Editing Tryptamine (section)

==Chemistry==
Tryptamine is a [[substituted tryptamine]] [[chemical derivative|derivative]] and [[trace amine]] and is [[structural analog|structurally related]] to the [[amino acid]] [[tryptophan]].

The experimental [[partition coefficient|log P]] of tryptamine is 1.55.<ref name="PubChem">{{cite web | title=Tryptamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/1150 | access-date=7 November 2024}}</ref>

===Derivatives===
{{Main|Substituted tryptamine}}

The [[endogenous]] [[monoamine neurotransmitter]]s [[serotonin]] (5-hydroxytryptamine or 5-HT) and [[melatonin]] (5-methoxy-''N''-acetyltryptamine), as well as trace amines like [[N-methyltryptamine|''N''-methyltryptamine]] (NMT), [[dimethyltryptamine|''N'',''N''-dimethyltryptamine]] (DMT), and [[bufotenin]] (''N'',''N''-dimethylserotonin), are [[chemical derivative|derivative]]s of tryptamine.

[[File:Tryptamine Alkaloids 2.png|class=skin-invert-image|thumb|483x483px|All tryptamine derivatives possess a modified 2-aminoethyl group and/or the addition of a substituent on the indole.]]

A variety of drugs, including both [[natural product|naturally occurring]] and [[pharmaceutical drug|pharmaceutical]] substances, are derivatives of tryptamine. These include the tryptamine psychedelics like [[psilocybin]], [[psilocin]], DMT, and [[5-MeO-DMT]]; tryptamine [[stimulant]]s, [[entactogen]]s, psychedelics, and/or [[antidepressant]]s like [[α-methyltryptamine]] (αMT) and [[α-ethyltryptamine]] (αET); [[triptan]] [[antimigraine agent]]s like [[sumatriptan]]; certain [[antipsychotic]]s like [[oxypertine]]; and the [[sleep aid]] [[melatonin (medication)|melatonin]].

Various other drugs, including [[ergoline]]s and [[lysergamide]]s like the psychedelic [[lysergic acid diethylamide]] (LSD), the antimigraine agents [[ergotamine]], [[dihydroergotamine]], and [[methysergide]], and the [[antiparkinsonian agent]]s [[bromocriptine]], [[cabergoline]], [[lisuride]], and [[pergolide]]; [[β-carboline]]s like [[harmine]] (some of which are [[monoamine oxidase inhibitor]]s (MAOIs)); [[Iboga-type alkaloid|''Iboga'' alkaloid]]s like the [[hallucinogen]] [[ibogaine]]; [[yohimban]]s like the [[alpha-2 blocker|α<sub>2</sub> blocker]] [[yohimbine]]; antipsychotics like [[ciclindole]] and [[flucindole]]; and the MAOI antidepressant [[metralindole]], can all be thought of as [[cyclic compound|cyclized]] 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]].