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Chemical Compound Review

Aminotoluene     phenylmethanamine

Synonyms: Moringine, BENZYLAMINE, N-Benzylamine, CHEMBL522, SureCN373, ...
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Disease relevance of alpha-Aminotoluene

  • A novel series of benzylamine, potassium channel openers (KCOs) is presented as part of our program toward designing new, bladder-selective compounds for the treatment of urge urinary incontinence (UUI) [1].
  • Butenafine (N-4-tert-butylbenzyl-N-methyl-1-naphtalenemethylamine hydrochloride) is an antifungal agent of the benzylamine class that has excellent therapeutic efficacy and a remarkably long duration of action when applied topically to treat various mycoses [2].
  • Isolation of an N-alkylated benzylamine derivative from Pseudomonas putida BTP1 as elicitor of induced systemic resistance in bean [3].
  • Several compounds that were structurally related to PM-THIQ (N-ethyl-PCA, 2-methyl-PCA, N-methyl-PM-THIQ, tetrahydroisoquinoline and benzylamine) also blocked MES seizures and caused motor impairment, but failed to show as great a separation between MES anticonvulsant activity and motor toxicity [4].
  • OBJECTIVE: We evaluated short-term treatment of tinea corporis with butenafine hydrochloride, a new benzylamine with in vitro fungicidal activity [5].

High impact information on alpha-Aminotoluene


Chemical compound and disease context of alpha-Aminotoluene


Biological context of alpha-Aminotoluene

  • The higher affinities toward both benzylamine and epsilon ACA indicate that a free carboxylate group is not, by itself, a main determinant of ligand-binding to kringle 5 [15].
  • As far as mechanisms of action, we have found that benzylamine/vanadate causes enhanced tyrosine phosphorylation of proteins and reduced protein tyrosine phosphatase activity in adipocytes [9].
  • We show that 4 catalyzes the aerobic oxidative deamination of benzylamine, though turnover eventually ceases on account of oxidation of the dihydrobenzoxazole tautomer of the "product Schiff base" to form a benzoxazole, a reaction that may be physiologically relevant [16].
  • Enzyme inactivated with N-[1-3H]C alpha MBA is reactivated by benzylamine with the release of 1 equiv of [3H]acrolein, which must have come from an adduct attached to an active site amino acid residue.(ABSTRACT TRUNCATED AT 250 WORDS)[17]
  • 1. The kinetics of benzylamine oxidation by a soluble preparation of rat liver mitochondrial monoamine oxidase were investigated and were shown to conform to adouble-displacement (or Ping Pong) mechanism [18].

Anatomical context of alpha-Aminotoluene


Associations of alpha-Aminotoluene with other chemical compounds

  • Benzamidine and p-benzylaminesulfonic acid associate with kringle 5 with similar affinities (Ka approximately 3.4 and 2.2 mM-1, respectively) while benzylamine binds about twice as tightly (Ka approximately 6.3 mM-1) [15].
  • These data show that mutation of Y444F in MAO A results in a mutant that has lost its ability to efficiently oxidize serotonin (its physiological substrate) but, however, exhibits unaltered quantitative structure-activity parameters in the binding and rate of benzylamine analogues [24].
  • It is shown that the radical signal is not affected during substrate (either benzylamine or phenylethylamine) turnover, by anaerobic incubation with substrate, or by covalent modification of the active site flavin cofactor in the catalytically active dimer [25].
  • MAO-A and MAO-B activities were measured using octopamine and benzylamine respectively [26].
  • These values were similar to or even better than those of kynuramine and benzylamine, good substrates for MAO-A and MAO-B, respectively [27].

Gene context of alpha-Aminotoluene

  • The KI values for 1-PCPA and N-C alpha MBA, analogues of the MAO B substrate benzylamine, are much higher with MAO A than with MAO B [28].
  • Quantitative structure-activity relationship (QSAR) analysis of dissociation constants shows that the binding of para-substituted benzylamine analogues to MAO A is best correlated with the van der Waals volume of the substituent, with larger substituents binding most tightly [29].
  • We have synthesized a series of conformationally defined analogues of benzylamine in order to probe the effect of conformation, as well as the influence of steric bulk, on PNMT inhibition by this class of ligands [30].
  • Benzylamine derivatives containing para substituents of differing electronegativity as well as isomers of aminomethylpyridine have been assessed for their substrate and inhibitor potentials toward lysyl oxidase [31].
  • MPTP was actively oxidized by the mitochondrial preparations, with Km and Vmax values very similar to those of benzylamine, a typical substrate for MAO-B [32].

Analytical, diagnostic and therapeutic context of alpha-Aminotoluene


  1. Design and SAR of novel potassium channel openers targeted for urge urinary incontinence. 2. Selective and potent benzylamino cyclobutenediones. Gilbert, A.M., Antane, M.M., Argentieri, T.M., Butera, J.A., Francisco, G.D., Freeden, C., Gundersen, E.G., Graceffa, R.F., Herbst, D., Hirth, B.H., Lennox, J.R., McFarlane, G., Norton, N.W., Quagliato, D., Sheldon, J.H., Warga, D., Wojdan, A., Woods, M. J. Med. Chem. (2000) [Pubmed]
  2. Experimental and conformational analyses of interactions between butenafine and lipids. Mingeot-Leclercq, M.P., Gallet, X., Flore, C., Van Bambeke, F., Peuvot, J., Brasseur, R. Antimicrob. Agents Chemother. (2001) [Pubmed]
  3. Isolation of an N-alkylated benzylamine derivative from Pseudomonas putida BTP1 as elicitor of induced systemic resistance in bean. Ongena, M., Jourdan, E., Schäfer, M., Kech, C., Budzikiewicz, H., Luxen, A., Thonart, P. Mol. Plant Microbe Interact. (2005) [Pubmed]
  4. Anticonvulsant activities of 1-phenylcyclohexylamine and its conformationally restricted analog 1,1-pentamethylenetetrahydroisoquinoline. Rogawski, M.A., Thurkauf, A., Yamaguchi, S., Rice, K.C., Jacobson, A.E., Mattson, M.V. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  5. A randomized trial to assess once-daily topical treatment of tinea corporis with butenafine, a new antifungal agent. Greer, D.L., Weiss, J., Rodriguez, D.A., Hebert, A.A., Swinehart, J.M. J. Am. Acad. Dermatol. (1997) [Pubmed]
  6. Monoamine metabolism in human brain. Robinson, D.S., Sourkes, T.L., Nies, A., Harris, L.S., Spector, S., Bartlett, D.L., Kaye, I.S. Arch. Gen. Psychiatry (1977) [Pubmed]
  7. Amine-synthesizing enzyme N-substituted formamide deformylase: screening, purification, characterization, and gene cloning. Fukatsu, H., Hashimoto, Y., Goda, M., Higashibata, H., Kobayashi, M. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Expression and purification of enzymatically active forms of the human lysyl oxidase-like protein 4. Kim, M.S., Kim, S.S., Jung, S.T., Park, J.Y., Yoo, H.W., Ko, J., Csiszar, K., Choi, S.Y., Kim, Y. J. Biol. Chem. (2003) [Pubmed]
  9. Semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 activity exerts an antidiabetic action in Goto-Kakizaki rats. Abella, A., Marti, L., Camps, M., Claret, M., Fernández-Alvarez, J., Gomis, R., Gumà, A., Viguerie, N., Carpéné, C., Palacín, M., Testar, X., Zorzano, A. Diabetes (2003) [Pubmed]
  10. Amine dehydrogenase of Pseudomonas putida: properties of the heme-prosthetic group. Durham, D.R., Perry, J.J. J. Bacteriol. (1978) [Pubmed]
  11. Overview of topical therapy for common superficial fungal infections and the role of new topical agents. Brennan, B., Leyden, J.J. J. Am. Acad. Dermatol. (1997) [Pubmed]
  12. Relation of blood serotonin and benzylamine oxidase to clinical symptoms and prognosis in Parkinson's disease. Ishizaki, F., Nishikawa, S. Eur. Neurol. (1988) [Pubmed]
  13. Comparative toxicity of allylamine and acrolein in cultured myocytes and fibroblasts from neonatal rat heart. Toraason, M., Luken, M.E., Breitenstein, M., Krueger, J.A., Biagini, R.E. Toxicology (1989) [Pubmed]
  14. Prion-derived copper-binding peptide fragments catalyze the generation of superoxide anion in the presence of aromatic monoamines. Kawano, T. Int. J. Biol. Sci. (2007) [Pubmed]
  15. Ligand interactions with the kringle 5 domain of plasminogen. A study by 1H NMR spectroscopy. Thewes, T., Constantine, K., Byeon, I.J., Llinás, M. J. Biol. Chem. (1990) [Pubmed]
  16. Catalytic turnover of benzylamine by a model for the lysine tyrosylquinone (LTQ) cofactor of lysyl oxidase. Ling, K.Q., Kim, J., Sayre, L.M. J. Am. Chem. Soc. (2001) [Pubmed]
  17. Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine. Vazquez, M.L., Silverman, R.B. Biochemistry (1985) [Pubmed]
  18. Rat liver mitochondrial monoamine oxidase. A change in the reaction mechanism on solubilization. Houslay, M.D., Tipton, K.F. Biochem. J. (1975) [Pubmed]
  19. Role of semicarbazide-sensitive amine oxidase on glucose transport and GLUT4 recruitment to the cell surface in adipose cells. Enrique-Tarancón, G., Marti, L., Morin, N., Lizcano, J.M., Unzeta, M., Sevilla, L., Camps, M., Palacín, M., Testar, X., Carpéné, C., Zorzano, A. J. Biol. Chem. (1998) [Pubmed]
  20. Endogenous and endobiotic induced reactive oxygen species formation by isolated hepatocytes. Siraki, A.G., Pourahmad, J., Chan, T.S., Khan, S., O'Brien, P.J. Free Radic. Biol. Med. (2002) [Pubmed]
  21. The presence of an inhibitor of benzylamine oxidase in human blood plasma. Buffoni, F., Banchelli, G., Ignesti, G., Pirisino, R., Raimondi, L. Biochem. J. (1983) [Pubmed]
  22. Monoamine oxidase (MAO) of platelets, plasma, lymphocytes and granulocytes in schizophrenia. Bond, P.A., Cundall, R.L., Falloon, I.R. The British journal of psychiatry : the journal of mental science. (1979) [Pubmed]
  23. The regional distribution of monoamine oxidase activities towards different substrates: effects in rat brain of chronic administration of manganese chloride and of ageing. Leung, T.K., Lai, J.C., Lim, L. J. Neurochem. (1981) [Pubmed]
  24. Loss of serotonin oxidation as a component of the altered substrate specificity in the Y444F mutant of recombinant human liver MAO A. Nandigama, R.K., Miller, J.R., Edmondson, D.E. Biochemistry (2001) [Pubmed]
  25. Observation of a flavin semiquinone in the resting state of monoamine oxidase B by electron paramagnetic resonance and electron nuclear double resonance spectroscopy. DeRose, V.J., Woo, J.C., Hawe, W.P., Hoffman, B.M., Silverman, R.B., Yelekci, K. Biochemistry (1996) [Pubmed]
  26. Monoamine oxidase isoenzymes in rat brain: differential changes during postnatal development but not aging. Rao, K., Nagendra, S.N., Subhash, M.N. Neurobiol. Aging (1995) [Pubmed]
  27. Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products. Youngster, S.K., McKeown, K.A., Jin, Y.Z., Ramsay, R.R., Heikkila, R.E., Singer, T.P. J. Neurochem. (1989) [Pubmed]
  28. Inactivation of monoamine oxidase A by the monoamine oxidase B inactivators 1-phenylcyclopropylamine, 1-benzylcyclopropylamine, and N-cyclopropyl-alpha-methylbenzylamine. Silverman, R.B., Hiebert, C.K. Biochemistry (1988) [Pubmed]
  29. Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A. Miller, J.R., Edmondson, D.E. Biochemistry (1999) [Pubmed]
  30. Conformational and steric aspects of the inhibition of phenylethanolamine N-methyltransferase by benzylamines. Grunewald, G.L., Sall, D.J., Monn, J.A. J. Med. Chem. (1988) [Pubmed]
  31. Electronegativity of aromatic amines as a basis for the development of ground state inhibitors of lysyl oxidase. Williamson, P.R., Kagan, H.M. J. Biol. Chem. (1987) [Pubmed]
  32. Studies on the oxidation of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase B. Heikkila, R.E., Manzino, L., Cabbat, F.S., Duvoisin, R.C. J. Neurochem. (1985) [Pubmed]
  33. Endogenous hydroperoxide formation, cell volume and cellular K+ balance in perfused rat liver. Saha, N., Schreiber, R., vom Dahl, S., Lang, F., Gerok, W., Häussinger, D. Biochem. J. (1993) [Pubmed]
  34. Well-defined azlactone-functionalized (co)polymers on a solid support: synthesis via supported living radical polymerization and application as nucleophile scavengers. Fournier, D., Pascual, S., Montembault, V., Haddleton, D.M., Fontaine, L. Journal of combinatorial chemistry. (2006) [Pubmed]
  35. The effects of lysosomotropic amines on protein degradation, migration of nonhistone proteins to the nucleus, and cathepsin D in lymphocytes. Polet, H. J. Cell. Physiol. (1985) [Pubmed]
  36. Benzylamine exhibits insulin-like effects on glucose disposal, glucose transport, and fat cell lipolysis in rabbits and diabetic mice. Iglesias-Osma, M.C., Garcia-Barrado, M.J., Visentin, V., Pastor-Mansilla, M.F., Bour, S., Prévot, D., Valet, P., Moratinos, J., Carpéné, C. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  37. Imaging the serotonin transporter with positron emission tomography: initial human studies with [11C]DAPP and [11C]DASB. Houle, S., Ginovart, N., Hussey, D., Meyer, J.H., Wilson, A.A. European journal of nuclear medicine. (2000) [Pubmed]
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