3-Nitrobenzanthrone

Last updated
3-Nitrobenzanthrone
3-Nitrobenzanthrone.png
Names
Preferred IUPAC name
3-Nitro-7H-benzo[de]anthracen-7-one
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C17H9NO3/c19-17-12-5-2-1-4-10(12)11-8-9-15(18(20)21)13-6-3-7-14(17)16(11)13/h1-9H Yes check.svgY
    Key: QAJOWHGESRCVLY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H9NO3/c19-17-12-5-2-1-4-10(12)11-8-9-15(18(20)21)13-6-3-7-14(17)16(11)13/h1-9H
    Key: QAJOWHGESRCVLY-UHFFFAOYAK
  • O=C2C1=CC=CC=C1C4=C3C2=CC=CC3C([N+]([O-])=O)C=C4
  • [O-][N+](=O)c2c1cccc4c1c(cc2)c3c(cccc3)C4=O
Properties
C17H9NO3
Molar mass 275.26 g/mol
Melting point 248 °C (478 °F; 521 K) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
extremely carcinogenic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

3-Nitrobenzanthrone (3-nitro-7H-benz[de]anthracen-7-one) is a chemical compound emitted in diesel exhaust; it is a potent carcinogen. [2] It produced the highest score ever reported in the Ames test, a standard measure of the cancer-causing potential of toxic chemicals, far greater than the previous known strongest (1,8-dinitropyrene, which is also found in diesel exhaust). [3]

See also

Related Research Articles

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The Ames test is a widely employed method that uses bacteria to test whether a given chemical can cause mutations in the DNA of the test organism. More formally, it is a biological assay to assess the mutagenic potential of chemical compounds. A positive test indicates that the chemical is mutagenic and therefore may act as a carcinogen, because cancer is often linked to mutation. The test serves as a quick and convenient assay to estimate the carcinogenic potential of a compound because standard carcinogen assays on mice and rats are time-consuming and expensive. However, false-positives and false-negatives are known.

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruses and bacteria. Most carcinogens act by creating mutations in DNA that disrupt a cell's normal processes for regulating growth, leading to uncontrolled cellular proliferation. This occurs when the cell's DNA repair processes fail to identify DNA damage allowing the defect to be passed down to daughter cells. The damage accumulates over time. This is typically a multi-step process during which the regulatory mechanisms within the cell are gradually dismantled allowing for unchecked cellular division.

<span class="mw-page-title-main">Mutagen</span> Physical or chemical agent that increases the rate of genetic mutation

In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes.

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<span class="mw-page-title-main">Carbon black</span> Chemical compound

Carbon black is a material produced by the incomplete combustion of coal tar, vegetable matter, or petroleum products, including fuel oil, fluid catalytic cracking tar, and ethylene cracking in a limited supply of air. Carbon black is a form of paracrystalline carbon that has a high surface-area-to-volume ratio, albeit lower than that of activated carbon. It is dissimilar to soot in its much higher surface-area-to-volume ratio and significantly lower polycyclic aromatic hydrocarbon (PAH) content.

Benzo(<i>a</i>)pyrene Carcinogenic compound found in smoke and soot

Benzo[a]pyrene (BaP or B[a]P) is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C20H12 is one of the benzopyrenes, formed by a benzene ring fused to pyrene. Its diol epoxide metabolites, more commonly known as BPDE, react with and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already known to be connected to soot.

<span class="mw-page-title-main">Nitrosamine</span> Organic compounds of the form >N–N=O

In organic chemistry, nitrosamines are organic compounds with the chemical structure R2N−N=O, where R is usually an alkyl group. They feature a nitroso group bonded to a deprotonated amine. Most nitrosamines are carcinogenic in nonhuman animals. A 2006 systematic review supports a "positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, and between preserved fish, vegetable and smoked food intake and gastric cancer, but is not conclusive".

<span class="mw-page-title-main">Chemical hazard</span> Non-biological hazards of hazardous materials

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IARC group 1 Carcinogens are substances, chemical mixtures, and exposure circumstances which have been classified as carcinogenic to humans by the International Agency for Research on Cancer (IARC). This category is used when there is sufficient evidence of carcinogenicity in humans. Exceptionally, an agent may be placed in this category when evidence of carcinogenicity in humans is less than sufficient, but when there is sufficient evidence of carcinogenicity in experimental animals and strong evidence in exposed humans that the agent (mixture) acts through a relevant mechanism of carcinogenicity.

<span class="mw-page-title-main">DNA adduct</span> Segment of DNA bound to a cancer-causing chemical

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Chemophobia is an aversion to or prejudice against chemicals or chemistry. The phenomenon has been ascribed both to a reasonable concern over the potential adverse effects of synthetic chemicals, and to an irrational fear of these substances because of misconceptions about their potential for harm, particularly the possibility of certain exposures to some synthetic chemicals elevating an individual's risk of cancer. Consumer products with labels such as "natural" and "chemical-free" appeal to chemophobic sentiments by offering consumers what appears to be a safer alternative.

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<span class="mw-page-title-main">Dibenzopyrenes</span> Chemical compound

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References

  1. Hansen, Tanja; Seidel, Albrecht; Borlak, Juergen (2007). "The environmental carcinogen 3-nitrobenzanthrone and its main metabolite 3-aminobenzanthrone enhance formation of reactive oxygen intermediates in human A549 lung epithelial cells". Toxicology and Applied Pharmacology . 221 (2): 222–234. doi:10.1016/j.taap.2007.03.003. PMID   17477947. S2CID   25295474.
  2. Volker M. Arlt (2005). "3-Nitrobenzanthrone, a potential human cancer hazard in diesel exhaust and urban air pollution: a review of the evidence". Mutagenesis. 20 (6): 399–410. CiteSeerX   10.1.1.1001.7655 . doi: 10.1093/mutage/gei057 . PMID   16199526.
  3. Fred Pearce (Oct 25, 1997). "Devil in the diesel". New Scientist: 4.