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Chemical Compound Review

Indoleamine     1H-indol-3-amine

Synonyms: SureCN37668, AG-K-88384, CHEBI:28626, NSC-24933, WTI-11954, ...
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Disease relevance of C01819


Psychiatry related information on C01819

  • CONCLUSIONS: While the prevailing view was that the activation of 5-HT(2) receptors is solely responsible for hallucinogenic drug effects, these results support a role for 5-HT(1A) receptors in the effects of the indoleamine hallucinogen 5-MeO-DMT on locomotor activity and PPI in rats [6].
  • The effects of psychological stress on catecholamine and indoleamine metabolism were examined in various brain regions of rats [7].
  • As such, monitoring tryptophan metabolism in chronic immunopathology provides a better understanding of the association between immune activation and IDO and its role in the development of immunodeficiency, anemia and mood disorders [8].
  • To further characterize the effects of this indoleamine on the macrostructure of feeding, a computer-automated data acquisition system was used to analyze macronutrient feeding patterns in freely feeding animals maintained on the pure diets of protein, carbohydrate, and fat [9].
  • The data show that systemic chronic immune activation in patients with Alzheimer's disease and Huntington's disease is associated with significant degradation of tryptophan, which is most likely due to activation of indoleamine (2,3)-dioxygenase by immunologic stimuli [10].

High impact information on C01819


Chemical compound and disease context of C01819


Biological context of C01819


Anatomical context of C01819


Associations of C01819 with other chemical compounds


Gene context of C01819

  • Cells expressing CTLA4-KDEL do not up-regulate the indoleamine 2, 3-dioxygenase enzyme, unlike cells treated with soluble CTLA4-immunoglobin (Ig) [35].
  • An antibody to IFN-gamma, but not IFN-alpha, inhibited the induction of IDO activity by this secreted factor [36].
  • In both cell lines, IFN-gamma induced the expression of indoleamine 2,3-dioxygenase (IDO) activity [37].
  • The IL-1-mediated inhibition of IDO activity and of subsequent antibacterial effect is due to the production of NO [38].
  • The most prominent gamma interferon (IFN-gamma)-induced antimicrobial effector mechanisms are the induction of nitric oxide (NO) synthase (NOS) and of indoleamine 2,3-dioxygenase (IDO) activity [38].

Analytical, diagnostic and therapeutic context of C01819


  1. Mitochondrial respiratory inhibition by N-methylated beta-carboline derivatives structurally resembling N-methyl-4-phenylpyridine. Albores, R., Neafsey, E.J., Drucker, G., Fields, J.Z., Collins, M.A. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  2. Induction of indoleamine 2,3-dioxygenase in mouse lung during virus infection. Yoshida, R., Urade, Y., Tokuda, M., Hayaishi, O. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  3. Inhibition of indoleamine 2,3-dioxygenase (IDO) enhances elimination of virus-infected macrophages in an animal model of HIV-1 encephalitis. Potula, R., Poluektova, L., Knipe, B., Chrastil, J., Heilman, D., Dou, H., Takikawa, O., Munn, D.H., Gendelman, H.E., Persidsky, Y. Blood (2005) [Pubmed]
  4. Morphological and immunocytochemical identification of indoleamine-accumulating neurons in the cat retina. Wässle, H., Voigt, T., Patel, B. J. Neurosci. (1987) [Pubmed]
  5. Melatonin inhibits expression of the inducible NO synthase II in liver and lung and prevents endotoxemia in lipopolysaccharide-induced multiple organ dysfunction syndrome in rats. Crespo, E., Macías, M., Pozo, D., Escames, G., Martín, M., Vives, F., Guerrero, J.M., Acuña-Castroviejo, D. FASEB J. (1999) [Pubmed]
  6. The roles of 5-HT(1A) and 5-HT (2) receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats. Krebs-Thomson, K., Ruiz, E.M., Masten, V., Buell, M., Geyer, M.A. Psychopharmacology (Berl.) (2006) [Pubmed]
  7. Psychological stress increases dopamine turnover selectively in mesoprefrontal dopamine neurons of rats: reversal by diazepam. Kaneyuki, H., Yokoo, H., Tsuda, A., Yoshida, M., Mizuki, Y., Yamada, M., Tanaka, M. Brain Res. (1991) [Pubmed]
  8. Monitoring tryptophan metabolism in chronic immune activation. Schröcksnadel, K., Wirleitner, B., Winkler, C., Fuchs, D. Clin. Chim. Acta (2006) [Pubmed]
  9. Effects of serotonin and the serotonin blocker metergoline on meal patterns and macronutrient selection. Leibowitz, S.F., Alexander, J.T., Cheung, W.K., Weiss, G.F. Pharmacol. Biochem. Behav. (1993) [Pubmed]
  10. Degradation of tryptophan in neurodegenerative disorders. Widner, B., Leblhuber, F., Walli, J., Tilz, G.P., Demel, U., Fuchs, D. Adv. Exp. Med. Biol. (1999) [Pubmed]
  11. Circadian clock in Xenopus eye controlling retinal serotonin N-acetyltransferase. Besharse, J.C., Iuvone, P.M. Nature (1983) [Pubmed]
  12. Prevention of allogeneic fetal rejection by tryptophan catabolism. Munn, D.H., Zhou, M., Attwood, J.T., Bondarev, I., Conway, S.J., Marshall, B., Brown, C., Mellor, A.L. Science (1998) [Pubmed]
  13. Long-term neuropathological and neurochemical effects of nucleus basalis lesions in the rat. Arendash, G.W., Millard, W.J., Dunn, A.J., Meyer, E.M. Science (1987) [Pubmed]
  14. Prevention of T cell-driven complement activation and inflammation by tryptophan catabolism during pregnancy. Mellor, A.L., Sivakumar, J., Chandler, P., Smith, K., Molina, H., Mao, D., Munn, D.H. Nat. Immunol. (2001) [Pubmed]
  15. Tryptophan recycling is responsible for the interferon-gamma resistance of Chlamydia psittaci GPIC in indoleamine dioxygenase-expressing host cells. Wood, H., Roshick, C., McClarty, G. Mol. Microbiol. (2004) [Pubmed]
  16. Myoclonus after 5-hydroxytryptophan in rats with lesions of indoleamine neurons in the central nervous system. Stewart, R.M., Growdon, J.H., Cancian, D., Baldessarini, R.J. Neurology (1976) [Pubmed]
  17. Protective effect of melatonin against alpha-naphthylisothiocyanate-induced liver injury in rats. Ohta, Y., Kongo, M., Sasaki, E., Ishiguro, I., Harada, N. J. Pineal Res. (2000) [Pubmed]
  18. Alterations in brain 5HT and tryptamine content during indoleamine-induced myoclonus in guinea pigs. Luscombe, G., Jenner, P., Marsden, C.D. Biochem. Pharmacol. (1983) [Pubmed]
  19. Tryptamine-induced myoclonus in guinea-pigs pretreated with a monoamine oxidase inhibitor indicates pre- and post-synaptic actions of tryptamine upon central indoleamine systems. Luscombe, G., Jenner, P., Marsden, C.D. Neuropharmacology (1982) [Pubmed]
  20. Retinal rhythms in chicks: circadian variation in melantonin and serotonin N-acetyltransferase activity. Hamm, H.E., Menaker, M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  21. Modulation of human dendritic-cell function following transduction with viral vectors: implications for gene therapy. Tan, P.H., Beutelspacher, S.C., Xue, S.A., Wang, Y.H., Mitchell, P., McAlister, J.C., Larkin, D.F., McClure, M.O., Stauss, H.J., Ritter, M.A., Lombardi, G., George, A.J. Blood (2005) [Pubmed]
  22. Cooperative role of interferon regulatory factor 1 and p91 (STAT1) response elements in interferon-gamma-inducible expression of human indoleamine 2,3-dioxygenase gene. Chon, S.Y., Hassanain, H.H., Gupta, S.L. J. Biol. Chem. (1996) [Pubmed]
  23. Suppression of memory CD8 T cell generation and function by tryptophan catabolism. Liu, Z., Dai, H., Wan, N., Wang, T., Bertera, S., Trucco, M., Dai, Z. J. Immunol. (2007) [Pubmed]
  24. Monooxygenase activities of dioxygenases. Benzphetamine demethylation and aniline hydroxylation reactions catalyzed by indoleamine 2,3-dioxygenase. Takikawa, O., Yoshida, R., Hayaishi, O. J. Biol. Chem. (1983) [Pubmed]
  25. The number of unidentified amacrine cells in the mammalian retina. Strettoi, E., Masland, R.H. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  26. A two-step induction of indoleamine 2,3 dioxygenase (IDO) activity during dendritic-cell maturation. Braun, D., Longman, R.S., Albert, M.L. Blood (2005) [Pubmed]
  27. An indoleamine system in photoreceptor cell terminals of the Long-Evans rat retina. Redburn, D.A., Churchill, L. J. Neurosci. (1987) [Pubmed]
  28. A system of indoleamine-accumulating neurons in the rabbit retina. Sandell, J.H., Masland, R.H. J. Neurosci. (1986) [Pubmed]
  29. FcepsilonRI induces the tryptophan degradation pathway involved in regulating T cell responses. von Bubnoff, D., Matz, H., Frahnert, C., Rao, M.L., Hanau, D., de la Salle, H., Bieber, T. J. Immunol. (2002) [Pubmed]
  30. Serotonin transporter overexpression is responsible for pulmonary artery smooth muscle hyperplasia in primary pulmonary hypertension. Eddahibi, S., Humbert, M., Fadel, E., Raffestin, B., Darmon, M., Capron, F., Simonneau, G., Dartevelle, P., Hamon, M., Adnot, S. J. Clin. Invest. (2001) [Pubmed]
  31. Dopaminergic and indoleamine-accumulating amacrine cells express GABA-like immunoreactivity in the cat retina. Wässle, H., Chun, M.H. J. Neurosci. (1988) [Pubmed]
  32. Intracellular utilization of superoxide anion by indoleamine 2,3-dioxygenase of rabbit enterocytes. Taniguchi, T., Hirata, F., Hayaishi, O. J. Biol. Chem. (1977) [Pubmed]
  33. Magnetic and natural circular dichroism of L-tryptophan 2,3-dioxygenases and indoleamine 2,3-dioxygenase. II. Spectra of their ferric cyanide and ferrous carbon monoxide complexes and an oxygenated form. Uchida, K., Shimizu, T., Makino, R., Sakaguchi, K., Iizuka, T., Ishimura, Y., Nozawa, T., Hatano, M. J. Biol. Chem. (1983) [Pubmed]
  34. IDO and interferon-alpha-induced depressive symptoms: a shift in hypothesis from tryptophan depletion to neurotoxicity. Wichers, M.C., Koek, G.H., Robaeys, G., Verkerk, R., Scharpé, S., Maes, M. Mol. Psychiatry (2005) [Pubmed]
  35. Creation of tolerogenic human dendritic cells via intracellular CTLA4: a novel strategy with potential in clinical immunosuppression. Tan, P.H., Yates, J.B., Xue, S.A., Chan, C., Jordan, W.J., Harper, J.E., Watson, M.P., Dong, R., Ritter, M.A., Lechler, R.I., Lombardi, G., George, A.J. Blood (2005) [Pubmed]
  36. A human 15-kDa IFN-induced protein induces the secretion of IFN-gamma. Recht, M., Borden, E.C., Knight, E. J. Immunol. (1991) [Pubmed]
  37. Regulation of the kynurenine metabolic pathway by interferon-gamma in murine cloned macrophages and microglial cells. Alberati-Giani, D., Ricciardi-Castagnoli, P., Köhler, C., Cesura, A.M. J. Neurochem. (1996) [Pubmed]
  38. Interleukin-1 inhibits gamma interferon-induced bacteriostasis in human uroepithelial cells. Däubener, W., Hucke, C., Seidel, K., Hadding, U., MacKenzie, C.R. Infect. Immun. (1999) [Pubmed]
  39. Marrying immunotherapy with chemotherapy: why say IDO? Muller, A.J., Prendergast, G.C. Cancer Res. (2005) [Pubmed]
  40. Terminal autoreceptor control of 5-hydroxytryptamine release as measured by in vivo microdialysis in the conscious guinea-pig. Lawrence, A.J., Marsden, C.A. J. Neurochem. (1992) [Pubmed]
  41. A high-affinity, tryptophan-selective amino acid transport system in human macrophages. Seymour, R.L., Ganapathy, V., Mellor, A.L., Munn, D.H. J. Leukoc. Biol. (2006) [Pubmed]
  42. Melatonin disrupts circadian rhythms of glutamate and GABA in the neostriatum of the aware rat: a microdialysis study. Marquez de Prado, B., Castañeda, T.R., Galindo, A., del Arco, A., Segovia, G., Reiter, R.J., Mora, F. J. Pineal Res. (2000) [Pubmed]
  43. Regional brain indoleamine metabolism following chronic portacaval anastomosis in the rat. Cummings, M.G., Soeters, P.B., James, J.H., Kean, J.M., Fischer, J.E. J. Neurochem. (1976) [Pubmed]
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