N,N-Dimethylformamide (BioDeep_00000003143)
Secondary id: BioDeep_00000266745, BioDeep_00000866930
natural product human metabolite blood metabolite
代谢物信息卡片
Dimethylamid kyseliny mravenci
化学式: C3H7NO (73.0528)
中文名称: N,N-二甲基甲酰胺, 甲酰胺，N,N-二甲基
谱图信息:
最多检出来源 Homo sapiens(blood) 17.29%
分子结构信息
SMILES: CN(C)C=O
InChI: InChI=1/C3H7NO/c1-4(2)3-5/h3H,1-2H3
描述信息
Dimethylformamide is a polar (hydrophilic) Aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions. Dimethylformamide can be synthesized from methyl formate and dimethyl amine or reaction of dimethyl amine and carbon monoxide. Dimethylformamide is not stable in the presence of strong bases like sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid and is hydrolyzed back into formic acid and dimethylamine, especially at elevated temperatures.; Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated DMF (though this acronym is sometimes used for dimethylfuran), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Pure dimethylformamide is odorless whereas technical grade or degraded dimethylformamide often has a fishy smell due to impurity of dimethylamine. Its name is derived from the fact that it is a derivative of formamide, the amide of formic acid.; N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals.; The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace. (PMID: 17254560). N,N-Dimethylformamide is found in papaya.
N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals. The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace. (PMID: 17254560).
Acquisition and generation of the data is financially supported in part by CREST/JST.
同义名列表
20 个代谢物同义名
Dimethylamid kyseliny mravenci; N,N-Dimethylmethanamide; N,N- Dimethyl formamide; N,N- Dimethylformamide; N,N-Dimethyl-formamide; N,N Dimethylformamide; N-Formyldimethylamine; N,N-DIMETHYLFORMAMIDE; Formyldimethylamine; Dimethyl-formamide; Dimethyl formamide; dimethylformamide; Dwumetyloformamid; Dimetylformamidu; Dimetilformamide; Dimethylformamid; Dimethylforamide; DMF; N,N-Dimethylformamide; Formamide,N,N-dimethyl-
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:17741
- KEGG: C03134
- PubChem: 6228
- HMDB: HMDB0001888
- Metlin: METLIN34471
- DrugBank: DB01844
- ChEMBL: CHEMBL268291
- Wikipedia: Dimethylformamide
- MeSH: Dimethylformamide
- MetaCyc: CPD-581
- foodb: FDB004724
- chemspider: 5993
- CAS: 68-12-2
- MoNA: PS105601
- MoNA: PR100424
- MoNA: PS105604
- MoNA: PS105602
- MoNA: PR100423
- PMhub: MS000008258
- PubChem: 6023
- PDB-CCD: DMF
- 3DMET: B00545
- NIKKAJI: J1.923B
- RefMet: N,N-Dimethylformamide
- KNApSAcK: 17741
分类词条
相关代谢途径
Reactome(0)
BioCyc(7)
- NADH to cytochrome bo oxidase electron transfer I
- succinate to cytochrome bo oxidase electron transfer
- NADH to cytochrome bo oxidase electron transfer II
- D-lactate to cytochrome bo oxidase electron transfer
- glycerol-3-phosphate to cytochrome bo oxidase electron transfer
- proline to cytochrome bo oxidase electron transfer
- pyruvate to cytochrome bo oxidase electron transfer
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)
2 个相关的物种来源信息
- 590725 - Cystoseira barbata: 10.1016/S0031-9422(96)00588-2
- 9606 - Homo sapiens: -
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
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PloS one.
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The Analyst.
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Cryobiology.
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10.1016/j.cryobiol.2015.01.001. [PMID: 25595634] - Jinjiang He, Jie Liu, Yulin Kong, Weiwei Yang, Zengli Zhang. Serum activities of liver enzymes in workers exposed to sub-TLV levels of dimethylformamide.
International journal of occupational medicine and environmental health.
2015; 28(2):395-8. doi:
10.13075/ijomeh.1896.00086. [PMID: 26182934] - Massimiliano Sgroi, Paolo Roccaro, Gregg L Oelker, Shane A Snyder. N-nitrosodimethylamine formation upon ozonation and identification of precursors source in a municipal wastewater treatment plant.
Environmental science & technology.
2014 Sep; 48(17):10308-15. doi:
10.1021/es5011658. [PMID: 25029629] - Zeyou Chen, Hui Li, Anping Peng, Yanzheng Gao. Oxidation of polycyclic aromatic hydrocarbons by horseradish peroxidase in water containing an organic cosolvent.
Environmental science and pollution research international.
2014 Sep; 21(18):10696-705. doi:
10.1007/s11356-014-3005-6. [PMID: 24894750] - Suresh Ramraj Subashchandrabose, Kannan Krishnan, Enrico Gratton, Mallavarapu Megharaj, Ravi Naidu. Potential of fluorescence imaging techniques to monitor mutagenic PAH uptake by microalga.
Environmental science & technology.
2014 Aug; 48(16):9152-60. doi:
10.1021/es500387v. [PMID: 25020149] - Cui Wang, Canke Huang, Yumei Wei, Qi Zhu, Weili Tian, Qingyu Zhang. Short-term exposure to dimethylformamide and the impact on digestive system disease: an outdoor study for volatile organic compound.
Environmental pollution (Barking, Essex : 1987).
2014 Jul; 190(?):133-8. doi:
10.1016/j.envpol.2014.03.026. [PMID: 24747345] - B S Paulsen, D J Craik, D E Dunstan, B A Stone, A Bacic. The Yariv reagent: behaviour in different solvents and interaction with a gum arabic arabinogalactan-protein.
Carbohydrate polymers.
2014 Jun; 106(?):460-8. doi:
10.1016/j.carbpol.2014.01.009. [PMID: 24721102] - Mingluan Xing, Qing Chen, Xiaoming Lou, Meibian Zhang, Delei Cai, Yong Xia. [Toxicity of intragastrically administered N, N-dimethylformamide in female Wistar rats].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2014 May; 32(5):370-3. doi:
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Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2014 May; 32(5):361-4. doi:
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Clinica chimica acta; international journal of clinical chemistry.
2014 Feb; 429(?):123-8. doi:
10.1016/j.cca.2013.11.027. [PMID: 24296265] - Juan Cheng, Qiang Liu, Bo Xu, Zhijun Wu, Meng Ye, Xiao Jiang, Chunmin Wang. [Effect of N, N-dimethylformamide on oxidation or antioxidation status among occupational exposed workers].
Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine].
2014 Jan; 48(1):28-32. doi:
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Journal of occupational health.
2014; 56(4):252-9. doi:
10.1539/joh.13-0228-oa. [PMID: 24826962] - Hiroyuki Miyauchi, Yoko Tsuda, Aoi Minozoe, Shigeru Tanaka, Heihachiro Arito, Teruomi Tsukahara, Tetsuo Nomiyama. Occupational exposure to N,N-dimethylformamide in the summer and winter.
Industrial health.
2014; 52(6):512-20. doi:
10.2486/indhealth.2014-0070. [PMID: 25224331] - Nivedita Jaiswal, Om Prakash. An organic solvent and surfactant stable α-amylase from soybean seeds.
Acta biochimica Polonica.
2013; 60(3):387-93. doi:
10.18388/abp.2013_1997. [PMID: 24066306] - A Morillo Rodriguez, C Balao da Silva, B Macías-García, J M Gallardo Bolaños, J A Tapia, I M Aparicio, C Ortega-Ferrusola, F J Peña. Dimethylformamide improves the in vitro characteristics of thawed stallion spermatozoa reducing sublethal damage.
Reproduction in domestic animals = Zuchthygiene.
2012 Dec; 47(6):995-1002. doi:
10.1111/j.1439-0531.2012.02005.x. [PMID: 22384798] - K Udeni Alwis, Benjamin C Blount, April S Britt, Dhrusti Patel, David L Ashley. Simultaneous analysis of 28 urinary VOC metabolites using ultra high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (UPLC-ESI/MSMS).
Analytica chimica acta.
2012 Oct; 750(?):152-60. doi:
10.1016/j.aca.2012.04.009. [PMID: 23062436] - Nasr-Eldin M Aref, A Mahdi Saeed. Generation of high-titer of neutralizing polyclonal antibodies against heat-stable enterotoxin (STa) of enterotoxigenic Escherichia coli.
Vaccine.
2012 Oct; 30(45):6341-6. doi:
10.1016/j.vaccine.2012.06.064. [PMID: 22766246] - Qi Zhang, Bo Hong, Lihong Zheng, Xiuhua Wang, Defu Cai. Matrix solid-phase dispersion extraction followed by HPLC-diode array detection method for the determination of major constituents in a traditional Chinese medicine Folium isatidis (Da-qing-ye).
Journal of separation science.
2012 Sep; 35(18):2453-9. doi:
10.1002/jssc.201200422. [PMID: 22997033] - Carlos Barea, Adriana Pabón, Silvia Galiano, Silvia Pérez-Silanes, German Gonzalez, Chloe Deyssard, Antonio Monge, Eric Deharo, Ignacio Aldana. Antiplasmodial and leishmanicidal activities of 2-cyano-3-(4-phenylpiperazine-1-carboxamido) quinoxaline 1,4-dioxide derivatives.
Molecules (Basel, Switzerland).
2012 Aug; 17(8):9451-61. doi:
10.3390/molecules17089451. [PMID: 22871647] - Kanagaraj Jyothi, Durai Kalyani, Vasanthi Nachiappan. Effect of acute exposure of N,N-dimethylformamide, an industrial solvent on lipid peroxidation and antioxidants in liver and kidney of rats.
Indian journal of biochemistry & biophysics.
2012 Aug; 49(4):279-84. doi:
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Archiv der Pharmazie.
2012 Aug; 345(8):663-9. doi:
10.1002/ardp.201200021. [PMID: 22592977] - Yoon Shin Park, Goh-Woon Lim, Kyung-Ah Cho, So-Youn Woo, Meeyoung Shin, Eun-Sun Yoo, Jeong Chan Ra, Kyung-Ha Ryu. Improved viability and activity of neutrophils differentiated from HL-60 cells by co-culture with adipose tissue-derived mesenchymal stem cells.
Biochemical and biophysical research communications.
2012 Jun; 423(1):19-25. doi:
10.1016/j.bbrc.2012.05.049. [PMID: 22609208] - Yoshiko Nakae, Olivier M Dorchies, Peter J Stoward, Benno F Zimmermann, Christina Ritter, Urs T Ruegg. Quantitative evaluation of the beneficial effects in the mdx mouse of epigallocatechin gallate, an antioxidant polyphenol from green tea.
Histochemistry and cell biology.
2012 Jun; 137(6):811-27. doi:
10.1007/s00418-012-0926-3. [PMID: 22331205] - Maria Pia Donzello, Elisa Viola, Mauro Giustini, Claudio Ercolani, Fabrizio Monacelli. Tetrakis(thiadiazole)porphyrazines. 8. Singlet oxygen production, fluorescence response and liposomal incorporation of tetrakis(thiadiazole)porphyrazine macrocycles [TTDPzM] (M = Mg(II)(H2O), Zn(II), Al(III)Cl, Ga(III)Cl, Cd(II), Cu(II), 2H(I)).
Dalton transactions (Cambridge, England : 2003).
2012 May; 41(20):6112-21. doi:
10.1039/c2dt12381a. [PMID: 22481095] - R A Forero-Gonzalez, E C C Celeghini, C F Raphael, A F C Andrade, F F Bressan, R P Arruda. Effects of bovine sperm cryopreservation using different freezing techniques and cryoprotective agents on plasma, acrosomal and mitochondrial membranes.
Andrologia.
2012 May; 44 Suppl 1(?):154-9. doi:
10.1111/j.1439-0272.2010.01154.x. [PMID: 22506813] - Nico C Houter, Thijs L Pons. Ontogenetic changes in leaf traits of tropical rainforest trees differing in juvenile light requirement.
Oecologia.
2012 May; 169(1):33-45. doi:
10.1007/s00442-011-2175-x. [PMID: 22038060] - Jing-Wei Lei, Cai-Xia Xie, Huai-Xia Yang. Poly[[diaqua-bis-(μ(3)-3,5-dicarb-oxy-benzo-ato-κ(3)O(1):O(3):O(5))bis-(μ(3)-5-carb-oxy-ben-zene-1,3-dicarboxyl-ato-κ(3)O(1):O(3):O(5))tetrakis(methylformamide-κO)tri-man-ganese(II)] dimethyl-formamide tetra-solvate].
Acta crystallographica. Section E, Structure reports online.
2012 May; 68(Pt 5):m697-8. doi:
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BMC musculoskeletal disorders.
2012 Apr; 13(?):54. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2012 Mar; 109(13):5016-21. doi:
10.1073/pnas.1119303109. [PMID: 22411801] - Aliaksei Dubavik, Erdinc Sezgin, Vladimir Lesnyak, Nikolai Gaponik, Petra Schwille, Alexander Eychmüller. Penetration of amphiphilic quantum dots through model and cellular plasma membranes.
ACS nano.
2012 Mar; 6(3):2150-6. doi:
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BMC complementary and alternative medicine.
2012 Mar; 12(?):15. doi:
10.1186/1472-6882-12-15. [PMID: 22405256] - Stefanie Volland, Cornelius Lütz, Bernhard Michalke, Ursula Lütz-Meindl. Intracellular chromium localization and cell physiological response in the unicellular alga Micrasterias.
Aquatic toxicology (Amsterdam, Netherlands).
2012 Mar; 109(?):59-69. doi:
10.1016/j.aquatox.2011.11.013. [PMID: 22204989] - Xiao-Feng Yuan, Hai-Yan Tian, Jin-Hang Li, Tong Yu, Ren-Wang Jiang. Secohellebrigeninamide.
Acta crystallographica. Section E, Structure reports online.
2012 Mar; 68(Pt 3):o682. doi:
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Chemical research in toxicology.
2012 Feb; 25(2):454-61. doi:
10.1021/tx200494h. [PMID: 22211372] - Lan Liu, Klaus Michelsen, Elena N Kitova, Paul D Schnier, John S Klassen. Energetics of lipid binding in a hydrophobic protein cavity.
Journal of the American Chemical Society.
2012 Feb; 134(6):3054-60. doi:
10.1021/ja208909n. [PMID: 22280480] - Romina Pedreschi, Jørgen Nørgaard, Alain Maquet. Current challenges in detecting food allergens by shotgun and targeted proteomic approaches: a case study on traces of peanut allergens in baked cookies.
Nutrients.
2012 02; 4(2):132-50. doi:
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European journal of pharmacology.
2012 Jan; 675(1-3):32-9. doi:
10.1016/j.ejphar.2011.11.049. [PMID: 22169772] - Pinki Nandi, Swatilekha Ghosh, Kuladip Jana, Parimal C Sen. Elucidation of the involvement of p14, a sperm protein during maturation, capacitation and acrosome reaction of caprine spermatozoa.
PloS one.
2012; 7(1):e30552. doi:
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International journal of nanomedicine.
2012; 7(?):417-33. doi:
10.2147/ijn.s26485. [PMID: 22334775] - Peizhong Mao, Charles K Meshul, Philippe Thuillier, Natalie R S Goldberg, P Hemachandra Reddy. CART peptide is a potential endogenous antioxidant and preferentially localized in mitochondria.
PloS one.
2012; 7(1):e29343. doi:
10.1371/journal.pone.0029343. [PMID: 22235287] - Rajesh Vasita, Dhirendra S Katti. Structural and functional characterization of proteins adsorbed on hydrophilized polylactide-co-glycolide microfibers.
International journal of nanomedicine.
2012; 7(?):61-71. doi:
10.2147/ijn.s26453. [PMID: 22275823] - Norbert Kummerfeld, Marko Legler, Peter Wohlsein, Maren Kummerfeld. [Morphological studies in different avian species on artefacts induced by euthanasia with T 61 " or Pentobarbital (Narcoren)].
Berliner und Munchener tierarztliche Wochenschrift.
2012 Jan; 125(1-2):27-31. doi:
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PloS one.
2012; 7(2):e32077. doi:
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PloS one.
2012; 7(5):e37080. doi:
10.1371/journal.pone.0037080. [PMID: 22606332] - Bo Li, Hui Xu, Zhen Li, Mingfei Yao, Meng Xie, Haijun Shen, Song Shen, Xinshi Wang, Yi Jin. Bypassing multidrug resistance in human breast cancer cells with lipid/polymer particle assemblies.
International journal of nanomedicine.
2012; 7(?):187-97. doi:
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Viruses.
2012 01; 4(1):167-83. doi:
10.3390/v4010167. [PMID: 22355457] - Graziano Colombo, Ranieri Rossi, Nicoletta Gagliano, Nicola Portinaro, Marco Clerici, Andrea Annibal, Daniela Giustarini, Roberto Colombo, Aldo Milzani, Isabella Dalle-Donne. Red blood cells protect albumin from cigarette smoke-induced oxidation.
PloS one.
2012; 7(1):e29930. doi:
10.1371/journal.pone.0029930. [PMID: 22238677] - Luc H Boudreau, Jacques Maillet, Luc M LeBlanc, Jacques Jean-François, Mohamed Touaibia, Nicolas Flamand, Marc E Surette. Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes.
PloS one.
2012; 7(2):e31833. doi:
10.1371/journal.pone.0031833. [PMID: 22347509] - Yingwei Zhang, Yonglan Luo, Jingqi Tian, Abdullah M Asiri, Abdulrahman O Al-Youbi, Xuping Sun. Rectangular coordination polymer nanoplates: large-scale, rapid synthesis and their application as a fluorescent sensing platform for DNA detection.
PloS one.
2012; 7(1):e30426. doi:
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