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PsychedeliaDokholyan Laboratory
Plate 184 of 545Verified

5-Methoxytryptamine

Also known asMethoxytryptamine · O-Methylserotonin · 3-(2-Aminoethyl)-5-methoxyindole · 5MOT · 5-Mot · 5-MeOT · 5-methoxy-1H-indole-3-ethanamine · 5 Methoxytryptamine

2-(5-methoxy-1H-indol-3-yl)ethanamine

PubChem CID
1833
Measurements
179
InChIKey
JTEJPPKMYBDEMY-UHFFFAOYSA-N

I · Summary

What is known

Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.

What it is

  • 5-methoxytryptamine is a member of the class of tryptamines that is the methyl ether derivative of serotonin. It has a role as a 5-hydroxytryptamine 2B receptor agonist, a 5-hydroxytryptamine 2C receptor agonist, a 5-hydroxytryptamine 2A receptor agonist, an antioxidant, a serotonergic agonist, a neuroprotective agent, a radiation protective agent, a mouse metabolite, a cardioprotective agent and a human metabolite. It is a member of tryptamines, an aromatic ether and a primary amino compound. It is functionally related to a serotonin. It is a conjugate base of a 5-methoxytryptamine(1+).

    ChEBI

  • 5-methoxytryptamine has been reported in Mimosa somnians, Cinchona calisaya, and other organisms with data available.

    LOTUS - the natural products occurrence database

  • Serotonin derivative proposed as potentiator for hypnotics and sedatives.

    Medical Subject Headings (MeSH)

In the body

  • 5-methoxytryptamine has known human metabolites that include serotonin.

    NORMAN Suspect List ExchangeS73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

History, discovery and cultural use

— Not in this archive. PubChem, ChEMBL and the Human Protein Atlas publish pharmacology, regulation and toxicology, and none of them publishes a heading for when 5-Methoxytryptamine was first made, by whom, or how it has been used. That is a gap in the databases this site reads and not a gap in the literature — the history of these compounds is written, at length and under peer review, in the works below. This site does not summarize them; it says where they are. Where a published passage above happens to touch origin or traditional use, it appears inside the entry that carries it.

Histories of this field

Scholarship on psychedelics generally, not on 5-Methoxytryptamine specifically. Whether any of these treats this compound is a question for the book, not for this page.

  • Mescaline: A Global History of the First Psychedelic

    Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.

    Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.

  • Expanding Mindscapes: A Global History of Psychedelicsopen access

    Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.

    Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.

  • Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers

    Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.

    Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.

  • Psychonauts: Drugs and the Making of the Modern Mind

    The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.

    Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.

  • Ancient Psychoactive Substances

    Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.

    Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.

  • History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders

    A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.

    Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.

    Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.

  • Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions

    Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.

    Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.

Institutional archives

  • Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
  • Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.

The rest of this dossier

  • Affinity — 179 measurements in this archive, equilibrium constants kept apart from functional readouts.
  • Toxicology — nothing published for 5-Methoxytryptamine. An absent record is an absence of study, not evidence of safety.
  • Legal — no DEA record is held here — which is not a finding that this compound is uncontrolled.
  • Systems — where this compound’s targets are transcribed, by brain region and tissue.

Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about 5-Methoxytryptamine is the history note, which says so on its face and carries a reference for every claim in it.

II · Identity

Structure and descriptors

Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.

2D structural depiction of 5-Methoxytryptamine
Depiction served by PubChem for CID 1833. Not redrawn here, so the picture and the identity come from the same record.
Formula
C11H14N2OR
Molecular weight
190.25g/molR
Exact mass
190.1106DaR
cLogP
1.68R
TPSA
51.0ŲR
H-bond donors
2R
H-bond acceptors
2R
Rotatable bonds
3R
Aromatic rings
2R
Heavy atoms
14R
Fraction sp³
0.273R
Formal charge
0R

Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.

Bemis–Murcko scaffold

c1ccc2[nH]ccc2c1

Shared with 1-Acetyl-5-MeO-DMT, 1-Methylpsilocin, 2-Me-DET, 2-Methyltryptamine, 2,N,N-TMT, 4-AcO-DALT and 81 more. All families

III · Behavior

Behavioral summary

Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.

Classification

MeSH indexes no pharmacological class for this compound.

Duration of acute subjective effects

—

No controlled human trial reporting a duration for this compound is cited here. The archive holds no other record of one either. A duration is not inferred from a chemical relative.

Plasma elimination half-life

How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.

No half-life is published for this compound in the sources this site reads.

Primary pharmacological drivers

ChEMBL holds no curated mechanism-of-action record for this compound. The measured affinities below are the evidence this archive has for what it binds.

Nothing about this compound’s pharmacology is published with a citation in the sources this site reads. The measured binding data below is what the archive can show.

IV · Clinical

Clinical description

Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.

No diagnostic chapter is shown for this compound. Either PubChem records no MeSH pharmacological class for it, or the class it records is not one of the substance classes ICD-11 gives a chapter to. Inferring a chapter from the compound’s name or its binding profile would be a diagnosis this archive is in no position to make.

How much has been written about each domain

The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.

None of the 0 records this archive holds for this compound uses a term from any of the clinical domains. That is a statement about the literature recorded here, not about the compound.

V · Systems

Systems physiology

Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.

Brain

cerebral cortex — 18.2 nTPM, from HTR2A, HTR1A, HTR1Ecerebellum — 1.0 nTPM, from HTR1E, HTR2A, HTR2Bhippocampal formation — 6.1 nTPM, from HTR1A, HTR2A, HTR2Camygdala — 3.5 nTPM, from HTR2A, HTR2C, HTR1Ahypothalamus — 12.6 nTPM, from HTR2C, HTR2A, HTR7thalamus — no resolved target expressed herebasal ganglia — 28.2 nTPM, from HTR2C, HTR6, HTR1Dmedulla oblongata — no resolved target expressed here

basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.

Measured but not drawn — this anatomogram has no outline for them: retina 3.3, midbrain 2.2, spinal cord 1.0, pituitary gland 0.7.

Body

heart — 4.6 nTPM, from HTR2B, HTR4, HTR2Asmooth muscle — 15.7 nTPM, from HTR2B, HTR2A, HTR1Elung — 0.8 nTPM, from HTR2B, HTR1B, HTR2Aliver — 3.3 nTPM, from HTR2B, HTR7, HTR2Akidney — 3.1 nTPM, from HTR2B, HTR1B, HTR1Fstomach — 4.7 nTPM, from HTR1B, HTR2B, HTR1Eduodenum — 8.0 nTPM, from HTR1D, HTR4, HTR2Bsmall intestine — 8.5 nTPM, from HTR4, HTR1D, HTR2Bcolon — 8.5 nTPM, from HTR2B, HTR4, HTR7adrenal gland — 17.2 nTPM, from HTR2B, HTR4, HTR1Bthyroid gland — 3.2 nTPM, from HTR2B, HTR1E, HTR1Fpancreas — 0.2 nTPM, from HTR2B, HTR1D, HTR1Furinary bladder — 2.1 nTPM, from HTR7, HTR2B, HTR1Bskeletal muscle — 0.9 nTPM, from HTR7, HTR2A, HTR2Bspleen — 1.0 nTPM, from HTR7, HTR1F, HTR2Bsalivary gland — 0.4 nTPM, from HTR2B, HTR7, HTR1B
028 nTPM

Square-root ramp · shared scale across both plates

Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.

Brain regions

Regions where this compound's measured targets are transcribed. Linked from the plate above.

  1. basal ganglia

    28.2 nTPM

  2. cerebral cortex

    18.2 nTPM

  3. hypothalamus

    12.6 nTPM

  4. hippocampal formation

    6.1 nTPM

  5. amygdala

    3.5 nTPM

  6. retina

    3.3 nTPM

  7. midbrain

    2.2 nTPM

  8. spinal cord

    1.0 nTPM

  9. cerebellum

    1.0 nTPM

  10. pituitary gland

    0.7 nTPM

Peripheral & autonomic

Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.

  1. adrenal gland

    17.2 nTPM

  2. smooth muscle

    15.7 nTPM

  3. small intestine

    8.5 nTPM

  4. colon

    8.5 nTPM

  5. duodenum

    8.0 nTPM

  6. stomach 1

    4.7 nTPM

  7. heart muscle

    4.6 nTPM

  8. liver

    3.3 nTPM

  9. thyroid gland

    3.2 nTPM

  10. kidney

    3.1 nTPM

  11. urinary bladder

    2.1 nTPM

  12. spleen

    1.0 nTPM

  13. skeletal muscle

    0.9 nTPM

  14. lung

    0.8 nTPM

  15. salivary gland

    0.4 nTPM

  16. pancreas

    0.2 nTPM

Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.

7 of this compound’s targets could not be resolved to a gene and are absent from both columns: 5-HT1, 5-HT2, 5-HT4A, 5-HT4B, 5-HT4C, 5-HT4D, 5-HT7B.

Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.

VI · Profile

Affinity rosette

The strongest measurement at each of 18 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.

5-HT7 — Ki 9.60 pX5-HT2B — Ki 9.29 pX5-HT7B — Ki 9.28 pX5-HT1B — Ki 9.12 pX5-HT1D — Ki 8.77 pX5-HT1 — Ki 8.70 pX5-HT1A — Ki 8.60 pX5-HT6 — Ki 8.43 pX5-HT2 — Ki 8.32 pX5-HT2A — Ki 8.32 pX5-HT2C — Ki 8.10 pX5-HT4 — Ki 7.40 pX5-HT4B — Ki 6.60 pX5-HT4A — Ki 6.50 pX5-HT4D — Ki 6.26 pX5-HT4C — Ki 5.99 pX5-HT1F — Ki 5.93 pX5-HT1E — Ki 5.50 pX5-HT75-HT2B5-HT7B5-HT1B5-HT1D5-HT15-HT1A5-HT65-HT25-HT2A5-HT2C5-HT45-HT4B5-HT4A5-HT4D5-HT4C5-HT1F5-HT1E579
Fig. Radius is pX = −log₁₀(value in M), that is 9 − log₁₀(value in nM), computed from the normalized measurement. Hatched wedges are equilibrium binding constants (Ki, Kd); dashed outlines are functional readouts (IC₅₀, EC₅₀, AC₅₀, potency), which answer a different question and are not pooled with them. Rings mark whole pX units from 5 to 10, labeled every second ring in the gutter at the top. Where a target carries several measurements, the strongest is drawn.

VII · Toxicology

Toxicological profile

What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.

Measured in this archive

Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.

No hERG, cytochrome, cytotoxicity or transport measurement exists for 5-Methoxytryptamine in this archive.

Published toxicology

— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for 5-Methoxytryptamine. They index compounds that have been studied for decades, so most of this archive has no entry. An absent record is an absence of study, not evidence of safety.

Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.

VIII · Evidence

Every measurement

One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.

Equilibrium binding constants 179

Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.

TargetClassTypeValue (nM)pXOrganismAssay
5-HT7Serotonin receptorsKi0.2519.60GUINEA PIGPMID 10051134
5-HT7Serotonin receptorsKi0.5019.30HUMANPMID 9149537
5-HT7Serotonin receptorsKi0.5019.30GUINEA PIGPMID 9149537
5-HT2BSerotonin receptorsKi0.5109.29HUMANPMID 9225287
5-HT7Serotonin receptorsKi0.5209.28GUINEA PIGPMID 7647964
5-HT7BSerotonin receptorsKi0.5209.28HUMANPMID 9298538
5-HT7Serotonin receptorsKi0.5709.24RATPMID 7984267
5-HT7Serotonin receptorsKi0.5709.24RATPMID 8394362
5-HT7Serotonin receptorsKi0.6319.20RATPMID 10051134
5-HT1BSerotonin receptorsKi0.7509.12HUMANPMID 7984267
5-HT1BSerotonin receptorsKi0.7509.12HUMANPMID 1315531
5-HT7Serotonin receptorsKi0.9309.03RATPMID 7984267
5-HT7Serotonin receptorsKi0.9339.03Rattus norvegicusCHEMBL620766
5-HT7Serotonin receptorsKi0.9409.03MammalianPMID 7696602
5-HT7Serotonin receptorsKi0.9409.03RATPMID 8397408
5-HT7Serotonin receptorsKi1.009.00RATPMID 9149537
5-HT7Serotonin receptorsKi1.009.00GUINEA PIGPMID 7518496
5-HT7Serotonin receptorsKi1.588.80GUINEA PIGPMID 7647964
5-HT7Serotonin receptorsKi1.588.80RATPMID 9149537
5-HT1BSerotonin receptorsKi1.698.77RATPMID 7984267
5-HT1DSerotonin receptorsKi1.708.77HUMANPMID 9303569
5-HT1BSerotonin receptorsKi1.718.77RATPMID 19912901
5-HT7Serotonin receptorsKi1.778.75RATPMID 7984267
5-HT7Serotonin receptorsKi1.788.75RATPMID 8394362
5-HT1Serotonin receptorsKi2.008.70Rattus norvegicusCHEMBL615400
5-HT7Serotonin receptorsKi2.008.70Homo sapiensCHEMBL619855
5-HT1DSerotonin receptorsKi2.188.66HUMANPMID 7984267
5-HT1DSerotonin receptorsKi2.208.66HUMANPMID 1652050
5-HT1DSerotonin receptorsKi2.398.62RATPMID 7984267
5-HT1DSerotonin receptorsKi2.408.62RATPMID 19912901
5-HT1ASerotonin receptorsKi2.508.60RATPDSP
5-HT1DSerotonin receptorsKi2.508.60BOVINEPDSP
5-HT1ASerotonin receptorsKi3.208.49Rattus norvegicusCHEMBL616081
5-HT1ASerotonin receptorsKi3.208.49Rattus norvegicusCHEMBL616423
5-HT1ASerotonin receptorsKi3.208.49Homo sapiensCHEMBL615759
5-HT1BSerotonin receptorsKi3.508.46Homo sapiensCHEMBL617320
5-HT6Serotonin receptorsKi3.718.43RATPMID 9225298
5-HT1DSerotonin receptorsKi3.988.40CALFPDSP
5-HT1DSerotonin receptorsKi3.988.40CALFPDSP
5-HT1DSerotonin receptorsKi3.988.40CALFPDSP
5-HT1DSerotonin receptorsKi3.988.40COWPDSP
5-HT1BSerotonin receptorsKi4.008.40RATPMID 1738111
5-HT1BSerotonin receptorsKi4.008.40Rattus norvegicusCHEMBL616775
5-HT1DSerotonin receptorsKi4.008.40BOVINEPMID 1565658
5-HT1DSerotonin receptorsKi4.788.32HUMANPMID 7984267
5-HT1BSerotonin receptorsKi4.808.32HUMANPMID 1565658
5-HT2Serotonin receptorsKi4.808.32Rattus norvegicusCHEMBL617034
5-HT2ASerotonin receptorsKi4.808.32Homo sapiensCHEMBL617384
5-HT1ASerotonin receptorsKi5.008.30Rattus norvegicusCHEMBL616691
5-HT7Serotonin receptorsKi5.008.30HUMANPMID 8226867
5-HT6Serotonin receptorsKi5.018.30MOUSEPMID 8169832
5-HT7Serotonin receptorsKi5.018.30HUMANPMID 7984267
5-HT7Serotonin receptorsKi5.018.30HUMANPMID 9149537
5-HT1DSerotonin receptorsKi5.408.27Homo sapiensCHEMBL617303
5-HT1DSerotonin receptorsKi6.178.21HUMANPDSP
5-HT1DSerotonin receptorsKi6.308.20DogPMID 7984267
5-HT6Serotonin receptorsKi6.308.20MOUSEPMID 8394987
5-HT7Serotonin receptorsKi6.308.20MOUSEPMID 7984267
5-HT1ASerotonin receptorsKi6.408.19RATPDSP
5-HT2BSerotonin receptorsKi7.078.15RATPMID 7984267
5-HT1DSerotonin receptorsKi7.088.15PIGPDSP
5-HT1DSerotonin receptorsKi7.088.15PIGPDSP
5-HT1DSerotonin receptorsKi7.308.14HUMANPDSP
5-HT2CSerotonin receptorsKi7.908.10PIGPDSP
5-HT1ASerotonin receptorsKi9.008.05Rattus norvegicusCHEMBL615963
5-HT2BSerotonin receptorsKi9.128.04RATPMID 7984267
5-HT2BSerotonin receptorsKi9.158.04RATPMID 8632342
5-HT1ASerotonin receptorsKi10.727.97Rattus norvegicusCHEMBL616344
5-HT2Serotonin receptorsKi14.007.85Rattus norvegicusCHEMBL617413
5-HT2Serotonin receptorsKi14.007.85Rattus norvegicusCHEMBL617414
5-HT2CSerotonin receptorsKi14.007.85RATPMID 9928251
5-HT2CSerotonin receptorsKi14.007.85RATPMID 10611640
5-HT1BSerotonin receptorsKi15.007.82RATPDSP
5-HT2BSerotonin receptorsKi16.407.79HUMANPMID 8632342
5-HT6Serotonin receptorsKi18.007.74HUMANPMID 8226867
5-HT6Serotonin receptorsKi18.007.74RATPMID 7680751
5-HT6Serotonin receptorsKi18.197.74RATPMID 7984267
5-HT6Serotonin receptorsKi22.397.65RATPMID 14645659
5-HT2CSerotonin receptorsKi23.407.63PIGPDSP
5-HT2CSerotonin receptorsKi23.407.63PIGPDSP
5-HT2CSerotonin receptorsKi23.407.63PIGPDSP
5-HT6Serotonin receptorsKi23.447.63MOUSEPMID 14645659
5-HT2CSerotonin receptorsKi25.107.60PIGPDSP
5-HT1BSerotonin receptorsKi30.907.51RATPMID 7984267
5-HT1DSerotonin receptorsKi30.907.51DogPMID 7984267
5-HT1ASerotonin receptorsKi31.947.50RATPDSP
5-HT1BSerotonin receptorsKi33.887.47HUMANPMID 7984267
5-HT1DSerotonin receptorsKi34.007.47HUMANPMID 1565658
5-HT1BSerotonin receptorsKi35.007.46HUMANPMID 9303569
5-HT1ASerotonin receptorsKi35.147.45RATPDSP
5-HT1BSerotonin receptorsKi38.007.42HUMANPMID 9303569
5-HT2ASerotonin receptorsKi38.007.42HUMANPMID 10611640
5-HT6Serotonin receptorsKi38.907.41RATPMID 7680751
5-HT6Serotonin receptorsKi38.907.41RATPMID 7984267
5-HT6Serotonin receptorsKi39.007.41RATPMID 7696602
5-HT4Serotonin receptorsKi39.817.40RATPMID 9225293
5-HT6Serotonin receptorsKi43.007.37HUMANPMID 8522988
5-HT2CSerotonin receptorsKi43.707.36PIGPDSP
5-HT2CSerotonin receptorsKi43.807.36PIGPDSP
5-HT2CSerotonin receptorsKi45.007.35Homo sapiensCHEMBL616819
5-HT1BSerotonin receptorsKi45.707.34RATPMID 7984267
UncheckedUnclassifiedKi45.807.34— organism not recordedCHEMBL1013929
5-HT2ASerotonin receptorsKi50.107.30PIGPDSP
5-HT2CSerotonin receptorsKi52.487.28HUMANPMID 9225287
5-HT2ASerotonin receptorsKi61.657.21HUMANPMID 9225287
5-HT2CSerotonin receptorsKi63.097.20RATPMID 9225287
5-HT6Serotonin receptorsKi69.187.16HUMANPMID 14645659
5-HT1DSerotonin receptorsKi70.007.15RATPDSP
5-HT1DSerotonin receptorsKi72.007.14RATPDSP
5-HT4Serotonin receptorsKi1126.95RATPMID 8813606
5-HT4Serotonin receptorsKi1236.91RATPMID 9351641
5-HT6Serotonin receptorsKi1296.89RATPMID 9225298
5-HT2ASerotonin receptorsKi1416.85RATPMID 9225287
5-HT2ASerotonin receptorsKi1436.84RATPDSP
5-HT4Serotonin receptorsKi1556.81HUMANPMID 9351641
5-HT2CSerotonin receptorsKi2156.67RATPMID 10611640
5-HT2CSerotonin receptorsKi2156.67RATPMID 9928251
5-HT1ASerotonin receptorsKi2246.65RATPDSP
5-HT1ASerotonin receptorsKi2276.64RATPDSP
5-HT4Serotonin receptorsKi2296.64MOUSEPMID 8946946
5-HT4Serotonin receptorsKi2516.60GUINEA PIGPMID 9349523
5-HT4BSerotonin receptorsKi2516.60HUMANPMID 11218067
5-HT2ASerotonin receptorsKi2956.53HUMANPDSP
5-HT2ASerotonin receptorsKi3006.52RATPDSP
5-HT2ASerotonin receptorsKi3006.52Homo sapiensCHEMBL617385
5-HT2ASerotonin receptorsKi3006.52RATPDSP
5-HT2Serotonin receptorsKi3026.52Rattus norvegicusCHEMBL617535
5-HT2Serotonin receptorsKi3056.52Rattus norvegicusCHEMBL617035
5-HT2ASerotonin receptorsKi3056.52RATPDSP
5-HT2ASerotonin receptorsKi3056.52RATPDSP
5-HT4Serotonin receptorsKi3166.50RATPMID 8226867
5-HT4ASerotonin receptorsKi3166.50HUMANPMID 11218067
5-HT4Serotonin receptorsKi3166.50GUINEA PIGPMID 8867105
5-HT4Serotonin receptorsKi3166.50RATPMID 9225293
5-HT4Serotonin receptorsKi3166.50GUINEA PIGPMID 7984267
5-HT4Serotonin receptorsKi3166.50GUINEA PIGPMID 8358562
5-HT1BSerotonin receptorsKi3986.40RATPDSP
5-HT1BSerotonin receptorsKi3986.40RATPDSP
5-HT1BSerotonin receptorsKi3986.40RATPDSP
5-HT1BSerotonin receptorsKi3986.40RATPDSP
5-HT1BSerotonin receptorsKi3986.40RATPDSP
5-HT4Serotonin receptorsKi3986.40RATPMID 9349523
5-HT1BSerotonin receptorsKi4006.40Rattus norvegicusCHEMBL616773
5-HT1BSerotonin receptorsKi4006.40Rattus norvegicusCHEMBL616773
5-HT4Serotonin receptorsKi4016.40RATPMID 8813606
5-HT4Serotonin receptorsKi4016.40RATPMID 7796807
UncheckedUnclassifiedKi5006.30— organism not recordedCHEMBL1013930
5-HT4Serotonin receptorsKi5016.30RATPMID 9225293
5-HT4Serotonin receptorsKi5016.30HUMANPMID 8867105
5-HT4Serotonin receptorsKi5016.30HUMANPMID 9349523
5-HT4Serotonin receptorsKi5256.28MOUSEPMID 8867105
5-HT4Serotonin receptorsKi5256.28MOUSEPMID 8946946
5-HT4Serotonin receptorsKi5256.28MOUSEPMID 8867105
5-HT4DSerotonin receptorsKi5536.26HUMANPMID 9603189
5-HT2ASerotonin receptorsKi6176.21RATPDSP
5-HT4Serotonin receptorsKi6316.20GUINEA PIGPMID 8358562
5-HT4Serotonin receptorsKi6316.20GUINEA PIGPMID 7984267
5-HT2ASerotonin receptorsKi6846.16RATPDSP
5-HT2ASerotonin receptorsKi6866.16RATPDSP
5-HT2Serotonin receptorsKi6906.16Rattus norvegicusCHEMBL617447
5-HT2ASerotonin receptorsKi7246.14HUMANPMID 10611640
5-HT4BSerotonin receptorsKi7946.10HUMANPMID 10646498
5-HT4BSerotonin receptorsKi7946.10HUMANPMID 10646498
5-HT4Serotonin receptorsKi1,0006.00HUMANPMID 9349523
5-HT4ASerotonin receptorsKi1,0006.00HUMANPMID 10646498
5-HT4CSerotonin receptorsKi1,0205.99HUMANPMID 9603189
5-HT1FSerotonin receptorsKi1,1665.93HUMANPMID 8380639
5-HT2ASerotonin receptorsKi1,3825.86RATPDSP
5-HT4Serotonin receptorsKi1,5745.80PIGPMID 7984293
5-HT4ASerotonin receptorsKi2,0805.68HUMANPMID 9603189
5-HT4BSerotonin receptorsKi2,4435.61HUMANPMID 9603189
5-HT2Serotonin receptorsKi2,5705.59Rattus norvegicusCHEMBL617444
5-HT2ASerotonin receptorsKi2,5705.59RATPDSP
5-HT2ASerotonin receptorsKi2,5705.59RATPDSP
5-HT2ASerotonin receptorsKi2,7005.57RATPDSP
5-HT2ASerotonin receptorsKi2,9505.53RATPDSP
5-HT2ASerotonin receptorsKi3,1005.51RATPDSP
5-HT1ESerotonin receptorsKi3,1515.50HUMANPMID 1513320
5-HT2ASerotonin receptorsKi4,8325.32RATPDSP
P
PubChem
C
ChEMBL
R
Computed here with RDKit
D
Derived here from the stored measurement

IX · Trials

Registered clinical trials

Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.

6T

Registered studies

1T

Open or ongoing

6T

With a phase recorded

By phase

A study may carry two phase codes at once, so these count studies bearing each phase and do not sum to the total.

  • Phase 23
  • Phase 33
  • Phase 41
  • Not applicable1

By status

The registry’s own status for each record. Withdrawn and terminated studies are counted here rather than hidden — a stopped trial is part of what is known.

  • Completed3
  • Not yet recruiting1
  • Unknown status1
  • Terminated1

Every matched study

Newest first by start date. Each identifier opens the registry record it came from; the title is the sponsor’s own, quoted.

  • NCT07553143Not yet recruiting · Not applicable

    Effect of Preoperative Melatonin on Quality of Recovery After Elective Laparoscopic Cholecystectomy

    Enrollment
    84Testimated
    Started
    2026-05-01
    Sponsor
    Armed Forces Medical Institute Bangladesh

    Conditions Laparoscopic Cholecystectomy · Postoperative Quality of Recovery · Preoperative Anxiety · Postoperative Sleep Quality · Opioid Consumption, Postoperative · PONV in Laparoscopic Cholocystectomies

    Matched “5-Methoxytryptamine” in the study’s intervention “Melatonin (N-acetyl-5-methoxytryptamine)”

  • NCT06898463Completed · Phase 4

    Comparison Of The Effects Of Melatonin Premedication And Ketamine On Postoperative Sleep Quality İn Rhinoplasty

    Enrollment
    183Tactual
    Started
    2022-09-19
    Sponsor
    Konya City Hospital

    Conditions Postoperative Sleep Disturbances

    Matched “5-Methoxytryptamine” in the study’s intervention “Melatonin (N-acetyl-5-methoxytryptamine)”

  • NCT04229719Unknown status · Phase 3

    Effect of Topical Melatonin Application on Dental Implant Osseointegration and Marginal Bone Level

    Enrollment
    10Testimated
    Started
    2019-11-01
    Sponsor
    University of Baghdad

    Conditions Alveolar Bone Loss

    Matched “5-Methoxytryptamine” in the study’s intervention “N-acetyl-5-methoxytryptamine”

  • NCT02451293Completed · Phase 2 / Phase 3

    The Effect of MElatonin on Depression, Anxiety, CIrcadian and Sleep Disturbances in Patients After Acute Myocardial Syndrome

    Enrollment
    252Tactual
    Started
    2016-01-18
    Sponsor
    Zealand University Hospital

    Conditions Depression · Acute Coronary Syndrome

    Matched “5-Methoxytryptamine” in the study’s intervention “Melatonin (N-acetyl-5-methoxytryptamine)”

  • NCT01172171Completed · Phase 2

    The Effect of Melatonin on Ischemia-reperfusion Injury Following Acute Myocardial Infarction

    Enrollment
    41Tactual
    Started
    2013-06
    Sponsor
    Herlev Hospital

    Conditions Acute Myocardial Infarction · Ischemia-reperfusion Injury

    Matched “5-Methoxytryptamine” in the study’s intervention “Melatonin, N-acetyl-5-methoxytryptamine”

  • NCT01355523Terminated · Phase 2 / Phase 3

    The Effect of Melatonin on Depression, Anxiety, Cognitive Function and Sleep Disturbances in Breast Cancer Patients

    Enrollment
    54Tactual
    Started
    2011-07
    Sponsor
    Melissa Voigt Hansen

    Conditions Breast Cancer · Depression

    Matched “5-Methoxytryptamine” in the study’s intervention “Melatonin (N-acetyl-5-methoxytryptamine)”

Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.

Searched as 5-Methoxytryptamine · Methoxytryptamine · O-Methylserotonin. Run this search at the registry — it returns the unfiltered result, including studies this page rejected as belonging to a different molecule.

A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether 5-Methoxytryptamine worked.

XI · Literature

Sources behind this dossier

The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.

Every paper below is one some value on this page came from — a binding constant, a passage of pharmacology or toxicology, or a measured duration. Each entry says what this archive took from it. Nothing else is claimed about any of them: the title is the study’s own account of itself, and a summary written here would be an assertion with no source behind it.

  1. 01

    Molecular biology of 5-HT receptors

    Boess FG, Martin IL · Neuropharmacology 1994

    • · 21 measurements at 6 targets (Ki), strongest 5-HT7 at 9.24 pX

    PMID 7984267

  2. 02

    RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist

    Bonhaus DW, Weinhardt KK, Taylor M et al. · Neuropharmacology 1997

    • · 5 measurements at 3 targets (Ki), strongest 5-HT2B at 9.29 pX

    PMID 9225287

  3. 03

    The 5-HT7 receptor: orphan found

    Eglen RM, Jasper JR, Chang DJ et al. · Trends in pharmacological sciences 1997

    • · 5 measurements at 1 target (Ki), strongest 5-HT7 at 9.30 pX

    PMID 9149537

  4. 04

    Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors

    Egan C, Grinde E, Dupre A et al. · Synapse (New York, N.Y.) 2000

    • · 4 measurements at 2 targets (Ki), strongest 5-HT2C at 7.85 pX

    PMID 10611640

  5. 05

    Cloning, expression, and pharmacology of four human 5-hydroxytryptamine 4 receptor isoforms produced by alternative splicing in the carboxyl terminus

    Blondel O, Gastineau M, Dahmoune Y et al. · Journal of neurochemistry 1998

    • · 4 measurements at 4 targets (Ki), strongest 5-HT4D at 6.26 pX

    PMID 9603189

  6. 06

    Cloning and expression of a human serotonin 5-HT4 receptor cDNA

    Van den Wyngaert I, Gommeren W, Verhasselt P et al. · Journal of neurochemistry 1997

    • · 4 measurements at 1 target (Ki), strongest 5-HT4 at 6.60 pX

    PMID 9349523

  7. 07

    Pharmacological comparison between [3H]GR 113808 binding sites and functional 5-HT4 receptors in neurons

    Ansanay H, Sebben M, Bockaert J et al. · European journal of pharmacology 1996

    • · 4 measurements at 1 target (Ki), strongest 5-HT4 at 6.50 pX

    PMID 8867105

  8. 08

    Differences in the central nervous system distribution and pharmacology of the mouse 5-hydroxytryptamine-6 receptor compared with rat and human receptors investigated by radioligand binding, site-directed mutagenesis, and molecular modeling

    Hirst WD, Abrahamsen B, Blaney FE et al. · Molecular pharmacology 2003

    • · 3 measurements at 1 target (Ki), strongest 5-HT6 at 7.65 pX

    PMID 14645659

  9. 09

    Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant

    Bender E, Pindon A, van Oers I et al. · Journal of neurochemistry 2000

    • · 3 measurements at 2 targets (Ki), strongest 5-HT4B at 6.10 pX

    PMID 10646498

  10. 10

    [3H]RS 57639, a high affinity, selective 5-HT4 receptor partial agonist, specifically labels guinea-pig striatal and rat cloned (5-HT4S and 5-HT4L) receptors

    Bonhaus DW, Berger J, Adham N et al. · Neuropharmacology 1997

    • · 3 measurements at 1 target (Ki), strongest 5-HT4 at 7.40 pX

    PMID 9225293

  11. 11

    Characterization of human serotonin 1D and 1B receptors using [3H]-GR-125743, a novel radiolabelled serotonin 5HT1D/1B receptor antagonist

    Doménech T, Beleta J, Palacios JM · Naunyn-Schmiedeberg's archives of pharmacology 1997

    • · 3 measurements at 2 targets (Ki), strongest 5-HT1D at 8.77 pX

    PMID 9303569

  12. 12

    Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase

    Bard JA, Zgombick J, Adham N et al. · The Journal of biological chemistry 1993

    • · 3 measurements at 3 targets (Ki), strongest 5-HT7 at 8.30 pX

    PMID 8226867

  13. 13

    Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta

    Weinshank RL, Zgombick JM, Macchi MJ et al. · Proceedings of the National Academy of Sciences of the United States of America 1992

    • · 3 measurements at 2 targets (Ki), strongest 5-HT1D at 8.40 pX

    PMID 1565658

  14. 14

    5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle

    Bach T, Syversveen T, Kvingedal AM et al. · Naunyn-Schmiedeberg's archives of pharmacology 2001

    • · 2 measurements at 2 targets (Ki), strongest 5-HT4B at 6.60 pX

    PMID 11218067

  15. 15

    [3H]-Mesulergine labels 5-HT7 sites in rat brain and guinea-pig ileum but not rat jejunum

    Hemedah M, Coupar IM, Mitchelson FJ · British journal of pharmacology 1999

    • · 2 measurements at 1 target (Ki), strongest 5-HT7 at 9.60 pX

    PMID 10051134

  16. 16

    Pharmacological characterization of the constitutively activated state of the serotonin 5-HT2C receptor

    Herrick-Davis K, Grinde E, Gauthier C et al. · Annals of the New York Academy of Sciences 1998

    • · 2 measurements at 1 target (Ki), strongest 5-HT2C at 7.85 pX

    PMID 9928251

  17. 17

    Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase

    Claeysen S, Faye P, Sebben M et al. · Neuroreport 1997

    • · 2 measurements at 1 target (Ki), strongest 5-HT4 at 6.91 pX

    PMID 9351641

  18. 18

    Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells

    Boess FG, Monsma FJ Jr, Carolo C et al. · Neuropharmacology 1997

    • · 2 measurements at 1 target (Ki), strongest 5-HT6 at 8.43 pX

    PMID 9225298

  19. 19

    [3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor

    Adham N, Gerald C, Schechter L et al. · European journal of pharmacology 1996

    • · 2 measurements at 1 target (Ki), strongest 5-HT4 at 6.95 pX

    PMID 8813606

  20. 20

    Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor

    Claeysen S, Sebben M, Journot L et al. · FEBS letters 1996

    • · 2 measurements at 1 target (Ki), strongest 5-HT4 at 6.64 pX

    PMID 8946946

  21. 21

    Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences

    Wainscott DB, Lucaites VL, Kursar JD et al. · The Journal of pharmacology and experimental therapeutics 1996

    • · 2 measurements at 1 target (Ki), strongest 5-HT2B at 8.04 pX

    PMID 8632342

  22. 22

    Characterization and distribution of putative 5-ht7 receptors in guinea-pig brain

    To ZP, Bonhaus DW, Eglen RM et al. · British journal of pharmacology 1995

    • · 2 measurements at 1 target (Ki), strongest 5-HT7 at 9.28 pX

    PMID 7647964

  23. 23

    5-HT6 receptors positively coupled to adenylyl cyclase in striatal neurones in culture

    Sebben M, Ansanay H, Bockaert J et al. · Neuroreport 1994

    • · 2 measurements at 2 targets (Ki), strongest 5-HT7 at 9.03 pX

    PMID 7696602

  24. 24

    Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs

    Monsma FJ Jr, Shen Y, Ward RP et al. · Molecular pharmacology 1993

    • · 2 measurements at 1 target (Ki), strongest 5-HT6 at 7.74 pX

    PMID 7680751

  25. 25

    Development of a radioligand binding assay for 5-HT4 receptors in guinea-pig and rat brain

    Grossman CJ, Kilpatrick GJ, Bunce KT · British journal of pharmacology 1993

    • · 2 measurements at 1 target (Ki), strongest 5-HT4 at 6.50 pX

    PMID 8358562

  26. 26

    Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype

    Shen Y, Monsma FJ Jr, Metcalf MA et al. · The Journal of biological chemistry 1993

    • · 2 measurements at 1 target (Ki), strongest 5-HT7 at 9.24 pX

    PMID 8394362

  27. 27

    Distinct 5-HT(1B) and 5-HT(1D) serotonin receptors in rat: Structural and pharmacological comparison of the two cloned receptors

    Hamblin MW, McGuffin RW, Metcalf MA et al. · Molecular and cellular neurosciences 1992

    • · 2 measurements at 2 targets (Ki), strongest 5-HT1B at 8.77 pX

    PMID 19912901

  28. 28

    Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b)

    Jasper JR, Kosaka A, To ZP et al. · British journal of pharmacology 1997

    • · 1 measurement at 1 target (Ki), strongest 5-HT7B at 9.28 pX

    PMID 9298538

  29. 29

    Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor

    Kohen R, Metcalf MA, Khan N et al. · Journal of neurochemistry 1996

    • · 1 measurement at 1 target (Ki), strongest 5-HT6 at 7.37 pX

    PMID 8522988

  30. 30

    The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants

    Gerald C, Adham N, Kao HT et al. · The EMBO journal 1995

    • · 1 measurement at 1 target (Ki), strongest 5-HT4 at 6.40 pX

    PMID 7796807

  31. 31

    Characterization of a 5-hydroxytryptamine receptor in mouse neuroblastoma N18TG2 cells

    Unsworth CD, Molinoff PB · The Journal of pharmacology and experimental therapeutics 1994

    • · 1 measurement at 1 target (Ki), strongest 5-HT6 at 8.30 pX

    PMID 8169832

  32. 32

    Cloning and expression of a 5-hydroxytryptamine7 receptor positively coupled to adenylyl cyclase

    Tsou AP, Kosaka A, Bach C et al. · Journal of neurochemistry 1994

    • · 1 measurement at 1 target (Ki), strongest 5-HT7 at 9.00 pX

    PMID 7518496

  33. 33

    Identification of serotonin 5-HT4 recognition sites in the porcine caudate nucleus by radioligand binding

    Schiavi GB, Brunet S, Rizzi CA et al. · Neuropharmacology 1994

    • · 1 measurement at 1 target (Ki), strongest 5-HT4 at 5.80 pX

    PMID 7984293

  34. 34

    Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase

    Adham N, Kao HT, Schecter LE et al. · Proceedings of the National Academy of Sciences of the United States of America 1993

    • · 1 measurement at 1 target (Ki), strongest 5-HT1F at 5.93 pX

    PMID 8380639

  35. 35

    Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase

    Plassat JL, Amlaiky N, Hen R · Molecular pharmacology 1993

    • · 1 measurement at 1 target (Ki), strongest 5-HT6 at 8.20 pX

    PMID 8394987

  36. 36

    Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation

    Ruat M, Traiffort E, Leurs R et al. · Proceedings of the National Academy of Sciences of the United States of America 1993

    • · 1 measurement at 1 target (Ki), strongest 5-HT7 at 9.03 pX

    PMID 8397408

  37. 37

    Characterization of 5-hydroxytryptamine1B receptors in rat spinal cord via [125I]iodocyanopindolol binding and inhibition of [3H]-5-hydroxytryptamine release

    Matsumoto I, Combs MR, Jones DJ · The Journal of pharmacology and experimental therapeutics 1992

    • · 1 measurement at 1 target (Ki), strongest 5-HT1B at 8.40 pX

    PMID 1738111

  38. 38

    Human gene S31 encodes the pharmacologically defined serotonin 5-hydroxytryptamine1E receptor

    Zgombick JM, Schechter LE, Macchi M et al. · Molecular pharmacology 1992

    • · 1 measurement at 1 target (Ki), strongest 5-HT1E at 5.50 pX

    PMID 1513320

  39. 39

    Molecular cloning and functional characterization of a human 5-HT1B serotonin receptor: a homologue of the rat 5-HT1B receptor with 5-HT1D-like pharmacological specificity

    Hamblin MW, Metcalf MA, McGuffin RW et al. · Biochemical and biophysical research communications 1992

    • · 1 measurement at 1 target (Ki), strongest 5-HT1B at 9.12 pX

    PMID 1315531

  40. 40

    Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor

    Hamblin MW, Metcalf MA · Molecular pharmacology 1991

    • · 1 measurement at 1 target (Ki), strongest 5-HT1D at 8.66 pX

    PMID 1652050