Methylamine (BioDeep_00000004397)

 

Secondary id: BioDeep_00000268066, BioDeep_00000860588

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin


代谢物信息卡片


Methylamine hydrochloride, 14C-labeled

化学式: CH5N (31.042197)
中文名称: 氨基甲烷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN
InChI: InChI=1S/CH5N/c1-2/h2H2,1H3

描述信息

Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. Interestingly, methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide. Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. Such deamination has been shown capable of regulating glucose transport in adipose cells. It has been independently discovered that the primary structure of vascular adhesion protein-1 (VAP-1) is identical to SSAO. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimers disease. The SSAO-catalyzed deamination of endogenous substrates like methylamine led to production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Inhibition of this effect by the presence of semicarbazide and catalase led to the suggestion that the process is mediated by the hydrogen peroxide produced in the oxidation of these amines (PMID: 16049393 , 12686132 , 17406961). Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821).
Methylamine is a colourless gas derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It has a strong odor similar to fish. Methylamine is used as a building block for the synthesis of many other commercially available compounds. Hundreds of millions of kilograms are produced annually. Methylamine is found in many foods, some of which are french plantain, tea, barley, and wild celery.

同义名列表

45 个代谢物同义名

Methylamine hydrochloride, 14C-labeled; Methyl OF gamma-N-methylasparagine; Methylamine, monopotassium salt; Methylamine, monosodium salt; Methylamine hydrogen cyanide; Methylamine aqueous solution; Methylamine hydrofluoride; Methylamine hydrochloride; Methylamine sulfate (1:1); Methylamine sulfate (2:1); Methylamine, 13C-labeled; Methylamine, 14C-labeled; Methylamine, 15N-labeled; Methylamine hydrobromide; Methylamine, cesium salt; Methylamine hydroiodide; Methylamine perchlorate; Monomethylammonium ion; Methylamine bisulfite; Methylamine solutions; Methylamine anhydrous; Anhydrous methylamine; Methylamine ion (1-); Methylamine solution; Methylamine nitrate; Methylamine hydride; Methylammonium ion; Monomethylamine; Methylammonium; N-Methylamine; Methylaminen; Methyl group; Aminomethane; Mercurialin; METHYLAMINE; Metyloamina; Methanamine; Carbinamine; Metilamine; CH3-NH2; Imizin; MeNH2; NME; MMA; NMA



数据库引用编号

17 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

38 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(26)

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

  • Georges Jourdi, Johan Abdoul, Virginie Siguret, Xavier Decleves, Elisa Frezza, Claire Pailleret, Isabelle Gouin-Thibault, Sophie Gandrille, Nathalie Neveux, Charles Marc Samama, Samuela Pasquali, Pascale Gaussem. Induced forms of α2-macroglobulin neutralize heparin and direct oral anticoagulant effects. International journal of biological macromolecules. 2021 Aug; 184(?):209-217. doi: 10.1016/j.ijbiomac.2021.06.058. [PMID: 34126147]
  • Mansoore Esmaili, Brian P Tancowny, Xiongyao Wang, Audric Moses, Leonardo M Cortez, Valerie L Sim, Holger Wille, Michael Overduin. Native nanodiscs formed by styrene maleic acid copolymer derivatives help recover infectious prion multimers bound to brain-derived lipids. The Journal of biological chemistry. 2020 06; 295(25):8460-8469. doi: 10.1074/jbc.ra119.012348. [PMID: 32358064]
  • Wahiduzzaman, Md Imtaiyaz Hassan, Asimul Islam, Faizan Ahmad. Urea Stress: Myo-inositol's efficacy to counteract destabilization of TIM-β-globin complex by urea is as good as that of the methylamine. International journal of biological macromolecules. 2020 May; 151(?):1108-1115. doi: 10.1016/j.ijbiomac.2019.10.153. [PMID: 31751698]
  • Pascal Ganz, Toyosi Ijato, Romano Porras-Murrilo, Nils Stührwohldt, Uwe Ludewig, Benjamin Neuhäuser. A twin histidine motif is the core structure for high-affinity substrate selection in plant ammonium transporters. The Journal of biological chemistry. 2020 03; 295(10):3362-3370. doi: 10.1074/jbc.ra119.010891. [PMID: 31988244]
  • Dorna Davani-Davari, Iman Karimzadeh, Shahrokh Ezzatzadegan-Jahromi, Mohammad Mahdi Sagheb. Potential Adverse Effects of Creatine Supplement on the Kidney in Athletes and Bodybuilders. Iranian journal of kidney diseases. 2018 10; 12(5):253-260. doi: . [PMID: 30367015]
  • Xuelu Ding, Vannuruswamy Garikapati, Bernhard Spengler, Sven Heiles. Analysis of ketone-based neurosteroids by reactive low-temperature plasma mass spectrometry. Rapid communications in mass spectrometry : RCM. 2018 Aug; 32(16):1439-1450. doi: 10.1002/rcm.8180. [PMID: 29802658]
  • Jun-Sheng Tian, Lei Zhao, Xiao-Li Shen, Huan Liu, Xue-Mei Qin. 1H NMR-based metabolomics approach to investigating the renal protective effects of Genipin in diabetic rats. Chinese journal of natural medicines. 2018 Apr; 16(4):261-270. doi: 10.1016/s1875-5364(18)30056-6. [PMID: 29703326]
  • Haoxin Lv, Nurettin Sahin, Akio Tani. Isolation and genomic characterization of Novimethylophilus kurashikiensis gen. nov. sp. nov., a new lanthanide-dependent methylotrophic species of Methylophilaceae. Environmental microbiology. 2018 03; 20(3):1204-1223. doi: 10.1111/1462-2920.14062. [PMID: 29411502]
  • Bindu Prasuna Aloor, Uday Kiran Avasthi, Agepati S Raghavendra. Stimulation by abscisic acid of the activity of phosphoenolpyruvate carboxylase in leaf disks of Amaranthus hypochondriacus L., C4 plant: role of pH and protein levels. Protoplasma. 2017 Sep; 254(5):1973-1981. doi: 10.1007/s00709-017-1091-2. [PMID: 28251362]
  • Dongli Hao, Shunying Yang, Yanan Huang, Yanhua Su. Identification of structural elements involved in fine-tuning of the transport activity of the rice ammonium transporter OsAMT1;3. Plant physiology and biochemistry : PPB. 2016 Nov; 108(?):99-108. doi: 10.1016/j.plaphy.2016.07.003. [PMID: 27423220]
  • Tomoyuki Minami, Misue Anda, Hisayuki Mitsui, Masayuki Sugawara, Takakazu Kaneko, Shusei Sato, Seishi Ikeda, Takashi Okubo, Hirohito Tsurumaru, Kiwamu Minamisawa. Metagenomic Analysis Revealed Methylamine and Ureide Utilization of Soybean-Associated Methylobacterium. Microbes and environments. 2016 Sep; 31(3):268-78. doi: 10.1264/jsme2.me16035. [PMID: 27431374]
  • Indranil Mitra, Christa M Snyder, Xiaomei Zhou, Margit I Campos, William R Alley, Milos V Novotny, Stephen C Jacobson. Structural Characterization of Serum N-Glycans by Methylamidation, Fluorescent Labeling, and Analysis by Microchip Electrophoresis. Analytical chemistry. 2016 09; 88(18):8965-71. doi: 10.1021/acs.analchem.6b00882. [PMID: 27504786]
  • Imen Abbes, Christophe Rihouey, Julie Hardouin, Emmanuelle Dé, Thierry Jouenne, Stéphane Alexandre. Pseudomonas aeruginosa produces phosphatidyltris(hydroxymethyl)aminomethane and derivatives when grown in Tris-buffered medium. Biochimica et biophysica acta. 2016 Aug; 1861(8 Pt A):703-14. doi: 10.1016/j.bbalip.2016.04.017. [PMID: 27126915]
  • Chaoji Huangfu, Yuyuan Ma, Maomin Lv, Junting Jia, Xiong Zhao, Jingang Zhang. Purification of α2-macroglobulin from Cohn Fraction IV by immobilized metal affinity chromatography: A promising method for the better utilization of plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Jul; 1025(?):68-75. doi: 10.1016/j.jchromb.2016.05.013. [PMID: 27214605]
  • Gabriella Varga, Norbert Lajkó, Melinda Ugocsai, Dániel Érces, Gyöngyi Horváth, Gábor Tóth, Mihály Boros, Miklós Ghyczy. Reduced mucosal side-effects of acetylsalicylic acid after conjugation with tris-hydroxymethyl-aminomethane. Synthesis and biological evaluation of a new anti-inflammatory compound. European journal of pharmacology. 2016 Jun; 781(?):181-9. doi: 10.1016/j.ejphar.2016.04.019. [PMID: 27079640]
  • Ahmed Abdur Rehman, Haseeb Ahsan, Fahim Halim Khan. Identification of a new alpha-2-macroglobulin: Multi-spectroscopic and isothermal titration calorimetry study. International journal of biological macromolecules. 2016 Feb; 83(?):366-75. doi: 10.1016/j.ijbiomac.2015.11.043. [PMID: 26608004]
  • Safikur Rahman, Marina Warepam, Laishram R Singh, Tanveer Ali Dar. A current perspective on the compensatory effects of urea and methylamine on protein stability and function. Progress in biophysics and molecular biology. 2015 Nov; 119(2):129-36. doi: 10.1016/j.pbiomolbio.2015.06.002. [PMID: 26095775]
  • Kosuke Shiraishi, Masahide Oku, Daichi Uchida, Hiroya Yurimoto, Yasuyoshi Sakai. Regulation of nitrate and methylamine metabolism by multiple nitrogen sources in the methylotrophic yeast Candida boidinii. FEMS yeast research. 2015 Nov; 15(7):. doi: 10.1093/femsyr/fov084. [PMID: 26377403]
  • Phattara Boraphech, Paitip Thiravetyan. Removal of trimethylamine (fishy odor) by C₃ and CAM plants. Environmental science and pollution research international. 2015 Aug; 22(15):11543-57. doi: 10.1007/s11356-015-4364-3. [PMID: 25827651]
  • Tingting Wei, Liangcai Zhao, Jianmin Jia, Huanhuan Xia, Yao Du, Qiuting Lin, Xiaodong Lin, Xinjian Ye, Zhihan Yan, Hongchang Gao. Metabonomic analysis of potential biomarkers and drug targets involved in diabetic nephropathy mice. Scientific reports. 2015 Jul; 5(?):11998. doi: 10.1038/srep11998. [PMID: 26149603]
  • Sha-Sha Lv, Yi-Rong Liu, Teng Huang, Ya-Juan Feng, Shuai Jiang, Wei Huang. Stability of Hydrated Methylamine: Structural Characteristics and H2N···H-O Hydrogen Bonds. The journal of physical chemistry. A. 2015 Apr; 119(16):3770-9. doi: 10.1021/acs.jpca.5b00616. [PMID: 25843772]
  • Kosuke Shiraishi, Masahide Oku, Kosuke Kawaguchi, Daichi Uchida, Hiroya Yurimoto, Yasuyoshi Sakai. Yeast nitrogen utilization in the phyllosphere during plant lifespan under regulation of autophagy. Scientific reports. 2015 Apr; 5(?):9719. doi: 10.1038/srep09719. [PMID: 25900611]
  • Zsolt Baranyai, Ernő Brücher, Fulvio Uggeri, Alessandro Maiocchi, Imre Tóth, Melinda Andrási, Attila Gáspár, László Zékány, Silvio Aime. The role of equilibrium and kinetic properties in the dissociation of Gd[DTPA-bis(methylamide)] (Omniscan) at near to physiological conditions. Chemistry (Weinheim an der Bergstrasse, Germany). 2015 Mar; 21(12):4789-99. doi: 10.1002/chem.201405967. [PMID: 25678406]
  • Safikur Rahman, Md Tabish Rehman, Laishram R Singh, Marina Warepam, Faizan Ahmad, Tanveer Ali Dar. Salt potentiates methylamine counteraction system to offset the deleterious effects of urea on protein stability and function. PloS one. 2015; 10(3):e0119597. doi: 10.1371/journal.pone.0119597. [PMID: 25793733]
  • Ioana Alesutan, Katharina Musculus, Tatsiana Castor, Kousi Alzoubi, Jakob Voelkl, Florian Lang. Inhibition of Phosphate-Induced Vascular Smooth Muscle Cell Osteo-/Chondrogenic Signaling and Calcification by Bafilomycin A1 and Methylamine. Kidney & blood pressure research. 2015; 40(5):490-9. doi: 10.1159/000368524. [PMID: 26418500]
  • Wen-Hsiao Chuang, Ping-Chung Liu, Chia-Yu Hung, Kuo-Kau Lee. Purification, characterization and molecular cloning of alpha-2-macroglobulin in cobia, Rachycentron canadum. Fish & shellfish immunology. 2014 Dec; 41(2):346-55. doi: 10.1016/j.fsi.2014.09.016. [PMID: 25245622]
  • Majid Rezayi, Reza Karazhian, Yadollah Abdollahi, Leila Narimani, Seyedeh Belin Tavakoly Sany, Saeid Ahmadzadeh, Yatimah Alias. Titanium (III) cation selective electrode based on synthesized tris(2pyridyl) methylamine ionophore and its application in water samples. Scientific reports. 2014 Apr; 4(?):4664. doi: 10.1038/srep04664. [PMID: 24722576]
  • Yan Zhu, Xiao-Min Ge, Mi-Mi Wu, Xuan Li, Jun-Min He. The role and interactions of cytosolic alkalization and hydrogen peroxide in ultraviolet B-induced stomatal closure in Arabidopsis. Plant science : an international journal of experimental plant biology. 2014 Feb; 215-216(?):84-90. doi: 10.1016/j.plantsci.2013.11.010. [PMID: 24388518]
  • Mélanie Boeckstaens, Elisa Llinares, Pascale Van Vooren, Anna Maria Marini. The TORC1 effector kinase Npr1 fine tunes the inherent activity of the Mep2 ammonium transport protein. Nature communications. 2014; 5(?):3101. doi: 10.1038/ncomms4101. [PMID: 24476960]
  • Libo Li, Igor Vorobyov, Toby W Allen. The different interactions of lysine and arginine side chains with lipid membranes. The journal of physical chemistry. B. 2013 Oct; 117(40):11906-20. doi: 10.1021/jp405418y. [PMID: 24007457]
  • Inga Rempe, Ulrike Brezina, Susanne Kersten, Sven Dänicke. Effects of a Fusarium toxin-contaminated maize treated with sodium metabisulphite, methylamine and calcium hydroxide in diets for female piglets. Archives of animal nutrition. 2013 Aug; 67(4):314-29. doi: 10.1080/1745039x.2013.818762. [PMID: 23859352]
  • Sheeza Khan, Zehra Bano, Laishram R Singh, Md Imtaiyaz Hassan, Asimul Islam, Faizan Ahmad. Why is glycine not a part of the osmoticum in the urea-rich cells?. Protein and peptide letters. 2013 Jan; 20(1):61-70. doi: NULL. [PMID: 22670764]
  • Sheeza Khan, Zehra Bano, Laishram R Singh, Md Imtaiyaz Hassan, Asimul Islam, Faizan Ahmad. Testing the ability of non-methylamine osmolytes present in kidney cells to counteract the deleterious effects of urea on structure, stability and function of proteins. PloS one. 2013; 8(9):e72533. doi: 10.1371/journal.pone.0072533. [PMID: 24039776]
  • Raymond J Ritchie. The ammonia transport, retention and futile cycling problem in cyanobacteria. Microbial ecology. 2013 Jan; 65(1):180-96. doi: 10.1007/s00248-012-0111-1. [PMID: 22940733]
  • Yongqian Zhang, Jian Mao, Peter H Yu, Shengyuan Xiao. A micro trapping system coupled with a high performance liquid chromatography procedure for methylamine determination in both tissue and cigarette smoke. Analytica chimica acta. 2012 Nov; 752(?):106-11. doi: 10.1016/j.aca.2012.09.027. [PMID: 23101659]
  • Liangcai Zhao, Hongchang Gao, Yongxiang Zhao, Donghai Lin. Metabonomic analysis of the therapeutic effect of Zhibai Dihuang Pill in treatment of streptozotocin-induced diabetic nephropathy. Journal of ethnopharmacology. 2012 Aug; 142(3):647-56. doi: 10.1016/j.jep.2012.05.031. [PMID: 22687255]
  • Chen Gui-Rong, Cai Li-Ping, Dou De-Qiang, Kang Ting-Guo, Li Hong-Fu, Li Fu-Rui, Jiang Ning. Synthesis of (-)-arctigenin derivatives and their anticancer activity. Natural product research. 2012; 26(2):177-81. doi: 10.1080/14786419.2010.541874. [PMID: 21867457]
  • Zhexuan Lin, Hui Li, Hongjun Luo, Yuan Zhang, Wenhong Luo. Benzylamine and methylamine, substrates of semicarbazide-sensitive amine oxidase, attenuate inflammatory response induced by lipopolysaccharide. International immunopharmacology. 2011 Aug; 11(8):1079-89. doi: 10.1016/j.intimp.2011.03.002. [PMID: 21414430]
  • A Olivieri, K Tipton. Inhibition of bovine plasma semicarbazide-sensitive amine oxidase by caffeine. Journal of biochemical and molecular toxicology. 2011 Jan; 25(1):26-7. doi: 10.1002/jbt.20356. [PMID: 21322095]
  • Nazih L Nakhoul, Solange M Abdulnour-Nakhoul, Emile L Boulpaep, Edd Rabon, Eric Schmidt, L Lee Hamm. Substrate specificity of Rhbg: ammonium and methyl ammonium transport. American journal of physiology. Cell physiology. 2010 Sep; 299(3):C695-705. doi: 10.1152/ajpcell.00019.2010. [PMID: 20592240]
  • Soojung Lee, Hye Jeong Lee, Han Soo Yang, Ian M Thornell, Mark O Bevensee, Inyeong Choi. Sodium-bicarbonate cotransporter NBCn1 in the kidney medullary thick ascending limb cell line is upregulated under acidic conditions and enhances ammonium transport. Experimental physiology. 2010 Sep; 95(9):926-37. doi: 10.1113/expphysiol.2010.053967. [PMID: 20591978]
  • Elena V Ermilova, Zhanneta M Zalutskaya, Maxim M Nikitin, Tatyana V Lapina, Emilio Fernández. Regulation by light of ammonium transport systems in Chlamydomonas reinhardtii. Plant, cell & environment. 2010 Jun; 33(6):1049-56. doi: 10.1111/j.1365-3040.2010.02126.x. [PMID: 20132518]
  • Manish P Ponda, Zhe Quan, Michal L Melamed, Amanda Raff, Timothy W Meyer, Thomas H Hostetter. Methylamine clearance by haemodialysis is low. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2010 May; 25(5):1608-13. doi: 10.1093/ndt/gfp629. [PMID: 20019016]
  • C Michele Nawata, Chris M Wood, Michael J O'Donnell. Functional characterization of Rhesus glycoproteins from an ammoniotelic teleost, the rainbow trout, using oocyte expression and SIET analysis. The Journal of experimental biology. 2010 Apr; 213(Pt 7):1049-59. doi: 10.1242/jeb.038752. [PMID: 20228341]
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