4,4'-Methylenedianiline (BioDeep_00000002226)
human metabolite
代谢物信息卡片
4,4-Diaminodiphenylmethane, sodium chloride (3:1)
化学式: C13H14N2 (198.1157)
中文名称: 4,4'-亚甲基二苯胺, 4,4-二氨基二苯甲烷
谱图信息:
最多检出来源 not specific(not specific) 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
4,4’-Methylenedianiline (MDA) is an industrial chemical that is produced and used industrially as a precursor to polyamides, epoxy resins, and polyurethane foams (PMID: 20621954). It is a primary aromatic amine, belonging to the family of compounds known as Diphenylmethanes. Diphenylmethanes are compounds consisting of methane with two of the hydrogen atoms replaced by phenyl groups. MDA is used mainly as a precursor to 4,4 ́-methylene diphenyl diisocyanate (MDI), which is a precursor to many polyurethane foams. To generate MDI, which is a highly reactive isocyanate, MDA is treated with phosgene. Workers exposed to MDI may develop sensitization, leading to occupational asthma. MDI is metabolized in the body and secreted in the urine as MDA, Therefore MDA is a urinary biomarker of MDI exposure. On its own, MDA is a known animal carcinogen, and human hepatotoxin. MDA produces genotoxic effects by forming DNA adducts in the liver and inducing DNA damage to hepatocytes (PMID: 32038824). The Occupational Safety and Health Administration has set a permissible exposure limit at 0.01 ppm over an eight-hour time-weighted average, and a short-term exposure limit at 0.10 ppm.
D009676 - Noxae > D002273 - Carcinogens
同义名列表
57 个代谢物同义名
4,4-Diaminodiphenylmethane, sodium chloride (3:1); 4-(4-Aminobenzyl)phenylamine (acd/name 4.0); 4,4-Diaminodiphenylmethane dihydrochloride; alpha-(p-Aminophenyl)-p-toluidine; 4-[(4-aminophenyl)methyl]aniline; 4,4-Methylenebis(benzeneamine); Α-(p-aminophenyl)-p-toluidine; a-(p-Aminophenyl)-p-toluidine; 4,4-Methylenebis-benzenamine; 4, 4-Diphenylmethanediamine; p,P-diaminodiphenylmethane; 4,4-Diaminodiphenylmethane; 4,4-Diphenylmethanediamine; 4, 4-Methylenebis(aniline); 4,4-Methylenedibenzenamine; Bis(4-aminophenyl)methane; 4,4-Diaminodiphenylmethan; 4,4-Methylene(bisaniline); Di-(4-aminophenyl)methane; Bis(p-aminophenyl)methane; Di-(p-aminophenyl)methane; 4,4-Methylenebis[aniline]; p,P-diaminodifenylmethan; Di(4-aminophenyl)methane; 4-(4-Aminobenzyl)aniline; Bis-p-aminophenylmethane; 4,4′-methylenedianiline; p, P-methylenedianiline; 4,4-Methylenedi-aniline; 4,4-Methylene dianiline; 4,4-Methylenebisaniline; 4,4-Methylene-dianiline; Bis(aminophenyl)methane; 4,4-Methylenedianiline; Diaminodiphenylmethane; p,P-methylenedianiline; Bis-p-aminofenylmethan; Araldite hardener 972; Methylenebis(aniline); Methylenebis[aniline]; Methylenedianiline; Dianilinemethane; Dianilinomethane; Jeffamine ap-20; Ancamine TL; Epikure DDM; Epicure DDM; Sumicure m; Curithane; 4,4-MDA; Tonox; DADPM; DAPM; DDM; MDA; 4,4'-Methylenedianiline; 4,4'-Methylenedianiline
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:32506
- KEGG: C14288
- PubChem: 7577
- HMDB: HMDB0041808
- Metlin: METLIN69942
- ChEMBL: CHEMBL85728
- Wikipedia: 4,4-Methylenedianiline
- chemspider: 7296
- CAS: 1219795-26-2
- CAS: 101-77-9
- PMhub: MS000002171
- PubChem: 17395288
- NIKKAJI: J4.995F
- 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)
1 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.
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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.
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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:
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Journal of toxicology and environmental health. Part A.
2001 Mar; 62(6):467-83. doi:
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Chemical research in toxicology.
2000 Feb; 13(2):82-9. doi:
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Journal of biomedical materials research.
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Occupational and environmental medicine.
1998 Dec; 55(12):805-11. doi:
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American Industrial Hygiene Association journal.
1997 Aug; 58(8):587-91. doi:
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Journal of toxicology. Clinical toxicology.
1997; 35(1):35-40. doi:
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Carcinogenesis.
1996 May; 17(5):1069-73. doi:
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International archives of occupational and environmental health.
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Chemico-biological interactions.
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Carcinogenesis.
1995 Mar; 16(3):573-82. doi:
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