N-Methylformamide (BioDeep_00000008683)

 

Secondary id: BioDeep_00001873566

human metabolite Endogenous


代谢物信息卡片


N-Monomethylformamide

化学式: C2H5NO (59.037112)
中文名称: N-甲基甲酰胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN=CO
InChI: InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)

描述信息

N-Methylformamide (NMF) is one of the two major urinary biomarkers of exposure to N,N-Dimethylformamide (DMF), a compound widely used in industries because of its extensive miscibility with water and solvents. Metabolism of NMF results in the formation of N-methylcarbamoyl adducts at the N-terminal valine and lysine in blood protein globin. (PMID: 17254560, 17254560, 16289959) [HMDB]
N-Methylformamide (NMF) is one of the two major urinary biomarkers of exposure to N,N-Dimethylformamide (DMF), a compound widely used in industries because of its extensive miscibility with water and solvents. Metabolism of NMF results in the formation of N-methylcarbamoyl adducts at the N-terminal valine and lysine in blood protein globin. (PMID: 17254560, 17254560, 16289959).
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C798 - Radiosensitizing Agent
D011838 - Radiation-Sensitizing Agents
D000970 - Antineoplastic Agents

同义名列表

9 个代谢物同义名

N-Monomethylformamide; Monomethylformamide; N-Methyl-formamide; N-METHYLFORMAMIDE; Methylformamide; HCONHCH3; NMF; NMF; N-Methylformamide



数据库引用编号

15 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)

2 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

  • Xubin Zheng, Ruiqing Fan, Haoyang Lu, Bowen Wang, Jingkun Wu, Ping Wang, Yulin Yang. A dual-emitting Tb(iii)&Yb(iii)-functionalized coordination polymer: a "turn-on" sensor for N-methylformamide in urine and a "turn-off" sensor for methylglyoxal in serum. Dalton transactions (Cambridge, England : 2003). 2019 Oct; 48(38):14408-14417. doi: 10.1039/c9dt02643f. [PMID: 31509135]
  • Yogesh Soni, T R Talluri, Ashok Kumar, S K Ravi, J S Mehta, B N Tripathi. Effects of different concentration and combinations of cryoprotectants on sperm quality, functional integrity in three Indian horse breeds. Cryobiology. 2019 02; 86(?):52-57. doi: 10.1016/j.cryobiol.2018.12.005. [PMID: 30576666]
  • S Macedo, M Bliebernicht, J Carvalheira, A Costa, F Ribeiro, A Rocha. Effects of two freezing methods and two cryopreservation media on post-thaw quality of stallion spermatozoa. Reproduction in domestic animals = Zuchthygiene. 2018 Apr; 53(2):519-524. doi: 10.1111/rda.13140. [PMID: 29383772]
  • Robert Hermes, Thomas Bernd Hildebrandt, Frank Göritz. Cryopreservation in rhinoceros-Setting a new benchmark for sperm cryosurvival. PloS one. 2018; 13(7):e0200154. doi: 10.1371/journal.pone.0200154. [PMID: 29995941]
  • Zhijun Wu, Qiang Liu, Chunmin Wang, Bo Xu, Mingyue Guan, Meng Ye, Hai Jiang, Min Zheng, Man Zhang, Wenjin Zhao, Xiao Jiang, Shuguang Leng, Juan Cheng. A Comparative Benchmark Dose Study for N, N-Dimethylformamide Induced Liver Injury in a Chinese Occupational Cohort. Toxicological sciences : an official journal of the Society of Toxicology. 2017 07; 158(1):140-150. doi: 10.1093/toxsci/kfx076. [PMID: 28505332]
  • Juliana P Alves, Carine D Corcini, Estela F Silva, Josie S Caldas, Tainã F Cardoso, Sergio R N Piedras, Rodrigo D Jardim, Antonio S Varela. The role of amides in seminal cryopreservation of wild silverside, Odontesthes bonariensis. Cryobiology. 2016 12; 73(3):383-387. doi: 10.1016/j.cryobiol.2016.09.001. [PMID: 27609248]
  • Sonja Kilo, Thomas Göen, Hans Drexler. Cross-sectional study on N,N-dimethylformamide (DMF); effects on liver and alcohol intolerance. International archives of occupational and environmental health. 2016 Nov; 89(8):1309-1320. doi: 10.1007/s00420-016-1164-0. [PMID: 27587219]
  • Elizabeth G Crichton, Budhan S Pukazhenthi, M Billah, Julian A Skidmore. Cholesterol addition aids the cryopreservation of dromedary camel (Camelus dromedarius) spermatozoa. Theriogenology. 2015 Jan; 83(2):168-74. doi: 10.1016/j.theriogenology.2014.09.005. [PMID: 25312816]
  • 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]
  • Yoko Tsuda, Hiroyuki Miyauchi, Aoi Minozoe, Shigeru Tanaka, Heihachiro Arito, Teruomi Tsukahara, Tetsuo Nomiyama. Seasonal difference in percutaneous absorption of N,N-dimethylformamide as determined using two urinary metabolites. Journal of occupational health. 2014; 56(4):252-9. doi: 10.1539/joh.13-0228-oa. [PMID: 24826962]
  • Mi-Young Lee, Jeong Sun Yang, Seong-Kyu Kang. External quality assessment scheme for biological monitoring of occupational exposure to toxic chemicals. Safety and health at work. 2011 Sep; 2(3):229-35. doi: 10.5491/shaw.2011.2.3.229. [PMID: 22953206]
  • Ya-Ling Qian, Cheng-Min Xu, Yan-Yan Lu, Yan-Hua Wang, Hao Wu, Xing Zhang. [The interventions effect-assessment of the workers exposed to N, N-dimethylformamide by percutaneous in a synthetic leather factory]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2011 Jun; 29(6):405-8. doi: NULL. [PMID: 22096848]
  • N Hoffmann, H Oldenhof, C Morandini, K Rohn, H Sieme. Optimal concentrations of cryoprotective agents for semen from stallions that are classified 'good' or 'poor' for freezing. Animal reproduction science. 2011 May; 125(1-4):112-8. doi: 10.1016/j.anireprosci.2011.03.001. [PMID: 21470802]
  • Philippe Hantson, Antoine Villa, Anne-Cécile Galloy, Sara Negri, Giulia Esabon, Fabien Lambiotte, Vincent Haufroid, Robert Garnier. Dimethylformamide metabolism following self-harm using a veterinary euthanasia product. Clinical toxicology (Philadelphia, Pa.). 2010 Aug; 48(7):725-9. doi: 10.3109/15563650.2010.498790. [PMID: 20849330]
  • Jun He, Jing-ping Zhou, Pei Wang. [High performance liquid chromatography for determination of N-acetyl-S-(N-methylformamide) cysteine in human urine derivative oscillopolarography for determination of urine arsenic]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2009 Feb; 27(2):103-4. doi: NULL. [PMID: 19351480]
  • Ven-Shing Wang, Ming-Yen Lu. Application of solid-phase microextraction and gas chromatography-mass spectrometry for measuring chemicals in saliva of synthetic leather workers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Jan; 877(1-2):24-32. doi: 10.1016/j.jchromb.2008.11.006. [PMID: 19036646]
  • Shih-Min Wang, Yao-Ming Chu, Shih-Chun Candice Lung, Tung-Sheng Shih, Yue-Ching Lin, Ho-Yuan Chang. Combining novel strategy with kinetic approach in the determination of respective respiration and skin exposure to N,N-dimethylformamide vapor. The Science of the total environment. 2007 Dec; 388(1-3):398-404. doi: 10.1016/j.scitotenv.2007.08.007. [PMID: 17854864]
  • Ya-Ling Qian, Hong-Fang Tang, Zheng Ruan. [Determination of N-methylformamide in urine with capillary gas chromatography.]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2007 Nov; 25(11):676-7. doi: NULL. [PMID: 18226374]
  • Dan Zhao, N D Sonawane, Marc H Levin, Baoxue Yang. Comparative transport efficiencies of urea analogues through urea transporter UT-B. Biochimica et biophysica acta. 2007 Jul; 1768(7):1815-21. doi: 10.1016/j.bbamem.2007.04.010. [PMID: 17506977]
  • Dar-Bin Shieh, Chia-Chun Chen, Tung-Sheng Shih, Huo-Mu Tai, Yau-Hui Wei, Ho-Yuan Chang. Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide. Chemico-biological interactions. 2007 Feb; 165(3):211-9. doi: 10.1016/j.cbi.2006.12.008. [PMID: 17254560]
  • S-M Wang, T-S Shih, Y-S Huang, M-R Chueh, J-S Chou, H-Y Chang. Evaluation of the effectiveness of personal protective equipment against occupational exposure to N,N-dimethylformamide. Journal of hazardous materials. 2006 Dec; 138(3):518-25. doi: 10.1016/j.jhazmat.2006.05.072. [PMID: 16846682]
  • Eleonora Pagnotta, Natalia Calonghi, Carla Boga, Lanfranco Masotti. N-methylformamide and 9-hydroxystearic acid: two anti-proliferative and differentiating agents with different modes of action in colon cancer cells. Anti-cancer drugs. 2006 Jun; 17(5):521-6. doi: 10.1097/00001813-200606000-00005. [PMID: 16702808]
  • In-Sung Chung, Jon-Ghan Kim, Sang-Kug Choi, Jong-Youn Bae, Mi-Young Lee. [Influencing factors that affect the biological monitoring of workers exposed to N,N-dimethylformamide in textile coating factories]. Journal of preventive medicine and public health = Yebang Uihakhoe chi. 2006 Mar; 39(2):171-6. doi: NULL. [PMID: 16615273]
  • Vagner Fernandes Knupp, Edna Maria Alvarez Leite, Zenilda de Lourdes Cardeal. Development of a solid phase microextraction-gas chromatography method to determine N-hydroxymethyl-N-methylformamide and N-methylformamide in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Dec; 828(1-2):103-7. doi: 10.1016/j.jchromb.2005.09.030. [PMID: 16221575]
  • H U Käfferlein, C Ferstl, A Burkhart-Reichl, K Hennebrüder, H Drexler, T Brüning, J Angerer. The use of biomarkers of exposure of N,N-dimethylformamide in health risk assessment and occupational hygiene in the polyacrylic fibre industry. Occupational and environmental medicine. 2005 May; 62(5):330-6. doi: 10.1136/oem.2004.017129. [PMID: 15837855]
  • Ho-Yuan Chang, Yuan-Der Yun, Yi-Chun Yu, Tung-Sheng Shih, Ming-Song Lin, Hsien-Wen Kuo, Kuo-Ming Chen. The effects of simultaneous exposure to methyl ethyl ketone and toluene on urinary biomarkers of occupational N,N-dimethylformamide exposure. Toxicology letters. 2005 Mar; 155(3):385-95. doi: 10.1016/j.toxlet.2004.11.005. [PMID: 15649622]
  • Jae Ho Sohn, Min Jeong Han, Mi Young Lee, Seong-Kyu Kang, Jeong Sun Yang. Simultaneous determination of N-hydroxymethyl-N-methylformamide, N-methylformamide and N-acetyl-S-(N-methylcarbamoyl)cystein in urine samples from workers exposed to N,N-dimethylformamide by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2005 Feb; 37(1):165-70. doi: 10.1016/j.jpba.2004.10.001. [PMID: 15664757]
  • Hideki Igisu, Takafumi Ezaki. [N-methylformamide in urine]. Nihon rinsho. Japanese journal of clinical medicine. 2004 Dec; 62 Suppl 12(?):488-90. doi: NULL. [PMID: 15658371]
  • E L Squires, S L Keith, J K Graham. Evaluation of alternative cryoprotectants for preserving stallion spermatozoa. Theriogenology. 2004 Sep; 62(6):1056-65. doi: 10.1016/j.theriogenology.2003.12.024. [PMID: 15289047]
  • Lu-Ming Li, Ming-Long Wang, Xiao-Lou Sun, Ya-Ling Qian, Bu-Yun Zheng, Yu-Fang Gu. [Study on the relationship between the level of urinary monomethylfomamide and the injury of liver and kidney in workers exposed to dimethylfomamide]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2004 Aug; 22(4):270-1. doi: NULL. [PMID: 15355706]
  • H U Käfferlein, J Mráz, C Ferstl, J Angerer. Analysis of metabolites of N,N-dimethylformamide in urine samples. International archives of occupational and environmental health. 2004 Aug; 77(6):427-32. doi: 10.1007/s00420-004-0538-x. [PMID: 15309551]
  • Ho-Yuan Chang, Tung-Sheng Shih, Yueliang Leon Guo, Ching-Yi Tsai, Ping-Chi Hsu. Sperm function in workers exposed to N,N-dimethylformamide in the synthetic leather industry. Fertility and sterility. 2004 Jun; 81(6):1589-94. doi: 10.1016/j.fertnstert.2003.10.033. [PMID: 15193482]
  • Ho-Yuan Chang, Ching-Yi Tsai, Yu-Qun Lin, Tung-Sheng Shih, Yun-Chin Lin. Urinary biomarkers of occupational N,N-dimethylformamide (DMF) exposure attributed to the dermal exposure. Journal of exposure analysis and environmental epidemiology. 2004 May; 14(3):214-21. doi: 10.1038/sj.jea.7500316. [PMID: 15141150]
  • Hyoung-Ah Kim, Kangyoon Kim, Yong Heo, Se-Hoon Lee, Ho-Chun Choi. Biological monitoring of workers exposed to N, N-dimethylformamide in synthetic leather manufacturing factories in Korea. International archives of occupational and environmental health. 2004 Feb; 77(2):108-12. doi: 10.1007/s00420-003-0474-1. [PMID: 14663587]
  • Ho-Yuan Chang, Tung-Sheng Shih, Ching-Chang Cheng, Ching-Yi Tsai, Jim-Shoung Lai, Ven-Shing Wang. The effects of co-exposure to methyl ethyl ketone on the biological monitoring of occupational exposure to N,N-dimethylformamide. International archives of occupational and environmental health. 2003 Mar; 76(2):121-8. doi: 10.1007/s00420-002-0371-z. [PMID: 12733084]
  • M Imbriani, L Maestri, P Marraccini, G Saretto, A Alessio, S Negri, S Ghittori. Urinary determination of N-acetyl- S-( N-methylcarbamoyl)cysteine and N-methylformamide in workers exposed to N, N-dimethylformamide. International archives of occupational and environmental health. 2002 Sep; 75(7):445-52. doi: 10.1007/s00420-002-0335-3. [PMID: 12172890]
  • Anette Gemal Jensen, Steen Honoré Hansen. Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow. Journal of pharmaceutical and biomedical analysis. 2002 Jan; 27(1-2):167-76. doi: 10.1016/s0731-7085(01)00548-9. [PMID: 11682223]
  • S Negri, A Alessio, L Maestri, M Sgroi, S Ghittori, M Imbriani. [High-pressure liquid chromatography (HPLC) with UV developer for the analysis of N-acetyl-S-(N-methylcarbomoyl)cysteine (AMCC)]. Giornale italiano di medicina del lavoro ed ergonomia. 2001 Oct; 23(4):461-6. doi: . [PMID: 11758151]
  • T Osunsanya, B Adejoro, B King. Biological monitoring of workers exposed to dimethylformamide in a textile polyurethane unit. Occupational medicine (Oxford, England). 2001 Sep; 51(6):374-9. doi: 10.1093/occmed/51.6.374. [PMID: 11584115]
  • T Nomiyama, V Haufroid, J P Buchet, H Miyauchi, S Tanaka, T Yamauchi, S Imamiya, Y Seki, K Omae, D Lison. Insertion polymorphism of CYP2E1 and urinary N-methylformamide after N,N- dimethylformamide exposure in Japanese workers. International archives of occupational and environmental health. 2001 Sep; 74(7):519-22. doi: 10.1007/s004200100252. [PMID: 11697456]
  • T Nomiyama, H Nakashima, L L Chen, S Tanaka, H Miyauchi, T Yamauchi, H Sakurai, K Omae. N,N-dimethylformamide: significance of dermal absorption and adjustment method for urinary N-methylformamide concentration as a biological exposure item. International archives of occupational and environmental health. 2001 Apr; 74(3):224-8. doi: 10.1007/s004200000207. [PMID: 11355298]
  • T Nomiyama, H Nakashima, Y Sano, L L Chen, S Tanaka, H Miyauchi, T Yamauchi, H Sakurai, K Omae. Does the polymorphism of cytochrome P-450 2E1 affect the metabolism of N,N-dimethylformamide? Comparison of the half-lives of urinary N-methylformamide. Archives of toxicology. 2001 Feb; 74(12):755-9. doi: 10.1007/s002040000197. [PMID: 11305777]
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  • H U Käfferlein, T Göen, J Müller, R Wrbitzky, J Angerer. Biological monitoring of workers exposed to N,N-dimethylformamide in the synthetic fibre industry. International archives of occupational and environmental health. 2000 Mar; 73(2):113-20. doi: 10.1007/s004200050016. [PMID: 10741509]
  • M Imbriani, P Marraccini, G Saretto, L Abatangelo, S Ghittori, A Cavalleri. [Measurement of N-methylformamide in occupational exposure to N,N-dimethylformamide]. La Medicina del lavoro. 2000 Mar; 91(2):114-24. doi: . [PMID: 10920619]
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