Methylone
1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one
Overview
Methylone belongs to Entactogens/Empathogens / Cathinones.
Effects
- Euphoria, emotional warmth, empathy and sociability with stimulation, increased energy and talkativeness: an MDMA-like entactogenic effect but generally milder, more stimulant and shorter-lived, with less of MDMA's depth of empathy.
- Sympathetic effects: raised heart rate and blood pressure, dilated pupils, jaw clenching/teeth grinding, sweating, raised body temperature and reduced appetite.
- The brief, less-satisfying reward encourages compulsive redosing. Comedowns bring anxiety, low mood, irritability, insomnia, cognitive fatigue and craving, and can last well into the next day.
Dosing & duration
Oral (swallowed) or insufflated. The values below are approximate ORAL figures.. Not a recommendation. Methylone is short-acting and reinforcing, which drives compulsive redosing and binges: the biggest source of harm. Insufflated doses are lower and faster in onset but harsher and shorter. Use a milligram scale, start low, space out or avoid redosing, keep cool and hydrated (but not excessively), and never combine with other stimulants or serotonergic drugs. Grey-market powders are frequently mis-sold or cut: test the substance.
Dose ranges
75 mg
75–150 mg
150–225 mg
225–325 mg
325 mg +
Duration
15–45 min (oral)
2.5–4 h (oral)
6–24 h (anxiety, low mood, fatigue, craving)
Chemical & Physical Properties
| Formula | C11H13NO3 |
| Molar mass | 207.23 g/mol |
| State | Solid (usually the hydrochloride salt, white to off-white crystalline powder or crystals) |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 0.6 (predicted, XLogP3, free base) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 186028-79-5 |
| CAS (enantiomer) | |
| PubChem CID | 45789647 |
| InChIKey | VKEQBMCRQDSRET-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3 |
| SMILES | CC(C(=O)C1=CC2=C(C=C1)OCO2)NC |
Synonyms
- 3,4-Methylenedioxy-N-methylcathinone
- βk-MDMA
- MDMC
- M1
- Explosion
Pharmacodynamics & Biochemistry
Methylone (3,4-methylenedioxy-N-methylcathinone, βk-MDMA) is the β-keto ('cathinone') analogue of MDMA: MDMA with a ketone on the β-carbon of the side chain. Like MDMA it is a non-selective, substrate-type releaser at the dopamine (DAT), noradrenaline (NET) and serotonin (SERT) transporters, and a much weaker reuptake inhibitor, giving it a mixed stimulant–entactogen profile. It is broadly MDMA-like but somewhat less potent, with a relatively larger dopaminergic contribution and weaker serotonin release, which is thought to underlie its more stimulant and less profoundly empathogenic character. It has essentially no affinity for the 5-HT2A/5-HT2C receptors and is inactive at TAAR1, and it is a considerably weaker substrate for the vesicular monoamine transporter VMAT2 than MDMA (~13-fold), a difference that may shape its serotonergic/neurotoxic profile. In rat brain synaptosomes methylone behaves as a monoamine-releasing agent with release EC50 values of ~133 nM (DAT), ~152 nM (NET) and ~242 nM (SERT): a non-selective releaser of MDMA-like potency and balance. In transfected human (HEK293) cells it inhibits monoamine uptake far more weakly and with a dopamine-over-serotonin bias: IC50 ≈ 0.54 µM (NET), 4.8 µM (DAT) and 15.5 µM (SERT): consistent with a compound that primarily carries monoamines out of the nerve terminal (a releaser) rather than simply blocking their reuptake. Its faster onset and shorter duration than MDMA tend to promote compulsive redosing.
Biological targets
- DAT
- NET
- SERT
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| Dopamine transporter | Ki 2,730 ± 200 nM | Human |
Pharmacokinetics
| Bioavailability | Oral or insufflated, rapid onset |
| Tmax | Not reported |
| Half-life | Reported elimination half-life on the order of a few hours (≈2–7 h across studies), subjective effects are shorter (≈2.5–4 h), which encourages redosing |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic: N-demethylation to methylenedioxycathinone (MDC), and O-demethylenation of the methylenedioxy ring followed by O-methylation (COMT) to hydroxy-methoxy metabolites. CYP enzymes implicated include CYP2D6, CYP2B6, CYP1A2 and CYP2C19 |
| Excretion | Renal |
Toxicology & Safety
Not reported
Methylone is a synthetic cathinone (a β-keto MDMA analogue) sold as a 'bath salts'/'research chemical' powder or crystal, often mis-sold as or cut into 'ecstasy'/MDMA. Its shorter, less euphoric effect than MDMA encourages compulsive redosing and binges, which are the main source of harm. Acute risks are those of a serotonergic stimulant: tachycardia, hypertension, palpitations and cardiovascular strain, hyperthermia (worsened by hot, crowded settings and dehydration), sweating, teeth-grinding, dilated pupils, anxiety, agitation and, at high doses or in binges, stimulant psychosis, seizures and serotonin toxicity. It carries a real serotonin-syndrome risk when combined with MAOIs, SSRIs/SNRIs or other serotonergic drugs, and deaths have occurred, frequently with co-used alcohol or other stimulants. Because identity and strength of grey-market powders vary widely, test the substance, use a milligram scale, start low, avoid or space out redosing, keep cool and hydrated (but do not over-drink water), and never combine with other stimulants or serotonergic medication.[4][5]
Legal Status
US: Schedule I. UK: Class B (since 2010). DE: BtMG Anlage II
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- A recreational stimulant–entactogen used for MDMA- and amphetamine-like euphoria, stimulation, warmth and sociability: usually swallowed or insufflated as a powder/crystal. It is frequently encountered mis-sold as or adulterating 'ecstasy'.
- First patented in 1996 (by Peyton Jacob III and Alexander Shulgin as a potential antidepressant), it re-emerged in the late 2000s as one of the earliest and most widespread 'bath salts'/'legal high' synthetic cathinones, its spread helping drive new-psychoactive-substance legislation.
- It has no accepted medical use and is now controlled in most jurisdictions (US Schedule I, UK Class B, DE Anlage II BtMG).
Sources & Evidence
- PubChem: Methylone (CID 45789647) — identifiers & computed properties
- Baumann MH, Ayestas MA Jr, Partilla JS, et al. (2012). The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology 37:1192-203.
PMID 22169943 · doi:10.1038/npp.2011.304
- 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
- Wikipedia: Methylone — pharmacology (substrate releaser at DAT/NET/SERT, weak VMAT2 substrate, inactive at TAAR1/5-HT2), metabolism, effects, harms & legal status CC BY-SA 4.0
- PsychonautWiki: Methylone — recreational dosage, duration & subjective effects CC BY-SA 4.0
- DEA Diversion Control Division: Controlled Substance Schedules (methylone is Schedule I)
- GOV.UK: Controlled drugs list — methylone is Class B (Misuse of Drugs Act 1971) OGL v3.0
- Anlage II BtMG — Betäubungsmittelgesetz (Gesetze im Internet): Methylon (3,4-Methylendioxy-N-methcathinon, MDMC), verkehrsfähiges aber nicht verschreibungsfähiges Betäubungsmittel