4,4'-Methylenebis(2-chloroaniline) (BioDeep_00000002750)

 

Secondary id: BioDeep_00001873592

human metabolite blood metabolite


代谢物信息卡片


4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline

化学式: C13H12Cl2N2 (266.0377492)
中文名称: 4.4-次甲基-双(2-氯苯胺)
谱图信息: 最多检出来源 Homo sapiens(blood) 2.27%

分子结构信息

SMILES: C1=CC(=C(C=C1CC2=CC(=C(C=C2)N)Cl)Cl)N
InChI: InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2

描述信息

KEIO_ID M142

同义名列表

10 个代谢物同义名

4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline; 3,3-Dichloro-4,4-diaminodiphenylmethane; 4,4-methylene-bis-(2-chloroaniline); 4,4-Methylene bis(o-chloroaniline); 4,4-METHYLENEBIS(2-CHLOROANILINE); Methylene bis(chloroaniline); Methylenebis(chloroaniline); bis amine; MBOCA; MOCA



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Nishikant Wase, Boqiang Tu, James W Allen, Paul N Black, Concetta C DiRusso. Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae. Plant physiology. 2017 Aug; 174(4):2146-2165. doi: 10.1104/pp.17.00433. [PMID: 28652262]
  • Chung-Ching Wang, Wei-Liang Chen, Chia-Ni Hsiung, Sheng-Ta Chiang, Ying-Chuan Wang, Ching-Hui Loh, I-Shen Lin, Hong-I Chen, Saou-Hsing Liou. Effect of CYP3A4 genetic polymorphisms on the genotoxicity of 4,4'-methylene-bis(2-chloroaniline)-exposed workers. Occupational and environmental medicine. 2017 01; 74(1):30-38. doi: 10.1136/oemed-2016-103816. [PMID: 27679675]
  • Akito Takeuchi, Akira Namera, Norihiro Sakui, Kenji Yamamuro, Toshio Kawai, Kimiaki Sumino. A method for routine analysis of urinary 4,4'-methylenebis (2-chloroaniline) by gas chromatography-electron capture detection. Journal of occupational health. 2014; 56(5):347-50. doi: 10.1539/joh.14-0052-br. [PMID: 25069897]
  • I-Shen Lin, Pao-Lou Fan, Hong-I Chen, Ching-Hui Loh, Tung-Sheng Shih, Saou-Hsing Liou. Rapid and intermediate N-acetylators are less susceptible to oxidative damage among 4,4'-methylenebis(2-chloroaniline) (MBOCA)-exposed workers. International journal of hygiene and environmental health. 2013 Jul; 216(4):515-20. doi: 10.1016/j.ijheh.2013.02.001. [PMID: 23491024]
  • C Keen, M Coldwell, K McNally, P Baldwin, J McAlinden, J Cocker. A follow up study of occupational exposure to 4,4'-methylene-bis(2-chloroaniline) (MbOCA) and isocyanates in polyurethane manufacture in the UK. Toxicology letters. 2012 Aug; 213(1):3-8. doi: 10.1016/j.toxlet.2011.04.003. [PMID: 21501672]
  • Abid Dost, J K Straughan, Tom Sorahan. Cancer incidence and exposure to 4,4'-methylene-bis-ortho-chloroaniline (MbOCA). Occupational medicine (Oxford, England). 2009 Sep; 59(6):402-5. doi: 10.1093/occmed/kqp093. [PMID: 19564173]
  • J Cocker, J R Cain, P Baldwin, K McNally, K Jones. A survey of occupational exposure to 4,4'-methylene-bis (2-chloroaniline) (MbOCA) in the UK. The Annals of occupational hygiene. 2009 Jul; 53(5):499-507. doi: 10.1093/annhyg/mep026. [PMID: 19447850]
  • Hong-I Chen, Saou-Hsing Liou, Shu-Fen Ho, Kuen-Yuh Wu, Chien-Wen Sun, Ming-Fong Chen, Li-Chuan Cheng, Tung-Sheng Shih, Ching-Hui Loh. Oxidative DNA damage estimated by plasma 8-hydroxydeoxyguanosine (8-OHdG): influence of 4, 4'-methylenebis (2-chloroaniline) exposure and smoking. Journal of occupational health. 2007 Sep; 49(5):389-98. doi: 10.1539/joh.49.389. [PMID: 17951971]
  • J Cocker, K Jones, J Morton, H J Mason. Biomonitoring at the UK Health and Safety Laboratory. International journal of hygiene and environmental health. 2007 May; 210(3-4):383-6. doi: 10.1016/j.ijheh.2007.01.028. [PMID: 17321210]
  • Wei-Chung Shih, Ming-Feng Chen, Chih-Chun Jean Huang, Shi-Nian Uang, Tung-Shen Shih, Saou-Hsing Liou, Kuen-Yuh Wu. Simultaneous analysis of urinary 4,4'-methylenebis(2-chloroaniline) and N-acetyl 4,4'-methylenebis(2-chloroaniline) using solid-phase extraction and liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2007; 21(24):4073-8. doi: 10.1002/rcm.3314. [PMID: 18008389]
  • Hong-I Chen, Saou-Hsing Liou, Ching-Hui Loh, Shi-Nian Uang, Yi-Chun Yu, Tung-Sheng Shih. Bladder cancer screening and monitoring of 4,4'-methylenebis(2-chloroaniline) exposure among workers in Taiwan. Urology. 2005 Aug; 66(2):305-10. doi: 10.1016/j.urology.2005.02.031. [PMID: 16098360]
  • E B Murray, J W Edwards. Differential induction of micronuclei in peripheral lymphocytes and exfoliated urothelial cells of workers exposed to 4,4'-methylenebis-(2-chloroaniline) (MOCA) and bitumen fumes. Reviews on environmental health. 2005 Jul; 20(3):163-76. doi: 10.1515/reveh.2005.20.3.163. [PMID: 16335575]
  • E B Murray, J W Edwards. Micronuclei in peripheral lymphocytes and exfoliated urothelial cells of workers exposed to 4,4'-methylenebis-(2-chloroaniline) (MOCA). Mutation research. 1999 Dec; 446(2):175-80. doi: 10.1016/s1383-5718(99)00180-1. [PMID: 10635339]
  • A Robert, P Ducos, J M Francin. Biological monitoring of workers exposed to 4,4'-methylene-bis-(2-orthochloroaniline) (MOCA). II. Comparative interest of 'free' and 'total' MOCA in the urine of exposed workers. International archives of occupational and environmental health. 1999 Jul; 72(4):229-37. doi: 10.1007/s004200050366. [PMID: 10491777]
  • A Robert, P Ducos, J M Francin. Biological monitoring of workers exposed to 4,4'-methylene-bis-(2-orthochloroaniline) (MOCA). I. A new and easy determination of 'free' and 'total' MOCA in urine. International archives of occupational and environmental health. 1999 Jul; 72(4):223-8. doi: 10.1007/s004200050365. [PMID: 10491776]
  • G T Vaughan, R S Kenyon. Monitoring for occupational exposure to 4,4'-methylenebis(2-chloroaniline) by gas chromatographic-mass spectrometric analysis of haemoglobin adducts, blood, plasma and urine. Journal of chromatography. B, Biomedical applications. 1996 Apr; 678(2):197-204. doi: 10.1016/0378-4347(95)00509-9. [PMID: 8738022]
  • W S Wu, R S Szklar, R Smith. Gas chromatographic determination and negative-ion chemical ionization mass spectrometric confirmation of 4,4'-methylenebis(2-chloroaniline) in urine via thin-layer chromatographic separation. The Analyst. 1996 Mar; 121(3):321-4. doi: 10.1039/an9962100321. [PMID: 8729654]
  • K R Kaderlik, G Talaska, D G DeBord, A M Osorio, F F Kadlubar. 4,4'-Methylene-bis(2-chloroaniline)-DNA adduct analysis in human exfoliated urothelial cells by 32P-postlabeling. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1993 Jan; 2(1):63-9. doi: . [PMID: 8420614]
  • K Jedrzejczak, V S Gaind. Determination of 4,4'-methylenebis(2-chloroaniline) in urine using capillary gas chromatography and negative ion chemical ionization mass spectrometry. The Analyst. 1992 Sep; 117(9):1417-20. doi: 10.1039/an9921701417. [PMID: 1443639]
  • J W Edwards, B G Priestly. Biological and biological-effect monitoring of workers exposed to 4,4'-methylene-bis(2-chloroaniline). Human & experimental toxicology. 1992 May; 11(3):229-36. doi: 10.1177/096032719201100312. [PMID: 1352119]
  • K L Cheever, D G DeBord, T F Swearengin. 4,4'-Methylenebis(2-chloroaniline) (MOCA): the effect of multiple oral administration, route, and phenobarbital induction on macromolecular adduct formation in the rat. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1991 Jan; 16(1):71-80. doi: 10.1016/0272-0590(91)90136-r. [PMID: 2019352]
  • E Ward, W Halperin, M Thun, H B Grossman, B Fink, L Koss, A M Osorio, P Schulte. Screening workers exposed to 4,4'-methylenebis(2-chloroaniline) for bladder cancer by cystoscopy. Journal of occupational medicine. : official publication of the Industrial Medical Association. 1990 Sep; 32(9):865-8. doi: 10.1097/00043764-199009000-00020. [PMID: 2074509]
  • J Cocker, A R Boobis, H K Wilson, D Gompertz. Evidence that a beta-N-glucuronide of 4,4'-methylenebis (2-chloroaniline) (MbOCA) is a major urinary metabolite in man: implications for biological monitoring. British journal of industrial medicine. 1990 Mar; 47(3):154-61. doi: 10.1136/oem.47.3.154. [PMID: 2328222]
  • A M Osorio, D Clapp, E Ward, H K Wilson, J Cocker. Biological monitoring of a worker acutely exposed to MBOCA. American journal of industrial medicine. 1990; 18(5):577-89. doi: 10.1002/ajim.4700180508. [PMID: 2244630]
  • G Sabbioni, H G Neumann. Quantification of haemoglobin binding of 4,4'-methylenebis(2-chloroaniline) (MOCA) in rats. Archives of toxicology. 1990; 64(6):451-8. doi: 10.1007/bf01977626. [PMID: 1703404]
  • K C Wan, B R Dare, N R Street. Biomedical surveillance of workers exposed to 4,4'-methylene-bis-(2-chloroaniline) (MBOCA) in Perth, Western Australia. Journal of the Royal Society of Health. 1989 Oct; 109(5):159-65. doi: 10.1177/146642408910900503. [PMID: 2509701]
  • J Cocker, H K Wilson. Determination of 4,4'-methylenebis(2-chloroaniline) in urine. Clinical chemistry. 1989 Mar; 35(3):506. doi: 10.1093/clinchem/35.3.506. [PMID: 2920428]
  • A Okayama, Y Ichikawa, M Yoshida, I Hara, K Morimoto. Determination of 4,4'-methylenebis(2-chloroaniline) in urine by liquid chromatography with ion-paired solid-phase extraction and electrochemical detection. Clinical chemistry. 1988 Oct; 34(10):2122-5. doi: 10.1093/clinchem/34.10.2122. [PMID: 3168228]
  • J Cocker, A R Boobis, D S Davies. Determination of the N-acetyl metabolites of 4,4'-methylene dianiline and 4,4'-methylene-bis(2-chloroaniline) in urine. Biomedical & environmental mass spectrometry. 1988 Sep; 17(3):161-7. doi: 10.1002/bms.1200170303. [PMID: 3214672]
  • K C Morton, M S Lee, P Siedlik, R Chapman. Metabolism of 4,4'-methylene-bis-2-chloroaniline (MOCA) by rats in vivo and formation of N-hydroxy MOCA by rat and human liver microsomes. Carcinogenesis. 1988 May; 9(5):731-9. doi: 10.1093/carcin/9.5.731. [PMID: 3365833]
  • E Ward, W Halperin, M Thun, H B Grossman, B Fink, L Koss, A M Osorio, P Schulte. Bladder tumors in two young males occupationally exposed to MBOCA. American journal of industrial medicine. 1988; 14(3):267-72. doi: 10.1002/ajim.4700140304. [PMID: 3189344]
  • P J McKerrell, G A Saunders, R Geyer. Determination of 4,4'-methylenebis(2-chloroaniline) in urine by high-performance liquid chromatography. Journal of chromatography. 1987 Nov; 408(?):399-401. doi: 10.1016/s0021-9673(01)81830-6. [PMID: 3429537]
  • E Ward, D Clapp, W Tolos, D Groth. Efficacy of urinary monitoring for 4,4'-methylenebis (2-chloroaniline). Journal of occupational medicine. : official publication of the Industrial Medical Association. 1986 Aug; 28(8):637-42. doi: 10.1097/00043764-198608000-00020. [PMID: 3746484]
  • M O Manis, W E Braselton. Metabolism of 4,4'-methylenebis(2-chloroaniline) by canine liver and kidney slices. Drug metabolism and disposition: the biological fate of chemicals. 1986 Mar; 14(2):166-74. doi: . [PMID: 2870890]
  • P Ducos, C Maire, R Gaudin. Assessment of occupational exposure to 4,4'-methylene-bis-(2-chloroaniline) "MOCA" by a new sensitive method for biological monitoring. International archives of occupational and environmental health. 1985; 55(2):159-67. doi: 10.1007/bf00378378. [PMID: 3988358]
  • M O Manis, W E Braselton. Structure elucidation and in vitro reactivity of the major metabolite of 4,4'-methylenebis(2-chloroaniline) (MBOCA) in canine urine. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1984 Dec; 4(6):1000-8. doi: 10.1016/0272-0590(84)90239-2. [PMID: 6549168]
  • J D Thomas, H K Wilson. Biological monitoring of workers exposed to 4,4'-methylenebis (2-chloroaniline) (MBOCA). British journal of industrial medicine. 1984 Nov; 41(4):547-51. doi: 10.1136/oem.41.4.547. [PMID: 6498117]
  • D H Groth, W W Weigel, W P Tolos, D E Brewer, K L Cheever, J R Burg. 4,4'-methylene-bis-ortho-chloro-aniline (MBOCA): absorption and excretion after skin application and gavage. Environmental research. 1984 Jun; 34(1):38-54. doi: 10.1016/0013-9351(84)90074-4. [PMID: 6723608]
  • W Gristwood, S M Robertson, H K Wilson. The determination of 4,4'-methylenebis (2-chloroaniline) in urine by electron capture gas chromatography. Journal of analytical toxicology. 1984 May; 8(3):101-5. doi: 10.1093/jat/8.3.101. [PMID: 6737997]
  • M O Manis, D E Williams, K M McCormack, R J Schock, L F Lepper, Y C Ng, W E Braselton. Percutaneous absorption, disposition, and excretion of 4,4'-methylenebis(2-chloroaniline) in dogs. Environmental research. 1984 Feb; 33(1):234-45. doi: 10.1016/0013-9351(84)90020-3. [PMID: 6692810]
  • M C Tobes, L E Brown, B Chin, D D Marsh. Kinetics of tissue distribution and elimination of 4,4'-methylene bis(2-chloroaniline) in rats. Toxicology letters. 1983 Jun; 17(1-2):69-75. doi: 10.1016/0378-4274(83)90037-1. [PMID: 6623511]
  • P B Van Roosmalen, A L Klein, I Drummond. Determination of 3,3'-dichloro-4,4'-diaminodiphenylmethane (MOCA) in urine. IARC scientific publications. 1981; ?(40):183-91. doi: NULL. [PMID: 7332716]
  • C Kommineni, D H Groth, I J Frockt, R W Voelker, R P Stanovick. Determination of the tumorigenic potential of methylene-bis-orthochloroaniline. Journal of environmental pathology and toxicology. 1979 May; 2(5):149-71. doi: . [PMID: 512554]
  • P B Van Roosmalen, A L Klein, I Drummond. An improved method for determination of 4,4'-methylene bis-(2-chloroaniline) (MOCA) in urine. American Industrial Hygiene Association journal. 1979 Jan; 40(1):66-9. doi: 10.1080/15298667991429336. [PMID: 484452]
  • E F Stula, J R Barnes, H Sherman, C F Reinhardt, J A Zapp. Urinary bladder tumors in dogs from 4,4'-methylene-bis (2-chloroaniline) (MOCA). Journal of environmental pathology and toxicology. 1978 Sep; 1(1):31-50. doi: . [PMID: 722185]
  • G Traina, C Sala, F Beretta, G Cortona. [Analysis of environmental MBOCA (4,4'-methylene-bis-(orthochloroaniline) pollution in a polyurethane elastomer plant]. La Medicina del lavoro. 1978 Jul; 69(4):530-6. doi: ". [PMID: 748736]
  • H R Hosein, P B Van Roosmalen. Acute exposure to methylene-bis-ortho chloroaniline (MOCA). American Industrial Hygiene Association journal. 1978 Jun; 39(6):496-7. doi: 10.1080/0002889778507795. [PMID: 685830]