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Plate 489 of 545Verified

Psilocin

Also known asPsilocine · 4-Hydroxy-N,N-dimethyltryptamine · Psilocyn · Psilotsin · N,N-Dimethyl-4-Hydroxytryptamine · 4-HO-DMT · Psilocin (1.0 mg/mL in Methanol) · CX-59

3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

PubChem CID
4980
Measurements
30
InChIKey
SPCIYGNTAMCTRO-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

  • Psilocin is a tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonancatl or "magic mushrooms"). It has a role as a hallucinogen, a serotonergic agonist, a drug metabolite, a fungal metabolite and a human xenobiotic metabolite. It is a member of phenols, a tryptamine alkaloid, a tertiary amino compound and a member of hydroxyindoles. It is functionally related to a N,N-dimethyltryptamine. It is a conjugate base of a psilocinium.
  • Psilocyn is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.
  • psilocin has been reported in Gymnopilus spectabilis, Deconica pseudobullacea, and other organisms with data available.
  • Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocin's ability to distort the perception of time. Sulfur analogs are k…

Recognized use

  • Psilocin is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms. (L1673)

In the body

  • Psilocin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

    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 Psilocin 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 Psilocin 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 — 30 measurements in this archive, equilibrium constants kept apart from functional readouts.
  • Toxicology — 1 published passage, plus any assay in this archive bearing on toxicity.
  • Legal — DEA Schedule I, with the passage it was read from.
  • 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 Psilocin 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 Psilocin
Depiction served by PubChem for CID 4980. Not redrawn here, so the picture and the identity come from the same record.
Formula
C12H16N2OR
Molecular weight
204.27g/molR
Exact mass
204.1263DaR
cLogP
1.98R
TPSA
39.3ŲR
H-bond donors
2R
H-bond acceptors
2R
Rotatable bonds
3R
Aromatic rings
2R
Heavy atoms
15R
Fraction sp³
0.333R
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

Duration of acute subjective effects

—

No controlled human trial reporting a duration for this compound is cited here. The archive does hold onset and duration ranges for it, inherited from an earlier build, but their source column is empty and so they cannot be shown. 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.

1.4–1.8 h

“Elimination half-lives were 1.8 hours (1.7-2.0), 1.4 hours (1.2-1.7), and 1.8 hours (1.6-1.9) for 15, 25, and 30 mg psilocybin, respectively”
Measured in plasma after oral psilocybin. Psilocin is the circulating species; trials dose psilocybin, so no duration is recorded here for psilocin as administered.Holze F et al., Clinical pharmacology and therapeutics 2023. PMID 36507738

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.

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.

Filed under Hallucinogens

  • 6C49Disorders due to use of hallucinogens

Diagnostic and Statistical Manual of Mental Disorders, Fifth Edition, Text Revision (DSM-5-TR): Hallucinogen-Related Disorders. Category names only — the manual is in copyright and no diagnostic criterion is reproduced here.

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 2 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.

038 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. retina

    7.8 nTPM
  5. amygdala

    6.4 nTPM
  6. hippocampal formation

    6.1 nTPM
  7. cerebellum

    5.8 nTPM
  8. pituitary gland

    4.7 nTPM
  9. midbrain

    2.5 nTPM
  10. spinal cord

    1.4 nTPM

Peripheral & autonomic

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

  1. small intestine

    38.0 nTPM
  2. kidney

    33.4 nTPM
  3. pancreas

    28.8 nTPM
  4. lung

    27.2 nTPM
  5. spleen

    20.8 nTPM
  6. adrenal gland

    17.2 nTPM
  7. smooth muscle

    15.7 nTPM
  8. urinary bladder

    14.8 nTPM
  9. duodenum

    9.7 nTPM
  10. heart muscle

    9.4 nTPM
  11. thyroid gland

    8.7 nTPM
  12. colon

    8.5 nTPM
  13. salivary gland

    6.5 nTPM
  14. liver

    6.3 nTPM
  15. skeletal muscle

    6.0 nTPM
  16. stomach 1

    4.7 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.

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 16 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.

5-HT2B — Ki 8.34 pX5-HT2C — Ki 8.00 pX5-HT2A — Ki 7.92 pX5-HT1D — Ki 7.73 pX5-HT1E — Ki 7.35 pX5-HT1A — Ki 7.31 pX5-HT5A — Ki 7.16 pX5-HT7 — Ki 7.15 pX5-HT6 — Ki 7.14 pX5-HT1B — Ki 6.52 pXD1 — Ki 7.70 pXD3 — Ki 6.99 pXAlpha2B — Ki 5.90 pXAlpha2A — Ki 5.69 pXAlpha2C — Ki 5.36 pXSERT — Ki 6.07 pX5-HT2B5-HT2C5-HT2A5-HT1D5-HT1E5-HT1A5-HT5A5-HT75-HT65-HT1BD1D3Alpha2BAlpha2AAlpha2CSERT579
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 Psilocin in this archive.

As published

Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.

Toxicity Summary

  • Psilocin acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is an 5-HT1A and 5-HT2A/2C agonist. (L1673)

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 27

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

TargetClassTypeValue (nM)pXOrganismAssay
5-HT2BSerotonin receptorsKi4.608.34Homo sapiensCHEMBL5346707
5-HT2BSerotonin receptorsKi4.708.33HUMANPMID 20126400
5-HT2CSerotonin receptorsKi10.008.00RATPMID 11101361
5-HT2ASerotonin receptorsKi12.007.92RATPMID 2795135
5-HT1DSerotonin receptorsKi18.607.73HUMANPMID 20126400
D1Dopamine receptorsKi19.907.70HUMANPMID 20126400
5-HT2ASerotonin receptorsKi25.007.60RATPMID 11101361
5-HT2ASerotonin receptorsKi25.007.60Rattus norvegicusCHEMBL617926
5-HT1ESerotonin receptorsKi44.307.35HUMANPMID 20126400
5-HT1ASerotonin receptorsKi49.007.31HUMANPMID 11101361
5-HT1ASerotonin receptorsKi62.607.20HUMANPMID 20126400
5-HT5ASerotonin receptorsKi69.907.16HUMANPMID 20126400
5-HT7Serotonin receptorsKi71.607.15HUMANPMID 20126400
5-HT6Serotonin receptorsKi71.707.14HUMANPMID 20126400
D3Dopamine receptorsKi1016.99HUMANPMID 20126400
5-HT2ASerotonin receptorsKi1076.97Homo sapiensCHEMBL5346705
5-HT2CSerotonin receptorsKi1416.85HUMANPMID 20126400
5-HT1BSerotonin receptorsKi3056.52HUMANPMID 20126400
5-HT2ASerotonin receptorsKi3236.49Rattus norvegicusCHEMBL980603
5-HT2ASerotonin receptorsKi3406.47HUMANPMID 20126400
5-HT2ASerotonin receptorsKi3706.43BOVINEPDSP
5-HT2ASerotonin receptorsKi3906.41Rattus norvegicusCHEMBL617465
5-HT2BSerotonin receptorsKi4506.35BOVINEPMID 2795135
SERTMonoamine transportersKi8526.07HUMANPMID 20126400
Alpha2BAdrenergic receptorsKi1,2715.90HUMANPMID 20126400
Alpha2AAdrenergic receptorsKi2,0445.69HUMANPMID 20126400
Alpha2CAdrenergic receptorsKi4,4045.36HUMANPMID 20126400

Functional readouts 3

IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.

TargetClassTypeValue (nM)pXOrganismAssay
5-HT2ASerotonin receptorsEC5075.207.12Homo sapiensCHEMBL4828616
5-HT1ASerotonin receptorsIC501966.71Homo sapiensCHEMBL6158869
5-HT2ASerotonin receptorsEC502,3005.64Rattus norvegicusCHEMBL617114
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.

2T

Registered studies

1T

Open or ongoing

2T

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 12

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.

  • Completed1
  • Active, not recruiting1

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.

  • NCT06035900Completed · Phase 1

    Evaluation of Safety, Rate and Extent of Absorption of Psilocin Mucate

    Enrollment
    10Tactual
    Started
    2023-06-21
    Sponsor
    Lobe Sciences Ltd.

    Conditions Side Effect of Drug

    Matched “Psilocin” in the study’s intervention “Psilocin”

  • NCT05317689Active, not recruiting · Phase 1

    Comparing the Effects of Psilocin and Psilocybin in Healthy Adults

    Enrollment
    20Testimated
    Started
    2022-05-26
    Sponsor
    University of California, San Francisco

    Conditions Healthy

    Matched “Psilocin” in the study’s intervention “Psilocin”

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 Psilocin · 4-Hydroxy-N,N-dimethyltryptamine · N,N-Dimethyl-4-Hydroxytryptamine. 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 Psilocin 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

    Psychedelics and the human receptorome

    Ray TS · PloS one 2010

    • · 16 measurements at 16 targets (Ki), strongest 5-HT2B at 8.33 pX

    PMID 20126400

  2. 02

    Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines

    Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D et al. · Journal of medicinal chemistry 2000

    • · 3 measurements at 3 targets (Ki), strongest 5-HT2C at 8.00 pX

    PMID 11101361

  3. 03

    Differentiation of 5-hydroxytryptamine2 receptor subtypes using 125I-R-(-)2,5-dimethoxy-4-iodo-phenylisopropylamine and 3H-ketanserin

    McKenna DJ, Peroutka SJ · The Journal of neuroscience : the official journal of the Society for Neuroscience 1989

    • · 2 measurements at 2 targets (Ki), strongest 5-HT2A at 7.92 pX

    PMID 2795135

  4. 04

    Psychedelics align brain activity with context

    Stoliker D, Novelli L, Khajehnejad M et al. · Nature 2026

    • · 3 timed observations on the simulation plate

    PMID 42618786

  5. 05

    Comparative acute effects of mescaline, lysergic acid diethylamide, and psilocybin in a randomized, double-blind, placebo-controlled cross-over study in healthy participants

    Ley L, Holze F, Arikci D et al. · Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 2023

    • · 2 timed observations on the simulation plate

    PMID 37231080

  6. 06

    Pharmacokinetics and Pharmacodynamics of Oral Psilocybin Administration in Healthy Participants

    Holze F, Becker AM, Kolaczynska KE et al. · Clinical pharmacology and therapeutics 2023

    • · Plasma elimination half-life

    PMID 36507738

  7. 07

    Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study

    Hasler F, Grimberg U, Benz MA et al. · Psychopharmacology 2004

    • · 1 timed observation on the simulation plate

    PMID 14615876