurs in cigarette smoke condensate...

The primary source of PAHs in air is the incomplete combustion of wood and fuel for residential heating. The PAHs are found in gasoline or diesel motor vehicle exhaust, by-products of open fires or refuse burning, coal tar, coal tar pitch, coke tars or coke oven emissions, creosote, mineral oils, bitumens, industrial smoke and soot, cigarette and cigar tobacco and smoke, tar, or smoke condensates, and charcoal-broiled foods(1). /Polycyclic aromatic hydrocarbons/

Other sources of incidentally generated PAHs include coal and coal combustion, petroleum refinery incinerators ... incomplete combustion of diesel and kerosene, soot, and marijuana smoke ... (1). /Polycyclic aromatic hydrocarbons/

Medical Surveillance · 1 Eintrag

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/

Soil Adsorption/Mobility · 1 Eintrag

The Koc of dibenz(a,h)acridine is estimated as 9.4X10+4(SRC), using a log Kow of 5.73(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibenz(a,h)acridine is expected to be immobile in soil. A log Koc of 6.44 has been measured using humic acid(4), corresponding to a Koc of 2.7X10+5(SRC). Using HPLC columns, capacity coefficients to humic and fulvic acid decrease in the order of dibenz(c,h)acridine, dibenz(a,c)acridine/dibenz(a,h)acridine, dibenz(a,j)acridine(5). Dibenz(a,h)acridine was readily absorbed by organic rich sludge at a 1:10,000 and 1:1000 water:biosludge ratio giving Koc values of 55167 for the neutral species and 2059 for the cationic species(pH < 3.0)(6). Dibenz(a,h)acridine was detected in a mixture of compounds during the investigation of bottom material from an overflow impoundment from an abandoned wood-treatment facility(7). Dibenz(a,h)acridine did not leach into a nearby shallow aquifer(7), again suggesting that this compound is essentially immobile in soil(SRC).

Atmospheric Concentrations · 1 Eintrag

URBAN/SUBURBAN: Dibenz(a,h)acridine was measured at concentrations of 0.2 and 0.08 ng/cu m air for a residential area and a busy street, respectively, in Copenhagen in February in 1976-1982(1). Urban atmospheric air from Tokyo showed dibenz(a,h)acridine at a concentration of 0.36 ug/g of particulates; this compares to a concentration of 0.6 ug/g of particulates measured in the United States and a concentration of 50 ug/g of particulates measured for coal tar pitch polluted air(2). Dibenzacridines were detected during the measurement of aerosols in Belgium at two monitoring stations from 1976-1979. The mass median equivalent diameter ranged from 0.61-1.2 um(3). The concentration of dibenz(a,h)acridine in the average American urban atmosphere was determined to be 0.6 ug/g airborne particles or 0.08 ug/1000 m cu air(5) up to 0.2 ug/cu m(6).

Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ Tumorigenic agents identified in particulate phase of tobacco smoke: dibenz(a,h)acridine--traces in cigarettes. /From table/
Artificial Pollution Sources · 1 Eintrag

Dibenz(a,h)acridine is directly released to the environment as an incomplete combustion product of organic compounds and is found in automobile exhaust, coal-burning effluent, and incinerator effluent(1). It is also found in cigarette smoke condensate(1).

Environmental Biodegradation · 1 Eintrag

AEROBIC: Dibenz(a,h)acridine at a concentration of 500 mg/L was incubated aerobically for 144 hours with activated sludge from three Tennessee municipal treatment plants (Ashland City, Franklin, and Nashville)(1). Ashland City at 2500 mg/L activated sludge gave 0.3%, 0.5% and 0.7% of the theoretical oxygen demand at 24, 72, 144 hours, respectively. At a sludge concentration of 5000 mg/L, 0.9 and 5.0% of the theoretical oxygen demand was reached at 24 and 144 hours, respectively. Nashville at 2500 mg/L activated sludge gave 0.9%, 3.1%, and 4.6% of the theoretical oxygen demand at 24, 72, and 144 hours, respectively. At a sludge concentration of 5000 mg/L, 1.2 and 17.3% of the theoretical oxygen demand was reached at 24 and 144 hours, respectively. Dibenz(a,h)acridine was toxic to the Franklin sludge except at the 24 hour timepoint (0.2% of the theoretical oxygen demand). At a sludge concentration of 5000 mg/L, however, 2.8 and 9.3% of the theoretical oxygen demand was reached at 24 and 144 hours, respectively(1).

Sediment/Soil Concentrations · 1 Eintrag

SEDIMENT: Dibenz(a,h)acridine was detected at unreported concentrations during investigations of bottom material from an overflow impoundment from an abandoned wood-treatment facility near Pensacola, Florida(1). Dibenz(a,c or a,h)acridine was detected in Lake Zurich surface sediments at a concentration of 35 ng/g and in Lake Lucerne sediments at a concentration of 5.0 ng/g(2). Street dust was measured at 260 ng/g dibenz(a,c or a,h)acridine(2).

Carcinogen Classification · 5 Einträge

Dibenz[a,h]acridine

Group 2B: Possibly carcinogenic to humans

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

2013

2011

Sicherheitsdaten

ridadr
2811
risk_code
22-40-41
hazard_code
Xn
safety_code
26-39
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
226-36-8(Hazardous Substances Data)

As part of a project to assess the effect of heterocyclic nitrogen in modifying the metabolism and mutagenicity of polycyclic aromatic hydrocarbons, /the authors/ investigated the metabolism of dibenz(a,h)acridine (DB(a,h)AC) by liver microsomes prepared from male Sprague-Dawley rats. During a 6-min incubation 21, 14, 0.7 or 0.2 nmol DB(a,h)AC per mg protein were metabolized by microsomes from rats pre-treated with DB(a,h)AC, 3-methylcholanthrene (3-MC), phenobarbital (PB) or corn oil, respectively. In each case the predominant metabolites were the dihydrodiols with bay-region double bonds, namely, DB(a,h)AC-3,4-dihydrodiol and DB(a,h)AC-10,11-dihydrodiol, each of which accounted for 21-23% of the total metabolism determined during a 7-min incubation with microsomes from 3-MC-treated rats. Other metabolites produced by these microsomes included DB(a,h)AC-1,2-dihydrodiol (approximately 5% of total metabolites); two K-region oxides (DB(a,h)AC-12,13- and 5,6-oxides (estimated to represent 5% and 2% of total metabolites, respectively)); several unidentified polar metabolites (10-15%) and several unidentified metabolites which co-eluted with 3-hydroxy-DB(a,h)AC (20%). DB(a,h)AC-8,9-dihydrodiol was not detected (less than 2%). The metabolite profiles produced by microsomes prepared from rats pretreated with DB(a,h)AC, PB or corn oil were very similar to the profile produced by 3-MC-induced microsomes. /Investigators/ conclude that: the potentially mutagenic benzo-ring dihydrodiols with bay-region double bonds are the predominant metabolite of DB(a,h)AC; the heterocyclic nitrogen atom has little effect in modifying the relative extents of formation of these two benzo-ring dihydrodiols with bay-region double bonds; metabolism at the K-region is only a minor pathway for DB(a,h)AC, as is also true for the carbon analogue dibenz(a,h)anthracene; and induction by a 3-MC-type inducer (e.g. DB(a,h)AC) is required for substantial metabolism to occur.

MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Verwendung und Herstellung

Uses · 2 Einträge

Produced from incomplete combustion of organic substances; Used for biochemical research; [HSDB]

BIOCHEMICAL RESEARCH

U.S. Production · 2 Einträge

(1975) NOT PRODUCED COMMERCIALLY IN US

(1977) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingFORMED FROM INCOMPLETE COMBUSTION OF ORGANIC MATERIALS (EG, REFUSE BURNING, OPERATION OF MOTOR VEHICLES, INDUST PROCESSES)

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

14-Butyldibenz[a,h]acridine

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