Tryptamine
Metabolite of the amino acid tryptophan / From Wikipedia, the free encyclopedia
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Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan.[2][3] 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).[2] 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.[4][5][6] Tryptamine has been shown to activate trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems.[7] [8] In the human gut, symbiotic bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility.[3][9][10] Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.[11][12][13]
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Preferred IUPAC name
2-(1H-Indol-3-yl)ethan-1-amine | |
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3D model (JSmol) |
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125513 | |
ChEBI | |
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DrugBank | |
ECHA InfoCard | 100.000.464 |
KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties[1] | |
C10H12N2 | |
Molar mass | 160.220 g·mol−1 |
Appearance | white to orange needles |
Melting point | 118˚C |
Boiling point | 137 °C (279 °F; 410 K) (0.15 mmHg) |
negligible solubility in water | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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For a list of tryptamine derivatives, see: List of substituted tryptamines.