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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-03-07 21:35:52 UTC |
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Update Date | 2022-03-07 03:17:38 UTC |
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HMDB ID | HMDB0059903 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dibromochloromethane |
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Description | Dibromochloromethane, also known as chlorodibromomethane, belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. Dibromochloromethane is possibly neutral. Dibromochloromethane is a potentially toxic compound. In humans and laboratory animals, dibromochloromethane (and bromoform) are generally absorbed quickly. If required provide artificial respiration. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. Dibromochloromethane (and bromoform) are thought to be metabolized by at least two route-independent pathways: oxidation by cytochrome P-450 mixed function oxidase system and conjugation via glutathione S-transferase. Some studies in animals indicate that exposure to high doses of dibromochloromethane may also lead to liver and the kidney injury within a short period of time. Exposure to dibromochloromethane leads to central nervous system depression, which is probably the chief cause of death in acute exposures. Dibromochloromethane is oxidized into trihalomethanol by the cytochrome P-450 mixed function oxidase system of liver. After ingestion, excretion occurs primarily by exhalation of the compound or of CO2. Trihalomethanol then decomposes by loss of hydrogen and halide ions to yield the dihalocarbonyl (an analogue of phosgene), which is a highly reactive molecule, and may undergo a number of reactions, including direct reaction with cellular nucleophiles to yield covalent adducts, reaction with two moles of glutathione (GSH) to yield CO and oxidized glutathione (GSSG), and hydrolysis to yield CO2. Rinse mouth with water (never give anything by mouth to an unconscious person). EYES: irrigate opened eyes for several minutes under running water. Seek immediate medical advice. |
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Structure | InChI=1S/CHBr2Cl/c2-1(3)4/h1H |
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Synonyms | Value | Source |
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Chlorodibromomethane | HMDB | Dibromo(chloro)methane | HMDB | Dibromo-chloro-methane | HMDB | Dibromochloromethane | KEGG |
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Chemical Formula | CHBr2Cl |
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Average Molecular Weight | 208.28 |
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Monoisotopic Molecular Weight | 205.813353033 |
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IUPAC Name | dibromo(chloro)methane |
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Traditional Name | dibromochloromethane |
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CAS Registry Number | Not Available |
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SMILES | ClC(Br)Br |
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InChI Identifier | InChI=1S/CHBr2Cl/c2-1(3)4/h1H |
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InChI Key | GATVIKZLVQHOMN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. |
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Kingdom | Organic compounds |
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Super Class | Organohalogen compounds |
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Class | Alkyl halides |
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Sub Class | Halomethanes |
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Direct Parent | Trihalomethanes |
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Alternative Parents | |
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Substituents | - Trihalomethane
- Hydrocarbon derivative
- Organochloride
- Organobromide
- Alkyl chloride
- Alkyl bromide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Dibromochloromethane EI-B (Non-derivatized) | splash10-004i-5900000000-0a5bd838330dc26d5a35 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibromochloromethane EI-B (Non-derivatized) | splash10-004i-5900000000-0a5bd838330dc26d5a35 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dibromochloromethane GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adi-0960000000-88b94675ee64d5a1fa39 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dibromochloromethane GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-004i-3900000000-2bd815439d7061bd9aa2 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Positive-QTOF | splash10-0a4i-0090000000-331858b80ef37cc92b57 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Positive-QTOF | splash10-0a4i-0090000000-331858b80ef37cc92b57 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Positive-QTOF | splash10-0a4i-0090000000-331858b80ef37cc92b57 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Negative-QTOF | splash10-0udi-0090000000-23f04d542b2a35b2e302 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Negative-QTOF | splash10-0udi-0090000000-23f04d542b2a35b2e302 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Negative-QTOF | splash10-0udi-0090000000-23f04d542b2a35b2e302 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Positive-QTOF | splash10-0a4i-0090000000-262798c8821c1a784f9f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Positive-QTOF | splash10-0a4i-0090000000-262798c8821c1a784f9f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Positive-QTOF | splash10-00b9-0900000000-30e20910a1b4ef59649f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 10V, Negative-QTOF | splash10-0udi-0090000000-1cd0365290e6754179c7 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 20V, Negative-QTOF | splash10-0udi-0090000000-1cd0365290e6754179c7 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibromochloromethane 40V, Negative-QTOF | splash10-0udi-0090000000-1cd0365290e6754179c7 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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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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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 29036 |
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KEGG Compound ID | C14692 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Dibromochloromethane |
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METLIN ID | Not Available |
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PubChem Compound | 31296 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Weaver WA, Li J, Wen Y, Johnston J, Blatchley MR, Blatchley ER 3rd: Volatile disinfection by-product analysis from chlorinated indoor swimming pools. Water Res. 2009 Jul;43(13):3308-18. doi: 10.1016/j.watres.2009.04.035. Epub 2009 May 3. [PubMed:19501873 ]
- Aguilera-Herrador E, Lucena R, Cardenas S, Valcarcel M: Determination of trihalomethanes in waters by ionic liquid-based single drop microextraction/gas chromatographic/mass spectrometry. J Chromatogr A. 2008 Oct 31;1209(1-2):76-82. doi: 10.1016/j.chroma.2008.09.030. Epub 2008 Sep 13. [PubMed:18817919 ]
- Panyakapo M, Soontornchai S, Paopuree P: Cancer risk assessment from exposure to trihalomethanes in tap water and swimming pool water. J Environ Sci (China). 2008;20(3):372-8. [PubMed:18595407 ]
- Chowdhury S, Champagne P, James McLellan P: Investigating effects of bromide ions on trihalomethanes and developing model for predicting bromodichloromethane in drinking water. Water Res. 2010 Apr;44(7):2349-59. doi: 10.1016/j.watres.2009.12.042. Epub 2010 Jan 6. [PubMed:20080279 ]
- Padhi RK, Sowmya M, Mohanty AK, Bramha SN, Satpathy KK: Formation and speciation characteristics of brominated trihalomethanes in seawater chlorination. Water Environ Res. 2012 Nov;84(11):2003-9. [PubMed:23356015 ]
- Ye B, Wang W, Yang L, Wei J, E X: Formation and modeling of disinfection by-products in drinking water of six cities in China. J Environ Monit. 2011 May;13(5):1271-5. doi: 10.1039/c0em00795a. Epub 2011 Mar 18. [PubMed:21416099 ]
- Carter JM, Moran MJ, Zogorski JS, Price CV: Factors associated with sources, transport, and fate of chloroform and three other trihalomethanes in untreated groundwater used for drinking water. Environ Sci Technol. 2012 Aug 7;46(15):8189-97. doi: 10.1021/es301839p. Epub 2012 Jul 25. [PubMed:22799526 ]
- Hansen KM, Zortea R, Piketty A, Vega SR, Andersen HR: Photolytic removal of DBPs by medium pressure UV in swimming pool water. Sci Total Environ. 2013 Jan 15;443:850-6. doi: 10.1016/j.scitotenv.2012.11.064. Epub 2012 Dec 14. [PubMed:23247288 ]
- Yamamoto K, Mori Y: Simulating distribution of trihalomethane in tap water in the area receiving a combination of advanced treated water and conventionally treated different source water: 1998, 1999 and 2002 data on Osaka Prefecture and its surrounding cities, Japan. Bull Environ Contam Toxicol. 2009 Nov;83(5):677-80. doi: 10.1007/s00128-009-9777-6. Epub 2009 May 28. [PubMed:19475326 ]
- Silva ZI, Rebelo MH, Silva MM, Alves AM, Cabral Mda C, Almeida AC, Aguiar FR, de Oliveira AL, Nogueira AC, Pinhal HR, Aguiar PM, Cardoso AS: Trihalomethanes in Lisbon indoor swimming pools: occurrence, determining factors, and health risk classification. J Toxicol Environ Health A. 2012;75(13-15):878-92. doi: 10.1080/15287394.2012.690706. [PubMed:22788374 ]
- Villanueva CM, Castano-Vinyals G, Moreno V, Carrasco-Turigas G, Aragones N, Boldo E, Ardanaz E, Toledo E, Altzibar JM, Zaldua I, Azpiroz L, Goni F, Tardon A, Molina AJ, Martin V, Lopez-Rojo C, Jimenez-Moleon JJ, Capelo R, Gomez-Acebo I, Peiro R, Ripoll M, Gracia-Lavedan E, Nieuwenhujsen MJ, Rantakokko P, Goslan EH, Pollan M, Kogevinas M: Concentrations and correlations of disinfection by-products in municipal drinking water from an exposure assessment perspective. Environ Res. 2012 Apr;114:1-11. doi: 10.1016/j.envres.2012.02.002. Epub 2012 Mar 20. [PubMed:22436294 ]
- Zhang L, Xu L, Zeng Q, Zhang SH, Xie H, Liu AL, Lu WQ: Comparison of DNA damage in human-derived hepatoma line (HepG2) exposed to the fifteen drinking water disinfection byproducts using the single cell gel electrophoresis assay. Mutat Res. 2012 Jan 24;741(1-2):89-94. doi: 10.1016/j.mrgentox.2011.11.004. Epub 2011 Nov 16. [PubMed:22108252 ]
- Silva LK, Backer LC, Ashley DL, Gordon SM, Brinkman MC, Nuckols JR, Wilkes CR, Blount BC: The influence of physicochemical properties on the internal dose of trihalomethanes in humans following a controlled showering exposure. J Expo Sci Environ Epidemiol. 2013 Jan-Feb;23(1):39-45. doi: 10.1038/jes.2012.80. Epub 2012 Jul 25. [PubMed:22829048 ]
- Cervera MI, Beltran J, Lopez FJ, Hernandez F: Determination of volatile organic compounds in water by headspace solid-phase microextraction gas chromatography coupled to tandem mass spectrometry with triple quadrupole analyzer. Anal Chim Acta. 2011 Oct 17;704(1-2):87-97. doi: 10.1016/j.aca.2011.08.012. Epub 2011 Aug 11. [PubMed:21907025 ]
- Jakubowska N, Henkelmann B, Schramm KW, Namiesnik J: Optimization of a novel procedure for determination of VOCs in water and human urine samples based on SBSE coupled with TD-GC-HRMS. J Chromatogr Sci. 2009 Sep;47(8):689-93. [PubMed:19772746 ]
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