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Chemical Compound Review

Ethamine     ethanamine

Synonyms: Ethylamin, Etilamina, ETHYLAMINE, Ethanamine, Etyloamina, ...
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Disease relevance of ethanamine

  • Combined effects of cisplatin and N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine HCl on the growth of human ovarian cancer xenografts in nude mice [1].
  • It was found that the intake of the 20% ACN fraction by gavage completely abrogated aromatase-induced hyperplasia and other changes in the mammary tissue [2].
  • Competition binding studies of 4-[125I]PEMP in melanoma (A375) and MCF-7 breast cancer cells showed a high affinity, dose-dependent inhibition of binding with known sigma ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl) ethylamine, BD1008 (Ki = 5, 11 nM, respectively), supporting the labeling of sigma sites in these cells [3].
  • Concentrated cell-extract of Pseudomonas taetrolens Y-30, isolated as a methylamine-assimilating organism, formed gamma-glutamylethylamide (theanine) from glutamic acid and ethylamine in a mixture containing the alcoholic fermentation system of baker's yeast for ATP-regeneration [4].

Psychiatry related information on ethanamine

  • The results presented illustrate how, for a partially reacted film resulting from a short reaction time, the extent of reaction with ferrocene ethylamine is not homogeneous throughout the thickness of the film, but occurs predominantly at the polymer/solution interface [5].

High impact information on ethanamine

  • Drinking tea, which contains l-theanine, a precursor of the nonpeptide antigen ethylamine, primed peripheral blood gammadelta T cells to mediate a memory response on reexposure to ethylamine and to secrete IFN-gamma in response to bacteria [6].
  • Beta-substituted ethylamine derivatives as suicide inhibitors of lysyl oxidase [7].
  • Raising the temperature beyond 320 K (the temperature of enantioselectivity collapse) leads either to irreversible dimerization with hydrogen elimination or to dissociation of the ethylamine moiety, depending on whether coadsorbed H(a) is present [8].
  • This small impact of Y305F on the rate of biogenesis contracts with a decrease in k(cat) (using ethylamine as the substrate) of 125-fold [9].
  • By contrast, significant recovery of function occurred when proteoliposomes were treated with MTSEA (methanethiosulfonate ethylamine), a thiol-specific reagent that implants a positively charged amino group [10].

Chemical compound and disease context of ethanamine


Biological context of ethanamine

  • Saturating concentrations of acetamidine increase, more than those of ethylamine, kcat for the hydrolysis of ZAlaONp [12].
  • Pre-steady-state data, analyzed in the framework of the three-step model, show that for b. beta-trypsin, b. thrombin, h.u. kallikrein, and h. urokinase the acylation step (k2) is rate limiting above pH 6 and the deacylation step (k3) below pH 4 in the hydrolysis of ZLysONp and of ZAlaONp in the presence of acetamidine or ethylamine [13].
  • Modifications of benzylphenoxy ethanamine antiestrogen molecules: influence affinity for antiestrogen binding site (AEBS) and cell cytotoxicity [14].
  • 2(2-Pyridyl) ethylamine administration resulted in renal vasodilatation, a 25% decrease in urinary sodium excretion and a significant increase in renin release [15].
  • In vivo, it dose dependently blocked induction of penile erections by the 5-HT2C agonists (S)-2-(6-chloro-5-fluoroindol-1-yl)-1-methylethylamine (Ro60,0175) and 1-methyl-2-(5,8,8-trimethyl-8H-3-aza-cyclopenta[a]inden-3-yl) ethylamine (Ro60,0332) [16].

Anatomical context of ethanamine

  • Modifications at the ring position para to the ethylamine chain, either with a sulfur atom, a longer alkyl chain, or both, lead to compounds of high central nervous system activity [17].
  • Furthermore, treatment of Vero cells with rIb in the presence of bafilomycin, methylamine, or ethylamine resulted in accumulation of the oligomer in the cells but had no effect on K(+) release [18].
  • The observation that a peroxisomal amine oxidase activity is specifically induced by ethylamine was used for the development of a plate assay screening procedure to isolate peroxisome degradation-defective mutants [19].
  • Apparent agonist potencies in the [35S]GTP gamma S binding assay to C6-glial/h5-HT1D membranes were, with the exception of 2-[5-[3-(4-methylsulphonylamino)benzyl-1 2,4-oxadiazol-5-yl]-1H-indol-3-yl] ethanamine (L694247), 5- to 13-times lower than in the cAMP assay on intact cells [20].
  • The diluents compared were Tes (N-tris(hydroxymethyl)methyl-2 aminoethane sulfonic acid)-Tris with 5% egg yolk and 6% glycerol (TEST) and Triladyl, yolk-citrate, Tris-trehalose, and Tris-lactose-all of them with 20% egg yolk and 6% (Triladyl) or 8% glycerol [21].

Associations of ethanamine with other chemical compounds

  • Using changes in the fluorescence of alpha 2M-bound 6-(p-toluidino)-2-naphthalenesulfonic acid, we have determined the rate constant for conformational change in human alpha 2M, following thiol ester cleavage by ammonia, methylamine, or ethylamine, both in the absence and in the presence of an SH-modifying group, methyl methanethiosulfate [22].
  • Successful results were obtained with a simple background electrolyte (BGE) containing 30 mM sodium tetraborate, pH 10.2, and ACN (75:25 v/v) [23].
  • The 400 nm species does not react with phenylhydrazine or ethylamine and is stable toward pH buffer exchange, long-term storage (>3 weeks), incubation at high temperatures, or incubation with reductants and colorimetric peroxide quenching reagents [9].
  • The cyclopropylamine moiety therefore appears to be a good strategy for rigidification of the ethylamine side chain only for tryptamines that bind to the 5-HT2C receptor isoform [24].
  • During the lag phase, Factor XIII is transformed by thrombin and Ca2+ into active transglutaminase (EC, which attaches the substrate ethylamine to a glutamine residue in acetylated, dephosphorylated beta-casein [25].

Gene context of ethanamine


Analytical, diagnostic and therapeutic context of ethanamine

  • Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction [31].
  • The inhibitory effect of 2-(2-pyridyl) ethylamine was completely abolished by reserpine or adrenalectomy [32].
  • Gastrin secretion was monitored in cell preparations further enriched in G cells (9% to 10%) by Percoll density gradient centrifugation either in the absence (basal) or presence of bombesin (1 mumol, 1 nmol/L), carbachol (1 mmol/L), leucine (10 mmol/L), and ethylamine (10 mmol/L) [33].
  • The method involves sensitive and selective detection of R(-)- and S(+)-prilocaine using normal-phase chiral HPLC on a pirkle-type naphthyl ethylamine stationary phase (Sumichiral OA-4700, 250 mm x 4 mm i.d.) at ambient temperature with a flow rate of 0.8 ml min-1 [34].
  • At 2 min after intravenous injection, the amino derivative, 2-(4-iodophenyl)-N,N-dimethyl ethylamine, displayed about twice the pancreatic uptake and a more than 8-fold higher pancreas/liver ratio than the carboxyl and methyl derivatives [35].


  1. Combined effects of cisplatin and N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine HCl on the growth of human ovarian cancer xenografts in nude mice. Hiramatsu, H., Kudoh, K., Kikuchi, Y., Hirata, J., Kita, T., Yamamoto, K., Tode, T., Nagata, I. Eur. J. Cancer (1997) [Pubmed]
  2. Suppression of aromatase (estrogen synthetase) by red wine phytochemicals. Eng, E.T., Williams, D., Mandava, U., Kirma, N., Tekmal, R.R., Chen, S. Breast Cancer Res. Treat. (2001) [Pubmed]
  3. Synthesis, in vitro validation and in vivo pharmacokinetics of [125I]N-[2-(4-iodophenyl)ethyl]-N-methyl-2-(1-piperidinyl) ethylamine: a high-affinity ligand for imaging sigma receptor positive tumors. John, C.S., Gulden, M.E., Vilner, B.J., Bowen, W.D. Nucl. Med. Biol. (1996) [Pubmed]
  4. Purification and characterization of glutamine synthetase of Pseudomonas taetrolens Y-30: an enzyme usable for production of theanine by coupling with the alcoholic fermentation system of baker's yeast. Yamamoto, S., Uchimura, K., Wakayama, M., Tachiki, T. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
  5. Temporal and spatial profiling of the modification of an electroactive polymeric interface using neutron reflectivity. Glidle, A., Bailey, L., Hadyoon, C.S., Hillman, A.R., Jackson, A., Ryder, K.S., Saville, P.M., Swann, M.J., Webster, J.R., Wilson, R.W., Cooper, J.M. Anal. Chem. (2001) [Pubmed]
  6. Antigens in tea-beverage prime human Vgamma 2Vdelta 2 T cells in vitro and in vivo for memory and nonmemory antibacterial cytokine responses. Kamath, A.B., Wang, L., Das, H., Li, L., Reinhold, V.N., Bukowski, J.F. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  7. Beta-substituted ethylamine derivatives as suicide inhibitors of lysyl oxidase. Tang, S.S., Simpson, D.E., Kagan, H.M. J. Biol. Chem. (1984) [Pubmed]
  8. Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111]. Bonello, J.M., Williams, F.J., Lambert, R.M. J. Am. Chem. Soc. (2003) [Pubmed]
  9. Role of a strictly conserved active site tyrosine in cofactor genesis in the copper amine oxidase from Hansenula polymorpha. DuBois, J.L., Klinman, J.P. Biochemistry (2006) [Pubmed]
  10. Analysis of substrate-binding elements in OxlT, the oxalate:formate antiporter of Oxalobacter formigenes. Wang, X., Sarker, R.I., Maloney, P.C. Biochemistry (2006) [Pubmed]
  11. Theanine production by coupled fermentation with energy transfer employing Pseudomonas taetrolens Y-30 glutamine synthetase and baker's yeast cells. Yamamoto, S., Wakayama, M., Tachiki, T. Biosci. Biotechnol. Biochem. (2005) [Pubmed]
  12. Catalytic properties of human urinary kallikrein. Antonini, E., Ascenzi, P., Menegatti, E., Bortolotti, F., Guarneri, M. Biochemistry (1982) [Pubmed]
  13. Catalytic properties of serine proteases. 2. Comparison between human urinary kallikrein and human urokinase, bovine beta-trypsin, bovine thrombin, and bovine alpha-chymotrypsin. Ascenzi, P., Menegatti, E., Guarneri, M., Bortolotti, F., Antonini, E. Biochemistry (1982) [Pubmed]
  14. Modifications of benzylphenoxy ethanamine antiestrogen molecules: influence affinity for antiestrogen binding site (AEBS) and cell cytotoxicity. Delarue, F., Kedjouar, B., Mésange, F., Bayard, F., Faye, J.C., Poirot, M. Biochem. Pharmacol. (1999) [Pubmed]
  15. The role of histamine receptors in the release of renin. Gerber, J.G., Nies, A.S. Br. J. Pharmacol. (1983) [Pubmed]
  16. The novel melatonin agonist agomelatine (S20098) is an antagonist at 5-hydroxytryptamine2C receptors, blockade of which enhances the activity of frontocortical dopaminergic and adrenergic pathways. Millan, M.J., Gobert, A., Lejeune, F., Dekeyne, A., Newman-Tancredi, A., Pasteau, V., Rivet, J.M., Cussac, D. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  17. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues. Jacob, P., Shulgin, A.T. J. Med. Chem. (1984) [Pubmed]
  18. Binding component of Clostridium perfringens iota-toxin induces endocytosis in Vero cells. Nagahama, M., Nagayasu, K., Kobayashi, K., Sakurai, J. Infect. Immun. (2002) [Pubmed]
  19. Selective peroxisome degradation in Yarrowia lipolytica after a shift of cells from acetate/oleate/ethylamine into glucose/ammonium sulfate-containing media. Gunkel, K., van der Klei, I.J., Barth, G., Veenhuis, M. FEBS Lett. (1999) [Pubmed]
  20. How efficacious are 5-HT1B/D receptor ligands: an answer from GTP gamma S binding studies with stably transfected C6-glial cell lines. Pauwels, P.J., Tardif, S., Palmier, C., Wurch, T., Colpaert, F.C. Neuropharmacology (1997) [Pubmed]
  21. Sperm cryopreservation in three species of endangered gazelles (Gazella cuvieri, G. dama mhorr, and G. dorcas neglecta). Garde, J.J., Soler, A.J., Cassinello, J., Crespo, C., Malo, A.F., Espeso, G., Gomendio, M., Roldan, E.R. Biol. Reprod. (2003) [Pubmed]
  22. Thiol ester cleavage-dependent conformational change in human alpha 2-macroglobulin. Influence of attacking nucleophile and of Cys949 modification. Gettins, P.G. Biochemistry (1995) [Pubmed]
  23. Development and validation of capillary electrophoresis method for tobramycin with precapillary derivatization and UV detection. Kaale, E., Van Schepdael, A., Roets, E., Hoogmartens, J. Electrophoresis (2002) [Pubmed]
  24. Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. Vangveravong, S., Kanthasamy, A., Lucaites, V.L., Nelson, D.L., Nichols, D.E. J. Med. Chem. (1998) [Pubmed]
  25. Kinetic determination of blood coagulation Factor XIII in plasma. Muszbek, L., Polgár, J., Fésüs, L. Clin. Chem. (1985) [Pubmed]
  26. Mechanisms of copper loading on the Schizosaccharomyces pombe copper amine oxidase 1 expressed in Saccharomyces cerevisiae. Laliberté, J., Labbé, S. Microbiology (Reading, Engl.) (2006) [Pubmed]
  27. N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine (DPPE) a chemopotentiating and cytoprotective agent in clinical trials: interaction with histamine at cytochrome P450 3A4 and other isozymes that metabolize antineoplastic drugs. Brandes, L.J., Queen, G.M., LaBella, F.S. Cancer Chemother. Pharmacol. (2000) [Pubmed]
  28. Prediction of differences in in vivo oral clearance of N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine monohydrochloride (NE-100) between extensive and poor metabolizers from in vitro metabolic data in human liver microsomes lacking CYP2D6 activity and recombinant CYPs. Yamamoto, T., Hagima, N., Nakamura, M., Kohno, Y., Nagata, K., Yamazoe, Y. Xenobiotica (2004) [Pubmed]
  29. A study of the vascular and acid-secretory responses of the rat gastric mucosa to histamine. Main, I.H., Whittle, B.J. J. Physiol. (Lond.) (1976) [Pubmed]
  30. The positive inotropic effect of alpha 1A-adrenoceptor stimulation is inhibited by 4-aminopyridine. Williamson, A.P., Seifen, E., Lindemann, J.P., Kennedy, R.H. Eur. J. Pharmacol. (1996) [Pubmed]
  31. Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction. Merkx, R., Brouwer, A.J., Rijkers, D.T., Liskamp, R.M. Org. Lett. (2005) [Pubmed]
  32. The inhibitory effect of histamine on the motility of rat uterus in vivo. Cortijo, J., Esplugues, J., Morales-Olivas, F.J., Rubio, E. Eur. J. Pharmacol. (1984) [Pubmed]
  33. Hyperplastic G cell responsiveness in vitro. Gower, W.R., McSweeney, E.M., Fabri, P.J. Surgery (1985) [Pubmed]
  34. Stereoselective determination of R(-)- and S(+)-prilocaine in human serum using a brush-type chiral stationary phase, solid-phase extraction and UV detection. Siluveru, M., Stewart, J.T. Journal of pharmaceutical and biomedical analysis. (1996) [Pubmed]
  35. Investigation of radiopharmaceuticals for pancreatic imaging: accumulation of amines in the pancreas. Saji, H., Kuge, Y., Magata, Y., Fujibayashi, Y., Yokoyama, A. Chem. Pharm. Bull. (1992) [Pubmed]
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