| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-10-14 21:19:36 UTC |
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| Update Date | 2014-12-24 20:27:01 UTC |
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| Accession Number | T3D4984 |
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| Identification |
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| Common Name | Aniline |
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| Class | Small Molecule |
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| Description | Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue. |
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| Compound Type | - Carcinogen
- Dye
- Industrial/Workplace Toxin
- Metabolite
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | Aminobenzene | | Aminophen | | Anilin | | Anilina | | Aniline hydrobromide | | Aniline oil | | Aniline oil, phenylamine | | Aniline reagent | | Aniline(S#299)-Liq | | Aniline, acs | | Anilinum | | Anyvim | | Arylamine | | Benzamine | | Benzenamine | | Benzene, amino | | Benzene,amino (aniline) | | Benzeneamine | | Benzidam | | BIDD:ER0581 | | Blue oil | | C.I. Oxidation base 1 | | CI Oxidation Base 1 | | Cyanol | | D'Aniline | | HSDB 43 | | Huile d'aniline | | Krystallin | | Kyanol | | nchembio.257-comp9 | | Phenylamine | | Phenyleneamine |
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| Chemical Formula | C6H7N |
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| Average Molecular Mass | 93.127 g/mol |
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| Monoisotopic Mass | 93.058 g/mol |
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| CAS Registry Number | 62-53-3 |
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| IUPAC Name | aniline |
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| Traditional Name | aniline |
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| SMILES | NC1=CC=CC=C1 |
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| InChI Identifier | InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 |
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| InChI Key | InChIKey=PAYRUJLWNCNPSJ-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Aniline and substituted anilines |
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| Direct Parent | Aniline and substituted anilines |
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| Alternative Parents | |
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| Substituents | - Aniline or substituted anilines
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | - Bladder
- Epidermis
- Prostate
- Spleen
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | -6 °C | | Boiling Point | 245 C | | Solubility | 36 mg/mL at 25 °C | | LogP | 0.9 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00kf-9000000000-9a543eee5081cc927e82 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-e04550d3cafee77e6192 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-b4213ef5f8ee4a3df612 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1900000000-b5d970641bbe63fdb366 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00kf-9000000000-9a543eee5081cc927e82 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-e04550d3cafee77e6192 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-b4213ef5f8ee4a3df612 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1900000000-b5d970641bbe63fdb366 | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-62eb000567821fbe8a22 | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-00di-0900000000-ed34a4f0bafc3ce06174 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9000000000-a23bad3a5415210b8e58 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9000000000-129ed2147aba87164399 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-9000000000-9e60a29bae11a3beb396 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-00kf-9000000000-8e5e6fec72fd720bd3bb | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive | splash10-0006-9000000000-e04550d3cafee77e6192 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0006-9000000000-4a2ea8998eab06e3b7fa | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-002f-9000000000-041fc0d729e6308b36ec | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-004i-9000000000-c0f67277e0af76d5d6e1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0fb9-9000000000-35b2093eb2c81ba07d17 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004i-9000000000-15d86b7cf94658003a7c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03di-9000000000-fc34fd188d386065c4f5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-03dl-9000000000-fbed3991af3afeea3a79 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0006-9000000000-0bea53746f5bc30ab770 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0007-9000000000-971619ea8bd73637ba14 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9000000000-2001822055db683e8999 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0006-9000000000-a5bc25b5010f2044b435 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-0006-9000000000-8ab282b725391b0d9923 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-4a2ea8998eab06e3b7fa | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-002f-9000000000-041fc0d729e6308b36ec | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-c0f67277e0af76d5d6e1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0fb9-9000000000-35b2093eb2c81ba07d17 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-15d86b7cf94658003a7c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-9000000000-fc34fd188d386065c4f5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03dl-9000000000-fbed3991af3afeea3a79 | JSpectraViewer | MoNA | | MS | Mass Spectrum (Electron Ionization) | splash10-00kf-9000000000-4ba5d22a406245826ca0 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| Toxicity Profile |
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| Route of Exposure | Toxic by ingestion and a skin and eye irritant. |
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| Mechanism of Toxicity | Aniline induces lipid peroxidation and protein oxidation in the spleen and that oxidative stress plays a role in the splenic toxicity of aniline. The hematopoietic system is the primary target of aniline insult in rats which is characterized by methemoglobinemia, hemolysis, and hemolytic anemia and by the development of splenic hyperplasia, siderosis, fibrosis, a variety of sarcomas, and, most commonly, fibrosarcomas on prolonged exposure. Many of the characteristics of splenotoxicity in rats, such as hyperplasia, hyperpigmentation, and/or formation of highly malignant tumors such as fibrosarcomas, are not restricted to aniline exposure, but also occur when animals are exposed to substituted anilines such as chloroaniline. Studies with aniline hydrochloride in rats indicate an association between erythrocyte damage and the severity of the splenotoxicity. Since one of the major functions of the spleen is to remove damaged erythrocytes, aniline-damaged erythrocytes would be expected to be scavenged by the spleen, especially by phagocytes. The deposition and subsequent breakdown of damaged erythrocytes will not only release aniline and/or its metabolites, but, most importantly, will also result in accumulation of iron in the spleen which may catalyze the generation of tissue-damaging oxygen radicals which can subsequently cause oxidation of biomolecules and result in lipid peroxidation and protein oxidation. It is also possible that during the scavenging of damaged erythrocytes, the splenic phagocytes, especially macrophages themselves, can become activated and release reactive oxygen species (ROS) which could further contribute to the oxidation of biomolecules leading to tissue injury. (14) |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (15) |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Aniline-induced splenic toxicity is characterized by hemorrhage, capsular hyperplasia, fibrosis, and a variety of sarcomas in rats. |
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| Treatment | Not Available |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB06728 |
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| HMDB ID | HMDB03012 |
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| PubChem Compound ID | 6115 |
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| ChEMBL ID | Not Available |
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| ChemSpider ID | 5889 |
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| KEGG ID | C00292 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 17296 |
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| BioCyc ID | 34-DICHLOROANILINE |
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| CTD ID | C023650 |
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| Stitch ID | Not Available |
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| PDB ID | ANL |
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| ACToR ID | Not Available |
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| Wikipedia Link | Aniline |
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| References |
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| Synthesis Reference | Michel Dury, “Method for preparing 2-trifluoro-methoxy-aniline.” U.S. Patent US6121492, issued 0000. |
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| MSDS | T3D4984.pdf |
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| General References | - Weiss T, Angerer J: Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Oct 5;778(1-2):179-92. [12376125 ]
- Hein DW, Doll MA, Xiao GH, Feng Y: Prostate expression of N-acetyltransferase 1 (NAT1) and 2 (NAT2) in rapid and slow acetylator congenic Syrian hamster. Pharmacogenetics. 2003 Mar;13(3):159-67. [12618593 ]
- Kuo HM, Ho HJ, Chao PD, Chung JG: Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. Phytomedicine. 2002 Oct;9(7):625-31. [12487326 ]
- Faraglia B, Chen SY, Gammon MD, Zhang Y, Teitelbaum SL, Neugut AI, Ahsan H, Garbowski GC, Hibshoosh H, Lin D, Kadlubar FF, Santella RM: Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke. Carcinogenesis. 2003 Apr;24(4):719-25. [12727801 ]
- Peluso M, Airoldi L, Magagnotti C, Fiorini L, Munnia A, Hautefeuille A, Malaveille C, Vineis P: White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. Carcinogenesis. 2000 Feb;21(2):183-7. [10657956 ]
- el-Bayoumy K, Donahue JM, Hecht SS, Hoffmann D: Identification and quantitative determination of aniline and toluidines in human urine. Cancer Res. 1986 Dec;46(12 Pt 1):6064-7. [3779628 ]
- Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504. [10570033 ]
- Bomhard EM, Herbold BA: Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol. 2005 Dec;35(10):783-835. [16468500 ]
- Iwersen-Bergmann S, Schmoldt A: Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. Int J Legal Med. 2000;113(3):171-4. [10876991 ]
- Gan J, Skipper PL, Gago-Dominguez M, Arakawa K, Ross RK, Yu MC, Tannenbaum SR: Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer. J Natl Cancer Inst. 2004 Oct 6;96(19):1425-31. [15467031 ]
- Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, Leclaire J: Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett. 2005 Sep 15;158(3):196-212. [15890478 ]
- Stanley LA, Coroneos E, Cuff R, Hickman D, Ward A, Sim E: Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J Histochem Cytochem. 1996 Sep;44(9):1059-67. [8773572 ]
- Vaziri SA, Hughes NC, Sampson H, Darlington G, Jewett MA, Grant DM: Variation in enzymes of arylamine procarcinogen biotransformation among bladder cancer patients and control subjects. Pharmacogenetics. 2001 Feb;11(1):7-20. [11207033 ]
- Khan MF, Boor PJ, Gu Y, Alcock NW, Ansari GA: Oxidative stress in the splenotoxicity of aniline. Fundam Appl Toxicol. 1997 Jan;35(1):22-30. [9024670 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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