Product Code Database
Tryptamine is an Indolamines metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic Neuromodulation including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.
Tryptamine has been shown to activate serotonin receptors and trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and Glutamic acid systems. In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility.
Multiple tryptamine-derived drugs have been developed to treat , while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.
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| Note: The smaller the value, the more avidly the compound binds to or activates the site. Footnotes: a = Neurotransmitter release. Refs: Main: Additional: (1997). 9780444820419, Elsevier. ISBN 9780444820419 | ||
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| Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The bioassay were done in rat brain and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: | ||||||
The TAAR1 is a stimulatory G protein-coupled receptor (GPCR) that is weakly gene expression in the intracellular compartment of both presynaptic and postsynaptic neurons. TAAR1 agonists have been implicated in regulating monoaminergic neurotransmission, for instance by activating G protein-coupled inwardly-rectifying potassium channels (GIRKs) and reducing action potential via facilitation of membrane hyperpolarization through the efflux of .
TAAR1 agonists are under investigation as a novel treatment for neuropsychiatric conditions like schizophrenia, drug addiction, and depression. The TAAR1 is expressed in brain structures associated with dopamine systems, such as the ventral tegmental area (VTA) and serotonin systems in the dorsal raphe nuclei (DRN). Additionally, the human TAAR1 gene is localized at 6q23.2 on the human chromosome, which is a susceptibility locus for and schizophrenia. Activation of TAAR1 suggests a potential novel treatment for neuropsychiatric disorders, as TAAR1 agonists produce antipsychotic-like, antiaddictive, and antidepressant-like effects in animals.
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| Tryptamine | 21,000 | N/A | 2,700 | 1,400 | 410 | 130 |
| Serotonin | >50,000 | N/A | >50,000 | N/A | 5,200 | N/A |
| Psilocin | >30,000 | N/A | 2,700 | 17,000 | 920 | 1,400 |
| Dimethyltryptamine | >10,000 | N/A | 1,200 | 3,300 | 1,500 | 22,000 |
| Notes: (1) EC50 and Ki values are in nanomolar (nM). (2) EC50 reflects the concentration required to elicit 50% of the maximum TAAR1 response. (3) The smaller the Ki value, the stronger the compound binds to the receptor. | ||||||
In animals, tryptamine, alone and/or in combination with a monoamine oxidase inhibitor (MAOI), produces behavioral changes such as hyperlocomotion and reversal of reserpine-induced hypoactivity. In addition, it produces effects like hyperthermia, tachycardia, myoclonus, and or , among others. Findings on tryptamine and the head-twitch response in rodents have been mixed, with some studies reporting no effect, some studies reporting induction of head twitches by tryptamine, and others reporting that tryptamine actually antagonized 5-hydroxytryptophan (5-HTP)-induced head twitches. Another study found that combination of tryptamine with an MAOI dose-dependently produced head twitches. (1984). 9781461297819, Humana Press. ISBN 9781461297819 Head twitches in rodents are a behavioral proxy of psychedelic-like effects. (2025). 9781461441205, Springer New York. ISBN 9781461441205 Many of the effects of tryptamine can be reversed by serotonin receptor antagonists like metergoline, metitepine (methiothepin), and cyproheptadine. Conversely, the effects of tryptamine in animals are profoundly augmented by MAOIs due to inhibition of its metabolism.
Tryptamine seems to also elevate prolactin and cortisol levels in animals and/or humans.
The values of tryptamine in animals include 100mg/kg i.p. in mice, 500mg/kg s.c. in mice, and 223mg/kg i.p. in rats.
Tryptamine is drug metabolism by monoamine oxidase (MAO) to form indole-3-acetic acid (IAA). Its metabolism is described as extremely rapid and its elimination half-life and duration as very short. In addition, its duration is described as shorter than that of dimethyltryptamine (DMT). Brain tryptamine levels are increased up to 300-fold by MAOIs in animals. In addition, the effects of exogenous tryptamine are strongly augmented by monoamine oxidase inhibitors (MAOIs).
Tryptamine is excretion in urine and its rate of urinary excretion has been reported to be pH-dependent.
The experimental log P of tryptamine is 1.55.
A variety of drugs, including both natural product and pharmaceutical substances, are derivatives of tryptamine. These include the tryptamine psychedelics like psilocybin, psilocin, DMT, and 5-MeO-DMT; tryptamine , , psychedelics, and/or like α-methyltryptamine (αMT) and α-ethyltryptamine (αET); triptan antimigraine agents like sumatriptan; certain like oxypertine; and the sleep aid melatonin.
Various other drugs, including and like the psychedelic lysergic acid diethylamide (LSD), the antimigraine agents ergotamine, dihydroergotamine, and methysergide, and the antiparkinsonian agents bromocriptine, cabergoline, lisuride, and pergolide; β-carbolines like harmine (some of which are monoamine oxidase inhibitors (MAOIs)); Iboga alkaloids like the hallucinogen ibogaine; like the α2 blocker yohimbine; antipsychotics like ciclindole and flucindole; and the MAOI antidepressant metralindole, can all be thought of as cyclic compound tryptamine derivatives.
Drugs very closely related to tryptamines, but technically not tryptamines themselves, include certain triptans like avitriptan and naratriptan; the antipsychotics sertindole and tepirindole; and the MAOI antidepressants pirlindole and tetrindole.
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