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PsychedeliaDokholyan Laboratory
Plate 511 of 545Verified

Tetrahydroharmine

Also known as(+)-Tetrahydroharmine · 1,2,3,4-Tetrahydroharmine · (R)-Tetrahydroharmine · AC1L9CA2 · (1r)-tetrahydroharmine

(1R)-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

PubChem CID
442118
Measurements
1
InChIKey
ZXLDQJLIBNPEFJ-MRVPVSSYSA-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

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 Tetrahydroharmine 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 Tetrahydroharmine 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 — 1 measurement in this archive, equilibrium constants kept apart from functional readouts.
  • Toxicology — nothing published for Tetrahydroharmine. An absent record is an absence of study, not evidence of safety.
  • Legal — listed by the DEA among its drugs of concern, with no schedule stated in the record held here.
  • 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 Tetrahydroharmine 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 Tetrahydroharmine
Depiction served by PubChem for CID 442118. Not redrawn here, so the picture and the identity come from the same record.
Formula
C13H16N2OR
Molecular weight
216.28g/molR
Exact mass
216.1263DaR
cLogP
2.38R
TPSA
37.0ŲR
H-bond donors
2R
H-bond acceptors
2R
Rotatable bonds
1R
Aromatic rings
2R
Heavy atoms
16R
Fraction sp³
0.385R
Formal charge
0R

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

Bemis–Murcko scaffold

c1ccc2c3c([nH]c2c1)CNCC3

Shared with 6-MeO-THH, Pinoline. 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 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.

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 — 21.0 nTPM, from DYRK1Acerebellum — 22.2 nTPM, from DYRK1Ahippocampal formation — 16.5 nTPM, from DYRK1Aamygdala — 16.4 nTPM, from DYRK1Ahypothalamus — 15.6 nTPM, from DYRK1Athalamus — no resolved target expressed herebasal ganglia — 16.9 nTPM, from DYRK1Amedulla 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 25.7, pituitary gland 18.6, midbrain 13.4, spinal cord 12.6.

Body

heart — 27.1 nTPM, from DYRK1Asmooth muscle — 22.5 nTPM, from DYRK1Alung — 20.3 nTPM, from DYRK1Aliver — 18.5 nTPM, from DYRK1Akidney — 18.6 nTPM, from DYRK1Astomach — 21.5 nTPM, from DYRK1Aduodenum — 17.6 nTPM, from DYRK1Asmall intestine — 19.7 nTPM, from DYRK1Acolon — 19.8 nTPM, from DYRK1Aadrenal gland — 19.2 nTPM, from DYRK1Athyroid gland — 24.1 nTPM, from DYRK1Apancreas — 20.3 nTPM, from DYRK1Aurinary bladder — 21.8 nTPM, from DYRK1Askeletal muscle — 43.4 nTPM, from DYRK1Aspleen — 28.6 nTPM, from DYRK1Asalivary gland — 19.1 nTPM, from DYRK1A
043 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. retina

    25.7 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX25.7

  2. cerebellum

    22.2 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX22.2

  3. cerebral cortex

    21.0 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX21.0

  4. pituitary gland

    18.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX18.6

  5. basal ganglia

    16.9 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX16.9

  6. hippocampal formation

    16.5 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX16.5

  7. amygdala

    16.4 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX16.4

  8. hypothalamus

    15.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX15.6

  9. midbrain

    13.4 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX13.4

  10. spinal cord

    12.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX12.6

Peripheral & autonomic

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

  1. skeletal muscle

    43.4 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX43.4

  2. spleen

    28.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX28.6

  3. heart muscle

    27.1 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX27.1

  4. thyroid gland

    24.1 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX24.1

  5. smooth muscle

    22.5 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX22.5

  6. urinary bladder

    21.8 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX21.8

  7. stomach 1

    21.5 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX21.5

  8. lung

    20.3 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX20.3

  9. pancreas

    20.3 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX20.3

  10. colon

    19.8 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX19.8

  11. small intestine

    19.7 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX19.7

  12. adrenal gland

    19.2 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX19.2

  13. salivary gland

    19.1 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX19.1

  14. kidney

    18.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX18.6

  15. liver

    18.5 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX18.5

  16. duodenum

    17.6 nTPM
    • Dual specificity tyrosine-phosphorylation-regulated kinase 1ADYRK1A5.5 pX17.6

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

Dual specificity tyrosine-phosphorylation-regulated kinase 1A — AC50 5.52 pXDual specificity…579
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 Tetrahydroharmine in this archive.

Published toxicology

— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for Tetrahydroharmine. 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.

Functional readouts 1

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

TargetClassTypeValue (nM)pXOrganismAssay
Dual specificity tyrosine-phosphorylation-regulated kinase 1AEnzymesAC502,9875.52Rattus norvegicusCHEMBL1794557
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.

— No registered study names Tetrahydroharmine as an intervention. That is an absence of registered research, not evidence about the compound. Most of this archive has never been the subject of a registered trial.

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 Tetrahydroharmine · (+)-Tetrahydroharmine · 1,2,3,4-Tetrahydroharmine. Run this search at the registry.

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

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.