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Tryptamine

Also called Indolylethylamine, 1H-Indole-3-ethanamine, Indol-3-ethylamine, 3-Indoleethylamine

Original Wikipedia articleen.wikipedia.org/wiki/Tryptamine revision used (24 October 2026)

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Part of the metabolic pathway of DMT and Tryptamine (compound). See the timeline on the metabolic highway.

Enzymes that break it down: monoamine oxidase (MAO). Wikipedia’s drug infobox says: “Very rapid (oxidative deamination by MAO)” (revision 1369726329).

Dosage

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Mixing

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Overview

Tryptamine is a monoamine alkaloid found in animals, plants and fungi. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter.[1] PW⚠ PsychonautWiki itself has flagged this text: citation needed.

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.[2–6] WP

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.[3][7–12] WP

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.[13][14][15] WP

History

History

Tryptamine, referred to by the name 3-β-aminoethylindole, was first synthesized by Arthur James Ewins and Patrick Laidlaw in 1910. Subsequently, they referred to it by the name indolethylamine in 1912 and 1913. The name tryptamine first emerged by at least 1918.[16–25] WP

Following tryptamine's synthesis, N-methylated tryptamines like N-methyltryptamine (NMT) and dimethyltryptamine (DMT) were synthesized by Richard Manske in 1931. Subsequently, the chemical structure of serotonin (5-hydroxytryptamine; 5-HT) was identified—and hence serotonin was first "truly" discovered (having been isolated earlier in the 1930s)—by Maurice M. Rapport in 1949. The structural similarity between serotonin and the psychedelic drug LSD, a lysergamide and cyclized tryptamine that contains tryptamine within its structure, was noticed and described by Dilworth Wayne Woolley and Elliott Shaw in 1954. The hallucinogenic effects of simple tryptamines themselves were not discovered until those of bufotenin and DMT were elucidated in 1955 and 1956, for instance by Stephen Szára, soon after their first isolation from hallucinogenic snuffs.[17][26–35] WP

The psychedelic effects of tryptamine itself in humans were first reported by W. R. Martin and J. W. Sloan in 1970.[7][36][37][38] WP

Pharmacology

Pharmacokinetics

Tryptamine produced endogenously or administered peripherally is readily able to cross the blood–brain barrier and enter the central nervous system. This is in contrast to serotonin, which is peripherally selective. However, it has been reported that tryptamine also shows partial peripheral selectivity.[51][52][53] WP

Tryptamine is metabolized 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).[1][7][36][37][38][51][52] WP

Tryptamine is excreted in urine and its rate of urinary excretion has been reported to be pH-dependent.[38][54][55] WP

Receptor binding · Wikipedia

Tryptamine target activities

Every row cites [7][39–50]

TargetAffinity (Kᵢ, nM)Species
5-HT1A32–685 (Kᵢ); 899–>10,000 (EC₅₀ (half-maximal effective concentration)); ND (No data) (Eₘₐₓ (maximal efficacy))Human; Human; Human WP
5-HT1B36–525Human WP
5-HT1D23–521Human WP
5-HT1E2,559Human WP
5-HT1F2,409Human WP
5-HT2A37–4,070 (Kᵢ); 7.4–257 (EC₅₀ (half-maximal effective concentration)); 71–104% (Eₘₐₓ (maximal efficacy))Human; Human; Human WP
5-HT2B25–113 (Kᵢ); 29.5 (EC₅₀ (half-maximal effective concentration)); 92% (Eₘₐₓ (maximal efficacy))Human; Human; Human WP
5-HT2C17–3,000 (Kᵢ); 1.17–45.7 (EC₅₀ (half-maximal effective concentration)); 85–108% (Eₘₐₓ (maximal efficacy))Human; Human; Human WP
5-HT₃ND (No data)ND (No data) WP
5-HT₄>10,000; 13,500 (EC₅₀ (half-maximal effective concentration)); 96% (Eₘₐₓ (maximal efficacy))Mouse; Pig; Pig WP
5-HT5AND (No data)ND (No data) WP
5-HT₆70–1,130Human WP
5-HT₇148–596Human WP
α2A19,000Rat WP
D₂>10,000Human WP
TAAR1 (Human trace amine-associated receptor 1)1,400 (Kᵢ); 2,700 (EC₅₀ (half-maximal effective concentration)); 117% (Eₘₐₓ (maximal efficacy)); 130 (Kᵢ); 410 (EC₅₀ (half-maximal effective concentration)); 91% (Eₘₐₓ (maximal efficacy)); 1,084 (Kᵢ); 2,210–21,000 (EC₅₀ (half-maximal effective concentration)); 73% (Eₘₐₓ (maximal efficacy))Mouse; Mouse; Mouse; Rat; Rat; Rat; Human; Human; Human WP
SERT (Serotonin transporter)32.6 (EC₅₀ (half-maximal effective concentration)) ᵃRat WP
NET (Norepinephrine transporter)716 (EC₅₀ (half-maximal effective concentration)) ᵃRat WP
DAT (Dopamine transporter)164 (EC₅₀ (half-maximal effective concentration)) ᵃRat WP

TAAR1 affinities and activational potencies of tryptamines

Every row cites [43][44]

Human TAAR1Mouse TAAR1Rat TAAR1
CompoundHuman TAAR1 EC₅₀ (nM)Human TAAR1 Kᵢ (nM)Mouse TAAR1 EC₅₀ (nM)Mouse TAAR1 Kᵢ (nM)Rat TAAR1 EC₅₀ (nM)Rat TAAR1 Kᵢ (nM)
Tryptamine21,000N/A2,7001,400410130 WP
Serotonin>50,000N/A>50,000N/A5,200N/A WP
Psilocin>30,000N/A2,70017,0009201,400 WP
Dimethyltryptamine>10,000N/A1,2003,3001,50022,000 WP

Chemistry

Formula
C10H12N2 PC
CAS number
61-54-1 PC
Molar mass (g/mol)
160.22 PC
IUPAC name (computed by PubChem)
2-(1H-indol-3-yl)ethanamine PC
SMILES
C1=CC=C2C(=C1)C(=CN2)CCN PC
InChIKey
APJYDQYYACXCRM-UHFFFAOYSA-N PC
PubChem CID
1150

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References

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  39. Other PDSP Database
  40. Other Liu T. BindingDB BDBM50024210 1H-indole-3-ethanamine::2-(1H-indol-3-yl)ethanamine::2-(3-indolyl)ethylamine::CHEMBL6640::tryptamine
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Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.