Harmine
Also known asBanisterine · Telepathine · Leucoharmine · Yageine · Yajeine · 1-Methyl-7-methoxy-beta-carboline · Harmin · Harmine (Telepathine)
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
- PubChem CID
- 5280953
- ChEMBL
- CHEMBL269538
- Measurements
- 143
- InChIKey
- BXNJHAXVSOCGBA-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
Harmine is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. It has a role as a metabolite, an EC 1.4.3.4 (monoamine oxidase) inhibitor and an anti-HIV agent. It derives from a hydride of a harman.
harmine has been reported in Passiflora phoenicia, Symplocos setchuensis, and other organisms with data available.
Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.
In the body
Harmine has known human metabolites that include Harmol and 6-Hydroxy-harmaline.
NORMAN Suspect List ExchangeS73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
History, discovery and cultural use
Written by this site · every claim referenced
Harmine is an alkaloid isolated from the seeds of Peganum harmala, and is identical to the compound described as banisterine, or telepathine, from Banisteria caapi 1. It is one of the active ingredients of the hallucinogenic drinks prepared in the western Amazon from related plants 1. Under the name banisterine it was, in the 1920s, hailed as a cure for postencephalitic Parkinson's disease 1.
All three sentences follow the MeSH descriptor held in this archive, which states the botanical source, the synonymy with banisterine and telepathine, the Amazonian preparations and the 1920s Parkinson's claim. Nothing above is quoted from Harmine’s own database records; those appear as quotations elsewhere on this plate.
Histories of this field
Scholarship on psychedelics generally, not on Harmine 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 — 143 measurements in this archive, equilibrium constants kept apart from functional readouts.
- Toxicology — nothing published for Harmine. 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 Harmine 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
- C13H12N2OR
- Molecular weight
- 212.25g/molR
- Exact mass
- 212.0950DaR
- cLogP
- 3.03R
- TPSA
- 37.9ŲR
- H-bond donors
- 1R
- H-bond acceptors
- 2R
- Rotatable bonds
- 1R
- Aromatic rings
- 3R
- Heavy atoms
- 16R
- Fraction sp³
- 0.154R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
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.
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.
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 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
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: retina 123.5, spinal cord 116.1, midbrain 93.6, pituitary gland 85.7.
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.
retina
123.5 nTPMspinal cord
116.1 nTPMhypothalamus
103.9 nTPMmidbrain
93.6 nTPMhippocampal formation
86.2 nTPM- Dual specificity protein kinase CLK1CLK17.9 pX86.2
- Serine/threonine-protein kinase pim-3PIM35.4 pX28.4
- Dual specificity protein kinase CLK3CLK35.5 pX22.2
- Dual specificity tyrosine-phosphorylation-regulated kinase 1BDYRK1B6.8 pX17.2
- Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A8.3 pX16.5
- and 15 more
pituitary gland
85.7 nTPMcerebellum
82.9 nTPMbasal ganglia
66.4 nTPMamygdala
65.1 nTPMcerebral cortex
50.9 nTPM
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
liver
3367.1 nTPMsmall intestine
754.5 nTPMduodenum
713.0 nTPMskeletal muscle
152.9 nTPMstomach 1
129.1 nTPMkidney
120.4 nTPMlung
117.8 nTPMspleen
113.2 nTPMthyroid gland
105.7 nTPMcolon
104.7 nTPMsalivary gland
102.9 nTPMurinary bladder
90.0 nTPMheart muscle
82.5 nTPMpancreas
80.2 nTPMadrenal gland
77.8 nTPMsmooth muscle
28.7 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.
12 of this compound’s targets could not be resolved to a gene and are absent from both columns: Casein kinase I delta/epsilon, Casein kinase I isoform delta, Cholinesterase, Cyclin-dependent kinase 1, Cyclin-dependent kinase 1/cyclin B, Cyclin-dependent kinase 2, Cyclin-dependent kinase 2/cyclin A, Cyclin-dependent kinase 5, and 4 more.
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 26 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.
Cytochrome P450 inhibition 1
Inhibition of a drug-metabolising enzyme, which is how interactions arise — the harmala alkaloids' MAO inhibition is the same kind of fact, and appears with the measurements above.
- Cytochrome P450 3A4Potency15,849nMCHEMBL1613886
Published toxicology
— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for Harmine. 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 20
Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| Amine oxidase [flavin-containing] A | Enzymes | Ki | 1.00 | 9.00 | Homo sapiens | CHEMBL5235560 |
| Amine oxidase [flavin-containing] A | Enzymes | Ki | 5.00 | 8.30 | Homo sapiens | CHEMBL1074724 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 1A | Enzymes | Kd | 5.47 | 8.26 | Homo sapiens | CHEMBL5251383 |
| Dual specificity protein kinase CLK1 | Enzymes | Kd | 12.11 | 7.92 | Homo sapiens | CHEMBL5251384 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 1A | Enzymes | Kd | 13.40 | 7.87 | Homo sapiens | CHEMBL5251692 |
| Amine oxidase [flavin-containing] A | Enzymes | Ki | 17.00 | 7.77 | Homo sapiens | CHEMBL1817453 |
| Nischarin | Unclassified | Ki | 22.00 | 7.66 | Homo sapiens | CHEMBL841867 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 1A | Enzymes | Ki | 33.00 | 7.48 | Homo sapiens | CHEMBL2394349 |
| Unchecked | Unclassified | Ki | 49.00 | 7.31 | — organism not recorded | CHEMBL881456 |
| Dual specificity tyrosine-phosphorylation-regulated kinase 1B | Enzymes | Ki | 166 | 6.78 | Homo sapiens | CHEMBL2394348 |
| Alpha2C | Adrenergic receptors | Ki | 810 | 6.09 | Homo sapiens | CHEMBL648620 |
| Alpha2B | Adrenergic receptors | Ki | 1,130 | 5.95 | Homo sapiens | CHEMBL646281 |
| 5-HT6 | Serotonin receptors | Ki | 1,480 | 5.83 | Homo sapiens | CHEMBL618121 |
| Alpha2A | Adrenergic receptors | Ki | 2,540 | 5.60 | Homo sapiens | CHEMBL647969 |
| NET | Monoamine transporters | Ki | 3,260 | 5.49 | Homo sapiens | CHEMBL872666 |
| Glycogen synthase kinase-3 beta | Enzymes | Kd | 3,560 | 5.45 | Homo sapiens | CHEMBL5251694 |
| 5-HT7 | Serotonin receptors | Ki | 5,500 | 5.26 | Homo sapiens | CHEMBL620826 |
| 5-HT2A | Serotonin receptors | Ki | 7,790 | 5.11 | Rattus norvegicus | CHEMBL618693 |
| 5-HT2C | Serotonin receptors | Ki | 9,340 | 5.03 | Homo sapiens | CHEMBL617276 |
| Nischarin | Unclassified | Ki | 13,800 | 4.86 | Homo sapiens | CHEMBL841854 |
Functional readouts 123
IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.
- 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.
3T
Registered studies
0T
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.
- Early phase 11
- Phase 11
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
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.
- NCT05526430Completed · Phase 1
Study of Harmine in Healthy Subjects
- Enrollment
- 27Tactual
- Started
- 2022-09-13
- Sponsor
- James Murrough
Conditions Diabetes Mellitus
Matched “Harmine” in the study’s intervention “Harmine Hydrochloride Capsules”
- NCT04716335Completed · Early phase 1
Neurodynamics of Prosocial Emotional Processing Following Serotonergic Stimulation With N,N-Dimethyltryptamine (DMT) and Harmine in Healthy Subjects
- Enrollment
- 34Tactual
- Started
- 2020-12-01
- Sponsor
- Psychiatric University Hospital, Zurich
Conditions Emotions · Mood · Cognitive Function 1, Social · Empathy
Matched “Harmine” in the study’s intervention “Harmine”
- NCT02379767Completed
Effects of ECT on Monoamine Oxidase A in Depression Investigated With PET
- Enrollment
- 27Tactual
- Started
- 2015-03
- Sponsor
- Medical University of Vienna
Conditions Major Depression
Matched “Harmine” in the study’s intervention “Positron emission tomography of the brain using [11C]harmine”
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 Harmine · Banisterine · Telepathine. 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 Harmine worked.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds. Not legal advice, and an absent record is not a finding that a compound is uncontrolled.
An absent DEA record is not a finding that Harmine is legal. It means this archive holds no DEA passage for it. The Controlled Substances Analogue Enforcement Act reaches substances that appear on no schedule by name, and many compounds here are ring-substituted analogues of scheduled drugs. Nothing on this plate should be read as saying a compound may lawfully be made, held or supplied.
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.
No reference is recorded against any value for this compound. Its measurements come from ChEMBL assay records that carry an assay identifier but no publication, so there is no paper to cite here — an absence in the upstream record, not a judgment about the evidence. The assay identifiers in Every measurement resolve to the records the values were read from.