Methylone

Not to be confused with ethylone.

Methylone
Clinical data
Other names3,4-Methylenedioxy-N-methylcathinone; 3,4-Methylenedioxymethcathinone; MDMC; MDMCAT; β-Keto-MDMA; βk-MDMA; M1; TSND-201; TSND201; MeONE; EASE; EMM; Explosion
Routes of
administration		Common: oral, insufflation[1]
Uncommon: IV or IM injection, rectal[1]
ATC code
  • None
Legal status
Legal status
  • AU: Unscheduled
  • BR: Class F2 (Prohibited psychotropics)[2]
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Schedule II [1]
  • PL: I-P[3]
Pharmacokinetic data
Onset of action0.5 hours[4]
Elimination half-life5.8–6.9 hours[4]
Duration of action2.5–3.0 hours[4]
Identifiers
IUPAC name
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13NO3
Molar mass207.229 g·mol−1
3D model (JSmol)
Solubility in water357 mg/mL (20 °C)
SMILES
  • CC(NC)C(=O)C1=CC=C(OCO2)C2=C1
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 Y
  • Key:VKEQBMCRQDSRET-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an entactogen and stimulant drug of the amphetamine, cathinone, and benzodioxole families related to 3,4-methylenedioxymethamphetamine (MDMA; "ecstasy").[5][1][6] It is the β-keto or cathinone analogue of MDMA.[6][1] Methylone is usually taken orally, but is also used by other routes.[5][1]

The drug acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][7][8][9] It has much less activity at the vesicular monoamine transporter 2 (VMAT2) than MDMA[5][10] and may have less serotonergic neurotoxicity.[5][11][12][7] In contrast to certain other entactogens like MDMA, methylone does not appear to be a significant agonist of the serotonin 5-HT2 receptors.[5][12][13][14] Methylone is similar in its effects to MDMA, producing entactogenic effects and euphoria, but has a reputation of being gentler than MDMA and only lasts about half as long.[5][15] Side effects of methylone include tachycardia, hangover, and insomnia.[5] It may have reduced negative after-effects compared to MDMA.[5] Methylone's onset is about 0.5 hours and its duration is about 2 to 3 hours.[5][4]

Methylone was first synthesized by Peyton Jacob III and Alexander Shulgin in the mid-1990s[16] and was first described in the literature in 1996.[1][17] It was patented by Jacob and Shulgin as a potential antidepressant and antiparkinsonian agent, but was never developed or marketed for such uses.[1][17] Methylone was encountered as a designer and recreational drug by 2004 and has become a controlled substance in many countries.[6][1] Similarly to MDMA, it is being developed for the treatment of post-traumatic stress disorder (PTSD).[18][19][20]

  1. ^ a b c d e f g h Karila L, Billieux J, Benyamina A, Lançon C, Cottencin O (September 2016). "The effects and risks associated to mephedrone and methylone in humans: A review of the preliminary evidences". Brain Res Bull. 126 (Pt 1): 61–67. doi:10.1016/j.brainresbull.2016.03.005. PMID 26995278.
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.
  4. ^ a b c d Poyatos L, Lo Faro AF, Berardinelli D, Sprega G, Malaca S, Pichini S, et al. (November 2022). "Methylone and MDMA Pharmacokinetics Following Controlled Administration in Humans". International Journal of Molecular Sciences. 23 (23): 14636. doi:10.3390/ijms232314636. PMC 9736016. PMID 36498963.
  5. ^ a b c d e f g h i j Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  6. ^ a b c Shulgin A, Manning T, Daley PF (2011). "#93. Methylone". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. pp. 228–230. ISBN 978-0-9630096-3-0.
  7. ^ a b Cite error: The named reference BaumannAyestasPartilla2012 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference BaumannPartillaLehner2013 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference ElmoreDillon-CarterPartilla2017 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference CozziSievertShulgin1999 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference DazianiLoFaroMontana2023 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference López-ArnauCamarasaCarbó2022 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Warner-SchmidtStogniew2024 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference LuethiKolaczynskaWalter2019 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Shulgin2004 was invoked but never defined (see the help page).
  16. ^ James W. Jesso (1 June 2023). "Entactogens, MDMA, and Bringing New Love Drugs To Market (with Matthew Baggott)". Adventures Through The Mind (Podcast). Retrieved 27 January 2025.
  17. ^ a b WO 9639133, Jacob III P, Shulgin AT, "Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones", published 1996-12-12, assigned to Neurobiological Technologies Inc. 
  18. ^ Cite error: The named reference AdisInsight was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Synapse was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference FierceBiotech2023 was invoked but never defined (see the help page).
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