Methylone
Also known asmdmc · BK-MDMA · BETAK-MDMA · .BETA.K-MDMA · M1 (PSYCHEDELIC) · (RS)-methylone
1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one
- PubChem CID
- 45789647
- ChEMBL
- CHEMBL3604010
- Measurements
- 0
- InChIKey
- VKEQBMCRQDSRET-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.
How it acts
A reproducible, simple, and small-scale method for determining the re-uptake and release of monoamines (dopamine, serotonin (5-HT) and norepinephrine) using rat brain synaptosomes /was developed/. These assays were then applied to study the effects of different kinds of non-medically used psychoactive drugs on monoamine re-uptake and release. The phenethylamine derivatives, 4-fluoroamphetamine, 2-methylamino-3,4-methylene-dioxy-propiophenone (methylone), 1-(1,3-benzodioxol-5-yl)-2-butanamine (BDB), and N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), had strong inhibitory effects on the re-uptake of dopamine, 5-HT and norepinephrine. 4-Fluoroamphetamine, methylone and BDB also strongly…
Hazardous Substances Data Bank (HSDB)PMID 17223101Nagai F et al; Eur J Pharmacol 559 (2-3): 132-7 (2007)
Methcathinone and methylone, the beta-ketone analogues of methamphetamine and 3,4-methylenedioxymethamphetamine (MDMA), respectively, were tested for neurotransmitter uptake inhibition in vitro. The beta-ketones were threefold less potent than the nonketo drugs at inhibiting platelet serotonin accumulation, with IC(50)'s of 34.6+/-4.8uM and 5.8+/-0.7 uM, respectively. Methcathinone and methylone were similar in potency to methamphetamine and MDMA at catecholamine transporters individually expressed in transfected glial cells. For dopamine uptake, IC(50)'s were 0.36+/-0.06 uM and 0.82+/-0.17 uM, respectively; for noradrenaline uptake, IC(50) values were 0.51+/-0.10 uM and 1. 2+/-0.1 microM, r…
Hazardous Substances Data Bank (HSDB)PMID 10528135Cozzi NV et al; Eur J Pharmacol 381 (1): 63-9 (1999)
Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.
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 Methylone 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 Methylone 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
- Toxicology — nothing published for Methylone. An absent record is an absence of study, not evidence of safety.
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 Methylone 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
- C11H13NO3R
- Molecular weight
- 207.23g/molR
- Exact mass
- 207.0895DaR
- cLogP
- 1.21R
- TPSA
- 47.6ŲR
- H-bond donors
- 1R
- H-bond acceptors
- 4R
- Rotatable bonds
- 3R
- Aromatic rings
- 1R
- Heavy atoms
- 15R
- Fraction sp³
- 0.364R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
c1ccc2c(c1)OCO2
Shared with 1,3-Benzodioxolyl-N-ethylbutanamine, 1,3-Benzodioxolyl-N-ethylpentanamine, 1,3-Benzodioxolyl-N-methylpentanamine, 1,3-Benzodioxolylbutanamine, 2-Bromo-4,5-methylenedioxyamphetamine, 2,3-Dimethoxy-4,5-methylenedioxyamphetamine and 31 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.
Mechanism, as published
Quoted verbatim from the database named after each passage, never summarized.
A reproducible, simple, and small-scale method for determining the re-uptake and release of monoamines (dopamine, serotonin (5-HT) and norepinephrine) using rat brain synaptosomes /was developed/. These assays were then applied to study the effects of different kinds of non-medically used psychoactive drugs on monoamine re-uptake and rele…
Hazardous Substances Data Bank (HSDB)PMID 17223101Nagai F et al; Eur J Pharmacol 559 (2-3): 132-7 (2007) Methcathinone and methylone, the beta-ketone analogues of methamphetamine and 3,4-methylenedioxymethamphetamine (MDMA), respectively, were tested for neurotransmitter uptake inhibition in vitro. The beta-ketones were threefold less potent than the nonketo drugs at inhibiting platelet serotonin accumulation, with IC(50)'s of 34.6+/-4.8uM a…
Hazardous Substances Data Bank (HSDB)PMID 10528135Cozzi NV et al; Eur J Pharmacol 381 (1): 63-9 (1999) Methylone (2-methylamino-1-[3,4-methylenedioxyphenyl]propane-1-one) is a synthetic hallucinogenic amphetamine analog, like MDMA (3,4-methylenedioxy- methamphetamine), considered to act on monoaminergic systems. However, the psychopharmacological profile of its cytotoxicity as a consequence of monoaminergic deficits remains unclear. We exa…
Hazardous Substances Data Bank (HSDB)PMID 21886563Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3137202
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.
- Perception 1
- matched on “hallucinogen” · in PMID 21886563
- Cognition 1
- matched on “concentrat” · in PMID 21886563
VI · Profile
Affinity rosette
No measurement for Methylone converts to an affinity at a molecular target, so there is no rosette to draw. This is an absence of data, not a finding about the compound.
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 Methylone in this archive.
Published toxicology
— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for Methylone. 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.
No bioactivity measurement is recorded for this compound in the archive.
- 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.
5T
Registered studies
0T
Open or ongoing
5T
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 13
- Phase 23
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.
- Completed4
- Unknown status1
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.
- NCT06215261Completed · Phase 2
An Evaluation of the Safety and Efficacy of Methylone for the Treatment of PTSD
- Enrollment
- 62Tactual
- Started
- 2024-04-04
- Sponsor
- Transcend Therapeutics
Conditions Post Traumatic Stress Disorder
Matched “Methylone” in the study’s intervention “Methylone”
- NCT06303648Completed · Phase 1
A Single, Ascending Dose Evaluation of the Safety, Pharmacokinetics of Methylone in Healthy Subjects
- Enrollment
- 40Tactual
- Started
- 2024-03-20
- Sponsor
- Transcend Therapeutics
Conditions Post Traumatic Stress Disorder
Matched “Methylone” in the study’s intervention “Methylone”
- NCT06237426Completed · Phase 2
An Evaluation of the Long-term Efficacy and Safety of Methylone for the Treatment of PTSD
- Enrollment
- 44Tactual
- Started
- 2024-03-06
- Sponsor
- Transcend Therapeutics
Conditions Post Traumatic Stress Disorder
Matched “Methylone” in the study’s intervention “Methylone”
- NCT05741710Completed · Phase 1 / Phase 2
A Study to Assess the Use of Methylone in the Treatment of PTSD
- Enrollment
- 79Tactual
- Started
- 2023-03-01
- Sponsor
- Transcend Therapeutics
Conditions Post Traumatic Stress Disorder
Matched “Methylone” in the study’s intervention “Methylone”
- NCT05488171Unknown status · Phase 1
Abuse Potential and Human Pharmacology of Methylone
- Enrollment
- 17Tactual
- Started
- 2021-12-01
- Sponsor
- Germans Trias i Pujol Hospital
Conditions Substance Use · Healthy Subjects
Matched “Methylone” in the study’s intervention “Methylone”
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 Methylone · BETAK-MDMA · .BETA.K-MDMA. 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 Methylone 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 Methylone 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.
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
Methylone and monoamine transporters: correlation with toxicity
Sogawa C, Sogawa N, Ohyama K et al. · Current neuropharmacology 2011
- · Mechanism of Action
- 02
The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain
Nagai F, Nonaka R, Satoh Hisashi Kamimura K · European journal of pharmacology 2007
- · Mechanism of Action
- 03
Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines
Cozzi NV, Sievert MK, Shulgin AT et al. · European journal of pharmacology 1999
- · Mechanism of Action