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Chemical Compound Review

Tryptamin     2-(1H-indol-3-yl)ethanamine

Synonyms: tryptamine, PubChem9450, CHEMBL6640, SureCN26725, AGN-PC-006Z67, ...
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Disease relevance of tryptamine

  • Although tryptamine secretion by carcinoid tumors is rare, 5-hydroxytryptophan secretion may be more common than is recognized [1].
  • Stability of Lambdoid bacteriophage heads: antagonism between polyamines and tryptamine [2].
  • Tryptamine-induced PI breakdown could be partially inhibited by pretreatment with 4 beta-phorbol 12-myristate 13-acetate but not pertussis toxin [3].
  • By pursuing urinary excretion of serotonin and tryptamine after oral loading with L-tryptophan (30 mg per kilogram body weight), our method proves that urinary excretion of both indoleamines increases immediately after loading and reaches a maximum in about 45 min [4].
  • The findings of decreased densities of [3H]tryptamine binding sites taken in conjunction with previous reports of increased CSF and brain tryptamine concentrations in HE suggest a pathogenic role for this neuroactive amine in HE resulting from chronic liver failure [5].

Psychiatry related information on tryptamine


High impact information on tryptamine

  • The crystal structures of STR1 in complex with its natural substrates tryptamine and secologanin provide structural understanding of the observed substrate preference and identify residues lining the active site surface that contact the substrates [10].
  • Platelet monoamine oxidase (MAO) activity was determined with tryptamine as substrate for 61 drug-free patients who had a primary major depressive disorder and for 32 normal controls [11].
  • Carbidopa, a decarboxylase inhibitor that does not cross the blood-brain barrier, inhibits the peripheral synthesis of nor-adrenaline, serotonin, and tryptamine [12].
  • There may exist a rostrally projecting neuronal tryptamine containing system arising from cell bodies in or close to the nucleus raphé medianus [13].
  • Localization of AT transcripts in the pineal gland and in specific cells of the intestine, cerebral cortex, pituitary, and lung identifies cells that may be important to the neurotransmitter and hormonal roles of the tryptamine derivatives [14].

Chemical compound and disease context of tryptamine

  • The cDNA for strictosidine synthase, the enzyme catalyzing the stereospecific condensation of tryptamine with secologanin producing strictosidine, the key intermediate in indole alkaloid biosynthesis, has been expressed in an enzymatically active form in Escherichia coli [15].
  • Tryptamine-induced myoclonus in guinea-pigs pretreated with a monoamine oxidase inhibitor indicates pre- and post-synaptic actions of tryptamine upon central indoleamine systems [16].
  • In rats, tryptamine-induced clonic seizure, a 5-HT2 receptor-mediated behavior, was also dose-dependently inhibited by NRA0045 (ED50 = 1.7 mg/kg i.p.). Norepinephrine-induced lethality is regarded as being induced through the alpha-1 adrenoceptor [17].
  • F 11356 thus is a selective, high-potency agonist at 5-HT1B/1D receptors, which distinguishes itself from tryptamine and derivatives in exerting high intrinsic activity at these receptors in vascular and neuronal models relevant to migraine [18].
  • High yielding Lewis acid-catalysed one-pot Pictet-Spengler reactions of tryptophan methyl ester and tryptamine with aliphatic and aromatic aldehydes were achieved in short reaction times with the aid of microwave irradiation [19].

Biological context of tryptamine


Anatomical context of tryptamine


Associations of tryptamine with other chemical compounds


Gene context of tryptamine


Analytical, diagnostic and therapeutic context of tryptamine


  1. Serotonin metabolism in patients with carcinoid tumors: incidence of 5-hydroxytryptophan-secreting tumors. Feldman, J.M. Gastroenterology (1978) [Pubmed]
  2. Stability of Lambdoid bacteriophage heads: antagonism between polyamines and tryptamine. Deeb, S.S., Moyle, E.A. J. Virol. (1982) [Pubmed]
  3. Tryptamine induces phosphoinositide turnover and modulates adrenergic and muscarinic cholinergic receptor function in cultured cerebellar granule cells. Ishitani, R., Kimura, M., Takeichi, M., Chuang, D.M. J. Neurochem. (1994) [Pubmed]
  4. High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Tsuchiya, H., Hayashi, T., Tatsumi, M., Hoshino, Y., Ohtani, S., Takagi, N. Clin. Chem. (1989) [Pubmed]
  5. Region-selective decreases in densities of [3H]tryptamine binding sites in autopsied brain tissue from cirrhotic patients with hepatic encephalopathy. Mousseau, D.D., Layrargues, G.P., Butterworth, R.F. J. Neurochem. (1994) [Pubmed]
  6. 3-Aminotetrahydrocarbazoles as a new series of central nervous system agents. Mooradian, A., Dupont, P.E., Hlavec, A.G., Aceto, M.D., Pearl, J. J. Med. Chem. (1977) [Pubmed]
  7. Effect of tryptamine antagonists on self-stimulation. Interaction with amphetamine. Silveira Filho, N.G., Graeff, F.G. Psychopharmacology (Berl.) (1977) [Pubmed]
  8. LSD and tryptamine effects on sleep/wakefulness and electrocorticogram patterns in intact cats. Kay, D.C., Martin, W.R. Psychopharmacology (Berl.) (1978) [Pubmed]
  9. Injections of deuterated tryptamine into the nucleus accumbens of the rat: effects on locomotor activity and monoamine metabolism. Marien, M.R., Gerber, R., Boyar, W.C., Altar, C.A. Neuropharmacology (1987) [Pubmed]
  10. The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins. Ma, X., Panjikar, S., Koepke, J., Loris, E., Stöckigt, J. Plant Cell (2006) [Pubmed]
  11. Platelet monoamine oxidase in affective disorders. Edwards, D.J., Spiker, D.G., Kupfer, D.J., Foster, G., Neil, J.F., Abrams, L. Arch. Gen. Psychiatry (1978) [Pubmed]
  12. CNS monoamine metabolism in bipolar affective disorder. Evaluation using a peripheral decarboxylase inhibitor. Garfinkel, P.E., Warsh, J.J., Stancer, H.C., Godse, D.D. Arch. Gen. Psychiatry (1977) [Pubmed]
  13. Tryptamine: a neuromodulator or neurotransmitter in mammalian brain? Jones, R.S. Prog. Neurobiol. (1982) [Pubmed]
  14. Histological localization of messenger RNAs for rat acetyltransferases that acetylate serotonin and genotoxic arylamines. Debiec-Rychter, M., Land, S.J., King, C.M. Cancer Res. (1996) [Pubmed]
  15. Expression of enzymatically active cloned strictosidine synthase from the higher plant Rauvolfia serpentina in Escherichia coli. Kutchan, T.M. FEBS Lett. (1989) [Pubmed]
  16. 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]
  17. In vitro and in vivo characterization of the dopamine D4 receptor, serotonin 5-HT2A receptor and alpha-1 adrenoceptor antagonist (R)-(+)-2-amino-4-(4-fluorophenyl)-5-[1-[4-(4-fluorophenyl)-4-oxobutyl] pyrrolidin-3-yl]thiazole (NRA0045). Okuyama, S., Chaki, S., Yoshikawa, R., Suzuki, Y., Ogawa, S., Imagawa, Y., Kawashima, N., Ikeda, Y., Kumagai, T., Nakazato, A., Nagamine, M., Tomisawa, K. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  18. F 11356, a novel 5-hydroxytryptamine (5-HT) derivative with potent, selective, and unique high intrinsic activity at 5-HT1B/1D receptors in models relevant to migraine. John, G.W., Pauwels, P.J., Perez, M., Halazy, S., Le Grand, B., Verscheure, Y., Valentin, J.P., Palmier, C., Wurch, T., Chopin, P., Marien, M., Kleven, M.S., Koek, W., Assie, M.B., Carilla-Durand, E., Tarayre, J.P., Colpaert, F.C. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  19. Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening. Srinivasan, N., Ganesan, A. Chem. Commun. (Camb.) (2003) [Pubmed]
  20. Serotonin autoreceptors on dorsal raphe neurons: structure-activity relationships of tryptamine analogs. Rogawski, M.A., Aghajanian, G.K. J. Neurosci. (1981) [Pubmed]
  21. Complete amino acid analysis of proteins from a single hydrolysate. Simpson, R.J., Neuberger, M.R., Liu, T.Y. J. Biol. Chem. (1976) [Pubmed]
  22. Arylamine N-methyltransferase. Methylation of the indole ring. Lyon, E.S., Jakoby, W.B. J. Biol. Chem. (1982) [Pubmed]
  23. Targeting tryptophan decarboxylase to selected subcellular compartments of tobacco plants affects enzyme stability and in vivo function and leads to a lesion-mimic phenotype. Di Fiore, S., Li, Q., Leech, M.J., Schuster, F., Emans, N., Fischer, R., Schillberg, S. Plant Physiol. (2002) [Pubmed]
  24. X-ray crystallographic studies of serotonin N-acetyltransferase catalysis and inhibition. Wolf, E., De Angelis, J., Khalil, E.M., Cole, P.A., Burley, S.K. J. Mol. Biol. (2002) [Pubmed]
  25. Autoradiographic localization of tryptamine binding sites in the rat and dog central nervous system. McCormack, J.K., Beitz, A.J., Larson, A.A. J. Neurosci. (1986) [Pubmed]
  26. Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Anderson, G.M., Gerner, R.H., Cohen, D.J., Fairbanks, L. Biol. Psychiatry (1984) [Pubmed]
  27. Benzodiazepine receptor affinity and interaction of some N-(indol-3-ylglyoxylyl)amine derivatives. Bianucci, A.M., Da Settimo, A., Da Settimo, F., Primofiore, G., Martini, C., Giannaccini, G., Lucacchini, A. J. Med. Chem. (1992) [Pubmed]
  28. Effect of intranigral administration of 6-hydroxydopamine and 5,7-dihydroxytryptamine on rat brain tryptamine. Juorio, A.V., Greenshaw, A.J., Nguyen, T.V. J. Neurochem. (1987) [Pubmed]
  29. Tryptamine: a possible endogenous substrate for CYP2D6. Martínez, C., Agúndez, J.A., Gervasini, G., Martín, R., Benítez, J. Pharmacogenetics (1997) [Pubmed]
  30. Ligands which effect human protein C activation by thrombin. Musci, G., Berliner, L.J. J. Biol. Chem. (1987) [Pubmed]
  31. Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. Bunzow, J.R., Sonders, M.S., Arttamangkul, S., Harrison, L.M., Zhang, G., Quigley, D.I., Darland, T., Suchland, K.L., Pasumamula, S., Kennedy, J.L., Olson, S.B., Magenis, R.E., Amara, S.G., Grandy, D.K. Mol. Pharmacol. (2001) [Pubmed]
  32. Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor. Boess, F.G., Monsma, F.J., Meyer, V., Zwingelstein, C., Sleight, A.J. Mol. Pharmacol. (1997) [Pubmed]
  33. Evidence that 5-methoxy-N, N-dimethyl tryptamine is a specific substrate for MAO-A in the rat: implications for the indoleamine dependent behavioural syndrome. Squires, R.F. J. Neurochem. (1975) [Pubmed]
  34. Serotoninergic system in hamster skin. Slominski, A., Pisarchik, A., Semak, I., Sweatman, T., Szczesniewski, A., Wortsman, J. J. Invest. Dermatol. (2002) [Pubmed]
  35. Interactions of tryptamine derivatives with serotonin transporter species variants implicate transmembrane domain I in substrate recognition. Adkins, E.M., Barker, E.L., Blakely, R.D. Mol. Pharmacol. (2001) [Pubmed]
  36. Modulation of CYP1A2 enzyme activity by indoleamines: inhibition by serotonin and tryptamine. Agúndez, J.A., Gallardo, L., Martínez, C., Gervasini, G., Benítez, J. Pharmacogenetics (1998) [Pubmed]
  37. Human indolethylamine N-methyltransferase: cDNA cloning and expression, gene cloning, and chromosomal localization. Thompson, M.A., Moon, E., Kim, U.J., Xu, J., Siciliano, M.J., Weinshilboum, R.M. Genomics (1999) [Pubmed]
  38. Purification of endogenous modulators of monoamine oxidase from plasma. Giambalvo, C.T. Biochem. Pharmacol. (1984) [Pubmed]
  39. Isolation, crystallization, and properties of indolyl-3-alkane alpha-hydroxylase. A novel tryptophan-metabolizing enzyme. Roberts, J., Rosenfeld, H.J. J. Biol. Chem. (1977) [Pubmed]
  40. Determination of kinetic properties of serotonin-N-acetyltransferase in bovine pineal gland using HPLC with fluorimetric detection. Fajardo, N., Abreu, P., Alonso, R. J. Pineal Res. (1992) [Pubmed]
  41. Effect of L-tryptophan on mouse brain 5-hydroxytryptamine: comparison of values obtained using a fluorimetric assay and a liquid Chromatographic assay with electrochemical detection. Marsden, C.A. J. Neurochem. (1981) [Pubmed]
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