Eutylone
1-(1,3-benzodioxol-5-yl)-2-(ethylamino)butan-1-one
Overview
Eutylone belongs to Entactogens/Empathogens / Cathinones.
Effects
- A stimulant-leaning cathinone: strong stimulation and alertness with only mild entactogenic warmth: generally described as less euphoric and less empathogenic than MDMA.
- Long-lasting, with pronounced and persistent insomnia a hallmark complaint.
- A harsh comedown, anxiety and a strong urge to redose are commonly reported: especially by people who took it believing it was MDMA.
- Common sympathomimetic effects: raised heart rate and body temperature, jaw tension, appetite loss and next-day fatigue.
Dosing & duration
Not reported
Dose ranges
Duration
Chemical & Physical Properties
| Formula | C13H17NO3 |
| Molar mass | 235.28 g/mol |
| State | Solid (usually the hydrochloride salt) |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 2.3 (predicted, XLogP3) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 802855-66-9 |
| CAS (enantiomer) | |
| PubChem CID | 57360686 |
| InChIKey | YERSNXHEOIYEGX-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H17NO3/c1-3-10(14-4-2)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10,14H,3-4,8H2,1-2H3 |
| SMILES | CCC(C(=O)C1=CC2=C(C=C1)OCO2)NCC |
Synonyms
- Eutylone
- βk-EBDB
- N-Ethylbutylone
- β-keto-1,3-benzodioxolyl-N-ethylbutanamine
Pharmacodynamics & Biochemistry
Eutylone (βk-EBDB, N-ethylbutylone) is a substituted cathinone stimulant–entactogen: the N-ethyl homologue of butylone and a member of the methylenedioxy ('methylone-type') cathinone family. It interacts with the monoamine transporters with dopamine-transporter–preferring potency (uptake IC50 ≈120 nM at DAT, ≈690 nM at SERT, ≈1,280 nM at NET), raising extracellular dopamine, serotonin and noradrenaline. Its marked dopamine preference gives it a more stimulant and less empathogenic character than MDMA or its N-methyl homologue butylone: users typically report weaker euphoria and emotional warmth but strong, long-lasting stimulation and pronounced insomnia. Harm-reduction significance: from 2019–2020 eutylone spread worldwide (after bans on the related ephylone) and was frequently mis-sold as, or used to cut, MDMA: by 2021 it was the most common cathinone identified by the US DEA. Because it feels 'weaker' and less euphoric than the MDMA a buyer expects, redosing is common, which drives stimulant toxicity and days-long insomnia.
Biological targets
- DAT
- SERT
- NET
Binding & functional measurements
Pharmacokinetics
| Bioavailability | Oral |
| Tmax | Not well characterised |
| Half-life | Not established in humans (effects reported as long-lasting) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic (N-deethylation, β-ketone reduction, demethylenation/O-methylation) |
| Excretion | Renal (presumed, hydroxy metabolites as conjugates) |
Toxicology & Safety
Not reported
Eutylone carries the sympathomimetic and serotonergic risks of an MDMA-like cathinone: raised heart rate and blood pressure, hyperthermia, agitation and anxiety, serotonin toxicity (especially combined with other serotonergic drugs) and hyponatraemia. Its most distinctive hazard is practical: it is frequently sold AS MDMA, but is more stimulant, less euphoric and much longer-lasting, with severe insomnia that can persist for days, so people redose expecting 'weak ecstasy', compounding cardiovascular strain and sleeplessness. It featured heavily in the 2019–2021 wave of cathinone-related hospitalisations and deaths. It has never been studied in controlled human trials and its safety margin is unknown. Missing data must never be read as evidence of safety.[2][3]
Legal Status
US: Schedule I. UK: Class B. DE: BtMG Anlage II
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- Developed in the 1960s. First reported to the EMCDDA in 2014.
- Became widespread internationally in 2019–2020 following bans on the related compound ephylone, and was widely mis-sold as MDMA. In 2021 it was the most common cathinone identified by the US DEA.
Sources & Evidence
- PubChem: Eutylone (CID 57360686) — identifiers & computed properties
- Wikipedia: Eutylone — pharmacology, prevalence as an MDMA substitute, history & legal status CC BY-SA 4.0
- Glatfelter GC, Walther D, Evans-Brown M, et al. (2021). Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation. ACS Chem Neurosci 12:1170-1177.
PMID 33689284 · doi:10.1021/acschemneuro.0c00797
- DEA Diversion Control Division: Controlled Substance Schedules (eutylone — Schedule I, positional isomer of pentylone)
- GOV.UK: Controlled drugs list (Misuse of Drugs legislation) — eutylone is a Class B cathinone OGL v3.0
- PubChem computed properties (CID 57360686)