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Chemical Compound Review

Donaxine     1-(1H-indol-3-yl)-N,N- dimethyl-methanamine

Synonyms: Donaxin, Gramine, Gramin, Prestwick_245, PubChem8121, ...
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Disease relevance of Gramine


High impact information on Gramine

  • The effect of gramine on the different stages of the cell division process has also been investigated [4].
  • Gramine causes a marked increase in radio-calcium efflux from the fertilized egg, and at the same time lowers the cAMP level [4].
  • The indole nucleus of these analogues was constructed by the reductive cyclization of the corresponding 2, beta-dinitrostyrenes, and the aminoethyl side chain was introduced via gramine methiodides [5].
  • The found anti/syn ratio of compound 8, which is a seco-ent-ardeemin analogue obtained by alkylation of 1 with gramine methiodide, confirms this computational model [6].
  • Gramine blocks the fast DSI-DFN EPSP, and has far less of an effect on the slow EPSP and the modulation [7].

Biological context of Gramine


Anatomical context of Gramine

  • 5 (+)-Lysergic diethylamide (LSD), methysergide or gramine did not alter the response to 5-HT, while LSD in low doses produced a marked increase in chemoreceptor discharges [12].
  • Voles fed 0.25 and 0.50% gramine had increased circulating reticulocyte levels (P less than 0.01) and those fed 0.125% gramine had higher alkaline phosphatase activity (P less than 0.05) than the control voles [3].
  • D98E also increased the efficacy of gramine relative to 5HT for inducing substrate-activated currents in Xenopus laevis oocytes, but these currents were noticeably dependent on extracellular medium acidification [13].

Associations of Gramine with other chemical compounds

  • The role of these substances in the cell division process has been studied by using the serotonin antagonists, gramine and metergoline [4].
  • A new indole alkaloid, N,N-methyl-3'-indolylmethyl-5-methoxytryptamine ( 4), as well as the known gramine, N,N-dimethyltryptamine and 6-methoxy-2-methyl-1,2,3,4-tetrahydro-beta-carboline were isolated from the roots of ANTIRHEA LUCIDA (Sw.) Hook (Rubiaceae) [14].
  • One hundred and twenty meadow voles, 31 days of age, were fed gramine (0, 0.125, 0.25, or 0.5% of a nutritionally complete diet) or hordenine sulfate (0, 0.15, 0.31, or 0.62% of the diet) for 21 days [3].
  • It is possible that the fluoride-induced concurrent increase in gramine concentration in barley leaves could override the eventual increase in nutritive value to herbivorous insects after fluoride exposure [15].
  • A new mechanism if proposed to explain the labile nature of the dimethylamino group of gramine and to account for the fact that NDMA is the only N-nitrosamine formed during the nitrosation of gramine [16].

Gene context of Gramine

  • Whole blood or urine, containing DMT and gramine (internal standard), was subjected to solid-phase extraction with a Sep-Pak C18 cartridge before analysis by GC-SID [17].
  • A gene sequence in barley that earlier was characterized as a jasmonate-induced O-methyltransferase (MT) (EC, GenBank accession U54767) was here found to be absent in some barley cultivars and breeding lines that all lacked gramine [18].


  1. Possible NMDA antagonist properties of drugs that affect high pressure neurological syndrome. Shuker, M.A., Bowser-Riley, F., Davies, S.N. Br. J. Pharmacol. (1994) [Pubmed]
  2. Role of dopamine and indolamine derivatives in the regulation of the sea urchin adenylate cyclase. Capasso, A., Cretì, P., De Petrocellis, B., De Prisco, P.P., Parisi, E. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  3. Some hematological and histopathological effects of the alkaloids gramine and hordenine on meadow voles (Microtus pennsylvanicus). Goelz, M.F., Rothenbacher, H., Wiggins, J.P., Kendall, W.A., Hershberger, T.V. Toxicology (1980) [Pubmed]
  4. On the role of serotonin and 5-methoxy-tryptamine in the regulation of cell division in sea urchin eggs. Renaud, F., Parisi, E., Capasso, A., De Prisco, P. Dev. Biol. (1983) [Pubmed]
  5. Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl-, and 4,7-dimethyl-5,6-dihydroxytryptamines. Sinhababu, A.K., Ghosh, A.K., Borchardt, R.T. J. Med. Chem. (1985) [Pubmed]
  6. Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment. Martín-Santamaría, S., Corzo-Suárez, R., Avendaño, C., Espada, M., Gago, F., García-Granda, S., Rzepa, H.S. J. Org. Chem. (2002) [Pubmed]
  7. Intrinsic neuromodulation in the Tritonia swim CPG: serotonin mediates both neuromodulation and neurotransmission by the dorsal swim interneurons. Katz, P.S., Frost, W.N. J. Neurophysiol. (1995) [Pubmed]
  8. Effects of gramine on energy metabolism of rat and bovine mitochondria. Niemeyer, H.M., Roveri, O.A. Biochem. Pharmacol. (1984) [Pubmed]
  9. Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. Iwata, S., Saito, S., Kon-ya, K., Shizuri, Y., Ohizumi, Y. Eur. J. Pharmacol. (2001) [Pubmed]
  10. Serotonin regulates repolarization of the C. elegans pharyngeal muscle. Niacaris, T., Avery, L. J. Exp. Biol. (2003) [Pubmed]
  11. Synthesis of N1-nitroso-3-nitromethylindole: a nonvolatile N-nitroso compound isolated from the nitrosation of the alkaloid gramine. Ahmad, M.U., Libbey, L.M., Scanlan, R.A. Food additives and contaminants. (1987) [Pubmed]
  12. The action of 5-hydroxytryptamine on chemoreceptor discharges of the cat's carotid body. Nishi, K. Br. J. Pharmacol. (1975) [Pubmed]
  13. Transmembrane domain I contributes to the permeation pathway for serotonin and ions in the serotonin transporter. Barker, E.L., Moore, K.R., Rakhshan, F., Blakely, R.D. J. Neurosci. (1999) [Pubmed]
  14. Indole Alkaloids from Antirhea lucida. Weniger, B., Rafik, W., Bastida, J., Quirion, J.C., Anton, R. Planta Med. (1995) [Pubmed]
  15. Gramine and free amino acids as indicators of fluoride-induced stress in barley and its consequences to insect herbivory. Hautala, E.L., Holopainen, J.K. Ecotoxicol. Environ. Saf. (1995) [Pubmed]
  16. Rapid formation of N-nitrosodimethylamine from gramine, a naturally occurring precursor in barley malt. Mangino, M.M., Scanlan, R.A. IARC Sci. Publ. (1984) [Pubmed]
  17. A simple and sensitive quantitation of N,N-dimethyltryptamine by gas chromatography with surface ionization detection. Ishii, A., Seno, H., Suzuki, O., Hattori, H., Kumazawa, T. Journal of analytical toxicology. (1997) [Pubmed]
  18. N-Methyltransferase involved in gramine biosynthesis in barley: Cloning and characterization. Larsson, K.A., Zetterlund, I., Delp, G., Jonsson, L.M. Phytochemistry (2006) [Pubmed]
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