5-Methylchrysene

242.31

242.31

O66195MC8L

407620

DTXSID6063143

C29804

Needles (recyrstallized from benzene/ethanol) with a brilliant bluish-violet fluorescence in ultraviolet light

2902909090

0

6.07 (est)

5-methylchrysene appears as purple crystals. Water insoluble.

1.2±0.1 g/cm3

117.5 °C

449.4±12.0 °C at 760 mmHg

217.8±13.7 °C

1.748

soluble in acetone

2-8°C

5.45X10-7 mm Hg at 25 deg C (est)

Henry's Law constant = 5.53X10-6 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.31X10-10 cu cm/molec-sec at 25 °C (est)

Dust/air mixture may ignite and explode. Insoluble in water.

Hydrocarbons, Aromatic

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 5-METHYLCHRYSENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

NONH for all modes of transport

22-50/53-40

60-61-36/37

Xn,N

Stable under recommended storage conditions.

P201-P202-P281-P308 + P313-P405-P501

H350

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|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.|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 5-Methylchrysene (8 total), please visit the HSDB record page.

Strong oxidizers.

National Toxicology Program. Fourteenth Report on Carcinogens (2016). 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. 5-Methylchrysene (3697-24-3) is listed as reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/[Available from, as of April 6, 2009: https://ntp.niehs.nih.gov/pubhealth/roc/index-1.html]

|Danger|H302 (76%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P310, P330, P391, P405, and P501|Aggregated GHS information provided by 53 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P391, and P501|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501

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/|Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: /Coal tar pitch volatiles/[Table#6550]|Respirator Recommendations: Escape conditions: /Coal tar pitch volatiles/[Table#6551]|Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|For more Personal Protective Equipment (PPE) (Complete) data for 5-Methylchrysene (7 total), please visit the HSDB record page.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

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/|ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

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 5-Methylchrysene (17 total), please visit the HSDB record page.

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/

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.2 mg/cu m. /Coal tar pitch volatiles (benzene soluble fraction), anthracene, BaP, phenanthrene, acridine, chrysene, pyrene/

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.1 mg/cu m (cyclohexane-extractable fraction). /Coal tar pitch volatiles/|NIOSH considers coal tar pitch volatiles to be potential occupational carcinogens. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration. /Coal tar pitch volatiles/

5-Methylchrysene has been identified in gasoline engine exhaust(1).

SEDIMENT: 5-Methylchrysene was detected at unreported concentrations in Black River sediment collected near the outfall of coking ovens used for the production of steel near Lorain, OH(1). The compound was detected <2.00 ng/g in 4 of 6 salt march sediments from the Bay of Cadiz, Spain, collected near the wastewater treatment plant outflows (cities of Chiclana de la Frontera, El Puerto de Santa Maria, and Rota. The remaining 2 of 6 sediment samples (Puerto Real and Cadiz) contained 5-methylchrysene at concentrations of 205.00-229.50 and 4.56-6.73 ng/g(2).

INDOOR: Indoor air particulate samples (<10 um) were collected in Chinese homes from Xuan Wei county burning smokey coal, smokeless coal, and wood in 1983 and 1984; the concentration of 5-methylchrysene was 1.6 to 17 ug/cu m, 0.21 to 3.5 ug/cu m, and 0.03 to 0.05 ug/cu m, respectively. Sampling was conducted in March and September, 2011(1).|SOURCE DOMINATED: 5-Methylchrysene was detected at 21 and 13 pg/cu m in PM2.5 samples within 10 m of an 8-lane highway in Raleigh, NC, with an annual average daily traffic count of 125,000 vehicles and a parallel secondary road of 200 vehicles/day 275 m distant from the highway collection site, respectively(1).

5-Methylchrysene has been detected, not quantified in mineral oil(1). The compound is a component of tobacco smoke(2,3) and marijuana smoke(4). Concentrations in mainstream smoke of US domestic brand cigarettes at a range of 2.5-3.9 ng/cigarette; limit of detection in smoke = 0.94 pg(5).

IDENTIFICATION AND USE: 5-Methylchrysene (5-MeC) is a solid polycyclic aromatic hydrocarbon. There is no commercial production or known use of this compound. Reference samples of certified high purity are available. HUMAN EXPOSURE AND TOXICITY: It is reasonably anticipated to be a human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals. ANIMAL STUDIES: A group of 25 male mice received sc injections of 0.05 mg highly purified5-MeC once every 2 weeks for 20 wk (total dose, 0.5 mg) and were observed for a further 12 weeks. A total of 22/25 mice had 24 fibrosarcomas, with an average latent period of 25 weeks. 5-MeC was found to be a potent lung carcinogen in strain A/J mice, inducing more than 100 tumors/mouse at a concentration of 200 mg/kg. 5-MeC induced both adenomas and DNA adducts in a dose-dependent manner in the lungs of mice. A strong correlation of lung adenoma induction with the time-integrated DNA adduct level values was observed. 5-MeC was a strong tumor initiator on mouse skin. The environmental carcinogen 5-MeC can be activated to mutagenic metabolites by several isozymes of cytochrome P-450. The resulting reactive diol-epoxides can be detoxified via conjugation by glutathione S-transferases.

5-Methylchrysene is one of many polycyclic aromatic hydrocarbons (PAH), a group of chemicals that are formed during the incomplete burning of coal, wood or other organic substances. PAHs generally occur as complex mixtures, for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in crude oil. They are found throughout the environment in the air, water, and soil(1). /Polycyclic aromatic hydrocarbons/

5-Methylchrysene is a member of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). 5-Methylchrysene is a product of incomplete combustion and as a component of tobacco and marijuana smoke(1), which will result in its direct release to the environment(SRC). There is no commercial production of this compound(1). 5-Methylchrysene is formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances. PAHs generally occur as complex mixtures, for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in substances such as crude oil and coal. They are found throughout the environment in the air, water, and soil(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.0X10+5(SRC), determined from a structure estimation method(2), indicates that 5-methylchrysene is expected to be immobile in soil(SRC). Volatilization of 5-methylchrysene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 5-Methylchrysene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). PAHs with four or more rings, such as 5-methylchrysene, are generally expected to be resistant to biodegradation(4). Chrysene (an analogous compound) has reported soil die-away half-lives ranging from 2 to 2.7 years(5), suggesting the biodegradationof 5-methylchyrsene is a slow environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.0X10+5(SRC), determined from a structure estimation method(2), indicates that 5-methylchrysene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 30 and 224 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 734 months if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 4700(SRC), from an estimated log Kow of 6.07(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC) provided the compound is not metabolized by the organism(SRC). Polycyclic aromatic hydrocarbons (PAHs) may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(7). PAHs with four or more rings, such as 5-methylchrysene, are generally expected to be resistant to biodegradation(8). For structurally analogous chrysene, half-lives in aerobic sediment slurry samples ranged from 153 to 189 days(9), suggesting that biodegradation may be a slow environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-methylchrysene, which has an estimated vapor pressure of 5.5X10-7 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. Vapor-phase 5-methylchrysene 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 0.1 days(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 5-methylchrysene may be removed from the air by wet and dry deposition(SRC). 5-Methylchrysene absorbs UV light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 5-methylchrysene with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 5-Methylchrysene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 5-Methylchrysene does absorb UV light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 4700 was calculated in fish for 5-methylchrysene(SRC), using an estimated log Kow of 6.07(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). PAHs may not bioconcentrate in aquatic organisms which contain microsomal oxidase, such as fish, as this enzyme enables the rapid metabolism of certain polycyclic aromatic hydrocarbons(3). Some marine organisms have no detectable aryl hydrocarbons hydroxylase enzyme systems, namely: phytoplankton, certain zooplankton, mussels (Mytilus edulis), scallops (Placopecten sp), and snails (Litternia littorea)(4). Those organisms which lack a metabolic detoxification enzyme system, tend to accumulate polycyclic aromatic hydrocarbons(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 5-methylchrysene can be estimated to be 3.0X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 5-methylchrysene is expected to be immobile in soil.

The Henry's Law constant for 5-methylchrysene is estimated as 5.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 5-methylchrysene 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 30 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 220 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 734 months if adsorption is considered(3). 5-Methylchrysene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 5-Methylchrysene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-7 mm Hg(SRC), determined from a fragment constant method(4).

Occupational exposure to 5-methylchrysene may occur through inhalation of dust particles contaminated with incomplete combustion products and dermal contact with incomplete combustion products containing 5-methylchrysene. Limited monitoring data indicate that the general population may be exposed to 5-methylchrysene via inhalation of cigarette smoke and inhalation of ambient air. (SRC)

Substances 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. (See all compounds classified as Carcinogens.)

The metabolic activation of the environmental carcinogen 5-methylchrysene was studied by combining high-pressure liquid chromatographic analysis of metabolites formed in vitro with assays of these metabolites for mutagenic activity toward Salmonella typhimurium. Metabolites were formed by incubation of 5-methylchrysene with the 9000 from Aroclor-treated rat livers. With the use of reverse-phase columns, the metabolites were resolved into 9 peaks, A to I. Each peak was collected and tested for mutagenicity with activation. Significant mutagenic activity was observed primarily in peak E and to a lesser extent in peak D. None of the other metabolites showed significant mutagenic activity. The major mutagenic metabolite (peak E) was identified as 1,2-dihydro-1,2-dihydroxy-5-methylchrysene (7.0% from 5-methylchrysene); peak D was 7,8-dihydro-7,8-dihydroxy-5-methylchrysene (2.6% from 5-methylchrysene). Other metabolites included 9,10-dihydro-9,10-dihydroxy-5-methylchrysene, 9-hydroxy-5-methylchrysene, 7-hydroxy-5-methylchrysene, 1-hydroxy-5-methylchrysene and 5-hydroxymethylchrysene. These results indicate that 1,2-dihydro-1,2-dihydroxy-5-methylchrysene is a major proximate mutagen of 5-methylchrysene.|1,2- & 7,8-Dihydrodiols were the major metabolites of 5-methylchrysene, 7 small amounts of the 9,10-dihydrodiol were also formed following incubation of the compound with rat-liver preparations. Other metabolites detected include 1-, 7- & 9-hydroxy-5-methylchrysene & 5-hydroxymethylchrysene.|The metabolic activation in mouse skin of the strong carcinogen, 5-methylchrysene (5-MeC) was compared to that of the inactive compound, 6-nitro-5-methylchrysene (6-NO2-5-MeC). Metabolites of 6-NO2-5-MeC, formed using rat liver homogenates, were identified based on their spectral properties and were used as markers for studies performed in vivo. In mouse epidermis in vivo, the identified metabolites of 6-NO2-5-MeC were trans-1,2-dihydro-1,2-dihydroxy-6-nitro-5-methylchrysene (6-NO2-5-MeC-1,2-diol), the precursor to a bay region dihydrodiol epoxide, trans-9,10-dihydro-9,10-dihydroxy-6-nitro-5-methylchrysene, and 6-nitro-5-hydroxymethylchrysene. The levels of 6-NO2-5-MeC-1,2-diol formed in mouse epidermis from 6-NO2-5-MeC were greater than those of the proximate carcinogen trans-1,2-dihydro-1,2-dihydroxy-5-methylchrysene (5-MeC-1,2-diol) formed from 5-MeC. The further metabolism of 6-NO2-5-MeC-1,2-diol was examined in mouse epidermis under conditions similar to those described previously for 5-MeC-1,2-diol. The extents of formation of 1,2,3,4-tetraols from both dihydrodiols were similar. The chromatographic patterns of DNA adducts formed in mouse epidermis from 6-NO2-5-MeC and 5-MeC were qualitatively similar; however, the extent of formation of DNA adducts from 5-MeC was 15-fold greater than from 6-NO2-5-MeC. The reactions between calf thymus DNA and the bay region 1,2-diol-3,4-epoxides of 5-MeC and 6-NO2-5-MeC were compared; the levels of adducts formed from the bay region diol epoxide of 5-MeC were about four times greater than those formed from the bay region diol epoxide of 6-NO2-5-MeC. The results indicate that the relatively low DNA binding in vivo of 6-NO2-5-MeC may be responsible for its apparent lack of tumorigenicity compared to 5-MeC. It is likely that nitro substitution at the 6-position of 5-MeC interferes with the structural requirements of the 1,2-diol-3,4-epoxide which are necessary for specific DNA interactions.|We have investigated the metabolism of chrysene (CHR) and 5-methychyrsene (5-MeCHR) by Shasta rainbow trout (Oncorhyncus mykiss) and Long Evans rat liver microsomes to assess the effect of a non-benzo ring methyl substituent on the reactions involved in the metabolism of polycyclic aromatic hydrocarbons (PAHs). Trout as well as rat liver microsomes metabolized both CHR and 5-MeCHR at essentially similar rates, indicating that the methyl substituent does not alter the substrate specificity of the cytochrome P450(s) involved in the metabolism of the two PAHs. Dihydrodiols were the major CHR metabolites formed by both trout and rat liver microsomes, whereas the trout liver microsomes formed a considerably higher proportion of 5-MeCHR phenols compared to diols, indicating that 5-methyl substitution alters the substrate specificity of trout microsomal epoxide hydrolase for 5-MeCHR epoxides. Unlike trout liver microsomes, rat liver microsomes formed a much greater proportion of 5-MeCHR diols compared to 5-MeCHR phenols, suggesting that 5-MeCHR epoxides are better substrates for the microsomal epoxide hydrolase present in rat liver than for the enzyme in trout liver. Both trout and rat liver microsomes are more efficient at attacking the bay-region bond versus the non-bay-region double bond in chrysene. In contrast the reverse is true in the case of 5-MeCHR, indicating that a non-benzo ring methyl substituent alters the regioselectivity of the enzymes involved in the oxidative metabolism of PAHs.|For more Metabolism/Metabolites (Complete) data for 5-Methylchrysene (10 total), please visit the HSDB record page.|5-methylchrysene has known human metabolites that include 5-Methyl-1,2-dihydrochrysene-1,2-diol.

Carcinogens

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

5-methylchrysene

There is no commercial production or known use of this compound. Reference samples of certified high purity are available....

Health Hazards -> Carcinogens