Skip to content
PsychedeliaDokholyan Laboratory
Plate 295 of 545Verified

DALT

PubChem records this structure as N,N-Diallyltryptamine.

Also known asN,N-Diallyltryptamine · Diallyltryptamine · 3-(2-(Diallylamino)ethyl)indole

N-[2-(1H-indol-3-yl)ethyl]-N-prop-2-enylprop-2-en-1-amine

PubChem CID
24839550
Measurements
40
InChIKey
LQEATNFJCMVKAC-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.

— No descriptive record. PubChem holds no attributed passage about DALT under any heading this site reads, and ChEMBL curates no mechanism for it. That is the common case for the research chemicals in this archive: they have structures and binding measurements, and nobody has written a monograph. The measurements are still on the plates that follow.

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 DALT 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 DALT 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 — 40 measurements in this archive, equilibrium constants kept apart from functional readouts.
  • Toxicology — nothing published for DALT. An absent record is an absence of study, not evidence of safety.
  • 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 DALT 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 DALT
Depiction served by PubChem for CID 24839550. Not redrawn here, so the picture and the identity come from the same record.
Formula
C16H20N2R
Molecular weight
240.35g/molR
Exact mass
240.1626DaR
cLogP
3.38R
TPSA
19.0ŲR
H-bond donors
1R
H-bond acceptors
1R
Rotatable bonds
7R
Aromatic rings
2R
Heavy atoms
18R
Fraction sp³
0.250R
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, ADRA1B, ADRA2Ccerebellum — 5.8 nTPM, from ADRA2A, ADRA2C, ADRA1Ahippocampal formation — 6.1 nTPM, from HTR1A, ADRA2C, ADRA1Bamygdala — 6.4 nTPM, from ADRA2C, ADRA1B, HTR2Ahypothalamus — 12.6 nTPM, from HTR2C, ADRA2A, ADRA1Bthalamus — no resolved target expressed herebasal ganglia — 28.2 nTPM, from HTR2C, ADRA2C, HTR6medulla 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: midbrain 92.9, pituitary gland 4.7, spinal cord 1.4, retina 0.7.

Body

heart — 9.4 nTPM, from ADRA2B, ADRA2C, ADRA1Asmooth muscle — 15.7 nTPM, from HTR2B, ADRA1A, ADRA2Alung — 27.2 nTPM, from SLC6A4, ADRA2A, ADRA2Cliver — 56.2 nTPM, from ADRA1A, ADRA1B, ADRA2Bkidney — 33.4 nTPM, from ADRA2C, ADRA2B, ADRA2Astomach — 4.4 nTPM, from HTR2B, ADRA2A, ADRA2Cduodenum — 9.7 nTPM, from SLC6A4, ADRA2A, HTR1Dsmall intestine — 38.0 nTPM, from SLC6A4, HTR1D, HTR2Bcolon — 8.5 nTPM, from HTR2B, ADRA2A, ADRA2Cadrenal gland — 17.2 nTPM, from HTR2B, SLC6A2, ADRA2Cthyroid gland — 8.7 nTPM, from ADRA2A, HTR2B, ADRA2Cpancreas — 28.8 nTPM, from ADRA2A, ADRA2C, SLC6A4urinary bladder — 14.8 nTPM, from ADRA2A, ADRA2C, ADRA2Bskeletal muscle — 6.0 nTPM, from ADRA2B, ADRA2C, ADRA2Aspleen — 20.8 nTPM, from ADRA2C, ADRA2A, ADRA1Bsalivary gland — 6.5 nTPM, from ADRA2A, ADRA1A, ADRA2B
093 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. midbrain

    92.9 nTPM

  2. basal ganglia

    28.2 nTPM

  3. cerebral cortex

    18.2 nTPM

  4. hypothalamus

    12.6 nTPM

  5. amygdala

    6.4 nTPM

  6. hippocampal formation

    6.1 nTPM

  7. cerebellum

    5.8 nTPM

  8. pituitary gland

    4.7 nTPM

  9. spinal cord

    1.4 nTPM

  10. retina

    0.7 nTPM

Peripheral & autonomic

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

  1. liver

    56.2 nTPM

  2. small intestine

    38.0 nTPM

  3. kidney

    33.4 nTPM

  4. pancreas

    28.8 nTPM

  5. lung

    27.2 nTPM

  6. spleen

    20.8 nTPM

  7. adrenal gland

    17.2 nTPM

  8. smooth muscle

    15.7 nTPM

  9. urinary bladder

    14.8 nTPM

  10. duodenum

    9.7 nTPM

  11. heart muscle

    9.4 nTPM

  12. thyroid gland

    8.7 nTPM

  13. colon

    8.5 nTPM

  14. salivary gland

    6.5 nTPM

  15. skeletal muscle

    6.0 nTPM

  16. stomach 1

    4.4 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.

2 of this compound’s targets could not be resolved to a gene and are absent from both columns: Sigma 1, Sigma 2.

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

5-HT2B — Ki 7.21 pX5-HT1A — Ki 7.00 pX5-HT1E — Ki 6.42 pX5-HT2C — Ki 6.41 pX5-HT1D — Ki 6.16 pX5-HT2A — Ki 6.15 pX5-HT6 — Ki 5.76 pXD3 — Ki 6.17 pXAlpha2A — Ki 6.91 pXAlpha2B — Ki 6.52 pXAlpha2C — Ki 6.05 pXAlpha1B — Ki 5.90 pXAlpha1A — Ki 5.78 pXKOR — Ki 5.61 pXSigma 1 — Ki 7.00 pXSigma 2 — Ki 6.45 pXSERT — Ki 6.82 pXNET — Ki 6.00 pXDAT — Ki 5.90 pX5-HT2B5-HT1A5-HT1E5-HT2C5-HT1D5-HT2A5-HT6D3Alpha2AAlpha2BAlpha2CAlpha1BAlpha1AKORSigma 1Sigma 2SERTNETDAT579
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 DALT in this archive.

Published toxicology

— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for DALT. 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 40

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

TargetClassTypeValue (nM)pXOrganismAssay
5-HT2BSerotonin receptorsKi61.007.21HUMANPMID 29499272
5-HT2BSerotonin receptorsKi61.667.21Homo sapiensCHEMBL3756280
5-HT1ASerotonin receptorsKi1007.00HUMANPMID 29499272
5-HT1ASerotonin receptorsKi1007.00Homo sapiensCHEMBL3756275
Sigma 1Sigma receptorsKi1007.00Homo sapiensCHEMBL3756496
Sigma 1Sigma receptorsKi1017.00RATPMID 29499272
Alpha2AAdrenergic receptorsKi1236.91Homo sapiensCHEMBL3756288
Alpha2AAdrenergic receptorsKi1246.91HUMANPMID 29499272
H1UnclassifiedKi1266.90Homo sapiensCHEMBL3756492
H1UnclassifiedKi1276.90HUMANPMID 29499272
SERTMonoamine transportersKi1506.82HUMANPMID 29499272
SERTMonoamine transportersKi1516.82Homo sapiensCHEMBL3756500
Alpha2BAdrenergic receptorsKi3026.52Homo sapiensCHEMBL3756488
Alpha2BAdrenergic receptorsKi3056.52HUMANPMID 29499272
UncheckedUnclassifiedKi3556.45— organism not recordedCHEMBL3756497
Sigma 2Sigma receptorsKi3566.45RATPMID 29499272
5-HT1ESerotonin receptorsKi3786.42HUMANPMID 29499272
5-HT1ESerotonin receptorsKi3806.42Homo sapiensCHEMBL3756278
5-HT2CSerotonin receptorsKi3856.41HUMANPMID 29499272
5-HT2CSerotonin receptorsKi3896.41Homo sapiensCHEMBL3756281
D3Dopamine receptorsKi6726.17HUMANPMID 29499272
D3Dopamine receptorsKi6766.17Homo sapiensCHEMBL3756491
5-HT1DSerotonin receptorsKi6896.16HUMANPMID 29499272
5-HT1DSerotonin receptorsKi6926.16Homo sapiensCHEMBL3756277
5-HT2ASerotonin receptorsKi7016.15HUMANPMID 29499272
5-HT2ASerotonin receptorsKi7086.15Homo sapiensCHEMBL3756279
Alpha2CAdrenergic receptorsKi8916.05Homo sapiensCHEMBL3756489
Alpha2CAdrenergic receptorsKi9016.05HUMANPMID 29499272
NETMonoamine transportersKi1,0006.00Homo sapiensCHEMBL3756499
NETMonoamine transportersKi1,1215.95HUMANPMID 29499272
Alpha1BAdrenergic receptorsKi1,2595.90Homo sapiensCHEMBL3756286
DATMonoamine transportersKi1,2595.90Homo sapiensCHEMBL3756498
Alpha1BAdrenergic receptorsKi1,3695.86HUMANPMID 29499272
DATMonoamine transportersKi1,4065.85HUMANPMID 29499272
Alpha1AAdrenergic receptorsKi1,6605.78Homo sapiensCHEMBL3756285
Alpha1AAdrenergic receptorsKi1,6635.78HUMANPMID 29499272
5-HT6Serotonin receptorsKi1,7185.76HUMANPMID 29499272
5-HT6Serotonin receptorsKi1,7385.76Homo sapiensCHEMBL3756283
KOROpioid receptorsKi2,4555.61Homo sapiensCHEMBL3756494
KOROpioid receptorsKi2,4775.61HUMANPMID 29499272
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 DALT 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 DALT · N,N-Diallyltryptamine · Diallyltryptamine. 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 DALT 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

    Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs

    Klein LM, Cozzi NV, Daley PF et al. · Neuropharmacology 2018

    • · 20 measurements at 20 targets (Ki), strongest 5-HT2B at 7.21 pX

    PMID 29499272