View source for Methcathinone

{{Short description|Psychoactive stimulant}}
{{More medical citations needed|date=February 2013}}
{{Infobox drug| Verifiedfields = changed
| verifiedrevid = 464193938
| IUPAC_name = (''RS'')-2-(methylamino)-1-phenyl-propan-1-one
| image = Methcathinone skeletal.svg
| image_class = skin-invert-image
| image2 = Methcathinone molecule ball.png
| alt2 = Ball-and-stick model of the methcathinone molecule
| chirality = [[Racemic mixture]]
<!--Clinical data-->
| legal_AU = S9
| 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=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_UK = Class B
| legal_US = Schedule I
| legal_UN = Psychotropic Schedule I
| routes_of_administration = [[Vaporize]]d, [[Insufflation (medicine)|insufflated]], [[Intravenous infusion|injected]], [[Mouth|orally]]

<!--Pharmacokinetic data-->
| excretion = [[Urine]]

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 5650-44-2
| CAS_supplemental = ([[Cahn–Ingold–Prelog priority rules|R]] form)<br />{{CAS|49656-78-2}} (R form · [[hydrochloride|HCl]])<br />{{CAS|112117-24-5}} (S form)<br />{{CAS|66514-93-0}} (S form · HCl)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 386QA522QG
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = S2Q5GUH10H
| ATC_prefix = none
| PubChem = 1576
| KEGG = C22263
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1519
| DrugBank = DB15339

<!--Chemical data-->
| C=10 | H=13 | N=1 | O=1 
| smiles = O=C(c1ccccc1)C(NC)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LPLLVINFLBSFRP-UHFFFAOYSA-N
}}

'''Methcathinone''' {{IPAc-en|ˌ|m|ɛ|θ|ˈ|k|æ|θ|ᵻ|ˌ|n|oʊ|n}} ('''α-[[methyl]][[amino]]-[[propiophenone]]''' or '''ephedrone''') (sometimes called "'''cat'''" or "'''jeff'''" or "'''catnip'''" or "'''M-Kat'''" or "'''kat'''" or "'''intash'''") is a [[monoamine]] [[alkaloid]] and [[psychoactive]] [[stimulant]], a substituted [[cathinone]]. It is used as a [[recreational drug]] due to its potent stimulant and [[euphoria|euphoric]] effects and is considered to be [[Substance use disorder|addictive]], with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration.<ref name="calkins 2005">{{cite journal | pmid = 8594170 | volume=27 | journal = Journal of Psychoactive Drugs | issue=3 | title = Methcathinone: the next illicit stimulant epidemic? | year=1995 | pages=277–85 |vauthors=Calkins RF, Aktan GB, Hussain KL | doi=10.1080/02791072.1995.10472472}}</ref> It is usually [[Nasal administration|snorted]], but can be smoked, injected, or taken orally.

Methcathinone is listed as a [[Convention on Psychotropic Substances#Schedule I|Schedule I controlled substance]] by the [[Convention on Psychotropic Substances]] and the [[United States]]' [[Controlled Substances Act]], and as such it is not considered to be safe or effective in the treatment, diagnosis, prevention, or cure of any disease, and has no approved medical use. Possession and distribution of methcathinone for the purpose of human consumption is illegal under any/all circumstances in the United States and is either illegal or highly regulated in most jurisdictions worldwide.

==History==
Methcathinone was first synthesized in 1928 in the United States<ref name="hyde1928">{{cite journal |vauthors=Hyde JF, Browning E, Adams R | year = 1928| title = Synthetic Homologs of d,l-Ephedrine |journal=Journal of the American Chemical Society   | volume = 50 | issue = 8| pages = 2287–2292 | doi = 10.1021/ja01395a032 | bibcode = 1928JAChS..50.2287H}}</ref> and was patented by [[Parke-Davis]] in 1957.<ref>US Patent 2802865 – Ethylaminopropiophenone compounds</ref> It was used in the [[Soviet Union]] during the 1930s and 1940s as an [[anti-depressant]] (under the name ''Эфедрон''—''ephedrone''). Methcathinone has long been used as a drug of abuse in the [[Soviet Union]] and [[Russia]].{{citation needed|date=January 2013}}

Circa 1994, the United States government recommended to the [[UN Secretary-General]] that methcathinone should be listed as a [[Convention on Psychotropic Substances#Schedule I|Schedule I controlled substance]] in the [[Convention on Psychotropic Substances]].<ref>[http://www.erowid.org/chemicals/chemicals_law1.shtml Erowid]</ref> In 1995, following US advice, [[China]] added the drug to its list of prohibited substances and discontinued its pharmaceutical use.<ref>{{Cite news|url=https://www.bbc.com/news/world-asia-china-32812621|title = Chinese professor accused in 'Breaking Bad' drugs plot|work = BBC News|date = 20 May 2015}}</ref>

It is currently a Schedule III drug in Canada along with codeine, anabolic steroids, and testosterone. It is legal to possess in Canada, but illegal to purchase. Methcathinone used to have the nick-name "bath salts", to avoid restrictions on importation.

==Chemistry==
{{More citations needed section|date=September 2014}}
Methcathinone is a beta-keto ''N''-methylamphetamine and is closely related to the naturally occurring compounds, [[cathinone]] and [[cathine]]. It is also very closely related to [[methamphetamine]], differing by only the β-[[ketone]] substituent and differing from [[amphetamine]] by both a keto and N-methyl substituent. Its carbon skeleton is identical to pseudoephedrine and methamphetamine. It differs from pseudoephedrine in that the hydroxyl beta to the aromatic ring is oxidized to a ketone.

Methcathinone possesses a [[chiral carbon]] atom, and therefore ''two'' enantiomers are possible. When it is made semi-synthetically  from pseudo/ephedrine as a starting material, then only a single enantiomer is produced. Given that the chiral center has an [[Alpha and beta carbon#Enols and enolates|alpha hydrogen]] and adjacent the carbonyl group, the molecule will [[racemization|racemize]] in solution via an [[enol]] intermediate. This process is known as [[keto–enol tautomerism]].

Methcathinone production utilizes the [[oxidation]] of [[pseudoephedrine]] or [[ephedrine]], the former being preferred because of much higher yields achieved. Oxidation of [[pseudoephedrine]] to methcathinone requires little [[chemistry]] experience, making it (relatively) easy to synthesize.<ref>[https://web.archive.org/web/20131113024319/http://www.scribd.com/doc/35411/The-Clandestine-Chemists-Notebook The Clandestine Chemists Notebook]</ref>{{unreliable source?|date=September 2014}} [[Potassium permanganate]] (KMnO<sub>4</sub>) is most commonly used as the oxidant.

In clandestine laboratories, synthesizing methcathinone using potassium permanganate is considered undesirable because of the low yields and the high toxicity of this oxidant {{crossreference|(see [[Manganism|Manganese toxicity]])}}; however, if done in a proper laboratory using the proper procedures potassium permanganate can be a high-yielding reactant. A method that yields more methcathinone is oxidizing (pseudo)ephedrine with [[Jones oxidation|chromium (VI)]] compounds, which are far more toxic than permanganate compounds.

Methcathinone as free base is very unstable; it easily loses its [[ketone]] group, which is substituted with a [[hydroxyl]] group, yielding [[pseudoephedrine]], in the reverse of the typical synthesis reaction.  Structurally, this occurs when the C=O bond at the Rβ-position is converted into a C-OH bond. Additionally, a dimerization reaction has been observed in solutions of freebase methcathinone, which yields a biologically inactive compound.<ref>{{Cite journal | doi=10.1093/chromsci/32.12.552| title=Methcathinone and Designer Analogues: Synthesis, Stereochemical Analysis, and Analytical Properties| journal=Journal of Chromatographic Science| volume=32| issue=12| pages=552–564| year=1994| vauthors = DeRuiter J, Hayes L, Valaer A, Clark CR, Noggle FT }}</ref>

== Effects ==

Methcathinone hydrochloride [[hyperlocomotion|increases spontaneous rodent locomotor activity]],<ref name="pmid3575369">{{cite journal |vauthors=Glennon RA, Yousif M, Naiman N, Kalix P |title=Methcathinone: a new and potent amphetamine-like agent |journal=Pharmacol. Biochem. Behav. |volume=26 |issue=3 |pages=547–51 |year=1987 |pmid=3575369 |doi=10.1016/0091-3057(87)90164-X|s2cid=5890314 }}</ref> potentiates the release of [[dopamine]] from [[dopaminergic|dopaminergic nerve]] terminals in the [[brain]],<ref name="pmid3575369" /> and causes [[appetite suppression]].{{Citation needed|date=April 2007}}  Users can easily forget to consume fluids leading to increased thirst and dehydration. The effects of methcathinone are similar to those of [[methamphetamine]], initially deemed to be less intense by the inexperienced user, and often more euphoric.{{Citation needed|date=April 2010}}  The effects have been compared to those of [[cocaine]], since it commonly causes [[hypertension]] (elevated blood pressure) and [[tachycardia]] (elevated heart rate).

Reported effects include:{{medical citation needed|date=September 2014}}

* Feelings of [[Euphoria (emotion)|euphoria]]
* Increased alertness
* Slurred speech
* Shaking of the limbs
* Increased heart rate
* Increased blood pressure, risk of stroke or heart attack
* Increased empathy and sense of communication
* Both decreased and increased sexual function and desire
* [[Bruxism]]
The effects of methcathinone usually last from four to six hours.{{Citation needed|date=August 2014}}

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatright" style="font-size:small;"
|+ {{Nowrap|[[Monoamine releasing agent|Monoamine release]] of methcathinone and related agents ({{Abbrlink|EC<sub>50</sub>|Half maximal effective concentration}}, nM)}}
|-
! Compound !! data-sort-type="number" | {{abbrlink|NE|Norepinephrine}} !! data-sort-type="number" | {{abbrlink|DA|Dopamine}} !! data-sort-type="number" | {{abbrlink|5-HT|Serotonin}} !! Ref
|-
| [[Phenethylamine]] || 10.9 || 39.5 || >10,000 || <ref name="ReithBLoughHong2015">{{cite journal | vauthors = Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL | title = Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter | journal = Drug and Alcohol Dependence | volume = 147 | issue =  | pages = 1–19 | date = February 2015 | pmid = 25548026 | pmc = 4297708 | doi = 10.1016/j.drugalcdep.2014.12.005 }}</ref><ref name="Forsyth2012" /><ref name="Blough2008" />
|-
| [[Amphetamine]] || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|-
| {{nbsp}}{{nbsp}}[[Dextroamphetamine]] || 6.6–7.2 || 5.8–24.8 || 698–1,765 || <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>
|-
| {{nbsp}}{{nbsp}}[[Levoamphetamine]] || 9.5 || 27.7 || {{abbr|ND|No data}} || <ref name="Forsyth2012">{{cite journal | vauthors = Forsyth AN | title=Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines | website=ScholarWorks@UNO | date=22 May 2012 | url=https://scholarworks.uno.edu/td/1436/ | access-date=4 November 2024}}</ref><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 [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref>
|-
| [[Methamphetamine]] || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|-
| {{nbsp}}{{nbsp}}[[Dextromethamphetamine]] || 12.3–13.8 || 8.5–24.5 || 736–1,292 || <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>
|-
| {{nbsp}}{{nbsp}}[[Levomethamphetamine]] || 28.5 || 416 || 4,640 || <ref name="RothmanBaumannDersch2001" />
|-
| [[Cathinone]] || 23.6–25.6 || 34.8–83.1 || 6,100–7,595 || <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 = | article-number = 109827 | date = March 2024 | pmid = 38154512 | doi = 10.1016/j.neuropharm.2023.109827 | pmc = 10842458 | url = }}</ref>
|-
| {{nbsp}}{{nbsp}}{{Small|D}}-Cathinone || 72.0 || 184 || >10,000 || <ref name="HutsellBaumannPartilla2016">{{cite journal | vauthors = Hutsell BA, Baumann MH, Partilla JS, Banks ML, Vekariya R, Glennon RA, Negus SS | title = Abuse-related neurochemical and behavioral effects of cathinone and 4-methylcathinone stereoisomers in rats | journal = Eur Neuropsychopharmacol | volume = 26 | issue = 2 | pages = 288–297 | date = February 2016 | pmid = 26738428 | pmc = 5331761 | doi = 10.1016/j.euroneuro.2015.12.010 | url = }}</ref>
|-
| {{nbsp}}{{nbsp}}{{Small|L}}-Cathinone || 12.4–28 || 18–24.6 || 2,366–9,267 || <ref name="RothmanVuPartilla2003">{{cite journal | vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 1 | pages = 138–145 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | s2cid = 19015584 }}</ref><ref name="ShalabiWaltherBaumann2017">{{cite journal | vauthors = Shalabi AR, Walther D, Baumann MH, Glennon RA | title = Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release | journal = ACS Chem Neurosci | volume = 8 | issue = 6 | pages = 1397–1403 | date = June 2017 | pmid = 28220701 | pmc = 7261150 | doi = 10.1021/acschemneuro.7b00055 | url = }}</ref><ref name="HutsellBaumannPartilla2016" />
|-
| Methcathinone || 22–26.1 || 12.5–49.9 || 2,592–5,853 || <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" />
|-
| {{nbsp}}{{nbsp}}{{Small|D}}-Methcathinone || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|IA|Inactive}} || <ref name="Davies2019">{{cite thesis | last=Davies | first=Rachel A | title=Structure-Activity Relationship Studies of Synthetic Cathinones and Related Agents | website=VCU Scholars Compass | date=10 July 2019 | doi=10.25772/TZSA-0396 | url=https://scholarscompass.vcu.edu/etd/5953/ | access-date=24 November 2024}}</ref>
|-
| {{nbsp}}{{nbsp}}{{Small|L}}-Methcathinone || 13.1 || 14.8 || 1,772 || <ref name="RothmanVuPartilla2003" /><ref name="GlennonDukat2017">{{cite book | vauthors = Glennon RA, Dukat M | title = Neuropharmacology of New Psychoactive Substances (NPS) | chapter = Structure-Activity Relationships of Synthetic Cathinones | series = Current Topics in Behavioral Neurosciences | volume = 32 | pages = 19–47 | date = 2017 | publisher = Springer | pmid = 27830576 | pmc = 5818155 | doi = 10.1007/7854_2016_41 | isbn = 978-3-319-52442-9 | chapter-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 [[bioassay|assay]]s were done in rat brain [[synaptosome]]s and human [[potency (pharmacology)|potencies]] may be different. See also [[Monoamine releasing agent#Activity profiles|Monoamine releasing agent § Activity profiles]] 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>
|}

Methcathinone is a [[norepinephrine–dopamine releasing agent]] (NDRA). Methcathinone has very strong [[affinity (pharmacology)|affinities]] for the [[dopamine transporter]] (DAT) and the [[norepinephrine transporter]] (NET). Its affinity for the [[serotonin transporter]] (SERT) is less than that of [[methamphetamine]].<ref>{{cite journal | vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | display-authors = 6 | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 1 | pages = 138–145 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | s2cid = 19015584 }}</ref>

The [[ketone|C=O bond]] at the ''R<sub>β</sub>''-position (directly right of the phenyl ring) is slightly polar, and as a result the drug does not cross the lipid [[blood–brain barrier]] quite as well as [[amphetamine]].{{citation needed|date=February 2013}} Nevertheless, it is a potent central nervous system (CNS) [[stimulant]] and [[dopamine reuptake inhibitor]]. Chronic high dosage use may result in acute mental confusion ranging from mild [[paranoia]] to [[psychosis]].{{citation needed|date=February 2013}} These symptoms typically disappear quickly if use is stopped.

Anecdotal reports have provided some information on patterns of methcathinone use. The most common [[route of administration]] is via [[human nose|nasal]] [[Insufflation (medicine)|insufflation]] (snorting).{{Citation needed|date=April 2007}} Other routes of administration include ''[[per os|oral]]'', [[intravenous injection|IV injection]] and [[Tobacco smoking|smoking]].

==Illicit usage==
Methcathinone binges resemble amphetamine binges in that the user may not sleep or eat, and takes in little in the way of liquids. The methcathinone binge is followed by long periods of sleep, excess eating, long-lasting nosebleeds ([[Insufflation (medicine)|insufflation]] of methcathinone is corrosive to the [[nasal mucosa]] in the same manner as methamphetamine) and, in some cases, [[clinical depression|depression]].{{Citation needed|date=April 2007}}

==Addiction==
In preclinical studies, methcathinone [[hydrochloride]] produces an abuse potential similar to that of the [[amphetamines]].<ref>{{cite journal | pmid = 8029273 | volume=47 | issue=4 | title=Intravenous self-injection of methcathinone in the baboon |date=April 1994 | pages=981–3 |vauthors=Kaminski BJ, Griffiths RR | journal=Pharmacol. Biochem. Behav. | doi=10.1016/0091-3057(94)90307-7| s2cid=40584010 | doi-access=free }}</ref>

Methcathinone can be highly psychologically addictive, and can produce a [[methamphetamine]]-like withdrawal.

In [[drug discrimination studies]], methcathinone hydrochloride evokes responses similar to those induced by both [[Dextroamphetamine|dextro{{shy}}amphetamine sulfate]] and [[cocaine]] hydrochloride.

==Intravenous usage==
Injecting this substance has been associated with symptoms similar to those seen in patients with [[Parkinson's disease]] ([[manganism]]) due to the compound [[manganese dioxide]] which is a byproduct of synthesis with [[permanganate]].<ref>{{cite journal |vauthors=De Bie RM, Gladstone RM, Strafella AP, Ko JH, Lang AE |date=Jun 2007 | title = Manganese-induced Parkinsonism associated with methcathinone (Ephedrone) abuse | journal = Archives of Neurology | volume = 64 | issue = 6| pages = 886–9 | pmid = 17562938 | doi=10.1001/archneur.64.6.886| doi-access =  }}</ref>

==Legal status==
The [[Convention on Psychotropic Substances]] lists methcathinone as a Schedule I substance which restricts its use for government-approved medical and scientific uses.<ref>{{cite web|url=https://www.unodc.org/pdf/convention_1971_en.pdf|title=Convention on Psychotropic Substances, 1971|publisher=United Nations Office on Drugs and Crime|access-date=9 January 2013}}</ref>

=== Australia ===
Methcathinone is a [[Standard for the Uniform Scheduling of Medicines and Poisons|Schedule 9]] prohibited substance in [[Australia]] under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (February 2021).<ref name=":0">{{Cite web|first=|date=February 2021|title=Poisons Standard February 2021|url=https://www.legislation.gov.au/Details/F2021C00098|website=Therapeutic Goods Administration|publisher=Australian Government Department of Health}}</ref> A Schedule 9 substance is defined as a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name=":0" />

=== United Kingdom ===
In the [[United Kingdom]], methcathinone is listed as a Class B drug with no clinical uses.<ref>{{cite web|url=http://www.statutelaw.gov.uk/content.aspx?ActiveTextDocId=2810429|archive-url=https://archive.today/20120805160900/http://www.statutelaw.gov.uk/content.aspx?ActiveTextDocId=2810429|url-status=dead|archive-date=August 5, 2012|title=The Misuse of Drugs Act 1971 (Modification) Order 1998 (SI 1998 No. 750)|date=1998-03-18|work=[[Statutory Instrument (UK)|Statutory Instrument]]|publisher=[[Ministry of Justice (United Kingdom)|Ministry of Justice]]|access-date=2008-07-06}}</ref>

=== United States ===
In the [[United States]], methcathinone is listed as a [[Controlled Substances Act#Schedule I controlled substances|Schedule I]] drug, for which there is no clinical use.<ref>{{cite web|url=http://www.drugfree.org/drug-guide/methcathinone |title=Methcathinone |work=Partnership for Drug-Free Kids |publisher=Drugfree.org |access-date=2015-12-23}}</ref>

=== Netherlands===
In the [[Netherlands]], methcathinone is listed as a Level I substance of the [[Opium Law]], for which there is no clinical use.

=== Finland ===
Methcathinone is illegal in [[Finland]]. It is scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".<ref>{{cite web | title=Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista &#124; 543/2008 &#124; Lainsäädäntö &#124; Finlex | url=https://www.finlex.fi/fi/lainsaadanto/2008/543 }}</ref>

== See also ==
* [[Substituted cathinone]]
* [[α-Methylmethcathinone]]

==References==
{{Reflist}}

==External links==
* [http://www.erowid.org/chemicals/cathinone/cathinone.shtml Cathinone & Methcathinone from Erowid]
* [http://www.erowid.org/chemicals/chemicals_law1.shtml International Drug Scheduling; Convention on Psychotropic Substances; Certain Stimulant/Hallucinogenic Drugs and Certain Nonbarbiturate Sedative Drugs], Food and Drug Administration, June 20, 1994.
* [https://web.archive.org/web/20060528001238/http://paranoia.lycaeum.org/stimulants/59.FR.31639 Methcathinone from lycaeum]

{{Stimulants}}
{{Monoamine releasing agents}}
{{Monoaminergic neurotoxins}}
{{Phenethylamines}}
{{Chemical classes of psychoactive drugs}}

[[Category:Cathinones]]
[[Category:Euphoriants]]
[[Category:Methamphetamines]]
[[Category:Monoaminergic neurotoxins]]
[[Category:Norepinephrine-dopamine releasing agents]]
[[Category:Stimulants]]