tryptamine
Also known as 1H-indole-3-ethanamine, 2-(3-indolyl)ethylamine, 2-(1H-indol-3-yl)ethanamine, Tryptamin, 2-Indol-3-yl-ethylamine, 3-Indoleethylamine, 2-(1H-Indol-3-yl)ethylamine, 3-(2-Aminoethyl)-1H-indole
Tryptamine, also known as 2-(3-indolyl)ethylamine, is an indolamine 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 neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.
Key facts
- Drug.image
- Tryptamine 2D.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 185px
- Drug.image2
- Tryptamine molecule from xtal ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175px
- Drug.routes_of_administration
- Intravenous injection
- Drug.class
- Serotonin receptor agonist; Trace amine-associated receptor 1 (TAAR1) agonist; Serotonin–norepinephrine–dopamine releasing agent; Serotonergic psychedelic; Hallucinogen
- Drug.ATC_prefix
- None
- Drug.legal_status
- Legal or unregulated
- Drug.bioavailability
- Oral: Very low
- Drug.metabolism
Article
23 sectionsContents
- Natural occurrences
- Mammalian brain
- Mammalian gut microbiome
- Metabolism
- Biosynthesis
- Catabolism
- Figure
- Biological activity
- Serotonin receptor agonist
- Gastrointestinal motility
- Monoamine releasing agent
- Monoaminergic activity enhancer
- TAAR1 agonist
- Effects in animals and humans
- Pharmacokinetics
- Chemistry
- Properties
- Synthesis
- Analogues and derivatives
- History
- See also
- References
- External links
Tryptamine, also known as 2-(3-indolyl)ethylamine, is an indolamine 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 neuromodulators 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 glutamatergic systems. In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility.
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Connections
Categories
5-HT1A agonists5-HT2A agonists5-HT2B agonists5-HT2C agonistsAminoethyl compoundsBiogenic aminesDrugs not assigned an ATC codeDrugs with non-standard legal statusECHA InfoCard ID from WikidataMonoaminergic activity enhancersPsychedelic drug metabolitesPsychedelic tryptaminesSerotonin-norepinephrine-dopamine releasing agents