DOET
PubChem records this structure as 2,5-Dimethoxy-4-ethylamphetamine.
Also known as2,5-Dimethoxy-4-ethylamphetamine · 4-Ethyl-2,5-dimethoxyamphetamine · HECATE · 2,5-DIMETHOXY-4-ETHYLAMPHETAMIN · DOET,(-)
1-(4-ethyl-2,5-dimethoxyphenyl)propan-2-amine
- PubChem CID
- 27402
- ChEMBL
- CHEMBL8224
- Measurements
- 14
- InChIKey
- HXJKWPGVENNMCC-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
2,5-Dimethoxy-4-ethylamphetamine is a member of amphetamines.
psychedelic agent; ethyl homolog of dimethoxymethylamphetamine; RN given refers to parent cpd without isomeric designation
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 DOET 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 DOET 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 — 14 measurements in this archive, equilibrium constants kept apart from functional readouts.
- Toxicology — nothing published for DOET. 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 DOET 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
- C13H21NO2R
- Molecular weight
- 223.32g/molR
- Exact mass
- 223.1572DaR
- cLogP
- 2.16R
- TPSA
- 44.5ŲR
- H-bond donors
- 1R
- H-bond acceptors
- 3R
- Rotatable bonds
- 5R
- Aromatic rings
- 1R
- Heavy atoms
- 16R
- Fraction sp³
- 0.538R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
c1ccccc1
Shared with 2-Bromomescaline, 2-TOET, 2-TOM, 2,3,4,5-Tetramethoxyamphetamine, 2,4-dimethoxyamphetamine, 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine and 129 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
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: midbrain 2.4, spinal cord 2.2, retina 0.7, pituitary gland 0.5.
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 nTPMhippocampal formation
6.1 nTPMamygdala
3.5 nTPMmidbrain
2.4 nTPMspinal cord
2.2 nTPMretina
0.7 nTPMcerebellum
0.5 nTPMpituitary gland
0.5 nTPM
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
lung
18.4 nTPMadrenal gland
17.2 nTPMsmooth muscle
15.7 nTPMliver
13.3 nTPMskeletal muscle
10.9 nTPMcolon
8.5 nTPMspleen
7.9 nTPMstomach 1
7.1 nTPMsalivary gland
6.9 nTPMurinary bladder
6.4 nTPMheart muscle
6.3 nTPMsmall intestine
5.0 nTPMthyroid gland
3.2 nTPMkidney
3.1 nTPMduodenum
1.8 nTPMpancreas
1.1 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.
3 of this compound’s targets could not be resolved to a gene and are absent from both columns: 5-HT1, 5-HT2, Serotonin (5-HT) receptor.
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 9 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 DOET in this archive.
Published toxicology
— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for DOET. 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 14
Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| 5-HT2A | Serotonin receptors | Ki | 0.540 | 9.27 | RAT | PMID 2795135 |
| 5-HT2A | Serotonin receptors | Ki | 53.00 | 7.28 | HUMAN | PDSP |
| Serotonin (5-HT) receptor | Serotonin receptors | Kd | 66.07 | 7.18 | Rattus norvegicus | CHEMBL619177 |
| Serotonin (5-HT) receptor | Serotonin receptors | Kd | 66.07 | 7.18 | Rattus norvegicus | CHEMBL619176 |
| 5-HT2B | Serotonin receptors | Ki | 80.00 | 7.10 | BOVINE | PMID 2795135 |
| 5-HT2 | Serotonin receptors | Ki | 100 | 7.00 | Rattus norvegicus | CHEMBL617438 |
| 5-HT2 | Serotonin receptors | Ki | 100 | 7.00 | Rattus norvegicus | CHEMBL617444 |
| 5-HT2A | Serotonin receptors | Ki | 100 | 7.00 | Rattus norvegicus | CHEMBL980602 |
| 5-HT2C | Serotonin receptors | Ki | 101 | 7.00 | Rattus norvegicus | CHEMBL616834 |
| 5-HT2C | Serotonin receptors | Ki | 101 | 7.00 | PIG | PDSP |
| 5-HT1B | Serotonin receptors | Ki | 2,451 | 5.61 | RAT | PDSP |
| 5-HT1A | Serotonin receptors | Ki | 3,930 | 5.41 | RAT | PDSP |
| 5-HT1 | Serotonin receptors | Ki | 4,570 | 5.34 | Rattus norvegicus | CHEMBL615400 |
| Beta2 | Adrenergic receptors | Ki | 8,000 | 5.10 | Mammalian | PMID 8699 |
- 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 DOET 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 DOET · 2,5-Dimethoxy-4-ethylamphetamine · 4-Ethyl-2,5-dimethoxyamphetamine. 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 DOET 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.
- DEA class
- Phenethylamines (D Series) (H)
- Added
- October 1998
As the DEA states it
Quoted whole. The badge above is a reading of these passages and adds nothing to them.
DOET (Class: Phenethylamines (D Series) (H), Added Date: 10-1998)
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
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 9.27 pX
- 02
Beta adrenergic receptor binding in membrane preparations from mammalian brain
Bylund DB, Snyder SH · Molecular pharmacology 1976
- · 1 measurement at 1 target (Ki), strongest Beta2 at 5.10 pX