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Revision as of 09:15, 24 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CAS_number').← Previous edit Latest revision as of 08:30, 16 January 2025 edit undoAlyInWikiWonderland (talk | contribs)Autopatrolled, Extended confirmed users83,252 edits →Pharmacodynamics: Trim a ref cite with duplicate vals. 
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{{Short description|Group of stereoisomers}}
{{Drugbox
{{Redirect|MDMC}}
| verifiedrevid = 455321417
{{Distinguish|ethylone}}
| IUPAC_name = (±)-2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one
{{cs1 config|name-list-style=vanc|display-authors=6}}
| image = MDMC.PNG
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457117430
| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
| image = MDMC.svg
| width =
| image2 = MDMC-3d-sticks.png | image2 = MDMC-3d-sticks.png
| width2 =
| imagename = 1 : 1 mixture (racemate)
| drug_name = Methylone


<!--Clinical data--> <!-- Clinical data -->
| tradename = | tradename =
| pregnancy_category = | pregnancy_category =
| legal_AU = Unscheduled | legal_AU = Unscheduled
| legal_CA = Unscheduled | legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_UK = Illegal (Class B)
| legal_CA = Schedule I
| legal_UK = Class B
| legal_US = Schedule I | legal_US = Schedule I
| legal_DE = Anlage II
| legal_status = I-P(])<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id = WDU20111050614 | publisher = Internetowy System Aktów Prawnych | accessdate = 17 June 2011}}</ref>
| legal_UN = Schedule II
| routes_of_administration = ], ], ]
| legal_status = <small>{{abbreviation|PL|Poland}}</small>: I-P<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 17 June 2011}}</ref>
| routes_of_administration = Common: ], ]<br />Uncommon: <abbr title="Intravenous">IV</abbr> or <abbr title="Intramuscular">IM</abbr> ], ]


<!--Identifiers--> <!-- Pharmacokinetic data -->
| bioavailability =
| CAS_number_Ref = {{cascite|correct|??}}
| protein_bound =
| CAS_number = <!-- blanked - oldvalue: 186028-79-5 -->
| metabolism =
| metabolites =
| onset = 0.5 hours<ref name="pmid36498963" />
| elimination_half-life = 5.8–6.9 hours<ref name="pmid36498963">{{cite journal | vauthors = Poyatos L, Lo Faro AF, Berardinelli D, Sprega G, Malaca S, Pichini S, Huestis MA, Papaseit E, Pérez-Mañá C, Busardò FP, Farré M | title = Methylone and MDMA Pharmacokinetics Following Controlled Administration in Humans | journal = International Journal of Molecular Sciences | volume = 23 | issue = 23 | page = 14636 | date = November 2022 | pmid = 36498963 | pmc = 9736016 | doi = 10.3390/ijms232314636 | doi-access = free }}</ref>
| duration_of_action = 2.5–3.0 hours<ref name="pmid36498963" />
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 186028-79-5
| CAS_supplemental = (racemic)<br />{{CAS|191916-41-3}} (+) | CAS_supplemental = (racemic)<br />{{CAS|191916-41-3}} (+)
| ATC_prefix = none | ATC_prefix = None
| ATC_suffix = | ATC_suffix =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = L4I4B1R01F
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C20126
| PubChem = 27281606
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106350
| synonyms = 3,4-Methylenedioxy-''N''-methylcathinone; Methylenedioxymethcathinone; MDMC; β-Keto-MDMA; βk-MDMA; M1; TSND-201; TSND201

<!-- Chemical data -->
| C=11 | H=13 | N=1 | O=3
| SMILES = CC(NC)C(=O)C1=CC=C(OCO2)C2=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VKEQBMCRQDSRET-UHFFFAOYSA-N | StdInChIKey = VKEQBMCRQDSRET-UHFFFAOYSA-N
| PubChem = 27281606
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106350


<!--Chemical data--> <!-- Physical data -->
| C=11 | H=13 | N=1 | O=3
| molecular_weight = 207.23 g/mol
| smiles = CC(NC)C(=O)C1=CC=C(OCO2)C2=C1
| solubility = 357 | solubility = 357
}} }}


'''Methylone''', also known as '''3,4-methylenedioxy-''N''-methylcathinone''' ('''MDMC'''), is an ] and ] ]. It is a member of the ], ] and ] classes.
'''Methylone''', also known as "M1", '''3,4-methylenedioxy-''N''-methylcathinone''', '''bk-MDMA''', and in the UK as '''Arlone''', is an ] and ] of the ], ], and ] classes. It was originally patented by Nick Wald and Adam Fantoma in 1996 as an antidepressant.<ref>{{Cite patent|WO|9639133}}</ref> The more intuitive abbreviation MDMC unfortunately can not be used for this chemical, since it had already been given to another earlier Shulgin creation, ]. Methylone is a close ] ] of ], differing by the addition of a β-] ].<ref name="pmid10528135">{{cite journal | author = Cozzi NV, Sievert MK, Shulgin AT, Jacob P, Ruoho AE | title = Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines | journal = European Journal of Pharmacology | volume = 381 | issue = 1 | pages = 63–9 | year = 1999 | month = September | pmid = 10528135 | doi = 10.1016/S0014-2999(99)00538-5| url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(99)00538-5}}</ref>


Methylone is a slight modification of ] (MDMA, also known as ecstasy). It was first synthesized by the chemists Peyton Jacob III and ] in 1996 for potential use as an antidepressant.<ref>{{Cite patent|country=WO|number=9639133|title=Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones|pubdate=1996-12-12|assign=]|inventor = Jacob III P, ] }}</ref> Methylone has been sold for ], taking advantage of the absence of legal prohibition of this compound in many countries.{{Citation needed|date=July 2018}}
== Recreational use ==


== Chemistry ==
]
Methylone is the substituted cathinone ] of 3,4-methylenedioxymethamphetamine (MDMA) and the 3,4-] analog of ]. The only structural difference of methylone with respect to MDMA is the substitution of 2 hydrogen atoms by 1 oxygen atom in the β position of the ] core, forming a ] ].<ref name="pmid10528135">{{cite journal | vauthors = Cozzi NV, Sievert MK, Shulgin AT, Jacob P, Ruoho AE | title = Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines | journal = European Journal of Pharmacology | volume = 381 | issue = 1 | pages = 63–69 | date = September 1999 | pmid = 10528135 | doi = 10.1016/S0014-2999(99)00538-5 }}</ref>

At the end of 2004, a new ] called "Explosion" appeared in the Netherlands. This drug was sold as a liquid via the internet and in ] "smartshops" (known as "headshops" in the United States and some other countries), stores selling at the time non-scheduled, usually becoming illegal within a year of becoming well-known, ] ]s such as '']'', ] and other ] substitutes like ] and ]. The product is advertised as a "room odorizer" and is sold in plastic tubes containing 5 mL of liquid. The tubes cost between €10 and €15 ($13–$20) and do not present any information about the composition of Explosion; they contain only a label saying "Room odorizer Vanilla. Do not ingest" and "Keep away from children. Never use more than one bottle". Users have mentioned ingesting the liquid to reach euphoric stimulating effects similar to those of MDMA.<ref>http://www.erowid.org/chemicals/methylone/methylone_info1.shtml</ref> The label circumvents Dutch regulations for illicit drugs and psychoactive substances when intentionally used for intoxication. Analysis of "Explosion" has confirmed that the active ingredient is methylone.{{Citation needed|date=January 2010}}


== Effects == == Effects ==
=== Resemblance to MDMA ===
{{See also|MDMA}}
], ] and ].<br />Right: ], ], and methylone]]


Methylone substitutes for MDMA in rats trained to discriminate MDMA from ]. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline.<ref>{{cite journal | vauthors = Dal Cason TA, Young R, Glennon RA | title = Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs | journal = Pharmacology, Biochemistry, and Behavior | volume = 58 | issue = 4 | pages = 1109–1116 | date = December 1997 | pmid = 9408221 | doi = 10.1016/s0091-3057(97)00323-7 | publisher = Elsevier BV | s2cid = 9704972 }}</ref> Further, also in common with MDMA, methylone acts on monoaminergic systems. '']'', methylone has one third the potency of MDMA at inhibiting platelet serotonin accumulation and about the same in its inhibiting effects on the dopamine and noradrenaline transporters.<ref>{{cite journal | vauthors = Cozzi NV, Sievert MK, Shulgin AT, Jacob III P, Ruoho AE |title=Methcathinone and 2 methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters |journal=Soc. Neurosci. Abs. |volume=24 |issue=341.8 |year=1998}}</ref><ref>{{cite journal | vauthors = Cozzi NV, Shulgin AT, Ruoho AE |title= Methcathinone (MCAT) and 2-methylamino-1-(3,4 methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit serotonin uptake into human platelets |journal=Amer. Chem. Soc. Div. Med. Chem. Abs. |volume=215 |issue=152 |year=1998}}</ref><ref name="pmid10528135"/>
Reported dosages range from 100 to 250&nbsp;mg orally.<ref name="erowid.org">http://www.erowid.org/chemicals/methylone/methylone_dose.shtml.</ref> Some respondents say that increasing dose with methylone beyond 100–180&nbsp;mg causes increased physical effects and does not substantially improve the empathic cognitive effects.<ref name="erowid.org"/>


In spite of these behavioral and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. ] wrote of the former:<ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online | url-status = dead | archive-url = https://web.archive.org/web/20100413235500/http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | archive-date = 2010-04-13 | access-date = 2010-01-17 }}</ref>
The effects of methylone may include the following:


{{blockquote|" has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA."}}
; ]
* ]
* ] or ], and ] or ], depending on the individual.
* An increase in ].
* ] and ]
* ]/], ]s, and ], depending on the individual, and in all individuals with high dosage or extended use.


In acute pharmacological studies of methylone (50–300{{nbsp}}mg) in humans, the drug produced physiological and psychological effects including increased ], ], ], ], ], ], feelings of ], enhanced ], increased ], and ].<ref name="pmid36873994">{{cite journal | vauthors = Poyatos L, Pérez-Mañá C, Hladun O, Núñez-Montero M, de la Rosa G, Martín S, Barriocanal AM, Carabias L, Kelmendi B, Taoussi O, Busardò FP, Fonseca F, Torrens M, Pichini S, Farré M, Papaseit E | title = Pharmacological effects of methylone and MDMA in humans | journal = Frontiers in Pharmacology | volume = 14 | issue = | pages = 1122861 | date = 2023 | pmid = 36873994 | pmc = 9981643 | doi = 10.3389/fphar.2023.1122861 | doi-access = free }}</ref><ref name="pmid34440023">{{cite journal | vauthors = Poyatos L, Papaseit E, Olesti E, Pérez-Mañá C, Ventura M, Carbón X, Grifell M, Fonseca F, Torrens M, de la Torre R, Farré M | title = A Comparison of Acute Pharmacological Effects of Methylone and MDMA Administration in Humans and Oral Fluid Concentrations as Biomarkers of Exposure | journal = Biology | volume = 10 | issue = 8 | page = 788 | date = August 2021 | pmid = 34440023 | pmc = 8389614 | doi = 10.3390/biology10080788 | doi-access = free }}</ref> The studies found that the effects of methylone were similar to or milder than those of MDMA.<ref name="pmid36873994" /><ref name="pmid34440023" /> Methylone had a faster ] and its subjective effects wore off sooner than MDMA, which might lead to a redosing pattern of use.<ref name="pmid36873994" /> The ] of methylone, as measured by for instance ] responses, appeared to be similar to that of MDMA.<ref name="pmid36873994" /> However it also has less off-target effects than MDMA which may be an advantage for medical applications.<ref>{{cite journal | vauthors = Warner-Schmidt J, Pittenger C, Stogniew M, Mandell B, Olmstead SJ, Kelmendi B | title = Methylone, a rapid acting entactogen with robust anxiolytic and antidepressant-like activity | journal = Frontiers in Psychiatry | volume = 13 | pages = 1041277 | date = 2022 | pmid = 36704743 | pmc = 9873307 | doi = 10.3389/fpsyt.2022.1041277 | doi-access = free }}</ref><ref name="pmid36873994" /><ref>{{cite journal | vauthors = Warner-Schmidt J, Stogniew M, Mandell B, Rowland RS, Schmidt EF, Kelmendi B | title = Methylone is a rapid-acting neuroplastogen with less off-target activity than MDMA | journal = Frontiers in Neuroscience | volume = 18 | pages = 1353131 | date = 2024-02-07 | pmid = 38389788 | pmc = 10882719 | doi = 10.3389/fnins.2024.1353131 | doi-access = free }}</ref>
; ]
* ] and ]
* ] and ]
* ] and ]
* ] and ]
* ]
* ] and ]


== Pharmacology ==
Most of these effects are very similar to those of other ]s.


=== Resemblance to MDMA === === Pharmacodynamics ===
Methylone acts as a mixed ] and ] of ], ], and ].<ref name="pmid10528135"/><ref name="pmid17223101">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref> In comparison to MDMA, it has approximately 3-fold lower ] for the ], while its affinity for the ] and ]s is similar.<ref name="pmid10528135"/><ref name="pmid17223101"/> Notably, methylone's affinity for the ] (VMAT2) is about 13-fold lower than that of MDMA.<ref name="pmid10528135"/> The results of these differences in pharmacology relative to MDMA are that methylone is less ] in terms of ], has more balanced ] effects relative to ], and behaves more like a reuptake inhibitor like ] than a releaser like ]; however, methylone still has relatively robust releasing capabilities,<ref name="pmid17223101"/> perhaps due to its ability to ] the ]s being similar in potency relative to MDMA.{{Citation needed|date=April 2010}}
{{See also|Effects of MDMA on the human body}}
], ] and ].<br/>Right: ], ], and methylone]]


In contrast to MDMA, methylone and its ]s lack significant affinity for the serotonin ] and ]s and similarly do not activate the serotonin ].<ref name="López-ArnauCamarasaCarbó2022" /><ref name="Warner-SchmidtStogniew2024">{{cite journal | vauthors = Warner-Schmidt J, Stogniew M, Mandell B, Rowland RS, Schmidt EF, Kelmendi B | title = Methylone is a rapid-acting neuroplastogen with less off-target activity than MDMA | journal = Front Neurosci | volume = 18 | issue = | pages = 1353131 | date = 2024 | pmid = 38389788 | pmc = 10882719 | doi = 10.3389/fnins.2024.1353131 | doi-access = free | url = }}</ref><ref name="LuethiKolaczynskaWalter2019">{{cite journal | vauthors = Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME | title = Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems | journal = J Psychopharmacol | volume = 33 | issue = 7 | pages = 831–841 | date = July 2019 | pmid = 31038382 | pmc = 8269116 | doi = 10.1177/0269881119844185 | url = }}</ref> This may make methylone safer than MDMA, for instance in terms of long-term ] risk.<ref name="TagenMantuanivanHeerden2023">{{cite journal | vauthors = Tagen M, Mantuani D, van Heerden L, Holstein A, Klumpers LE, Knowles R | title = The risk of chronic psychedelic and MDMA microdosing for valvular heart disease | journal = J Psychopharmacol | volume = 37 | issue = 9 | pages = 876–890 | date = September 2023 | pmid = 37572027 | doi = 10.1177/02698811231190865 | url = }}</ref><ref name="RouaudCalderHasler2024">{{cite journal | vauthors = Rouaud A, Calder AE, Hasler G | title = Microdosing psychedelics and the risk of cardiac fibrosis and valvulopathy: Comparison to known cardiotoxins | journal = J Psychopharmacol | volume = 38 | issue = 3 | pages = 217–224 | date = March 2024 | pmid = 38214279 | pmc = 10944580 | doi = 10.1177/02698811231225609 | url = }}</ref><ref name="RothmanBaumann2009">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Serotonergic drugs and valvular heart disease | journal = Expert Opin Drug Saf | volume = 8 | issue = 3 | pages = 317–329 | date = May 2009 | pmid = 19505264 | pmc = 2695569 | doi = 10.1517/14740330902931524 | url = }}</ref> Methylone is inactive at the mouse and rat ] (TAAR1).<ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = }}</ref><ref name="LuethiKolaczynskaWalter2019">{{cite journal | vauthors = Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME | title = Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems | journal = J Psychopharmacol | volume = 33 | issue = 7 | pages = 831–841 | date = July 2019 | pmid = 31038382 | pmc = 8269116 | doi = 10.1177/0269881119844185 | url = }}</ref>
Methylone resembles MDMA in its behavioural profile, as it substitutes for MDMA in rats trained to discriminate MDMA from saline. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline.<ref>TA Dal Cason, R Young, RA Glennon. Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs. ''Pharmacol. Biochem. Behav. 58'', 1109–1116 (1997)</ref> Further, also in common with MDMA, methylone acts on monoaminergic systems. In vitro, methylone has one third the potency of MDMA at inhibiting platelet serotonin accumulation and about the same in its inhibiting effects on the dopamine and noradrenaline transporters.<ref>NV Cozzi, MK Sievert, AT Shulgin, P Jacob III, AE Ruoho. Methcathinone and 2 methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters. ''Soc. Neurosci. Abs., 24'', 341.8 (1998).</ref><ref>NV Cozzi, AT Shulgin, AE Ruoho. Methcathinone (MCAT) and 2-methylamino-1-(3,4 methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit serotonin uptake into human platelets. ''Amer. Chem. Soc. Div. Med. Chem. Abs., 215'', 152 (1998).</ref><ref name="pmid10528135"/>


Similarly to MDMA, methylone has been found to be a ] in animals.<ref name="DazianiLoFaroMontana2023">{{cite journal | vauthors = Daziani G, Lo Faro AF, Montana V, Goteri G, Pesaresi M, Bambagiotti G, Montanari E, Giorgetti R, Montana A | title = Synthetic Cathinones and Neurotoxicity Risks: A Systematic Review | journal = Int J Mol Sci | volume = 24 | issue = 7 | date = March 2023 | page = 6230 | pmid = 37047201 | pmc = 10093970 | doi = 10.3390/ijms24076230 | doi-access = free | url = }}</ref> It has specifically been found to produce ] and ] in rodents.<ref name="DazianiLoFaroMontana2023" /> However, in one study, moderate doses of MDMA produced serotonergic neurotoxicity in rodents whereas methylone and mephedrone did not do so, suggesting that cathinones like methylone may be less neurotoxic than their corresponding amphetamine counterparts like MDMA.<ref name="López-ArnauCamarasaCarbó2022">{{cite journal | vauthors = López-Arnau R, Camarasa J, Carbó ML, Nadal-Gratacós N, Puigseslloses P, Espinosa-Velasco M, Urquizu E, Escubedo E, Pubill D | title = 3,4-Methylenedioxy methamphetamine, synthetic cathinones and psychedelics: From recreational to novel psychotherapeutic drugs | journal = Front Psychiatry | volume = 13 | issue = | pages = 990405 | date = 2022 | pmid = 36262632 | pmc = 9574023 | doi = 10.3389/fpsyt.2022.990405 | doi-access = free | url = }}</ref><ref name="BaumannAyestasPartilla2012" />
In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. ] wrote of the former:<ref name="urlCathinone | Ask Dr. Shulgin Online">{{cite web | url = http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm | title = Cathinone &#124; Ask Dr. Shulgin Online | work = | accessdate = }}</ref>


{| class="wikitable" style="font-size:small;"
{{quotation|" has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA."}}
|+ {{Nowrap|] of ] and related agents ({{Abbrlink|EC<sub>50</sub>|Half maximal effective concentration}}, nM)}}
|-
! Compound !! data-sort-type="number" | {{abbrlink|5-HT|Serotonin}} !! data-sort-type="number" | {{abbrlink|NE|Norepinephrine}} !! data-sort-type="number" | {{abbrlink|DA|Dopamine}} !! Ref
|-
| ] || 698–1,765 || 6.6–7.2 || 5.8–24.8 || <ref name="RothmanBaumannDersch2001">{{cite journal | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 | url = }}</ref><ref name="BaumannPartillaLehner2013">{{cite journal | vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | year = 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }}</ref>
|-
| ] || 736–1,292 || 12.3–13.8 || 8.5–24.5 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">{{cite journal | vauthors = Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV | title = The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue | journal = Neuropsychopharmacology | volume = 37 | issue = 5 | pages = 1192–1203 | year = 2012 | pmid = 22169943 | pmc = 3306880 | doi = 10.1038/npp.2011.304 }}</ref>
|-
| {{Abbrlink|MDA|Methylenedioxyamphetamine}} || 160–162 || 47–108 || 106–190 || <ref name="SetolaHufeisenGrande-Allen2003" /><ref name="Blough2008">{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref><ref name="BrandtWaltersPartilla2020" />
|-
| {{Abbrlink|MDMA|Methylenedioxymethamphetamine}} || 49.6–72 || 54.1–110 || 51.2–278 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012" /><ref name="MarusichAntonazzoBlough2016">{{cite journal | vauthors = Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH | title = The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue | journal = Neuropharmacology | volume = 101 | pages = 68–75 | date = February 2016 | pmid = 26362361 | pmc = 4681602 | doi = 10.1016/j.neuropharm.2015.09.004 }}</ref><ref name="SetolaHufeisenGrande-Allen2003">{{cite journal | vauthors = Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, Rothman RB, Roth BL | title = 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro | journal = Molecular Pharmacology | volume = 63 | issue = 6 | pages = 1223–1229 | date = June 2003 | pmid = 12761331 | doi = 10.1124/mol.63.6.1223 | s2cid = 839426 }}</ref><ref name="BrandtWaltersPartilla2020">{{cite journal | vauthors = Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH | title = The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats | journal = Psychopharmacology (Berl) | volume = 237 | issue = 12 | pages = 3703–3714 | date = December 2020 | pmid = 32875347 | doi = 10.1007/s00213-020-05648-z | url = | pmc = 7686291 }}</ref>
|-
| ] || 6,100–7,595 || 23.6–25.6 || 34.8–83.1 || <ref name="Blough2008" /><ref name="BloughDeckerLandavazo2019">{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 }}</ref><ref name="FitzgeraldGannonWalther2024">{{cite journal | vauthors = Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE | title = Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones | journal = Neuropharmacology | volume = 245 | issue = | pages = 109827 | date = March 2024 | pmid = 38154512 | doi = 10.1016/j.neuropharm.2023.109827 | pmc = 10842458 | pmc-embargo-date = March 1, 2025 | url = }}</ref>
|-
| ] || 2,592–5,853 || 22–26.1 || 12.5–49.9 || <ref name="Blough2008" /><ref name="BloughDeckerLandavazo2019" /><ref name="Shalabi2017">{{cite thesis | last=Shalabi | first=Abdelrahman R. | title=Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters | website=VCU Scholars Compass | date=14 December 2017 | doi=10.25772/M4E1-3549 | url=https://scholarscompass.vcu.edu/etd/5176/ | access-date=24 November 2024}}</ref><ref name="WaltherShalabiBaumann2019">{{cite journal | vauthors = Walther D, Shalabi AR, Baumann MH, Glennon RA | title = Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents | journal = ACS Chem Neurosci | volume = 10 | issue = 1 | pages = 740–745 | date = January 2019 | pmid = 30354055 | pmc = 8269283 | doi = 10.1021/acschemneuro.8b00524 | url = }}</ref><ref name="FitzgeraldGannonWalther2024" />
|-
| {{Abbrlink|MDC|Methylenedioxycathinone}} || 966 || 394 || 370 || <ref name="ElmoreDillon-CarterPartilla2017" />
|-
| ] ({{Abbr|MDMC|methylenedioxymethcathinone}}) || 234–708 || 140–270 || 117–220 || <ref name="BaumannAyestasPartilla2012" /><ref name="BaumannPartillaLehner2013" /><ref name="Sakloth2015">{{cite thesis | last=Sakloth | first=Farhana | title=Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action | website=VCU Scholars Compass | date=11 December 2015 | doi=10.25772/AY8R-PW77 | url=https://scholarscompass.vcu.edu/etd/4041/ | access-date=24 November 2024}}</ref><ref name="GlatfelterWaltherEvans-Brown2021">{{cite journal | vauthors = Glatfelter GC, Walther D, Evans-Brown M, Baumann MH | title = Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation | journal = ACS Chem Neurosci | volume = 12 | issue = 7 | pages = 1170–1177 | date = April 2021 | pmid = 33689284 | pmc = 9423000 | doi = 10.1021/acschemneuro.0c00797 | url = }}</ref><ref name="ElmoreDillon-CarterPartilla2017">{{cite journal | vauthors = Elmore JS, Dillon-Carter O, Partilla JS, Ellefsen KN, Concheiro M, Suzuki M, Rice KC, Huestis MA, Baumann MH | title = Pharmacokinetic Profiles and Pharmacodynamic Effects for Methylone and Its Metabolites in Rats | journal = Neuropsychopharmacology | volume = 42 | issue = 3 | pages = 649–660 | date = February 2017 | pmid = 27658484 | pmc = 5240186 | doi = 10.1038/npp.2016.213 | url = }}</ref>
|-
| ] || 118.3–122 || 58–62.7 || 49.1–51 || <ref name="BaumannAyestasPartilla2012" /><ref name="BaumannPartillaLehner2013" /><ref name="BloughDeckerLandavazo2019" /><ref name="WaltherShalabiBaumann2019" /><ref name="BonanoBanksKolanos2015">{{cite journal | vauthors = Bonano JS, Banks ML, Kolanos R, Sakloth F, Barnier ML, Glennon RA, Cozzi NV, Partilla JS, Baumann MH, Negus SS | title = Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues | journal = Br J Pharmacol | volume = 172 | issue = 10 | pages = 2433–2444 | date = May 2015 | pmid = 25438806 | pmc = 4409897 | doi = 10.1111/bph.13030 | url = }}</ref>
|-
| colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the drug releases the neurotransmitter. The ]s were done in rat brain ]s and human ] may be different. See also ] for a larger table with more compounds. '''Refs:''' <ref name="RothmanBaumann2003">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = Eur J Pharmacol | volume = 479 | issue = 1–3 | pages = 23–40 | date = October 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054 | url = }}</ref><ref name="RothmanBaumann2006">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Current Topics in Medicinal Chemistry | volume = 6 | issue = 17 | pages = 1845–1859 | year = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = https://zenodo.org/record/1235860 }}</ref>
|}


== Pharmacology == === Pharmacokinetics ===
The two major ]s in ]s for methylone are ''N''-] to ] (MDC), and ] followed by ''O''-] of the 3- or 4-] ] to ] (HMMC) or ] (3-OH-4-MeO-MC). When 5&nbsp;mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged).<ref>{{cite journal | vauthors = Kamata HT, Shima N, Zaitsu K, Kamata T, Miki A, Nishikawa M, Katagi M, Tsuchihashi H | title = Metabolism of the recently encountered designer drug, methylone, in humans and rats | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 36 | issue = 8 | pages = 709–723 | date = August 2006 | pmid = 16891251 | doi = 10.1080/00498250600780191 | s2cid = 10875717 }}</ref> The mean ] of methylone in humans following ] of doses of 50 to 200{{nbsp}}mg ranged from 5.8 to 6.9{{nbsp}}hours.<ref name="pmid36498963" /> The ] and ] of methylone in humans are 0.5{{nbsp}}hours and 2.5 to 3.0{{nbsp}}hours, respectively.<ref name="pmid36498963" />
=== Pharmacodynamics ===


== Commercial distribution ==
Methylone acts as a mixed ]/] of ], ], and ].<ref name="pmid10528135"/><ref name="pmid17223101">{{cite journal | author = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–7 | year = 2007 | month = March | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(06)01381-1}}</ref> In comparison to MDMA, it has approximately 3x lower ] for the ], while its affinity for the ] and ]s is similar.<ref name="pmid10528135"/><ref name="pmid17223101"/> Notably, methylone's affinity for the ] (VMAT2) is about 13x lower than that of MDMA.<ref name="pmid10528135"/> The results of these differences in pharmacology relative to MDMA are that methylone is less ] in terms of ], has more balanced ] effects relative to ], and behaves more like a reuptake inhibitor like ] than a releaser like ]; however, methylone has relatively robust releasing capabilities,<ref name="pmid17223101"/> perhaps due to its ability to ] the ]s being similar in potency relative to MDMA.{{Citation needed|date=April 2010}}
]


Analysis of "Explosion" has confirmed that the active ingredient is methylone.<ref>{{cite web |url=http://www.erowid.org/chemicals/methylone/methylone_info1.shtml |title=Methylone sold under "Explosion" and "Inpact" brand names in the Netherlands and Japan |archive-url=https://web.archive.org/web/20090304225847/http://www.erowid.org/chemicals/methylone/methylone_info1.shtml |archive-date=2009-03-04 |date=Apr 2005 |website=www.erowid.org}}</ref>{{Unreliable source?|date=May 2014}} Many other formulations marketed as household chemicals, as well as the pure powder, have been sold.
=== Pharmacokinetics ===


==Legal status==
Little is currently known about the pharmacokinetics of methylone, aside from metabolism.


==== Metabolism ==== ===Netherlands===
In the Netherlands, methylone is not yet listed under the ], but is covered under the medicine act. Because methylone is not registered officially, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group (CAM) to gather information about this substance, resulting possibly in an official risk assessment.<ref>{{cite journal | vauthors = van Amsterdam JG, Best W, Opperhuizen A, de Wolff FA | title = Evaluation of a procedure to assess the adverse effects of illicit drugs | journal = Regulatory Toxicology and Pharmacology | volume = 39 | issue = 1 | pages = 1–4 | date = February 2004 | pmid = 14746774 | doi = 10.1016/j.yrtph.2003.09.001 | publisher = Elsevier BV | hdl = 10029/12622 | hdl-access = free }}</ref> Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug.


===New Zealand===
The two major ]s in ]s for methylone are ''N''-] to ] (MDC), and ] followed by ''O''-] of the 3- or 4-] ] to ] (HMMC) or ] (3-OH-4-MeO-MC). When 5&nbsp;mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged).<ref> HT Kamata, N Shima, K Zaitsu, T Kamata, A Miki, M Nishikawa, M Katagi, H Tsuchihashi. (2006). Metabolism of methylone in humans and rats. Volume 36, Number 8 / August 2006.</ref>
In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an "amphetamine analogue" in the Misuse of Drugs Act, it is considered to be "substantially similar" to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government.<ref name="TVNZ_697050">{{cite news |url=http://tvnz.co.nz/view/page/411424/697050 |title=Party pill sparks official concern |date=7 April 2006 |work=] |access-date=23 October 2011 |url-status=live |archive-url=https://web.archive.org/web/20120209003752/http://tvnz.co.nz/view/page/411424/697050 |archive-date=9 February 2012 }}</ref><ref>{{cite web |url=http://www.scoop.co.nz/stories/GE0604/S00032.htm |title=EASE trial terminated after conflicting advice |archive-url=https://web.archive.org/web/20120929074649/http://www.scoop.co.nz/stories/GE0604/S00032.htm |archive-date=2012-09-29 |website=scoop.co.nz |date=April 9, 2006}}</ref>


== Legal status == ===UK===
In the UK, methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the ]. In March 2010, plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the ], the revision was rushed through by the government with little regard for the views of the council. The importation of the compound was banned immediately.<ref>{{cite news|url=http://news.bbc.co.uk/1/hi/uk/8599814.stm|title=Suspected mephedrone-type compound seized at airport |date=1 April 2010|publisher=BBC News|access-date=3 April 2010}}</ref>


===Sweden===
In the Netherlands, methylone is not yet scheduled as a drug of abuse, but is considered to be a psychoactive medicine. Because methylone is not registered officially, as such, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group (CAM) to gather information about this substance, resulting possibly in an official risk assessment.<ref>van Amsterdam et al., 2004</ref> Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug.
] added methylone to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Oct 1, 2010, published by ] in their regulation LVFS 2010:23 listed as Metylon, 2-metylamino-1-(3,4-metylendioxifenyl)propan-1-on.<ref>{{cite web |url=http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf |title=Läkemedelsverkets föreskrifter - LVFS och HSLF-FS |publisher=Läkemedelsverket - Swedish Medical Products Agency |access-date=2010-10-07 |url-status=live |archive-url=https://web.archive.org/web/20110216190305/http://www.lakemedelsverket.se/upload/lvfs/LVFS_2010_23.pdf |archive-date=2011-02-16 }}</ref> Methylone was first classified by ] health ministry {{ill|Statens folkhälsoinstitut|sv}} as "health hazard" under the act {{ill|Lagen om förbud mot vissa hälsofarliga varor|sv}} (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 3,4-metylendioximetkatinon (Metylon).<ref>{{cite web |url=http://www.notisum.se/rnp/sls/sfs/20050733.pdf |title=Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor; |website=notisum.se |language=sv|access-date=2015-10-10 |url-status=live |archive-url=https://web.archive.org/web/20160304112946/http://www.notisum.se/rnp/sls/sfs/20050733.pdf |archive-date=2016-03-04 }}</ref>


===Canada===
In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an "amphetamine analogue" in the Misuse of Drugs Act, it is considered to be "substantially similar" to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government.<ref name="TVNZ_697050">{{cite news |url=http://tvnz.co.nz/view/page/411424/697050 |title=Party pill sparks official concern |date=7 April 2006 |work=] |accessdate=23 October 2011}}</ref><ref></ref>
Although not listed as a ]<ref name="CDSA Schedule I: Amphetamines">{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C|title=Controlled Drugs and Substances Act : Legislative history · Schedule I · Section 19: Tramadol ; Amphetamines|website=isomerdesign.com|access-date=28 March 2018|url-status=live|archive-url=https://web.archive.org/web/20131110200556/http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C|archive-date=10 November 2013}}</ref> substance, Health Canada reports that methylone falls under the scheduling as an analogue of amphetamine. However, Methylone bears the exact chemical difference between amphetamine and ] – and cathinone is listed as not being an analogue of amphetamine, possibly implying that methylone is unscheduled in Canada.<ref name="Definitions and Interpretations">{{cite web|url=http://isomerdesign.com/Cdsa/definitions.php?structure=C|title=Controlled Drugs and Substances Act : Definitions and Interpretations|website=isomerdesign.com|access-date=28 March 2018|url-status=live|archive-url=https://web.archive.org/web/20131110213450/http://isomerdesign.com/Cdsa/definitions.php?structure=C|archive-date=10 November 2013}}</ref> The CDSA was updated as a result of the Safe Streets Act changing amphetamines from ] to ]; however, methylone was not added.<ref name="Safe Streets Act">{{cite web|url=http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html|title=The Safe Streets and Communities Act Four Components Coming into Force|date=18 October 2012|access-date=28 March 2018|url-status=dead|archive-url=https://web.archive.org/web/20121018122345/http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html|archive-date=18 October 2012}}</ref>


===United States===
In the UK, Methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the ]. In March 2010 plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the ], the revision was rushed through by the government with little regard for the views of the ACMD. The importation of the compounds was banned immediately.<ref>{{cite news|url=http://news.bbc.co.uk/1/hi/uk/8599814.stm|title=Suspected mephedrone-type compound seized at airport |date=1 April 2010|publisher=BBC News|accessdate=3 April 2010}}</ref>
In October 2011, the ] issued an emergency ban on methylone. It was made illegal to possess and distribute.<ref>{{cite web|title=Chemicals Used in 'Bath Salts' Now Under Federal Control and Regulation|url=https://www.justice.gov/dea/divisions/hq/2011/hq102111.shtml|publisher=USA Dept of Justice|access-date=22 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140425083923/http://www.justice.gov/dea/divisions/hq/2011/hq102111.shtml|archive-date=25 April 2014}}</ref><ref>{{cite web|title=Schedules of Controlled Substances: Placement of Methylone Into Schedule I|url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2012/fr1017.htm|access-date=22 April 2014 |website=usdoj.gov|url-status=live|archive-url=https://web.archive.org/web/20140417130900/http://www.deadiversion.usdoj.gov/fed_regs/rules/2012/fr1017.htm|archive-date=17 April 2014}}</ref> On April 4, 2013, the DEA placed methylone as a Schedule 1 substance under the CSA.<ref>{{cite web|title=Schedules of Controlled Substances: Placement of Methylone Into Schedule I|url=https://www.federalregister.gov/articles/2013/04/12/2013-08673/schedules-of-controlled-substances-placement-of-methylone-into-schedule-i |website=federalregister.gov|access-date=22 April 2014|date=2014-04-12|url-status=live|archive-url=https://web.archive.org/web/20141215042354/https://www.federalregister.gov/articles/2013/04/12/2013-08673/schedules-of-controlled-substances-placement-of-methylone-into-schedule-i|archive-date=15 December 2014}}</ref>


* Arizona:
In Sweden, methylone was classed as a Harmful Substance since 2007, but since 21 September 2010 the drug was actively scheduled as a narcotic.<ref name="SwedishMethyloneBan">, Förordning
::Effective February 16, 2012, methylenedioxymethcathinone (methylone) was classified as a dangerous drug, making it a felony to knowingly possess, use, possess for sale, manufacture, administer, transport for sale, import into the state, or offer to transport for sale or import into this state, sell, transfer or offer to sell or transfer. A.R.S. 13-3401(6)(c)(xliii), 2012 Ariz. Legis. Serv. Ch. 1 (H.B. 2356).
om ändring i förordningen (1992:1554) om kontroll
av narkotika</ref> In Sweden the name in the books for the substance classified is '''3,4-metylendioximetkatinon''' ('''Metylon''').<ref name="urlNotisum Sweden | Förordning (1999:58) om förbud mot vissa hälsofarliga varor">{{cite web |url=http://www.notisum.se/rnp/sls/lag/19990058.htm |title=http://www.notisum.se/rnp/sls/lag/19990058.htm – Förordning (1999:58) om förbud mot vissa hälsofarliga varor |work= |accessdate=}}</ref>

United States
: As of October 6, 2011 the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.
* Florida: * Florida:
::In January 2011, it was reported that Florida Attorney General Pam Bondi issued an emergency ban on MDPV, Methylone, Mephedrone, 3-methoxymethcathinon, 3-fluoromethcathinone, and 4-fluoromethcathinone as media attention on products labeled as "bath salts" grew. These chemicals are now Schedule I under Florida law. ::In January 2011, it was reported that Florida Attorney General Pam Bondi issued an emergency ban on MDPV, Methylone, Mephedrone, 3-methoxymethcathinone, 3-fluoromethcathinone, and 4-fluoromethcathinone as media attention on products labeled as "bath salts" grew. These chemicals are now Schedule I under Florida law.<ref>{{cite web |url=http://myfloridalegal.com/webfiles.nsf/WF/RMAS-98NQAK/$file/History-of-AGs-Scheduling-Actions.pdf |title=Florida Synthetic Drug Scheduling Actions - 2011-2014 |website=myfloridalegal.com|access-date=2017-04-08 |url-status=live |archive-url=https://web.archive.org/web/20150320074110/http://myfloridalegal.com/webfiles.nsf/WF/RMAS-98NQAK/$file/History-of-AGs-Scheduling-Actions.pdf |archive-date=2015-03-20 }}</ref>
* Louisiana: * Louisiana:
::In January 2011, the governor of Louisiana emergency scheduled 3,4-Methylenedioxymethcathinone (Methylone), 3,4-Methyenedioxypyrovalerone (]), 4-Methylmethcathinone (]), 4-methoxymethcathinone (]), 4-Fluoromethcathinone (]), and 3-Fluoromethcathinone (]). ::In January 2011, Louisiana Governor Bobby Jindal emergency scheduled 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (]), 4-methylmethcathinone (]), 4-methoxymethcathinone (]), 4-fluoromethcathinone (]), and 3-fluoromethcathinone (]).
* Tennessee: * Tennessee:
::On May 5, 2011, Tennessee Governor Bill Haslam signed a law making it a crime to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-Methylenedioxymethcathinone (Methylone), 3,4-Methyenedioxypyrovalerone (]), 4-Methylmethcathinone (]), 4-methoxymethcathinone (]), 4-Fluoromethcathinone (]), and 3-Fluoromethcathinone (]).<ref>http://state.tn.us/sos/acts/107/pub/pc0169.pdf</ref> ::On May 5, 2011, Tennessee Governor ] signed a law making it a crime to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (]), 4-methylmethcathinone (]), 4-methoxymethcathinone (]), 4-fluoromethcathinone (]), and 3-fluoromethcathinone (]).<ref>{{cite web|url=http://state.tn.us/sos/acts/107/pub/pc0169.pdf|title=Welcome to the Tennessee Secretary of State's Website – Tennessee Secretary of State|website=state.tn.us|access-date=28 March 2018|url-status=live|archive-url=https://web.archive.org/web/20130901093741/http://state.tn.us/sos/acts/107/pub/pc0169.pdf|archive-date=1 September 2013}}</ref>
* Texas:
::In September 2011, Texas added 3,4-methylenedioxy-''N''-methylcathinone to the Penalty Group 2 listing of the Health and Safety Code. Possession of a substance in penalty group 2 is a minimum of a state jail felony.
* Michigan:
::Schedule 1 controlled substance in 2012.


== Etymology == == Etymology ==

"Methylone" is also a trademarked brand name for an injectable form of ], a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. Aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug. "Methylone" is also a trademarked brand name for an injectable form of ], a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. Aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug.


A proposed alternate name is bk-MDMA, or beta-keto-MDMA. While this nomenclature has not caught on because the name "methylone" became widely used before the conflicting Methylone trademark was noticed, the analogous names for related chemicals ] and ] have become the established names for those substances. A proposed alternate name is βk-MDMA, or beta-keto-MDMA. While this nomenclature has not caught on because the name "methylone" became widely used before the conflicting Methylone trademark was noticed, the analogous names for related chemicals ] and ] have become the established names for those substances.


== See also == == Research ==
=== Post-traumatic stress disorder ===
* ]
Under the developmental code TSND-201, methylone is under ] by Transcend Therapeutics for the treatment of ] (PTSD).<ref name="AdisInsight">{{cite web | title=Methylone - Transcend Therapeutics | website=AdisInsight | date=24 July 2024 | url=https://adisinsight.springer.com/drugs/800072616 | access-date=24 October 2024}}</ref><ref name="Synapse">{{cite web | title=Delving into the Latest Updates on Methylone with Synapse | website=Synapse | date=20 September 2024 | url=https://synapse.patsnap.com/drug/2c777b7e3faf48f18fad88d817c0ec7f | access-date=24 October 2024}}</ref><ref name="FierceBiotech2023">{{cite web | last=Bayer | first=Max | title=PTSD treatment is on the cusp of a paradigm shift. This biotech hopes to Transcend the competition | website=Fierce Biotech | date=5 December 2023 | url=https://www.fiercebiotech.com/biotech/budding-psychiatry-biotech-looks-transcend-ptsd-competition-sample-phase-2-data | access-date=24 October 2024}}</ref> As of July 2024, it is in ] ]s for this indication.<ref name="AdisInsight" /><ref name="Synapse" />


== References == == References ==
{{Reflist|2}} {{Reflist}}

== External links ==
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{{Entactogens}} {{Entactogens}}
{{Stimulants}} {{Stimulants}}
{{Monoamine releasing agents}}
{{Adrenergics}}
{{Monoamine neurotoxins}}
{{Dopaminergics}}
{{Serotonergics}}
{{Phenethylamines}} {{Phenethylamines}}


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