Butylone
1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one
Overview
Butylone belongs to Entactogens/Empathogens / Cathinones.
Effects
- An MDMA-like entactogen: euphoria, emotional warmth, sociability and stimulation, but generally described as milder and more stimulant/less empathogenic than MDMA or methylone.
- Relatively short-lived (≈3–5 hours) with a rapid onset.
- A harsh comedown and a strong urge to redose are commonly reported, as with other cathinones.
- Common unwanted effects overlap with MDMA: jaw tension, raised heart rate and body temperature, anxiety, insomnia and next-day fatigue.
Dosing & duration
Oral. Not a recommendation. Butylone has never been studied in controlled human trials, so these are only commonly cited community ranges. Its serotonin-toxicity, hyponatraemia and cardiovascular risks, and the strong cathinone urge to redose, make repeated dosing especially dangerous. It is usually handled as the hydrochloride salt.
Dose ranges
≈20 mg
≈40–80 mg
≈80–125 mg
≈125–225 mg
Duration
≈15–60 min
≈1–2 h
≈3–5 h
Chemical & Physical Properties
| Formula | C12H15NO3 |
| Molar mass | 221.25 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 | 1.9 (predicted, XLogP3) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 802575-11-7 |
| CAS (enantiomer) | |
| PubChem CID | 56843046 |
| InChIKey | CGKQZIULZRXRRJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H15NO3/c1-3-9(13-2)12(14)8-4-5-10-11(6-8)16-7-15-10/h4-6,9,13H,3,7H2,1-2H3 |
| SMILES | CCC(C(=O)C1=CC2=C(C=C1)OCO2)NC |
Synonyms
- Butylone
- βk-MBDB
- β-Keto-MBDB
- 3,4-Methylenedioxy-α-ethyl-N-methylcathinone
Pharmacodynamics & Biochemistry
Butylone (βk-MBDB) is a substituted cathinone entactogen: the β-keto analogue of MBDB and the ethyl homologue of methylone (βk-MDMA), making it a cathinone cousin of MDMA. Like MDMA and methylone it raises extracellular serotonin, noradrenaline and dopamine, producing entactogenic and stimulant effects, but it is markedly less potent: acting in the low-micromolar range at the monoamine transporters versus low-nanomolar for MDMA. Its transporter action is mixed and asymmetric. At the noradrenaline and dopamine transporters it is a reuptake inhibitor / blocker (uptake IC50 ≈2.0 µM at NET, ≈2.9 µM at DAT) and does NOT release dopamine (release EC50 >100 µM). At the serotonin transporter it behaves instead as a substrate-type releaser (release EC50 ≈5.5 µM) as well as an uptake inhibitor (IC50 ≈6.2 µM). This 'DAT-blocker but SERT-substrate' profile distinguishes butylone from classical amphetamine-type releasers and underlies its comparatively mild, serotonin-tilted entactogenic character.
Biological targets
- SERT
- NET
- DAT
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| Serotonin transporter | EC50 5,500 nM | Human |
| Dopamine transporter | Ki 440 ± 30 nM | Human |
| Noradrenaline transporter | Ki 8,130 ± 700 nM | Human |
Pharmacokinetics
| Bioavailability | Oral |
| Tmax | Not well characterised (onset ≈15–60 min) |
| Half-life | Not established in humans (duration ≈3–5 h) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic (demethylenation/O-methylation, β-ketone reduction, N-demethylation) |
| Excretion | Renal (hydroxy metabolites as urinary conjugates) |
Toxicology & Safety
Not reported
Butylone carries the combined sympathomimetic and serotonergic risks of an MDMA-like cathinone: raised heart rate and blood pressure, hyperthermia, serotonin toxicity (especially combined with other serotonergic drugs) and hyponatraemia (dangerously low blood sodium from drinking too much plain water). As with other cathinones its relatively short duration and harsh comedown encourage compulsive redosing, which compounds cardiovascular and neurotoxic strain. 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][5]
Legal Status
US: Schedule I. UK: Class B. DE: BtMG Anlage II
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- First synthesised in 1967 (Koeppe, Ludwig & Zeile) but remained obscure until it entered the designer-drug / 'research chemical' market around 2005.
- Sold as a 'bath salt' / legal-high powder and used as an MDMA or methylone substitute before being scheduled in most jurisdictions.
Sources & Evidence
- PubChem: Butylone (CID 56843046) — identifiers & computed properties
- Wikipedia: Butylone — pharmacology, metabolism, effects, history & legal status CC BY-SA 4.0
- PsychonautWiki: Butylone — dosage & duration (community-derived, no controlled human data) CC BY-SA 4.0
- Simmler LD, Buser TA, Donzelli M, et al. (2013). Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458-70.
PMID 22897747 · doi:10.1111/j.1476-5381.2012.02145.x
- Saha K, Li Y, Holy M, et al. (2019). The synthetic cathinones, butylone and pentylone, are stimulants that act as dopamine transporter blockers but 5-HT transporter substrates. Psychopharmacology (Berl) 236:953-962.
PMID 30345459 · doi:10.1007/s00213-018-5075-5
- DEA Diversion Control Division: Controlled Substance Schedules (butylone — Schedule I)
- GOV.UK: Controlled drugs list (Misuse of Drugs legislation) — butylone is a Class B cathinone OGL v3.0
- PubChem computed properties (CID 56843046)