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
- ChEMBL
- CHEMBL65547
- 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.
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.
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.
- 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”
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.
Brain
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: retina 7.8, pituitary gland 4.7, midbrain 2.5, spinal cord 1.4.
Body
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.
basal ganglia
28.2 nTPMcerebral cortex
18.2 nTPMhypothalamus
12.6 nTPMretina
7.8 nTPMamygdala
6.4 nTPMhippocampal formation
6.1 nTPMcerebellum
5.8 nTPMpituitary gland
4.7 nTPMmidbrain
2.5 nTPMspinal cord
1.4 nTPM
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
small intestine
38.0 nTPMkidney
33.4 nTPMpancreas
28.8 nTPMlung
27.2 nTPMspleen
20.8 nTPMadrenal gland
17.2 nTPMsmooth muscle
15.7 nTPMurinary bladder
14.8 nTPMduodenum
9.7 nTPMheart muscle
9.4 nTPMthyroid gland
8.7 nTPMcolon
8.5 nTPMsalivary gland
6.5 nTPMliver
6.3 nTPMskeletal muscle
6.0 nTPMstomach 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.
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.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| 5-HT2B | Serotonin receptors | Ki | 4.60 | 8.34 | Homo sapiens | CHEMBL5346707 |
| 5-HT2B | Serotonin receptors | Ki | 4.70 | 8.33 | HUMAN | PMID 20126400 |
| 5-HT2C | Serotonin receptors | Ki | 10.00 | 8.00 | RAT | PMID 11101361 |
| 5-HT2A | Serotonin receptors | Ki | 12.00 | 7.92 | RAT | PMID 2795135 |
| 5-HT1D | Serotonin receptors | Ki | 18.60 | 7.73 | HUMAN | PMID 20126400 |
| D1 | Dopamine receptors | Ki | 19.90 | 7.70 | HUMAN | PMID 20126400 |
| 5-HT2A | Serotonin receptors | Ki | 25.00 | 7.60 | RAT | PMID 11101361 |
| 5-HT2A | Serotonin receptors | Ki | 25.00 | 7.60 | Rattus norvegicus | CHEMBL617926 |
| 5-HT1E | Serotonin receptors | Ki | 44.30 | 7.35 | HUMAN | PMID 20126400 |
| 5-HT1A | Serotonin receptors | Ki | 49.00 | 7.31 | HUMAN | PMID 11101361 |
| 5-HT1A | Serotonin receptors | Ki | 62.60 | 7.20 | HUMAN | PMID 20126400 |
| 5-HT5A | Serotonin receptors | Ki | 69.90 | 7.16 | HUMAN | PMID 20126400 |
| 5-HT7 | Serotonin receptors | Ki | 71.60 | 7.15 | HUMAN | PMID 20126400 |
| 5-HT6 | Serotonin receptors | Ki | 71.70 | 7.14 | HUMAN | PMID 20126400 |
| D3 | Dopamine receptors | Ki | 101 | 6.99 | HUMAN | PMID 20126400 |
| 5-HT2A | Serotonin receptors | Ki | 107 | 6.97 | Homo sapiens | CHEMBL5346705 |
| 5-HT2C | Serotonin receptors | Ki | 141 | 6.85 | HUMAN | PMID 20126400 |
| 5-HT1B | Serotonin receptors | Ki | 305 | 6.52 | HUMAN | PMID 20126400 |
| 5-HT2A | Serotonin receptors | Ki | 323 | 6.49 | Rattus norvegicus | CHEMBL980603 |
| 5-HT2A | Serotonin receptors | Ki | 340 | 6.47 | HUMAN | PMID 20126400 |
| 5-HT2A | Serotonin receptors | Ki | 370 | 6.43 | BOVINE | PDSP |
| 5-HT2A | Serotonin receptors | Ki | 390 | 6.41 | Rattus norvegicus | CHEMBL617465 |
| 5-HT2B | Serotonin receptors | Ki | 450 | 6.35 | BOVINE | PMID 2795135 |
| SERT | Monoamine transporters | Ki | 852 | 6.07 | HUMAN | PMID 20126400 |
| Alpha2B | Adrenergic receptors | Ki | 1,271 | 5.90 | HUMAN | PMID 20126400 |
| Alpha2A | Adrenergic receptors | Ki | 2,044 | 5.69 | HUMAN | PMID 20126400 |
| Alpha2C | Adrenergic receptors | Ki | 4,404 | 5.36 | HUMAN | PMID 20126400 |
Functional readouts 3
IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| 5-HT2A | Serotonin receptors | EC50 | 75.20 | 7.12 | Homo sapiens | CHEMBL4828616 |
| 5-HT1A | Serotonin receptors | IC50 | 196 | 6.71 | Homo sapiens | CHEMBL6158869 |
| 5-HT2A | Serotonin receptors | EC50 | 2,300 | 5.64 | Rattus norvegicus | CHEMBL617114 |
- 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.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds and shown with the passage each was read from. Not legal advice, and not necessarily current.
As the DEA states it
Quoted whole. The badge above is a reading of these passages and adds nothing to them.
Schedule I - 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.
United States federal status only. State law differs, and so does the law of every other country — none of it is represented here. Scheduling changes, and this reflects the DEA records held by PubChem descriptive sections when the monograph was last harvested, not necessarily today. This is a record of what a database publishes, not legal advice.
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.
- 01
Psychedelics and the human receptorome
Ray TS · PloS one 2010
- · 16 measurements at 16 targets (Ki), strongest 5-HT2B at 8.33 pX
- 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
- 03
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
- 04
Psychedelics align brain activity with context
Stoliker D, Novelli L, Khajehnejad M et al. · Nature 2026
- · 3 timed observations on the simulation plate
- 05
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
- 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
- 07
Hasler F, Grimberg U, Benz MA et al. · Psychopharmacology 2004
- · 1 timed observation on the simulation plate