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Chemical Compound Review

Methanaminium     methylazanium

Synonyms: Methylammonium, NH2-, CHEBI:57913, CHEBI:58855, CHEBI:59338, ...
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Disease relevance of methanamine


High impact information on methanamine

  • The substrates ammonium and methylammonium have been used for cocrystallization experiments with Amt-1, but the identification of binding sites that are distinct from water positions is not unambiguous [5].
  • Together with our previous studies, current results are in accord with the view that Amt and methylammonium/ammonium permease proteins increase the rate of diffusion of the uncharged species NH(3) across the cytoplasmic membrane [1].
  • Based on the organismal, organ, and tissue distribution of Rh proteins, and on our evidence that their only known paralogues, the ammonium and methylammonium transport proteins (also called methylammonium permeases), are gas channels for NH(3), we recently speculated that Rh proteins are biological gas channels for CO(2) [6].
  • In bacteria, however, ATP-dependent conversion of methylammonium to gamma-N-methylglutamine by glutamine synthetase precludes its use in assessing concentrative transport across the cytoplasmic membrane [7].
  • Thus, in fungi as in bacteria, subsequent energy-dependent utilization of methylammonium precludes its use in assessing active transport across the cytoplasmic membrane [7].

Chemical compound and disease context of methanamine


Biological context of methanamine


Anatomical context of methanamine

  • AtTIP2;1- and AtTIP2;3-mediated methylammonium detoxification in yeast depended on a functional vacuole, which was in agreement with the subcellular localization of green fluorescent protein-fusion proteins on the tonoplast in planta [10].
  • In accordance with its localization, human RhBG mediates saturable, electroneutral transport of the ammonium analogue methylammonium when heterologously expressed in Xenopus oocytes [11].
  • In rat yolk sacs incubated in vitro, the rates of degradation of endogenous [3H]leucine-labelled proteins and of pinocytically ingested 125I-labelled bovine serum albumin were both decreased in the presence of either ammonium, methylammonium or ethylammonium ions (0-20 mM) or much lower concentrations of chloroquine (0-500 microM) [12].
  • Thus, this work provides directly the missing evidence for the hypothesized role played by the wider vestibule site of AmtB at the periplasmic side of the membrane in "recruiting" NH(4)(+) or methylammonium ions as proposed by Khademi et al [13].
  • Glutamine synthetase activity of cells cultured with ammonium was 33% that of N2-fixing cultures, but activity was unaffected by incubation with methylammonium [14].

Associations of methanamine with other chemical compounds


Gene context of methanamine


Analytical, diagnostic and therapeutic context of methanamine

  • One mutant in the largest class had an insert in the AMT4 gene, and the insert cosegregated with methylammonium resistance in genetic crosses [24].
  • Sequence analysis revealed that one P(II) protein-encoding gene, glnB, was adjacent to a glnA gene (encoding glutamine synthetase) and that two other P(II) protein-encoding genes, identified as glnK1 and glnK2, were located upstream of amtB1 and amtB2, respectively, genes which in other organisms encode ammonium (or methylammonium) transporters [25].
  • The analysis of intracellular metabolites using thin-layer chromatography and matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry indicated that methylammonium was rapidly metabolized to N-methylglutamate via gamma-N-methylglutamine [26].
  • Discrimination of methylammonium from organic ammonium ions using ion-selective electrodes based on calix[4]arene-crown-6 conjugates [27].


  1. Ammonium/methylammonium transport (Amt) proteins facilitate diffusion of NH3 bidirectionally. Soupene, E., Lee, H., Kustu, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  2. Functional and genetic characterization of the (methyl)ammonium uptake carrier of Corynebacterium glutamicum. Siewe, R.M., Weil, B., Burkovski, A., Eikmanns, B.J., Eikmanns, M., Krämer, R. J. Biol. Chem. (1996) [Pubmed]
  3. Ammonium/methylammonium permeases of a Cyanobacterium. Identification and analysis of three nitrogen-regulated amt genes in synechocystis sp. PCC 6803. Montesinos, M.L., Muro-Pastor, A.M., Herrero, A., Flores, E. J. Biol. Chem. (1998) [Pubmed]
  4. Evidence for a methylammonium-binding site on methylamine dehydrogenase of Thiobacillus versutus. Gorren, A.C., Moenne-Loccoz, P., Backes, G., de Vries, S., Sanders-Loehr, J., Duine, J.A. Biochemistry (1995) [Pubmed]
  5. Crystal structure of the archaeal ammonium transporter Amt-1 from Archaeoglobus fulgidus. Andrade, S.L., Dickmanns, A., Ficner, R., Einsle, O. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  6. Rhesus expression in a green alga is regulated by CO(2). Soupene, E., King, N., Feild, E., Liu, P., Niyogi, K.K., Huang, C.H., Kustu, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  7. Evidence that fungal MEP proteins mediate diffusion of the uncharged species NH(3) across the cytoplasmic membrane. Soupene, E., Ramirez, R.M., Kustu, S. Mol. Cell. Biol. (2001) [Pubmed]
  8. NH4Cl-induced hypertrophy is mediated by weak base effects and is independent of cell cycle processes. Franch, H.A., Preisig, P.A. Am. J. Physiol. (1996) [Pubmed]
  9. Characterisation of the glnK-amtB operon and the involvement of AmtB in methylammonium uptake in Azorhizobium caulinodans. Michel-Reydellet, N., Desnoues, N., de Zamaroczy, M., Elmerich, C., Kaminski, P.A. Mol. Gen. Genet. (1998) [Pubmed]
  10. Tonoplast intrinsic proteins AtTIP2;1 and AtTIP2;3 facilitate NH3 transport into the vacuole. Loqué, D., Ludewig, U., Yuan, L., von Wirén, N. Plant Physiol. (2005) [Pubmed]
  11. Electroneutral ammonium transport by basolateral rhesus B glycoprotein. Ludewig, U. J. Physiol. (Lond.) (2004) [Pubmed]
  12. Effects of weak bases on the degradation of endogenous and exogenous proteins by rat yolk sacs. Livesey, G., Williams, K.E., Knowles, S.E., Ballard, F.J. Biochem. J. (1980) [Pubmed]
  13. Molecular determinants for binding of ammonium ion in the ammonia transporter AmtB-A quantum chemical analysis. Liu, Y., Hu, X. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  14. The role of glutamine in regulation of ammonium transport in Azotobacter vinelandii. Jayakumar, A., Barnes, E.M. Arch. Biochem. Biophys. (1984) [Pubmed]
  15. Regulation of yeast H(+)-ATPase by protein kinases belonging to a family dedicated to activation of plasma membrane transporters. Goossens, A., de La Fuente, N., Forment, J., Serrano, R., Portillo, F. Mol. Cell. Biol. (2000) [Pubmed]
  16. Monovalent and divalent cation permeability and block of neuronal nicotinic receptor channels in rat parasympathetic ganglia. Nutter, T.J., Adams, D.J. J. Gen. Physiol. (1995) [Pubmed]
  17. Ionic selectivity of Ih channels of rod photoreceptors in tiger salamanders. Wollmuth, L.P., Hille, B. J. Gen. Physiol. (1992) [Pubmed]
  18. The permeability of the cGMP-activated channel to organic cations in retinal rods of the tiger salamander. Picco, C., Menini, A. J. Physiol. (Lond.) (1993) [Pubmed]
  19. HOR7, a multicopy suppressor of the Ca2+-induced growth defect in sphingolipid mannosyltransferase-deficient yeast. Lisman, Q., Urli-Stam, D., Holthuis, J.C. J. Biol. Chem. (2004) [Pubmed]
  20. Different transport mechanisms in plant and human AMT/Rh-type ammonium transporters. Mayer, M., Schaaf, G., Mouro, I., Lopez, C., Colin, Y., Neumann, P., Cartron, J.P., Ludewig, U. J. Gen. Physiol. (2006) [Pubmed]
  21. Characterization of Arabidopsis AtAMT2, a novel ammonium transporter in plants. Sohlenkamp, C., Shelden, M., Howitt, S., Udvardi, M. FEBS Lett. (2000) [Pubmed]
  22. glnA mutations conferring resistance to methylammonium in Escherichia coli K12. Servín-González, L., Ortiz, M., González, A., Bastarrachea, F. J. Gen. Microbiol. (1987) [Pubmed]
  23. Double chromodomains cooperate to recognize the methylated histone H3 tail. Flanagan, J.F., Mi, L.Z., Chruszcz, M., Cymborowski, M., Clines, K.L., Kim, Y., Minor, W., Rastinejad, F., Khorasanizadeh, S. Nature (2005) [Pubmed]
  24. Spontaneous mutations in the ammonium transport gene AMT4 of Chlamydomonas reinhardtii. Kim, K.S., Feild, E., King, N., Yaoi, T., Kustu, S., Inwood, W. Genetics (2005) [Pubmed]
  25. Identification of three genes encoding P(II)-like proteins in Gluconacetobacter diazotrophicus: studies of their role(s) in the control of nitrogen fixation. Perlova, O., Ureta, A., Nordlund, S., Meletzus, D. J. Bacteriol. (2003) [Pubmed]
  26. Ammonium and methylammonium uptake in a fertilizer-degrading strain of Ochrobactrum anthropi. Ewen, H., Kaltwasser, H., Jahns, T. Antonie Van Leeuwenhoek (2000) [Pubmed]
  27. Discrimination of methylammonium from organic ammonium ions using ion-selective electrodes based on calix[4]arene-crown-6 conjugates. Katsu, T., Matsumoto, M. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. (2001) [Pubmed]
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