4,4-Methylenedianiline (BioDeep_00001873640)
代谢物信息卡片
4,4′-methylenedianiline
化学式: C13H14N2 (198.1157)
中文名称: 4,4-二氨基二苯甲烷, 4,4'-亚甲基二苯胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=CC=C1CC2=CC=C(C=C2)N)N
InChI: InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2
描述信息
D009676 - Noxae > D002273 - Carcinogens
同义名列表
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:32506
- PubChem: 7577
- ChEMBL: CHEMBL85728
- CAS: 1219795-26-2
- CAS: 101-77-9
- KEGG: C14288
- PubChem: 17395288
- KNApSAcK: 32506
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)
0 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
- Jeffrey Wight, William Doucette. Quantifying the Root-to-Shoot Transfer of 4,4'-Methylenedianiline Using Pressure Chamber and Intact Plant Methods.
Environmental toxicology and chemistry.
2023 Mar; 42(3):655-662. doi:
10.1002/etc.5549. [PMID: 36718782] - Md Nurul Huda Bhuiyan, Habyeong Kang, Jiwon Choi, Soyoung Lim, Younglim Kho, Kyungho Choi. Effects of 3,4-dichloroaniline (3,4-DCA) and 4,4'-methylenedianiline (4,4'-MDA) on sex hormone regulation and reproduction of adult zebrafish (Danio rerio).
Chemosphere.
2021 Apr; 269(?):128768. doi:
10.1016/j.chemosphere.2020.128768. [PMID: 33153842] - Maggy Lépine, Lekha Sleno, Jacques Lesage, Sébastien Gagné. A validated liquid chromatography/tandem mass spectrometry method for 4,4'-methylenedianiline quantitation in human urine as a measure of 4,4'-methylene diphenyl diisocyanate exposure.
Rapid communications in mass spectrometry : RCM.
2019 Mar; 33(6):600-606. doi:
10.1002/rcm.8380. [PMID: 30604511] - Erica E Carroll, Danielle L Ippolito, Matthew G Permenter, B Claire McDyre, Christine E Baer, David M Kumsher, Molly H Boyle, Valerie T DiVito, John A Lewis, Jason M Koontz. Utility of Serum miR-122, Liver Enzymes, and Hepatic Histopathology in Response to Hepatotoxicants in Sprague-Dawley Rats.
Toxicologic pathology.
2018 10; 46(7):835-846. doi:
10.1177/0192623318795435. [PMID: 30205766] - Danielle L Ippolito, Mohamed Diwan M AbdulHameed, Gregory J Tawa, Christine E Baer, Matthew G Permenter, Bonna C McDyre, William E Dennis, Molly H Boyle, Cheryl A Hobbs, Michael A Streicker, Bobbi S Snowden, John A Lewis, Anders Wallqvist, Jonathan D Stallings. Gene Expression Patterns Associated With Histopathology in Toxic Liver Fibrosis.
Toxicological sciences : an official journal of the Society of Toxicology.
2016 Jan; 149(1):67-88. doi:
10.1093/toxsci/kfv214. [PMID: 26396155] - Michelle Carroll-Turpin, Valeria Hebert, Tanya Chotibut, Heather Wensler, Dallas Krentzel, Kurt James Varner, Brendan R Burn, Yi-Fan Chen, Fleurette Abreo, Tammy Renee Dugas. 4,4'-Methylenedianiline Alters Serotonergic Transport in a Novel, Sex-Specific Model of Pulmonary Arterial Hypertension in Rats.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Sep; 147(1):235-45. doi:
10.1093/toxsci/kfv126. [PMID: 26116029] - Pablo Campo, William Platten, Makram T Suidan, Yunzhou Chai, John W Davis. Aerobic biodegradation of amines in industrial saline wastewaters.
Chemosphere.
2011 Nov; 85(7):1199-203. doi:
10.1016/j.chemosphere.2011.08.039. [PMID: 21925703] - Tobias Weiss, Hubert Schuster, Johannes Müller, Karl-Heinz Schaller, Hans Drexler, Jürgen Angerer, Heiko U Käfferlein. Dermal uptake and excretion of 4,4'-methylenedianiline during rotor blade production in helicopter industry--an intervention study.
The Annals of occupational hygiene.
2011 Oct; 55(8):886-92. doi:
10.1093/annhyg/mer051. [PMID: 21841153] - Lygia T Budnik, Dennis Nowak, Rolf Merget, Catherine Lemiere, Xaver Baur. Elimination kinetics of diisocyanates after specific inhalative challenges in humans: mass spectrometry analysis, as a basis for biomonitoring strategies.
Journal of occupational medicine and toxicology (London, England).
2011 Mar; 6(1):9. doi:
10.1186/1745-6673-6-9. [PMID: 21447151] - Anoop Kumar, Nagaraju Dongari, Gabriele Sabbioni. New isocyanate-specific albumin adducts of 4,4'-methylenediphenyl diisocyanate (MDI) in rats.
Chemical research in toxicology.
2009 Dec; 22(12):1975-83. doi:
10.1021/tx900270z. [PMID: 19928878] - Kenji Ishihara, Naruo Katsutani, Naoki Asai, Akira Inomata, Yuji Uemura, Akiyoshi Suganuma, Kohei Sawada, Tsuyoshi Yokoi, Toyohiko Aoki. Identification of urinary biomarkers useful for distinguishing a difference in mechanism of toxicity in rat model of cholestasis.
Basic & clinical pharmacology & toxicology.
2009 Sep; 105(3):156-66. doi:
10.1111/j.1742-7843.2009.00410.x. [PMID: 19486331] - Er-Jia Wang, Ronald D Snyder, Mark R Fielden, Roger J Smith, Yi-Zhong Gu. Validation of putative genomic biomarkers of nephrotoxicity in rats.
Toxicology.
2008 Apr; 246(2-3):91-100. doi:
10.1016/j.tox.2007.12.031. [PMID: 18289764] - Gabriele Sabbioni, Hansjörg Wesp, Jürgen Lewalter, Richard Rumler. Determination of isocyanate biomarkers in construction site workers.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2007 Sep; 12(5):468-83. doi:
10.1080/13547500701395636. [PMID: 17701746] - A Robert, P Ducos, J M Francin, P Marsan. Biological monitoring of workers exposed to 4,4'-methylenediphenyl diisocyanate (MDI) in 19 French polyurethane industries.
International archives of occupational and environmental health.
2007 Apr; 80(5):412-22. doi:
10.1007/s00420-006-0150-3. [PMID: 17061110] - Vicente Santa Cruz, Hanlin Liu, Lata Kaphalia, Mary F Kanz. Effects of methylenedianiline on tight junction permeability of biliary epithelial cells in vivo and in vitro.
Toxicology letters.
2007 Feb; 169(1):13-25. doi:
10.1016/j.toxlet.2006.11.007. [PMID: 17178199] - Masanori Ogawa, Tsunehiro Oyama, Toyohi Isse, Tetsunosuke Yamaguchi, Tomoe Murakami, Yoko Endo, Toshihiro Kawamoto. Hemoglobin adducts as a marker of exposure to chemical substances, especially PRTR class I designated chemical substances.
Journal of occupational health.
2006 Sep; 48(5):314-28. doi:
10.1539/joh.48.314. [PMID: 17053297] - C J Sennbro, C H Lindh, C Mattsson, B A G Jönsson, H Tinnerberg. Biological monitoring of exposure to 1,5-naphthalene diisocyanate and 4,4'-methylenediphenyl diisocyanate.
International archives of occupational and environmental health.
2006 Sep; 79(8):647-53. doi:
10.1007/s00420-006-0096-5. [PMID: 16506043] - Jürgen Pauluhn, William E Brown, Paul Hext, Edgar Leibold, Gabriele Leng. Analysis of biomarkers in rats and dogs exposed to polymeric methylenediphenyl diisocyanate (pMDI) and its glutathione adduct.
Toxicology.
2006 May; 222(3):202-12. doi:
10.1016/j.tox.2006.02.014. [PMID: 16574299] - Xiaoyan Zhang, Jason C Lambert, Mark A Doll, Jason M Walraven, Gavin E Arteel, David W Hein. 4,4'-methylenedianiline-induced hepatotoxicity is modified by N-acetyltransferase 2 (NAT2) acetylator polymorphism in the rat.
The Journal of pharmacology and experimental therapeutics.
2006 Jan; 316(1):289-94. doi:
10.1124/jpet.105.093302. [PMID: 16192314] - Carl Johan Sennbro, Christian H Lindh, Håkan Tinnerberg, Cecilia Gustavsson, Margareta Littorin, Hans Welinder, Bo A G Jönsson. Development, validation and characterization of an analytical method for the quantification of hydrolysable urinary metabolites and plasma protein adducts of 2,4- and 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate and 4,4'-methylenediphenyl diisocyanate.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2003 May; 8(3-4):204-17. doi:
10.1080/1354750031000090660. [PMID: 12944173] - Jürgen Pauluhn, Gabriele Leng. Concentration-dependence of biomarkers of exposure of methylenediphenyl-diisocyanate following acute inhalation exposure of rats.
Toxicology.
2003 Mar; 185(1-2):35-48. doi:
10.1016/s0300-483x(02)00585-1. [PMID: 12505443] - Christina Rosenberg, Kirsi Nikkilä, Maj-Len Henriks-Eckerman, Kimmo Peltonen, Kerstin Engströrm. Biological monitoring of aromatic diisocyanates in workers exposed to thermal degradation products of polyurethanes.
Journal of environmental monitoring : JEM.
2002 Oct; 4(5):711-6. doi:
10.1039/b206340a. [PMID: 12400919] - Antonietta Martelli, Roberto Carrozzino, Francesca Mattioli, Giovanni Brambilla. DNA damage induced by 4,4'-methylenedianiline in primary cultures of hepatocytes and thyreocytes from rats and humans.
Toxicology and applied pharmacology.
2002 Aug; 182(3):219-25. doi:
10.1006/taap.2002.9446. [PMID: 12183101] - K Kääriä, A Hirvonen, H Norppa, P Piirilä, H Vainio, C Rosenberg. Exposure to 4,4'-methylenediphenyl diisocyanate (MDI) during moulding of rigid polyurethane foam: determination of airborne MDI and urinary 4,4'-methylenedianiline (MDA).
The Analyst.
2001 Apr; 126(4):476-9. doi:
10.1039/b009549o. [PMID: 11340982] - T R Dugas, V Santa Cruz, H Liu, M F Kanz. Evaluation of the gender differences in 4,4'-methylenedianiline toxicity, distribution, and effects on biliary parameters.
Journal of toxicology and environmental health. Part A.
2001 Mar; 62(6):467-83. doi:
10.1080/00984100150501187. [PMID: 11289319] - G Sabbioni, R Hartley, D Henschler, A Höllrigl-Rosta, R Koeber, S Schneider. Isocyanate-specific hemoglobin adduct in rats exposed to 4, 4'-methylenediphenyl diisocyanate.
Chemical research in toxicology.
2000 Feb; 13(2):82-9. doi:
10.1021/tx990096e. [PMID: 10688531] - H M Do Luu, J C Hutter. Pharmacokinetic modeling of 4,4'-methylenedianiline released from reused polyurethane dialyzer potting materials.
Journal of biomedical materials research.
2000; 53(3):276-86. doi:
10.1002/(sici)1097-4636(2000)53:3<276::aid-jbm13>3.0.co;2-e. [PMID: 10813768] - L Robbiano, R Carrozzino, C P Puglia, C Corbu, G Brambilla. Correlation between induction of DNA fragmentation and micronuclei formation in kidney cells from rats and humans and tissue-specific carcinogenic activity.
Toxicology and applied pharmacology.
1999 Dec; 161(2):153-9. doi:
10.1006/taap.1999.8796. [PMID: 10581209] - D H Brouwer, L Hoogendoorn, P M Bos, P J Boogaard, J J van Hemmen. Proposal for the assessment to quantitative dermal exposure limits in occupational environments: Part 2. Feasibility study for application in an exposure scenario for MDA by two different dermal exposure sampling methods.
Occupational and environmental medicine.
1998 Dec; 55(12):805-11. doi:
10.1136/oem.55.12.805. [PMID: 9924441] - M Dalene, G Skarping, P Lind. Workers exposed to thermal degradation products of TDI- and MDI-based polyurethane: biomonitoring of 2,4-TDA, 2,6-TDA, and 4,4'-MDA in hydrolyzed urine and plasma.
American Industrial Hygiene Association journal.
1997 Aug; 58(8):587-91. doi:
10.1080/15428119791012522. [PMID: 9248033] - H L Tillmann, F N van Pelt, W Martz, T Luecke, H Welp, F Dörries, A Veuskens, M Fischer, M P Manns. Accidental intoxication with methylene dianiline p,p'-diaminodiphenylmethane: acute liver damage after presumed ecstasy consumption.
Journal of toxicology. Clinical toxicology.
1997; 35(1):35-40. doi:
10.3109/15563659709001163. [PMID: 9022650] - E H Vock, H G Hoymann, U Heinrich, W K Lutz. 32P-postlabeling of a DNA adduct derived from 4,4'-methylenedianiline, in the olfactory epithelium of rats exposed by inhalation to 4,4'-methylenediphenyl diisocyanate.
Carcinogenesis.
1996 May; 17(5):1069-73. doi:
10.1093/carcin/17.5.1069. [PMID: 8640915] - M Dalene, K Jakobsson, A Rannug, G Skarping, L Hagmar. MDA in plasma as a biomarker of exposure to pyrolysed MDI-based polyurethane: correlations with estimated cumulative dose and genotype for N-acetylation.
International archives of occupational and environmental health.
1996; 68(3):165-9. doi:
10.1007/bf00381626. [PMID: 8919844] - O Sepai, D Schütze, U Heinrich, H G Hoymann, D Henschler, G Sabbioni. Hemoglobin adducts and urine metabolites of 4,4'-methylenedianiline after 4,4'-methylenediphenyl diisocyanate exposure of rats.
Chemico-biological interactions.
1995 Jul; 97(2):185-98. doi:
10.1016/0009-2797(95)03615-s. [PMID: 7606816] - M F Kanz, A Wang, G A Campbell. Infusion of bile from methylene dianiline-treated rats into the common bile duct injures biliary epithelial cells of recipient rats.
Toxicology letters.
1995 Jul; 78(2):165-71. doi:
10.1016/0378-4274(95)03251-f. [PMID: 7618181] - H Shintani. Formation and elution of toxic compounds from sterilized medical products: methylenedianiline formation in polyurethane.
Journal of biomaterials applications.
1995 Jul; 10(1):23-58. doi:
10.1177/088532829501000102. [PMID: 7473051] - D Schütze, O Sepai, J Lewalter, L Miksche, D Henschler, G Sabbioni. Biomonitoring of workers exposed to 4,4'-methylenedianiline or 4,4'-methylenediphenyl diisocyanate.
Carcinogenesis.
1995 Mar; 16(3):573-82. doi:
10.1093/carcin/16.3.573. [PMID: 7697816] - G Skarping, M Dalene. Determination of 4,4'-methylenediphenyldianiline (MDA) and identification of isomers in technical-grade MDA in hydrolysed plasma and urine from workers exposed to methylene diphenyldiisocyanate by gas chromatography-mass spectrometry.
Journal of chromatography. B, Biomedical applications.
1995 Jan; 663(2):209-16. doi:
10.1016/0378-4347(94)00425-5. [PMID: 7735468] - P Brunmark, M Dalene, G Skarping. Gas chromatography-negative-ion chemical ionization mass spectrometry of hydrolysed human urine and blood plasma for the biomonitoring of occupational exposure to 4,4'-methylenebisaniline.
The Analyst.
1995 Jan; 120(1):41-5. doi:
10.1039/an9952000041. [PMID: 7710126] - A Robert, P Ducos, J M Francin. Determination of urinary 4,4'-methylenedianiline and its acetylated metabolites by solid-phase extraction and HPLC analysis with UV and electrochemical detection.
International archives of occupational and environmental health.
1995; 68(1):44-51. doi:
10.1007/bf01831632. [PMID: 8847112] - G Skarping, M Dalene, M Littorin. 4,4'-Methylenedianiline in hydrolysed serum and urine from a worker exposed to thermal degradation products of methylene diphenyl diisocyanate elastomers.
International archives of occupational and environmental health.
1995; 67(2):73-7. doi:
10.1007/bf00572229. [PMID: 7672860] - M Dalene, G Skarping, P Brunmark. Assessment of occupational exposure to 4,4'-methylenedianiline by the analysis of urine and blood samples.
International archives of occupational and environmental health.
1995; 67(2):67-72. doi:
10.1007/bf00572228. [PMID: 7672859] - P Brunmark, M Bruze, S Skerfving, G Skarping. Biomonitoring of 4,4'-methylene dianiline by measurement in hydrolysed urine and plasma after epicutaneous exposure in humans.
International archives of occupational and environmental health.
1995; 67(2):95-100. doi:
10.1007/bf00572232. [PMID: 7672863] - J Cocker, B P Nutley, H K Wilson. A biological monitoring assessment of exposure to methylene dianiline in manufacturers and users.
Occupational and environmental medicine.
1994 Aug; 51(8):519-22. doi:
10.1136/oem.51.8.519. [PMID: 7951775] - G M Liss, S S Guirguis. Follow-up of a group of workers intoxicated with 4,4'-methylenedianiline.
American journal of industrial medicine.
1994 Jul; 26(1):117-24. doi:
10.1002/ajim.4700260110. [PMID: 8074119] - M B Bailie, T P Mullaney, R A Roth. Characterization of acute 4,4'-methylene dianiline hepatotoxicity in the rat.
Environmental health perspectives.
1993 Jun; 101(2):130-3. doi:
10.1289/ehp.93101130. [PMID: 8354198] - M Kajbaf, O Sepai, J H Lamb, S Naylor. Identification of metabolites of 4,4'-diaminodiphenylmethane (methylene dianiline) using liquid chromatographic and mass spectrometric techniques.
Journal of chromatography.
1992 Nov; 583(1):63-76. doi:
10.1016/0378-4347(92)80345-q. [PMID: 1484093] - M F Kanz, L Kaphalia, B S Kaphalia, E Romagnoli, G A Ansari. Methylene dianiline: acute toxicity and effects on biliary function.
Toxicology and applied pharmacology.
1992 Nov; 117(1):88-97. doi:
10.1016/0041-008x(92)90221-d. [PMID: 1440618] - P Brunmark, P Persson, G Skarping. Determination of 4,4'-methylenedianiline in hydrolysed human urine by micro liquid chromatography with ultraviolet detection.
Journal of chromatography.
1992 Sep; 579(2):350-4. doi:
10.1016/0378-4347(92)80403-d. [PMID: 1429984] - A Seldén, P Berg, R Jakobsson, J de Laval. Methylene dianiline: assessment of exposure and cancer morbidity in power generator workers.
International archives of occupational and environmental health.
1992; 63(6):403-8. doi:
10.1007/bf00386936. [PMID: 1544689] - E Kusters. Biological monitoring of MDA.
British journal of industrial medicine.
1992 Jan; 49(1):72. doi:
10.1136/oem.49.1.72. [PMID: 1733462] - H Shintani, A Nakamura. Formation of 4,4'-methylenedianiline in polyurethane potting materials by either gamma-ray or autoclave sterilization.
Journal of biomedical materials research.
1991 Oct; 25(10):1275-86. doi:
10.1002/jbm.820251008. [PMID: 1812119] - G L Kennedy. Toxicity of 1,4-bis(aminocyclohexyl)methane.
Journal of applied toxicology : JAT.
1991 Oct; 11(5):367-71. doi:
10.1002/jat.2550110512. [PMID: 1783741] - H Shintani. Solid-phase extraction of a carcinogen, 4,4'-methylenedianiline, in serum.
Journal of analytical toxicology.
1991 Jul; 15(4):198-201. doi:
10.1093/jat/15.4.198. [PMID: 1943069] - J C Peterson, E C Estiva, D S Lyttle, R M Harris. High-performance liquid chromatographic determination of 4,4'-methylenedianiline in human urine.
Journal of chromatography.
1991 Mar; 564(1):205-12. doi:
10.1016/0378-4347(91)80082-n. [PMID: 1860914] - A Tiljander, G Skarping. Determination of 4,4'-methylenedianiline in hydrolysed human urine using liquid chromatography with UV detection and peak identification by absorbance ratio.
Journal of chromatography.
1990 Jul; 511(?):185-94. doi:
10.1016/s0021-9673(01)93284-4. [PMID: 2211910] - H Shintani, A Nakamura. Analysis of a carcinogen, 4,4'-methylenedianiline, from thermosetting polyurethane during sterilization.
Journal of analytical toxicology.
1989 Nov; 13(6):354-7. doi:
10.1093/jat/13.6.354. [PMID: 2607764] - M Larroque, L Vian, A Blaise, S Brun. [Determination of residual monomers of epoxy resins in wine simulants].
Journal of chromatography.
1988 Jul; 445(1):107-17. doi:
10.1016/s0021-9673(01)84512-x. [PMID: 3215966] - J Cocker, L C Brown, H K Wilson, K Rollins. A GC/MS method for the determination of 4,4'-diaminodiphenylmethane and substituted analogues in urine.
Journal of analytical toxicology.
1988 Jan; 12(1):9-14. doi:
10.1093/jat/12.1.9. [PMID: 3352246] - B K Leong, J E Lund, J A Groehn, J K Coombs, C P Sabaitis, R J Weaver, R L Griffin. Retinopathy from inhaling 4,4'-methylenedianiline aerosols.
Fundamental and applied toxicology : official journal of the Society of Toxicology.
1987 Nov; 9(4):645-58. doi:
. [PMID: 3692021] - R Berruet, E Vinard, A Calle, H L Tighzert, B Chabert, H Magloire, R Eloy. Mechanical properties and biocompatibility of two polyepoxy matrices: DGEBA-DDM and DGEBA-IPD.
Biomaterials.
1987 May; 8(3):162-71. doi:
10.1016/0142-9612(87)90058-5. [PMID: 3607148] - H Tsuda, T Ogiso, R Hasegawa, K Imaida, T Masui, N Ito. Inhibition of neoplastic development in rat liver, kidney, oesophagus and forestomach by 4,4'-diaminodiphenylmethane administration.
Carcinogenesis.
1987 May; 8(5):719-22. doi:
10.1093/carcin/8.5.719. [PMID: 3581430] - T Van Joost, F Heule, J de Boer. Sensitization to methylenedianiline and para-structures.
Contact dermatitis.
1987 May; 16(5):246-8. doi:
10.1111/j.1600-0536.1987.tb01446.x. [PMID: 3621924] - J Cocker, W Gristwood, H K Wilson. Assessment of occupational exposure to 4,4'-diaminodiphenylmethane (methylene dianiline) by gas chromatography-mass spectrometry analysis of urine.
British journal of industrial medicine.
1986 Sep; 43(9):620-5. doi:
10.1136/oem.43.9.620. [PMID: 3756114] - J C Lamb, J E Huff, J K Haseman, A S Murthy, H Lilja. Carcinogenesis studies of 4,4'-methylenedianiline dihydrochloride given in drinking water to F344/N rats and B6C3F1 mice.
Journal of toxicology and environmental health.
1986; 18(3):325-37. doi:
10.1080/15287398609530874. [PMID: 3712494] - S R Cohen. Yellow staining caused by 4,4'-methylenedianiline exposure. Occurrence among molded plastics workers.
Archives of dermatology.
1985 Aug; 121(8):1022-7. doi:
NULL. [PMID: 4026338] - K Tanaka, T Ino, T Sawahata, S Marui, H Igaki, H Yashima. Mutagenicity of N-acetyl and N,N'-diacetyl derivatives of 3 aromatic amines used as epoxy-resin hardeners.
Mutation research.
1985 May; 143(1-2):11-5. doi:
10.1016/0165-7992(85)90097-1. [PMID: 4000142] - A Takahara, J Tashita, T Kajiyama, M Takayanagi. Effect of aggregation state of hard segment in segmented poly(urethaneureas) on their fatigue behavior after interaction with blood components.
Journal of biomedical materials research.
1985 Jan; 19(1):13-34. doi:
10.1002/jbm.820190104. [PMID: 4077870] - Y Hiasa, Y Kitahori, N Enoki, N Konishi, T Shimoyama. 4,4'-Diaminodiphenylmethane: promoting effect on the development of thyroid tumors in rats treated with N-bis(2-hydroxypropyl)nitrosamine.
Journal of the National Cancer Institute.
1984 Feb; 72(2):471-6. doi:
. [PMID: 6582329] - S Sell. Comparison of oval cells induced in rat liver by feeding N-2-fluorenylacetamide in a choline-devoid diet and bile duct cells induced by feeding 4,4'-diaminodiphenylmethane.
Cancer research.
1983 Apr; 43(4):1761-7. doi:
. [PMID: 6187438] - S Fukushima, M Hirose, A Hagiwara, R Hasegawa, N Ito. Inhibitory effect of 4,4'-diaminodiphenylmethane on liver, kidney and bladder carcinogenesis in rats ingesting N-ethyl-N-hydroxyethylnitrosamine or N-butyl-N-(4-hydroxybutyl) nitros-amine.
Carcinogenesis.
1981; 2(10):1033-7. doi:
10.1093/carcin/2.10.1033. [PMID: 7296757] - P Schmidt, R Gohlke, A Just, R Rothe, D Burck, H Jäger. Combined action of hepatotoxic substances and increased environmental temperature on the liver of rats.
Journal of hygiene, epidemiology, microbiology, and immunology.
1980; 24(3):271-6. doi:
. [PMID: 7440962]
