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Chemical Compound Review

Metilamine     methanamine

Synonyms: Carbinamine, METHYLAMINE, Mercurialin, Methanamine, Metyloamina, ...
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Disease relevance of methanamine

  • We propose that PE enters mouse fibroblasts by receptor-mediated endocytosis and that chloroquine and methylamine, agents which are known to block this process, prevent expression of toxicity [1].
  • The complex is composed of three electron transfer proteins from Paracoccus denitrificans, the quinoprotein methylamine dehydrogenase, the blue copper protein amicyanin, and the cytochrome c551i [2].
  • The three-dimensional structure of quinoprotein methylamine dehydrogenase from Thiobacillus versutus has been determined at 2.25 A resolution by a combination of multiple isomorphous replacement, phase extension by solvent flattening and partial structure phasing using molecular dynamics refinement [3].
  • Urinary excretion of monomethylamine remained constant (1.3 to 1.5 mumol/24 h/kg of body weight) throughout the study [4].
  • In vivo 13C and 15N NMR studies of methylamine metabolism in Pseudomonas species MA [5].

Psychiatry related information on methanamine


High impact information on methanamine

  • We postulate that the primary amines, methylamine and mono-dansylcadaverine, interfere with the recycling of alpha 2M receptors, while the chemical nature of the amines and the conditions under which inhibition becomes apparent point to the involvement of transglutaminase in this recycling [7].
  • The sCR1 bivalently bound dimeric forms of its ligands, C3b and methylamine-treated C4 (C4-ma), and promoted their inactivation by factor I. In nanomolar concentrations, sCR1 blocked complement activation in human serum by the two pathways [8].
  • Increasing the vacuolar pH with chloroquine, ammonium chloride, methylamine, or monensin significantly inhibited the escape of the parasites into the cytosol [9].
  • SDS-PAGE and autoradiographic analysis of C3 extracted from bacteria opsonized with isolated proteins or EGTA-serum using methylamine and SDS demonstrated that the predominant form of C3 bound by ester bonds under both sets of conditions was iC3b [10].
  • When the C3d portion of C3b bound to zymosan particles via the metastable binding site was treated with radiolabeled methylamine, the fragment was released from the particles in radiolabeled form [11].

Chemical compound and disease context of methanamine


Biological context of methanamine

  • Alkylation experiments with [1-14C]iodoacetamide have further established a 1:1 correspondence between methylamine incorporation and expression of the reactive thiol [17].
  • In separate experiments in rats, intramuscular injections of 0.63M methylamine plus 0.079M hydroxylamine induced local egress of intravascular radiolabeled albumin within the injection site and endothelial gaps in venules detected with colloidal carbon--changes consistent with direct effects on vascular permeability [18].
  • Dansylcadaverine (20 microM), methylamine (20 mM), and bacitracin (2 mg/ml) prevented cell pair formation even when added poststarvation, after mixing of cells of opposite mating types (during the preparing interaction) [19].
  • Amino acid analysis of A. variabilis allophycocyanin subunits showed that the derivative at position 71 can account for the total methylamine released from the beta subunit, while hydrolysis of the alpha subunit released no methylamine [20].
  • The cytotoxicity seems, therefore, to be a consequence of the deamination of methylamine [21].

Anatomical context of methanamine

  • The effects on endocytic vesicle pH are rapidly reversible upon removal of the perturbant, but the effects on cell surface receptors are slowly reversible with methylamine and essentially irreversible with monensin [22].
  • Determination of CQ and methylamine accumulation in infected erythrocytes, in conjunction with morphometric determination of the relative sizes of the various cellular compartments, provided an independent assessment of the vacuolar pH, yielding a value of 5.0-5 [23].
  • Bacterial spores of various Bacillus species are impermeable or exhibit low permeability to many compounds that readily penetrate germinated spores, including methylamine [24].
  • Intracellular processing studies carried out in the presence and absence of methylamine suggested that mIL-3 is cleaved at two specific sites before its complete digestion within lysosomes [25].
  • In Wistar cells vesicular fluorescence could be increased by preincubation with monensin or methylamine, compounds that have been shown to interfere with plasma membrane recycling [26].

Associations of methanamine with other chemical compounds

  • Native C3 from fresh plasma did not bind to laminin but C3 from plasma treated with methylamine bound efficiently [27].
  • The methylamine uptake is optimal at pH 7 with a Km of 65 microM and a Ki for NH4+ of approximately 10 microM, is energy-dependent and can be inhibited by protonophores [28].
  • Studies of ET from tryptophan tryptophylquinone to copper to heme in the methylamine dehydrogenase-amicyanin-cytochrome c-551i ET complex, as well as studies of other physiologic redox protein complexes, are used to illustrate the combination of factors which control rates of interprotein ET reactions [29].
  • Intracellular pH was determined by 31P NMR and by equilibrium distribution studies with 5,5-dimethyloxazolidine-2,4-dione or methylamine [30].
  • Furthermore, as previously reported for alpha 2-macroglobulin in the presence of methylamine, dansylcadaverine, or bacitracin, clustering and internalization were inhibited but the overall fluorescence intensity of the cells did not appear to be affected [31].

Gene context of methanamine

  • In addition to finding label in the alpha-chains of the secreted (C4s) and predominant plasma (C4p) forms of C4, two additional molecules with apparent molecular weights of approximately 168,000 (p168) and approximately 125,000 (p125) covalently incorporated methylamine, indicating the presence of an internal thioester bond [32].
  • Reaction of alpha 2AP with SkPl in murine plasma was significant only after the alpha 2M was inactivated with methylamine [33].
  • Methylamine, which blocks protease binding to alpha 2M, increases the amount of 125I-bFGF that can be bound 2-fold [34].
  • Mutagenesis of Asn246 to Ala in Mep2 abolished transport and signalling with methylamine but had no effect with ammonium [35].
  • Ni2+ inhibited all of the specific binding of radiolabeled methylamine-activated alpha 2-macroglobulin (125I-alpha 2-M*) to rabbit aortic smooth muscle cells (SMC), rat hepatoma Fu5AH, and mouse fibroblast L cells [36].

Analytical, diagnostic and therapeutic context of methanamine


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  2. Structure of an electron transfer complex: methylamine dehydrogenase, amicyanin, and cytochrome c551i. Chen, L., Durley, R.C., Mathews, F.S., Davidson, V.L. Science (1994) [Pubmed]
  3. Structure of quinoprotein methylamine dehydrogenase at 2.25 A resolution. Vellieux, F.M., Huitema, F., Groendijk, H., Kalk, K.H., Jzn, J.F., Jongejan, J.A., Duine, J.A., Petratos, K., Drenth, J., Hol, W.G. EMBO J. (1989) [Pubmed]
  4. Increase in human exposure to methylamine precursors of N-nitrosamines after eating fish. Zeisel, S.H., DaCosta, K.A. Cancer Res. (1986) [Pubmed]
  5. In vivo 13C and 15N NMR studies of methylamine metabolism in Pseudomonas species MA. Jones, J.G., Bellion, E. J. Biol. Chem. (1991) [Pubmed]
  6. Methylamine, but not ammonia, is hypophagic in mouse by interaction with brain Kv1.6 channel subtype. Pirisino, R., Ghelardini, C., Pacini, A., Galeotti, N., Raimondi, L. Br. J. Pharmacol. (2004) [Pubmed]
  7. Primary amines inhibit recycling of alpha 2M receptors in fibroblasts. Van Leuven, F., Cassiman, J.J., Van Den Berghe, H. Cell (1980) [Pubmed]
  8. Soluble human complement receptor type 1: in vivo inhibitor of complement suppressing post-ischemic myocardial inflammation and necrosis. Weisman, H.F., Bartow, T., Leppo, M.K., Marsh, H.C., Carson, G.R., Concino, M.F., Boyle, M.P., Roux, K.H., Weisfeldt, M.L., Fearon, D.T. Science (1990) [Pubmed]
  9. The exit of Trypanosoma cruzi from the phagosome is inhibited by raising the pH of acidic compartments. Ley, V., Robbins, E.S., Nussenzweig, V., Andrews, N.W. J. Exp. Med. (1990) [Pubmed]
  10. Opsonization of bacteroides by the alternative complement pathway reconstructed from isolated plasma proteins. Bjornson, A.B., Magnafichi, P.I., Schreiber, R.D., Bjornson, H.S. J. Exp. Med. (1987) [Pubmed]
  11. Relation of putative thioester bond in C3 to activation of the alternative pathway and the binding of C3b to biological targets of complement. Pangburn, M.K., Müller-Eberhard, H.J. J. Exp. Med. (1980) [Pubmed]
  12. The reduced nicotinamide adenine nucleotide-activated phosphoenolpyruvate carboxylase from Pseudomonas MA. Further studies on regulatory properties. Millay, R.H., Schilling, H., Hersh, L.B. J. Biol. Chem. (1978) [Pubmed]
  13. Characterization of two inducible periplasmic c-type cytochromes from Paracoccus denitrificans. Husain, M., Davidson, V.L. J. Biol. Chem. (1986) [Pubmed]
  14. Crystallographic and spectroscopic studies of native, aminoquinol, and monovalent cation-bound forms of methylamine dehydrogenase from Methylobacterium extorquens AM1. Labesse, G., Ferrari, D., Chen, Z.W., Rossi, G.L., Kuusk, V., McIntire, W.S., Mathews, F.S. J. Biol. Chem. (1998) [Pubmed]
  15. Inhibition of human immunodeficiency virus type 1 Tat-dependent activation of translation in Xenopus oocytes by the benzodiazepine Ro24-7429 requires trans-activation response element loop sequences. Braddock, M., Cannon, P., Muckenthaler, M., Kingsman, A.J., Kingsman, S.M. J. Virol. (1994) [Pubmed]
  16. 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]
  17. Evidence for presence of an internal thiolester bond in third component of human complement. Tack, B.F., Harrison, R.A., Janatova, J., Thomas, M.L., Prahl, J.W. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  18. Intramuscular administration of human tissue-type plasminogen activator in rabbits and dogs and its implications for coronary thrombolysis. Sobel, B.E., Saffitz, J.E., Fields, L.E., Myears, D.W., Sarnoff, S.J., Robison, A.K., Owensby, D.A., Fox, K.A. Circulation (1987) [Pubmed]
  19. Role for endocytosis in conjugation in Tetrahymena. Rotheim, M.B., Love, B. Mol. Cell. Biol. (1982) [Pubmed]
  20. Post-translational methylation of asparaginyl residues. Identification of beta-71 gamma-N-methylasparagine in allophycocyanin. Klotz, A.V., Leary, J.A., Glazer, A.N. J. Biol. Chem. (1986) [Pubmed]
  21. Oxidative deamination of methylamine by semicarbazide-sensitive amine oxidase leads to cytotoxic damage in endothelial cells. Possible consequences for diabetes. Yu, P.H., Zuo, D.M. Diabetes (1993) [Pubmed]
  22. Rapid acidification of endocytic vesicles containing asialoglycoprotein in cells of a human hepatoma line. Tycko, B., Keith, C.H., Maxfield, F.R. J. Cell Biol. (1983) [Pubmed]
  23. Identification of the acidic compartment of Plasmodium falciparum-infected human erythrocytes as the target of the antimalarial drug chloroquine. Yayon, A., Cabantchik, Z.I., Ginsburg, H. EMBO J. (1984) [Pubmed]
  24. Lipids in the inner membrane of dormant spores of Bacillus species are largely immobile. Cowan, A.E., Olivastro, E.M., Koppel, D.E., Loshon, C.A., Setlow, B., Setlow, P. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  25. Interleukin-3 down-regulates its own receptor. Murthy, S.C., Sorensen, P.H., Mui, A.L., Krystal, G. Blood (1989) [Pubmed]
  26. Accumulation of organic anion in intracellular vesicles of cultured rat hepatocytes is mediated by the canalicular multispecific organic anion transporter. Oude Elferink, R.P., Bakker, C.T., Roelofsen, H., Middelkoop, E., Ottenhoff, R., Heijn, M., Jansen, P.L. Hepatology (1993) [Pubmed]
  27. C3d fragment of complement interacts with laminin and binds to basement membranes of glomerulus and trophoblast. Leivo, I., Engvall, E. J. Cell Biol. (1986) [Pubmed]
  28. Identification of a high affinity NH4+ transporter from plants. Ninnemann, O., Jauniaux, J.C., Frommer, W.B. EMBO J. (1994) [Pubmed]
  29. What controls the rates of interprotein electron-transfer reactions. Davidson, V.L. Acc. Chem. Res. (2000) [Pubmed]
  30. pH homeostasis in Leishmania donovani amastigotes and promastigotes. Glaser, T.A., Baatz, J.E., Kreishman, G.P., Mukkada, A.J. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  31. Receptor-mediated uptake of 3,3',5-triiodo-L-thyronine by cultured fibroblasts. Cheng, S.Y., Maxfield, F.R., Robbins, J., Willingham, M.C., Pastan, I.H. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  32. Identification and structural characterization of two incompletely processed forms of the fourth component of human complement. Chan, A.C., Atkinson, J.P. J. Clin. Invest. (1983) [Pubmed]
  33. Regulation of streptokinase-human plasmin complex by the plasma proteinase inhibitors alpha 2-antiplasmin and alpha 2-macroglobulin is species specific and temperature dependent. Gonias, S.L., Figler, N.L., Braud, L.L. Blood (1988) [Pubmed]
  34. Alpha 2-macroglobulin is a binding protein for basic fibroblast growth factor. Dennis, P.A., Saksela, O., Harpel, P., Rifkin, D.B. J. Biol. Chem. (1989) [Pubmed]
  35. Ammonium permease-based sensing mechanism for rapid ammonium activation of the protein kinase A pathway in yeast. Van Nuland, A., Vandormael, P., Donaton, M., Alenquer, M., Lourenço, A., Quintino, E., Versele, M., Thevelein, J.M. Mol. Microbiol. (2006) [Pubmed]
  36. Nickel is a specific inhibitor for the binding of activated alpha 2-macroglobulin to the low density lipoprotein receptor-related protein/alpha 2-macroglobulin receptor. Hussain, M.M., Kancha, R.K., Tulenko, T.N. Biochemistry (1995) [Pubmed]
  37. Sequence determination of the thiolester site of the fourth component of human complement. Harrison, R.A., Thomas, M.L., Tack, B.F. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  38. Cytotoxic necrotizing factor type 2 produced by virulent Escherichia coli modifies the small GTP-binding proteins Rho involved in assembly of actin stress fibers. Oswald, E., Sugai, M., Labigne, A., Wu, H.C., Fiorentini, C., Boquet, P., O'Brien, A.D. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  39. Methylamine reaction and denaturation-dependent fragmentation of complement component 3. Comparison with alpha2-macroglobulin. Howard, J.B. J. Biol. Chem. (1980) [Pubmed]
  40. A functional, thioester-containing alpha 2-macroglobulin homologue isolated from the hemolymph of the American lobster (Homarus americanus). Spycher, S.E., Arya, S., Isenman, D.E., Painter, R.H. J. Biol. Chem. (1987) [Pubmed]
  41. Control of C1 activation by nascent C3b and C4b: a mechanism of feedback inhibition. Ziccardi, R.J. J. Immunol. (1986) [Pubmed]
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