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HCID 62275Erstellt: 27. Oktober 2026

Meiqx

MEIQX · MelQx · Ccris 2536 · Brn 4188271 · 8-Methyl-iqx · MeIQx, Mutagenic agent · 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline · 3,8-Dimethyl-3H-Imidazo[4,5-f]quinoxalin-2-amine

https://huagongshe.com/de/chemical/62275

Molekülstruktur von Meiqx

Identifikatoren & physikalische Daten

CAS No.77500-04-0
SummenformelC11H11N5
Durchschnittliche Molmasse213,24 g/mol
Monoisotopische Masse213,10144535 g/mol
SMILESCc1cnc2ccc3c(nc(N)n3C)c2n1
InChIKeyDVCCCQNKIYNAKB-UHFFFAOYSA-N
PubChem CID62275
ChEBICHEBI:76604
EC No.690-718-6
DTXSIDDTXSID1020801

Chemische & physikalische Eigenschaften

XLogP1
Polarare Oberfläche (TPSA)69,6
H-Brücken-Donoren1
H-Brücken-Akzeptoren4
Frei drehbare Bindungen0
Schwere Atome16
Formalladung0
Komplexität271
StoffklassenNitrogen Compounds -> Other Aromatics (Nitrogen)
LogP (Verteilungskoeffizient)log Kow = 1.01
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt295 - 300 °C> 300°C
Dampfdruck0.00000002 [mmHg]
Physical DescriptionYellow solid[Toronto Research Chemicals MSDS]
Dissociation ConstantspKa1 = 1.43 (secondary amine)pKa2 = 5.23 (secondary amine)
Siedepunkt343.23°C (rough estimate)
Dichte1.2597 (rough estimate)
Brechungsindex1.6880 (estimate)
LagerbedingungenRefrigerator
LöslichkeitDMSO (Slightly, Heated), Methanol (Slightly, Heated)
AggregatzustandSolid
pKa (Säurekonstante)2.20±0.50(Predicted)
FarbeYellow to Green
Henry-Konstante6.2×107 mol/(m3Pa) at 25℃, HSDB (2015)
StabilitätHygroscopic

Sicherheit & Vorschriften

GHS-EinstufungWarningH351 (100%): Suspected of causing cancer [Warning Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Regulatorische InformationenHazard Traits - Carcinogenicity
GefahrenübersichtMay cause irritationSuspected mutagen and carcinogen[Toronto Research Chemicals MSDS]
Special ReportsIARC Monographs on the Evaluation of Carcinogenic Risks to Humans. MeIQx in: Some Naturally Occurring Substances: Food Items and Constituents, Heterocyclic Aromatic Amines and Mycotoxins (vol 56). p.210-228. (1993). IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Available from, as of November 18, 2009: http://monographs.iarc.fr/ENG/Monographs/vol56/mono56-12.pdf]National Toxicology Program. Eleventh Report on Carcinogens (2005). 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. 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) (77500-04-0) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of September 23, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s092vhca.pdf]
Hazard Classes and CategoriesCarc. 2 (100%)
Shipment Methods and RegulationsPRECAUTIONS 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/

Anwendungen & Verwendung

Verwenden

Diet meat mutagen heterocyclic amine colorectal adenoma recurrence.

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/
LagerbedingungenPRECAUTIONS 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/
ReinigungsverfahrenPRECAUTIONS 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/
EntsorgungsverfahrenPRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /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 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (6 total), please visit the HSDB record page.
Preventive MeasuresPRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/For more Preventive Measures (Complete) data for 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (9 total), please visit the HSDB record page.
Personal Protective Equipment (PPE)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/
Wechselwirkungen/It was/ previously demonstrated using a bacterial system that the antigenotoxic activity of the anthraquinone compounds purpurin and alizarin was due to the suppression of microsomal enzyme activity involved in the activation of mutagens. In the present study we determined the effect of purpurin and alizarin on (i) MeIQx-DNA-adduct formation in mouse tissues and (ii) the activity of phases I and II enzymes in liver fractions, the liver being the target tissue of MeIQx. The amount of MeIQx-DNA adduct formed was determined using (32P)-postlabeling methods. Methoxyresorufin-O-demethylase (MROD) and ethoxyresorufin-O-deethylase (EROD) enzyme activities, which reflect CYP 1A activity, were measured as markers for phase I enzymes, and UDP-glucuronyltransferase (UGT) and glutathione S-transferase (GST) activities were determined as markers for phase II enzymes. Mice fed with a diet containing 0.5% purpurin for 3 days prior to MeIQx administration had 70% fewer MeIQx-DNA adducts in the lung and kidney, and fewer DNA adducts (insignificant, statistically) in the liver compared with mice fed a diet lacking purpurin. MROD and EROD activities in the liver of these mice increased six- and eight-fold, respectively, and were higher than those determined for the control mice within 1 day following commencement of purpurin treatment. These elevated activities were maintained during treatment and declined immediately following removal of purpurin from the diet. GST and UGT activities gradually increased 2.5- and 3-fold, respectively, following purpurin treatment, and were maintained at significantly high levels even after purpurin administration ceased. Alizarin did not significantly affect DNA-adduct formation and enzyme activity, except in the case of UGT. Taken together, /the/ results show that purpurin reduced MeIQx-DNA-adduct formation by maintaining elevated phase II enzyme activities, thereby facilitating accelerated excretion of MeIQx.A single oral treatment of rats with MeIQx followed by phenobarbital, combined with further modulating procedures, stimulated development of foci of altered hepatocytes. Sequential administration of MeIQx after N-nitrosodiethylamine enhanced the appearance of foci of altered hepatocytes in rats.The modifying effects of cigarette smoke (CS) exposure on a heterocyclic amine (HCA) 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)-induced carcinogenesis were investigated in male F344 rats. Groups 1 and 2 were fed MeIQx at a dose of 300 ppm, and simultaneously received CS and sham smoke (SS) for 16 wk, respectively. Groups 3 - 5 were given the MeIQx diet for 4 wk, and simultaneously exposed to CS for 4 wk (group 3), exposed to CS for 12 wk after the MeIQx treatment (group 4), or received SS for 16 wk (group 5). Groups 6 and 7 were fed basal diet and respectively received CS and SS for 16 wk. In terms of the mean number or area, the development of glutathione S-transferase placental form-positive (GST-P(+)) liver cell foci was significantly (P < 0.01) greater in group 1 than in group 2. The mean number of colonic aberrant crypt foci (ACFs) per animal was increased by continuous CS exposure regardless of MeIQx feeding, the differences between groups 4 and 5 (P < 0.05), and between groups 6 and 7 (P < 0.05) being significant. Immunoblot analysis confirmed that the hepatic CYP1A2 level in group 6 was remarkably increased as compared to that in group 7. In addition, liver S9 from rats in group 6 consistently increased the mutagenic activities of six HCAs including MeIQx as compared to those in group 7. Thus, our results clearly indicate that CS enhances hepatocarcinogenesis when given in the initiation phase via increasing intensity of metabolic activation for MeIQx and possibly colon carcinogenesis when given in the post-initiation phase in rats induced by MeIQx.... The effects of low doses of 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline (MeIQx) /were examined/ in combination with carbon tetrachloride (CCl4) on the formation of glutathione S-transferase placental form (GST-P)-positive foci in rat liver. Administration of diet containing MeIQx at 0.4, 4, or 40 ppm, representing one-thousandth, one-hundredth, and one-tenth of the dose proved to induce hepatocellular carcinomas (400 ppm), for 8 or 12 wk did not induce GST-P-positive foci. However, 40 ppm of MeIQx when co-administered with CCl4 (0.7 mL/kg, sc twice a wk) induced preneoplastic lesions: 7- and 3-fold increases in the numbers and areas of GST-P positive foci in wk 8, and 8- and 6-fold increases respectively in wk 12, over those with CCl4 alone. Furthermore, a marked increase in the number of hyperplastic nodules was observed in this group of rats in wk 12. No significant increases of GST-P-positive foci were observed at doses of 0.4 or 4 ppm MeIQx in combination with CCl4. Thus, it is predicted that chronic exposure to 40 ppm of MeIQx eventually results in induction of hepatocellular carcinomas in injured rat liver.For more Interactions (Complete) data for 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (19 total), please visit the HSDB record page.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,500(SRC), determined from a structure estimation method(2), indicates that 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is expected to have slight mobility in soil(SRC). The pKa of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is estimated as 5.2(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-13 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(5). 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). Biodegradation in soil data were not available(SRC, 2009).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,500(SRC), determined from a structure estimation method(2), indicates that 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline 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 1.6X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2(SRC), from a log Kow of 1.01(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Amino-3,8-dimethylimidazo[4,5-f]quinoline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental condition(3). Biodegradation in water data were not available(SRC, 2009).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, which has an estimated vapor pressure of 1.7X10-8 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 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline may be removed from the air by wet or dry deposition(SRC). 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Lebensmitteluntersuchungswerte2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline was detected in meat and chicken purchased from local Okayama, Japan markets, following cooking and analysis on the same day: in chicken, pork, well done beef and medium beef at 77, 202, 198 and 138 pg/g of sample, respectively(1). Food purchased at a supermarket in Little Rock, AK and cooked, contained 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in pan fried beef at 1450, 3720 and 5310 pg/g of meat, in pan fried beef scrapings at 62,600 pg/g of meat, in barbequed beef at 527 and 1600 pg/g of meat, beef extract at 37,800 pg/g of meat and in barbequed chicken at 335 pg/g of meat(2).
Unerwünschte WirkungenIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Medical SurveillancePRECAUTIONS 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/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline can be estimated to be 2,500(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is expected to have slight mobility in soil. The pKa of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is estimated as 5.2(3), indicating that this compound will exist partially in the cation form in the environment and cations generally do adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Human Toxicity Excerpts/EPIDEMIOLOGY STUDIES/ Although evidence suggests that consumption of well-done or grilled meat may be associated with increased cancer risk in humans, the data are insufficient to support the conclusion that this risk is due specifically to MeIQx present in these foods ... The presence of an individual heterocyclic amine (HCA) in cooked meat is highly correlated with the presence of other HCAs and with many other constituents, including protein, animal fat, nitrosamines, and substances other than HCAs formed during cooking, such as polycyclic aromatic hydrocarbons. It is therefore difficult to establish associations between cancer risk and specific HCAs.[DHHS/National Toxicology ProgramEleventh Report on Carcinogens: 2-Amino-3,8-Dimethylimidazo/EPIDEMIOLOGY STUDIES/ ... During high temperature cooking of red meats, heterocyclic amines (HCAs) are generatedhowever, to be carcinogenic, they must be metabolized by enzymes including cytochrome P450 1A2 (CYP1A2) and N-acetyltransferase 1 (NAT1) and/or N-acetyltransferase 2 (NAT2) ... A clinic-based case-control study of colorectal adenomas ... focused on assessment of exposure to HCAs (estimated by use of a HCA database and meat cooking module) and modification of these exposures by genetic factors. /The authors/previously reported that intake of MeIQx was associated with an increased risk of colorectal adenomas [overall association at 80th percentile, > 27.00 ng/day: odds ratio (OR) = 2.68, 95% confidence interval (CI) 1.58-4.55]. Here, .... the evaluation of whether variation in CYP1A2, NAT1 and/or NAT2 modify the association between HCAs and colorectal adenoma formation in 146 cases and 228 frequency-matched controls /is reported/. The NAT1*10 allele was associated with a nonsignificant increased risk of colorectal adenomas (OR = 1.4395% CI 0.86-2.36). Further, when ... 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) intake /was analyzed/ as a categorical variable, ... a six-fold increase in adenoma risk among rapid NAT1 acetylators who consumed more than 27 ng/day (OR = 6.5095% CI 2.16-19.7) /was observed/, whereas among slow NAT1 acetylators, the increase in risk was two-fold (OR = 2.3295% CI 1.12-4.81). While suggestive, the results were not significantly different from each other on either an additive or multiplicative scale .../GENOTOXICITY/ In order to study the mutagenic effects of heterocyclic aromatic amines (HAAs) in cells of human origin, five compounds, namely 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ), 2-amino-3, 4-dimethyl-imidazo[4,5-f]quinoline (MeIQ), 2-amino-3, 8-dimethyl-imidazo[4,5-f]quinoxaline (MeIQx), the pyridoimidazo derivative 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), were tested in micronucleus (MN) assays with a human derived hepatoma (HepG2) cell line. All HAAs caused significant, dose-dependent effects. The activities of IQ, MeIQ, MeIQx, and PhIP were similar (lowest effective concentrations 25-50 uM), whereas Trp-P-1 was effective at a dose of >/= 2.1 uM./GENOTOXICITY/ A co-expression plasmid (p1A2OR) carrying human CYP1A2 and NADPH-P450 reductase cDNAs and an expression plasmid (pOAT) carrying Salmonella TA1538/ARO cells. The CYP and OAT expressed in the Salmonella cells showed catalytic activity. The TA1538/ARO strain exhibited high sensitivity to heterocyclic amines (HCAs) such as 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimenthylimidazo[4,5-f]quinoline (MeIQx), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) as compared with the parent Ames tester strain TA1538. It is suggested that the intracellular expression of drug-metabolizing enzymes makes the Salmonella cells highly sensitive to the HCAs.For more Human Toxicity Excerpts (Complete) data for 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (7 total), please visit the HSDB record page.
Fish/Seafood Concentrations2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline was detected in fish purchased from local Okayama, Japan markets, following cooking and analysis on the same day: in the skin and flesh of pacific saury 424 and 191 pg/gin the skin and flesh of sardine at 860 and 152 pg/gat 385 and 25 pg/g in the skin and flesh of horse mackerelin the skin and flesh of mackerel at 588 pg/g and not detectedin the skin and flesh of salmon at 593 and 99 pg/gnot detected in the skin and flesh of salted atka mackerelnot detected in seasoned eel skin and fleshin semi-dried horse mackerel skin and flesh at 420 pg/g(1).
Artificial Pollution Sources2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline is formed and released in cooking fish(1), beef and chicken(1,2), resulting in its direct release to the environment. Its limited production and use for research purposes(3) may result in its release to the environment through various waste streams(SRC).[(1) Kataoka H et alBull Environ Contam Toxicol 69: 682-89 (2002) (2) Turesky RJ et alJ Agric Food Chem 53: 3248-58 (2005) (3) DHHS/National Toxicology ProgramEleventh Report on Carcinogens: 2-Amino-3,8-Dimethylimidazo
Carcinogen ClassificationMeIQx (2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline)Group 2B: Possibly carcinogenic to humansVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print)19931992
Environmental BioconcentrationAn estimated BCF of 2 was calculated in fish for 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline(SRC), using a log Kow of 1.01(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilThe Henry's Law constant for 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is estimated as 1.6X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline is expected to be essentially nonvolatile from water surfaces(2). 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-8 mm Hg(SRC), determined from a fragment constant method(3).
Zollcode29334900
RTECS-Nr.NJ5925500
GefahrensymboleT
hazard_noteToxic
Gefahrstoffdaten77500-04-0(Hazardous Substances Data)