Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Mephedrone: Difference between pages

{{Short description|Synthetic stimulant drug}}

{{Distinguish|methedrine|methedrone|mephedrene|methadone|methylone|methcathinone|ephedrone}}

{{Use dmy dates|date=January 2020}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477169815

| IUPAC_name = (''RS'')-2-Methylamino-1-(4-methylphenyl)propan-1-one<ref name=emcdda/>{{rp|5|date=November 2012}}

| image = 4-Methylmethcathinone.svg

| width =

| image2 = Mephedrone-enantiomers-Spartan-HF-3-21G-3D-balls.png

| alt2 = The two [[enantiomer]]s of mephedrone: The potentially more potent ''S'' form is above the ''R'' form.

| width2 = 200

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YELGFTGWJGBAQU-UHFFFAOYSA-N

| smiles = CC1=CC=C(C(C(NC)C)=O)C=C1

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 1189805-46-6

| CAS_supplemental = <br />1189726-22-4 ([[hydrochloride|HCl]])<ref name=emcdda/>{{rp|5|date=November 2012}}

| ATC_prefix = none

| ATC_suffix =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 59331

| PubChem = 29982893

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21485694

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| KEGG = C22785

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8BA8T27317

| C = 11

| H = 15

| N = 1

| O = 1

| synonyms = 4-methyl-''N''-methylcathinone; 2-methylamino-1-''p''-tolylpropan-1-one<ref name=meyer2009 />

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

<!-- Legal status -->

| legal_AU = S8

| 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_DE = Anlage I

| legal_UK = Class B

| legal_US = Schedule I

| legal_UN = P II

| legal_UN_comment = <ref>{{Cite web |title=Substance Details 4-Methylmethcathinone |url=https://www.unodc.org/LSS/Substance/Details/26beacc1-da0e-4543-8f51-a3d54e6d6678 |access-date=2024-01-22}}</ref>

| legal_status =

| routes_of_administration = [[Mouth|Oral]], [[Insufflation (medicine)|insufflation]], [[Intravenous|IV]], [[Suppository|rectal]]

'''Mephedrone''', also known as '''{{nowrap|4-methylmethcathinone}}''', '''{{nowrap|4-MMC}}''', and '''{{nowrap|4-methylephedrone}}''', is a [[Organic compound#Synthetic compounds|synthetic]] [[stimulant]] [[drug]] of the [[substituted amphetamine|amphetamine]] and [[substituted cathinone|cathinone]] classes. Slang names include '''drone''',<ref name=Cumming/> '''{{nowrap|M-CAT}}''',<ref name=bbc0803/> '''White Magic''',<ref>{{cite journal| vauthors = Kihara R, Day E |title=Transient psychotic episodes following recreational use of NRG-3|journal=Progress in Neurology and Psychiatry|date=May 2014|volume=18|issue=3|pages=14–18|doi=10.1002/pnp.331|s2cid=70766780|doi-access=free}}</ref> '''meow meow''' and '''bubble'''.<ref>{{cite journal | vauthors = Schifano F, Albanese A, Fergus S, Stair JL, Deluca P, Corazza O, Davey Z, Corkery J, Siemann H, Scherbaum N, Farre' M, Torrens M, Demetrovics Z, Ghodse AH | display-authors = 6 | title = Mephedrone (4-methylmethcathinone; 'meow meow'): chemical, pharmacological and clinical issues | journal = Psychopharmacology | volume = 214 | issue = 3 | pages = 593–602 | date = April 2011 | pmid = 21072502 | doi = 10.1007/s00213-010-2070-x | url = http://uhra.herts.ac.uk/bitstream/2299/16594/2/904396.pdf | hdl = 2299/16594 | s2cid = 10529974 }}</ref> It is chemically similar to the cathinone compounds found in the [[Khat]] plant of [[eastern Africa]].<ref name="Cumming" /><ref name="acmdreport" /> It comes in the form of tablets or crystals,<ref>{{Cite web|date=2021-11-10|title=Mephedrone|url=https://adf.org.au/drug-facts/mephedrone/|url-status=live|archive-url=https://web.archive.org/web/20210418140939/https://adf.org.au/drug-facts/mephedrone/|archive-date=2021-04-18|access-date=2021-11-22|website=[[Alcohol and Drug Foundation]]|language=en}}</ref> which users can swallow, snort or inject, producing effects similar to those of [[MDMA]], [[amphetamine]]s and [[cocaine]].

In addition to its stimulant effects, mephedrone produces [[side effects]], of which [[bruxism]] is the most common. The [[drug metabolism|metabolism]] of mephedrone has been studied in rats and humans and the metabolites can be detected in urine after usage.

Mephedrone was first synthesised in 1929, but did not become widely known until it was rediscovered in 1999–2000 at which point it was legal to produce and possess in many countries. By 2000, mephedrone was reported to be available for sale on the internet, by 2008 law enforcement agencies had become aware of the compound, and by 2010, it had been reported in most of Europe, becoming particularly prevalent in the United Kingdom. Mephedrone was first made illegal in Israel in 2008, followed by Sweden later that year. In 2010, it was made illegal in many European countries and in December 2010, the EU ruled it illegal. In Australia, New Zealand and the United States, it is considered an [[structural analog|analog]] of other illegal drugs and can be controlled by laws similar to the US [[Federal Analog Act]]. In September 2011, the US temporarily classified mephedrone as a Schedule I drug, effective October 2011. This classification was made permanent in July 2012 with the passage of the Synthetic Drug Abuse Prevention Act (SDAPA).

== Uses ==

===Recreational===

Users have reported that mephedrone causes [[euphoria]], [[stimulation]], an enhanced appreciation for [[music]], an elevated [[mood (psychology)|mood]], decreased [[hostility]], improved [[mental function]] and mild [[sexual stimulation]]; these effects are similar to the effects of cocaine, amphetamines and MDMA, and last different lengths of time depending on the way the drug is taken. Of 70 Dutch users of mephedrone, 58 described it as an overall pleasant experience and 12 described it as an unpleasant experience.<ref name=brunt/> In a survey of UK users who had previously taken cocaine, most users found it produced a better-quality and longer-lasting high and was less addictive. The users were also asked to compare the "risk", and they answered that it was equal.<ref name=winstockaddiction/> A study of users in Northern Ireland found they did not equate the fact that mephedrone was legal with it being safe to use. This was contrary to another study in New Zealand, where users of [[benzylpiperazine]] thought that because it was legal, it was safe.<ref name=McElrath/>

===Available forms===

Mephedrone can come in the form of capsules, tablets or white powder that users may swallow, snort, inject, smoke or use rectally.<ref name=emcdda/>{{rp|12|date=November 2012}}<ref name=winstockaddiction/><ref name=matthews/> When taken orally, users reported they could feel the effects within 15–45 minutes; when snorted, the effects were felt within minutes and peaked within half an hour. The effects last for between two and three hours when taken orally or nasally, but only half an hour if taken intravenously.<ref name=emcdda/>{{rp|12|date=November 2012}} It is sometimes sold mixed with [[methylone]] in a product called '''bubbles''' in the UK<ref name=herald/> and also mixed with other cathinones, including [[ethcathinone]], [[butylone]], [[fluoromethcathinone]] and [[methedrone]].<ref name=emcdda/>{{rp|9|date=November 2012}}

====Purity====

One published study that analysed samples of mephedrone bought using the internet in the UK in 2010 found it was racemic (a mixture of both stereoisomers) and of high purity.<ref name=gibbons/> An unpublished study of six samples also ordered off the internet in the UK in 2010 found they contained very few organic impurities.<ref name=lough/> Four products sold in Irish head shops were tested in 2010 and were found to contain between 82% and 14% mephedrone, with some products containing [[benzocaine]] and [[caffeine]].<ref name=kavanagh/>

==Adverse effects==

===Short-term effects===

The [[EMCDDA]] reported mephedrone can cause various unintended [[acute (medicine)|side effects]] including: [[mydriasis|dilated pupils]],<ref name=winstock/> poor [[concentration]], [[bruxism|teeth grinding]], problems focusing visually, poor [[short-term memory]], [[hallucinations]], delusions, and erratic behaviour.<ref name=emcdda/>{{rp|13|date=November 2012}} They noted the most severe effects appear anecdotally to be linked with high doses or prolonged use, and the effects may be due to users taking other intoxicants at the same time. Other effects users in internet forums have noted include changes in body temperature, [[tachycardia|increased heart rate]], [[breathing difficulties]], loss of appetite, [[hyperhidrosis|increased sweating]], discolouration of extremities, [[anxiety]], [[paranoia]] and [[depression (mood)|depression]].<ref name=emcdda/>{{rp|13|date=November 2012}} When snorted, it can also cause [[nose bleed]]s and nose burns.<ref name=emcdda/>{{rp|13|date=November 2012}}<ref name=bbc2711/> A survey conducted by the UK National Addiction Centre found 67% of mephedrone users experienced sweating, 51% suffered from headaches, 43% from heart palpitations, 27% from nausea and 15% from cold or blue fingers,<ref name=reed1301/> indicative of [[vasoconstriction]] occurring.<ref name=james/> Doctors at [[Guy's Hospital]] in London reported that of 15 patients they treated after taking mephedrone in 2009, 53% were agitated, 40% had increased heart rates, 20% had [[systolic hypertension]] and 20% had seizures; three required treatment with [[benzodiazepines]], predominantly to control their agitation. They reported none of their patients suffered from cold or blue peripheries, contrary to other reports. Nine of the 15 of patients had a [[Glasgow coma scale]] (GCS) of 15, indicating they were in a normal mental state, four had a GCS below 8, but these patients all reported using a [[central nervous system]] depressant, most commonly [[gamma-Hydroxybutyric acid|GHB]], with mephedrone. The patients also reported [[polydrug use]] of a variety of compounds.<ref name=wood/>

===Neurotoxicity===

Mephedrone is neurotoxic and induces injury to the 5-HT neurons.<ref name="pmid26074741">{{cite journal |vauthors=Karch SB |title=Cathinone neurotoxicity (The "3Ms") |journal=Current Neuropharmacology |volume=13 |issue=1 |pages=21–5 |date=January 2015 |pmid=26074741 |pmc=4462040 |doi=10.2174/1570159X13666141210225009}}</ref><ref name="pmid27908258">{{cite journal |vauthors=Pantano F, Tittarelli R, Mannocchi G, Pacifici R, di Luca A, Busardò FP, Marinelli E |title=Neurotoxicity Induced by Mephedrone: An up-to-date Review |journal=Current Neuropharmacology |volume=15 |issue=5 |pages=738–749 |date=2017 |pmid=27908258 |pmc=5771050 |doi=10.2174/1570159X14666161130130718}}</ref><ref name="pmid32087112">{{cite journal |vauthors=Mead J, Parrott A |title=Mephedrone and MDMA: A comparative review |journal=Brain Res |volume=1735 |issue= |pages=146740 |date=May 2020 |pmid=32087112 |doi=10.1016/j.brainres.2020.146740}}</ref> Although some studies in animal models reported no damage to DA nerve endings in the [[striatum]] and no significant changes in brain [[monoamine]] levels, some others suggested a rapid reduction in [[Serotonin transporter|5-HT]] and [[Dopamine transporter|DA transporter]] function. Persistent serotonergic deficits were observed after binge like treatment in a warm environment and in both serotonergic and dopaminergic nerve endings at high ambient temperature. [[Oxidative stress]] [[cytotoxicity]] and an increase in [[frontal cortex]] [[lipid peroxidation]] were also reported.<ref name="pmid27908258"/><ref name="pmid29713996">{{cite journal |vauthors=Kamińska K, Noworyta-Sokołowska K, Górska A, Rzemieniec J, Wnuk A, Wojtas A, Kreiner G, Kajta M, Gołembiowska K |title=The Effects of Exposure to Mephedrone During Adolescence on Brain Neurotransmission and Neurotoxicity in Adult Rats |journal=Neurotox Res |volume=34 |issue=3 |pages=525–537 |date=October 2018 |pmid=29713996 |pmc=6154178 |doi=10.1007/s12640-018-9908-0}}</ref>

===Reinforcement disorders===

There have been reports of users craving mephedrone, suggesting it may be addictive.<ref name=emcdda/>{{rp|13|date=November 2012}}<ref name=brunt/>

==Overdose==

===Toxicity===

In 2009, one case of [[sympathomimetic]] toxicity was reported in the UK after a person took 0.2&nbsp;g of mephedrone [[per os|orally]], and after this did not achieve the desired effect, [[intramuscular injection| intramuscularly injected]] 3.8&nbsp;g mixed with water into his thighs. Shortly afterwards, the user "developed palpitations, blurred tunnel vision, chest pressure and sweating". The patient was treated with 1&nbsp;mg of [[lorazepam]] and the sympathomimetic features decreased and the user was discharged within six hours of arrival.<ref name=woodsubcataneous/> One case of [[serotonin syndrome]] has been reported, where the patient was already prescribed [[fluoxetine]] and [[olanzapine]], and then took 40 tablets containing mephedrone in one night. He was treated with lorazepam and discharged 15 hours after admission.<ref name=Garrett/> Both [[enantiomer]]s of [[methcathinone]], which differs only in the lack of the methyl group on the [[aryl]] ring when compared to mephedrone, have been shown to be toxic to rat [[dopamine]] neurons, and the ''S''-enantiomer was also toxic against [[serotonin]] neurons. Simon Gibbons and Mire Zloh of the School of Pharmacy, [[University of London]] stated, based on the chemical similarities between methcathinone and mephedrone, "it is highly likely that mephedrone will display neurotoxicity".<ref name=gibbons/> However, Brunt and colleagues stated, "extreme caution" should be used when inferring the toxicity of mephedrone from methcathinone, noting some of the toxicity associated with methcathinone is due to manganese impurities related to its synthesis, rather than the compound itself. They concluded more experimental research is needed to investigate the toxicity of mephedrone.<ref name=brunt/>

Doctors who treated a 15-year-old female suffering from mephedrone intoxication suggested in ''The Lancet'' that, like MDMA, mephedrone may promote serotonin-mediated release of [[antidiuretic hormone]], resulting in [[hyponatraemia]] and an altered mental state.<ref name=sammler/> In another case, a 19-year-old male was admitted to hospital suffering from [[myocarditis|inflammation of the heart]], 20 hours after taking one gram of mephedrone. The doctors treating the patient stated it was caused by either a direct toxic effect of mephedrone on the heart muscle, or by an immune response.<ref name=Nicholson/> One case of [[Methaemoglobinaemia#Acquired methemoglobinemia|acquired methaemoglobinaemia]], where a patient had "bluish lips and fingers", has also been reported, after the user snorted one gram of mephedrone. The patient started to recover after arriving at the hospital and it was not necessary to administer any medication.<ref name=ahmed/>

===Deaths===

====Sweden====

In 2008, an 18-year-old Swedish woman died in [[Stockholm]] after taking mephedrone. The newspaper ''[[Svenska Dagbladet]]'' reported the woman went into convulsions and turned blue in the face.<ref name=local/> Doctors reported she was comatose and suffering from [[hyponatremia]] and severe [[hypokalemia]]; the woman died one and a half days after the onset of symptoms. An autopsy showed severe brain swelling.<ref name=Gustavsson/> Mephedrone was scheduled to be classified as a "dangerous substance" in Sweden even before the woman's death at [[Karolinska University Hospital]] on 14 December, but the death brought more media attention to the drug. The possession of mephedrone became classified as a criminal offence in Sweden on 15 December 2008.<ref name=local/>

====United Kingdom====

In 2010, unconfirmed reports speculated about the role mephedrone has played in the deaths of several young people in the UK. By July 2010, mephedrone had been alleged to be involved in 52 fatalities in the UK, but detected in only 38 of these cases. Of the nine that coroners had finished investigating, two were caused directly by mephedrone.<ref name=npsad/> The first death reported to be caused by mephedrone use was that of 46-year-old, John Sterling Smith,<ref>[https://www.bbc.co.uk/news/10176982 "Man from Hove died after injecting mephedrone"], BBC News website, 27 May 2010; retrieved on 9 June 2012</ref> who had underlying health problems and repeatedly injected the drug.<ref name=bbc2805/> A report in ''[[Forensic Science International]]'' in August 2010 stated mephedrone intoxication has been recorded as the cause of death in two cases in Scotland. ''Post mortem'' samples showed the concentration of mephedrone in their blood was 22&nbsp;mg/L in one case and 3.3&nbsp;mg/L in the other.<ref name=Torrance/> The death of a teenager in the UK in November 2009 was widely reported as being caused by mephedrone, but a report by the coroner concluded she had died from natural causes.<ref name=fleming0504/> In March 2010, the deaths of two teenagers in [[Scunthorpe]] were widely reported by the media to be caused by mephedrone. Toxicology reports showed the teenagers had not taken any mephedrone and had died as a result of consuming alcohol and the synthetic [[opioid]] [[agonist]] [[methadone]].<ref name=bbc2805/><ref name=bbc2501/> According to Fiona Measham, a criminologist who is a member of the ACMD, the reporting of the unconfirmed deaths by newspapers followed "the usual cycle of 'exaggeration, distortion, inaccuracy and sensationalism{{'"}} associated with the reporting of recreational drug use.<ref name="Measham"/>

====United States====

Mephedrone has been implicated in the death of a 22-year-old man, who had also injected [[black tar heroin]]. Mephedrone was found in his blood at a concentration of 0.50&nbsp;mg/L and in his urine at a concentration of 198&nbsp;mg/L. The blood concentration of morphine, a metabolite of heroin, was 0.06&nbsp;mg/L.<ref name=dickson/> For comparison, the average blood morphine concentration resulting from deadly overdoses involving only heroin is around 0.34&nbsp;mg/L.<ref name=darke/>

==Pharmacology==

{{update|section|date=March 2015}}

===Pharmacodynamics===

Mephedrone is a [[monoamine releasing agent]]. It is a [[chiral centre|chiral]] compound and both of its [[enantiomer]]s display similar [[Potency (pharmacology)|potency]] as [[Substrate (chemistry)|substrates]] at [[dopamine transporter]]s. ''[[Absolute configuration|R]]''-Mephedrone is much less potent than ''S''-mephedrone as a substrate at [[serotonin transporter]]s.<ref name="pmid25255824">{{cite journal | vauthors = Gregg RA, Baumann MH, Partilla JS, Bonano JS, Vouga A, Tallarida CS, Velvadapu V, Smith GR, Peet MM, Reitz AB, Negus SS, Rawls SM | display-authors = 6 | title = Stereochemistry of mephedrone neuropharmacology: enantiomer-specific behavioural and neurochemical effects in rats | journal = British Journal of Pharmacology | volume = 172 | issue = 3 | pages = 883–94 | date = February 2015 | pmid = 25255824 | pmc = 4301696 | doi = 10.1111/bph.12951 }}</ref>

The [[Ketone|keto]] oxygen renders mephedrone more [[hydrophilic]] than the corresponding amphetamine [[4-Methylmethamphetamine]], which may account for the higher doses required to achieve a similar effect, because mephedrone is less able to cross the [[blood–brain barrier]].<ref name=emcdda/>{{rp|12|date=November 2012}}<ref name=gibbons/>

Mephedrone is often consumed with [[alcohol (drug)|alcohol]]. A study in mice investigated the interrelation between these two substances, focusing on the psychostimulant and rewarding properties of mephedrone. It found that at low (non-stimulant) doses alcohol significantly enhanced the psychostimulant effects of mephedrone. This effect was mediated by an increase in synaptic [[dopamine]], as [[haloperidol]], but not [[ketanserin]], was able to block the potentiation by alcohol. Similarly, the rewarding properties of mephedrone were enhanced by a low non-rewarding dose of alcohol.<ref>{{cite journal | vauthors = Ciudad-Roberts A, Camarasa J, Ciudad CJ, Pubill D, Escubedo E | title = Alcohol enhances the psychostimulant and conditioning effects of mephedrone in adolescent mice; postulation of unique roles of D3 receptors and BDNF in place preference acquisition | journal = British Journal of Pharmacology | volume = 172 | issue = 20 | pages = 4970–84 | date = October 2015 | pmid = 26228024 | pmc = 4621996 | doi = 10.1111/bph.13266 }}</ref>

===Pharmacokinetics===

Several articles published near the end of 2011 examined the effects of mephedrone, compared to the similar drugs MDMA and amphetamine in the [[nucleus accumbens]] of rats, as well as examining the reinforcing potential of mephedrone. [[Dopamine]] and [[serotonin]] were collected using microdialysis, and increases in dopamine and serotonin were measured using [[HPLC]]. Reward and drug seeking are linked to increases in dopamine concentrations in the nucleus accumbens, and drug half-life plays a role in drug seeking, as well. Based on histological examination, most of the author's probes were in the nucleus accumbens shell. Mephedrone administration caused about a 500% increase in dopamine, and about a 950% increase in serotonin. They reached their peak concentrations at 40 minutes and 20 minutes, respectively, and returned to baseline by 120 minutes after injection. In comparison, MDMA caused a roughly 900% increase in serotonin at 40 minutes, with an insignificant increase in dopamine. Amphetamine administration resulted in about a 400% increase in dopamine, peaking at 40 minutes, with an insignificant increase in serotonin. Analysis of the ratio of the AUC for dopamine (DA) and serotonin (5-HT) indicated mephedrone was preferentially a serotonin releaser, with a ratio of 1.22:1 (serotonin vs. dopamine). Additionally, half-lives for the decrease in DA and 5-HT were calculated for each drug. Mephedrone had decay rates of 24.5 minutes and 25.5 minutes, respectively. MDMA had decay values of 302.5 minutes and 47.9 minutes, respectively, while amphetamine values were 51 minutes and 84.1 minutes, respectively. Taken together, these findings show mephedrone induces a massive increase in both DA and 5-HT, combined with rapid clearance. The rapid rise and subsequent fall of DA levels could explain some of the addictive properties mephedrone displays in some users.<ref name=Kehr/><ref>{{cite journal | vauthors = Hadlock GC, Webb KM, McFadden LM, Chu PW, Ellis JD, Allen SC, Andrenyak DM, Vieira-Brock PL, German CL, Conrad KM, Hoonakker AJ, Gibb JW, Wilkins DG, Hanson GR, Fleckenstein AE | display-authors = 6 | title = 4-Methylmethcathinone (mephedrone): neuropharmacological effects of a designer stimulant of abuse | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 339 | issue = 2 | pages = 530–6 | date = November 2011 | pmid = 21810934 | pmc = 3200001 | doi = 10.1124/jpet.111.184119 }}</ref>

====Metabolism====

Based on the analysis of rat and human urine by [[gas chromatography]] and [[mass spectrometry]], mephedrone is thought to be [[drug metabolism|metabolised]] by three [[Phase 1 metabolism|phase 1 pathways]]. It can be [[demethylation|demethylated]] to the primary [[amine]] (producing compounds 2, 3 and 5), the [[ketone]] group can be [[redox|reduced]] (producing 3) or the [[tolyl]] group can be oxidised (producing 6). Both 5 and 6 are thought to be further metabolised by conjugation to the [[glucuronide]] and [[sulfate]] derivatives. Knowledge of the primary routes of metabolism should allow the intake of mephedrone to be confirmed by [[drug test]]s, as well as more accurate determination of the causes of side effects and potential for toxicity.<ref name=meyer2010/>

[[File:Mephedrone metabolism.png|thumb|center|600px|Proposed scheme for the [[drug metabolism|metabolism]] of mephedrone (1) based on the analysis of rat and human urine<ref name=meyer2010/>]]

===Detection in body fluids===

Mephedrone may be quantitated in blood, plasma or urine by gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalised patients or to provide evidence in a medicolegal death investigation. Blood or plasma mephedrone concentrations are expected to be in a range of 50–100 μg/L in persons using the drug recreationally, >100 μg/L in intoxicated patients and >500 μg/L in victims of acute overdosage.<ref>L.J. Marinetti and H.M. Antonides. Analysis of synthetic cathinones commonly found in bath salts in human performance and postmortem toxicology: method development, drug distribution and interpretation of results. J. Anal. Tox. 37: 135–146, 2013.</ref><ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 10th edition, Biomedical Publications, Seal Beach, CA, 2014, pp. 1226–1227. {{ISBN|978-0-9626523-9-4}}</ref>

==Chemistry==

===Appearance and odour===

Mephedrone is a white substance. It is sold most commonly as crystals or a powder, but also in the form of capsules or pills.<ref name=reed1301what/><ref name=roussel/> It can have a distinctive odour, reported to range the smell of [[vanilla]] and [[bleach]], stale [[urine]], or electric [[circuit board]]s.<ref name=psychoreport/> Synthesis byproducts or other contaminants are likely responsible for this, as the molecule itself is not an [[Aroma compound|odorant]].

===Synthesis===

Mephedrone can be synthesised in several ways. The simplest method, due to the availability of the compounds,<ref name=emcdda/>{{rp|17|date=November 2012}} is to add [[4-methylpropiophenone]] dissolved in [[glacial acetic acid]] to [[bromine]], creating an oil fraction of 4'-methyl-2-bromopropiophenone. The oil fraction can then be dissolved in [[dichloromethane]] (CH₂Cl₂) and drops of the solution added to another solution of CH₂Cl₂-containing [[Methylamine#Production|methylamine hydrochloride]] and [[triethylamine]]. [[Hydrochloric acid]] (HCl) is then added and the aqueous layer is removed and [[acid–base reaction|turned alkaline]] using [[sodium hydroxide]] before the amine is extracted using CH₂Cl₂. The CH₂Cl₂ is then evaporated using a vacuum, creating an oil which is then dissolved in a nonaqueous [[ether]]. Finally, HCl gas is bubbled through the mixture to produce 4-methylmethcathinone hydrochloride.<ref name=Camilleri/> This method produces a mixture of both [[enantiomer]]s and requires similar knowledge to that required to synthesise amphetamines and MDMA.<ref name=emcdda/>{{rp|17|date=November 2012}}

[[File:Mephedrone-synthesis-scheme-2D-skeletal-B.png|900px|thumb|center|Mephedrone synthesis scheme from 4-methylpropiophenone]]

It can also be produced by oxidising the ephedrine analogue [[4-methylephedrine]] using [[potassium permanganate]] dissolved in [[sulfuric acid]]. Because 4-methylephedrine can be obtained in a specific enantiomeric form, mephedrone consisting of only one enantiomer can be produced. The danger associated with this method is it may cause [[manganese poisoning]] if the product is not correctly purified.<ref name=emcdda/>{{rp|17|date=November 2012}}

===Analysis===

Mephedrone does not react with most [[reagent testing]] kits. The exception is the [[Liebermann reagent]], which gives a bright yellow reaction.<ref name='Microgram methcathinone'>{{cite journal | vauthors = Toole KE, Fu S, Shimmon RG, Kraymen N | title = Color Tests for the Preliminary Identification of Methcathinone and Analogues of Methcathinone | journal = Microgram Journal | volume = 9 | issue = 1 | pages = 27–32 | year = 2012 | url = http://www.justice.gov/dea/pr/microgram-journals/2012/mj9-1_27-32.pdf | access-date = 29 January 2016 | archive-date = 26 November 2013 | archive-url = https://web.archive.org/web/20131126123356/http://www.justice.gov/dea/pr/microgram-journals/2012/mj9-1_27-32.pdf | url-status = dead }}</ref>

==History==

[[File:Зиплок-пакет с веществом мефедрон.jpg|300px|thumb|Mephedrone. "Not for human consumption. For technical use only. Purity: 99+ %"]]

Mephedrone is one of hundreds of [[designer drug]]s or legal highs that have been reported in recent years, including artificial chemicals such as [[synthetic cannabis]] and semisynthetic substances such as [[methylhexanamine]]. These drugs are primarily developed to avoid being controlled by laws against illegal drugs, thus giving them the label of designer drugs.<ref name=McElrath/> According to the [[European Monitoring Centre for Drugs and Drug Addiction]], the synthesis of mephedrone was first reported in 1929 by Saem de Burnaga Sanchez in the ''[[Bulletin de la Société Chimique de France]]'', under the name "toluyl-alpha-monomethylaminoethylcetone",<ref name=emcdda/>{{rp|17|date=November 2012}}<ref name=Sanchez1929/> but the compound remained an obscure product of academia until 2003, when it was "re-discovered" and publicised by an [[unknown British/asianchemistry|underground chemist]] on [[The Hive (website)|The Hive]] website, registered to a Portuguese ip working under the pseudonym "Kinetic".<ref name=hamilton/> Kinetic posted on the site, "I've been bored over the last couple of days and had a few fun reagents lying around, so I thought I'd try and make some 1-(4-methylphenyl)-2-methylaminopropanone hydrochloride, or 4-methylmethcathinone." before going on to describe that after consuming it, the user had a "fantastic sense of well-being that I haven't got from any drug before except my beloved Ecstasy."<ref name=druglink0110power/> After the initial description of mephedrone's qualitative effects by Kinetic, the drug was commercially introduced in Israel by a mathematician named Ezekiel Golan or "Dr. Z".<ref name=slezak1/><ref name=slezak2/>

A drug similar to mephedrone, containing [[cathinone]], was sold legally in Israel from around 2004, under the name ''hagigat''. When this was made illegal, the cathinone was modified and the new products were sold by the Israeli company, Neorganics.<ref name=druglink0309/><ref name=doward2/><ref name=bentur/> The products had names such as Neodoves pills, but the range was discontinued in January 2008 after the Israeli government made mephedrone illegal.<ref name=Cumming/><ref name="Camilleri" /><ref name=davies09/> The Psychonaut Research Project, an EU organisation that searches the internet for information regarding new drugs, first identified mephedrone in 2008. Their research suggested the drug first became available to purchase on the internet in 2007, made available through British contacts, contact unknown, when it was also discussed on internet forums.<ref name=McElrath/><ref name=psycho/> Mephedrone was first seized in France in May 2007, after police sent a tablet they assumed to be ecstasy to be analysed, with the discovery published in a paper titled "Is 4-methylephedrone, an "Ecstasy" of the twenty-first century?"<ref name=roussel/> Mephedrone was reported as having been sold as [[ecstasy (drug)|ecstasy]] in the Australian city of [[Cairns]], along with [[ethylcathinone]], in 2008.<ref name=guppy/><ref name=abcnews/> An annual survey of regular ecstasy users in Australia in 2010 found 21% of those surveyed had used mephedrone, with 17% having done so in the previous six months. The price they paid per gram varied from [[Australian dollar|A$]]16 to $320.<ref name=matthews/>

[[Europol]] noted they became aware of it in 2008, after it was found in Denmark, Finland and the UK.<ref name=emcdda08/> The [[Drug Enforcement Administration]] noted it was present in the United States in July 2009.<ref name=dea/> By May 2010, mephedrone had been detected in all 22 [[EU member states]] that reported to Europol, as well as in Croatia and Norway.<ref name=emcdda/>{{rp|21|date=November 2012}} ''The Daily Telegraph'' reported in April 2009 that it was manufactured in [[China]], but it has since been made illegal there.<ref name=devlin/><ref name=china/> In March 2009, ''Druglink'' magazine reported it only cost a "couple of hundred pounds" to synthesise a kilogram of mephedrone,<ref name=druglink0309/> the same month, ''The Daily Telegraph'' reported manufacturers were making "huge amounts of money" from selling it.<ref name=Gammell/> In January 2010, ''Druglink'' magazine reported dealers in Britain spent £2,500 to ship one kilogram from China, but could sell it for £10 a gram, making a profit of £7,500.<ref name=druglink0110power/><ref name=Campbell1701/> A later report, in March 2010, stated the wholesale price of mephedrone was £4000 per kilogram.<ref name=fleming1803/>

In March 2011, the [[International Narcotics Control Board]] published a report about designer drugs, noting mephedrone was by then being used recreationally in Europe, North America, Southeast Asia, New Zealand and Australia.<ref name=incb/><ref name=incbreport/>

===United Kingdom===

[[File:Cathinones seizures.png|thumb|The number of samples analysed by the [[Forensic Science Service]] of seized [[MDMA]], [[piperazine]]s and [[cathinone]]s between the third quarter of 2005 and the first quarter of 2010: MDMA seizures in blue, piperazine seizures in orange and cathinone seizures in purple<ref name=emcddatechnical/>]]

Between the summer of 2009 and March 2010, the use of mephedrone grew rapidly in the UK, with it becoming readily available at [[music festival]]s, [[head shop]]s and on the internet.<ref name=Measham/> A survey of ''[[Mixmag]]'' readers in 2009, found it was the fourth most popular [[street drug]] in the [[United Kingdom]], behind [[Cannabis (drug)|cannabis]], [[cocaine]], and [[MDMA|ecstasy]].<ref name=fleming1803/> The drug was used by a diverse range of social groups. Whilst the evidence was anecdotal, researchers, charity workers, teachers and users reported widespread and increasing use of the drug in 2009. The drug's rapid growth in popularity was believed to be related to both its availability and legality.<ref name=Measham/>

In a book about drugs<ref>{{cite book |last1=Nutt |first1=David J. |title=Drugs without the hot air : making sense of legal and illegal drugs |date=2021 |location=Cambridge |isbn=9780857844989 |edition=Second |url=https://www.uit.co.uk/drugs-without-the-hot-air.html |access-date=27 September 2022}}</ref> [[David Nutt]] reports the re-popularization story of mephedrone in a way that can be cross referenced with a report by [[Chemistry World]] in an article.<ref>{{cite web |last1=Extance |first1=Andy |title=The rising tide of 'legal highs' |url=https://www.chemistryworld.com/features/the-rising-tide-of-legal-highs/3007738.article |website=Chemistry World |access-date=27 September 2022 |language=en}}</ref>

Fiona Measham, a criminologist at [[The University of Lancaster]], thought the emergence of mephedrone was also related to the decreasing purity of ecstasy and cocaine on sale in the UK,<ref name=Measham/> a view reinforced in a report by the [[National Treatment Agency for Substance Misuse]].<ref name=nmsta/> The average [[cocaine]] purity fell from 60% in 1999 to 22% in 2009 and about half of ecstasy pills seized in 2009 contained no [[MDMA]],<ref name=fleming2903/> and by June 2010 almost all ecstasy pills seized in the UK contained no MDMA.<ref name=Reed2006/> A similar pattern was observed in the Netherlands, with the number of ecstasy tablets containing no MDMA rising from 10% in mid-2008 to 60% by mid-2009, with mephedrone being detected in 20% of ecstasy tablets by mid-2009.<ref name=brunt/> The decrease of MDMA was thought to be partly due to the seizure of 33&nbsp;tonnes of [[sassafras oil]], the precursor to MDMA, in [[Cambodia]] in June 2008, which could have been used to make 245 million doses of MDMA.<ref name=druglink0110power/> According to John Ramsey, a [[toxicologist]] at [[St George's, University of London]], the emergence of mephedrone was also related to the UK government banning the [[benzylpiperazine]] class of drugs in December 2009.<ref name=druglink0309/><ref name=bzpmoda/> [[gamma-Butyrolactone|''gamma''-Butyrolactone]] (GBL), another previously "legal high", was also banned in August 2009 despite concerns it would be replaced by other drugs.<ref name=silverman/>

By December 2009 mephedrone was available on at least 31 websites based in the UK and by March 2010 there were at least 78 online shops, half of which sold amounts of less than 200&nbsp;grams and half that also sold bulk quantities. The price per gram varied from £9.50 to £14.<ref name=emcdda/>{{rp|11|date=November 2012}} Between July 2009 and February 2010, UK health professionals accessed the [[National Poisons Information Service]]{{'}}s (NPIS) entry on mephedrone 1664 times and made 157 telephone inquiries; the requests increased month on month over this period. In comparison, over a similar time period, the entries for cocaine and MDMA were accessed approximately 2400 times.<ref name=james/> After mephedrone was made illegal the number of inquiries to the NPIS fell substantially, to only 19 in June 2010.<ref name=press0410/>

Media organisations including the [[BBC]] and ''[[The Guardian]]'' incorrectly reported mephedrone was commonly used as a plant [[fertiliser]]. In fact sellers of the drug described it as "plant food" because it was illegal to sell the compound for human consumption.<ref name=fleming2903/> In late 2009 UK newspapers began referring to the drug as '''meow''' or '''miaow''' (sometimes doubled as '''meow meow''' or '''miaow miaow'''), a name that was almost unknown on the street at the time.<ref name=Eye/> In November 2009, the [[tabloid (newspaper format)|tabloid]] newspaper, ''[[The Sun (United Kingdom)|The Sun]]'' published a story stating that a man had ripped off his own [[scrotum]] whilst using mephedrone. The story was later shown to be an online joke posted on mephedrone.com, later included in a police report with the caveat that it could be unreliable. The police report was used as a source for the story in ''The Sun''.<ref name=fleming0504/><ref name=davey/> Other myths the media often repeated during 2010 were that mephedrone had led to the deaths of over 20 people, teachers were unable to confiscate the drug from pupils and the government was too slow to ban the drug.<ref name=greenslade/> Parallels were drawn between the media coverage of mephedrone and a piece of satire by [[Chris Morris (satirist)|Chris Morris]] in 1997 on ''[[Brass Eye]]'' when he tricked public figures into talking of the dangers of taking the fictional legal drug "cake".<ref name=fleming0504/> The [[Advisory Council on the Misuse of Drugs]] (ACMD) have suggested that the media coverage of the drug led to its increased usage.<ref name=lancet/> Jon Silverman, a former BBC Home Affairs Correspondent, has written two articles discussing how the media had a strong influence over the UK government's drugs policy, particularly in that the government wished to demonstrate they were being "tough" on drugs.<ref name=silverman/><ref name=silverman2/>

A survey of 1000 secondary school pupils and university students in [[Tayside]] conducted in February 2010 found 20% of them had previously taken mephedrone. Although at the time it was available legally over the internet, only 10% of users reported purchasing it online, with most purchasing it from street dealers. Of those who had used mephedrone, 97% said it was easy or very easy to obtain. Around 50% of users reported at least one negative effect associated with the use of mephedrone, of which [[bruxism|teeth grinding]] is the most common.<ref name=dargan/> Detailed interviews with users in Northern Ireland similarly found that few purchased mephedrone online, with most interviewees citing concerns that their address would be traced or that family members could intercept the package.<ref name=McElrath/>

On 30 March 2010, [[Alan Johnson]], the then [[Home Secretary]], announced mephedrone would be made illegal "within weeks" after the ACMD sent him a report on the use of cathinones.<ref name=acmdreport/><ref name=bbc2903/> The legislation would make all cathinones illegal, which Johnson said would "stop unscrupulous manufacturers and others peddling different but similarly harmful drugs".<ref name=kmietowicz/> The ACMD had run into problems with the UK Government in 2009 regarding drugs policy, after the government did not follow the advice of the ACMD to reclassify [[MDMA|ecstasy]] and [[Cannabis classification in the United Kingdom|cannabis]], culminating in the dismissal of the ACMD chairman, [[David Nutt]], after he reiterated the ACMD's findings in an academic lecture.<ref name=bbc2903letter/> Several members resigned after he was sacked, and prior to the announcement that mephedrone was to be banned, the trend continued when Dr Polly Taylor resigned, saying she "did not have trust" in the way the government would use the advice given by the ACMD.<ref name=bbc2903polly/> Eric Carlin, a member of the ACMD and former chairman of the English Drug Education Forum, also resigned after the announcement. He said the decision by the Home Secretary was "unduly based on media and political pressure" and there was "little or no discussion about how our recommendation to classify this drug would be likely to impact on young people's behaviour."<ref name=bbc0204/> Some former members of the ACMD and various charity groups expressed concern over the banning of the drug, arguing it would inevitably criminalise users, particularly young people.<ref name=TDPF/> Others expressed concern that the drug would be left in the hands of [[black market]] dealers, who will only compound the problem.<ref name=doward/> Carlin's resignation was specifically linked to the criminalisation of mephedrone; he stated: "We need to review our entire approach to drugs, dumping the idea that legally-sanctioned punishments for drug users should constitute a main part of the armoury in helping to solve our country's drug problems. We need to stop harming people who need help and support".<ref name=bbc0204letter/>

The parliamentary debate was held on 8 April, one day after the [[2010 United Kingdom general election|2010 general election]] had been announced, meaning it was during the so-called "[[wash-up period]]" when legislation is passed with little scrutiny. Only one hour was spent debating the ban and all three parties agreed, meaning no vote was required.<ref name=daat/> In an interview conducted in July 2010, when he was no longer a minister, Johnson admitted the decision to ban mephedrone was sped up after widespread reporting of deaths caused by the drug, and because the government wished to pass the law before parliament was dissolved prior to the upcoming general election.<ref name=silverman/> In January 2011, however, Johnson told the ''Scunthorpe Telegraph'' that the decision was based only on information from the ACMD.<ref name=scunthorpe/> An editorial in the April 2010 edition of ''[[The Lancet]]'' questioned the decision to ban mephedrone, saying the ACMD did not have enough evidence to judge the potential harms caused by mephedrone and arguing that policy makers should have sought to understand why young people took it and how they could be influenced to not take it.<ref name=lancet/> [[Evan Harris]], then the [[Liberal Democrats (UK)|Liberal Democrat]] science spokesman, stated the ACMD "was not 'legally constituted{{'"}} as required by the [[Misuse of Drugs Act 1971|Misuse of Drugs Act]], when the report on cathinones was published, since after Taylor resigned, it lacked a veterinary surgeon.<ref name=kmietowicz/> In the rush to make mephedrone illegal, the act that was passed specified the inactive enantiomer of mephedrone, leaving the active form legal until the loophole was closed in February 2011 by another act of parliament.<ref name=nutt11/> In ''[[Chemistry World]]'', John Mann, professor of chemistry at [[Queen's University Belfast]], suggested the UK create a law similar to the [[Federal Analog Act]] of the United States, which would have made mephedrone illegal as an analog of cathinone.<ref name=mann/> In August 2010, [[James Brokenshire]], the Home Office drugs minister, announced plans to create a new category in the Misuse of Drugs Act, through the [[Police Reform and Social Responsibility Bill]], that would allow new legal highs to be made temporarily illegal, without the need for a vote in parliament or advice from the ACMD, as was required to categorise mephedrone.<ref name=druglink0910sare/><ref name=stratton/><ref name=Noorden/>

According to the [[Independent Scientific Committee on Drugs]], after mephedrone was made illegal, a street trade in the drug emerged, with prices around double those prior to the ban, at £20–£25 per gram.<ref name=ISCoD/> In September 2010, ''Druglink'' reported the ban had a mixed effect on mephedrone use, with it decreasing in some areas, remaining similar in others and becoming more prevalent in some areas.<ref name=druglink0910daly/> In an online survey of 150 users after the ban, 63% said they were continuing to use mephedrone; of those, half claimed unchanged usage amounts (as to dosage and frequency) and half claimed decreased usage. Compared to previous surveys, more users purchased it from dealers, rather than the internet. The average price per gram was £16, compared to around £10 before the ban.<ref name=winstock1210/> The 2010 ''Mixmag'' survey of 2,500 nightclubbers found one quarter had used mephedrone in the previous month, the price had roughly doubled since it was made illegal, and it was more likely to be [[Lacing (drugs)|cut]] with other substances.<ref name=bbc0802/> Of those who had already used mephedrone prior to the ban, 75% had continued to use it after the ban. Of the various drugs used by the survey participants, users were more likely to have concerns about it<!-- in audio -->.<ref name=garnett/> Interviews with users in Northern Ireland also found the price had roughly doubled since it was made illegal, to around £30 a gram. Rather than the price rising due to increased scarcity of the drug, it is thought to have risen for two other reasons. Firstly, dealers knew there was still demand for mephedrone, but were aware the supplies may be exhausted in the future. Secondly, the dealers perceived customers were likely to be willing to pay more for an illegal substance.<ref name=McElrath/>

Professor Shiela Bird, a statistician at the [[Medical Research Council (UK)|Medical Research Council]], suggested the ban of mephedrone may lead to more cocaine-related deaths. In the first six months of 2009, the number of cocaine-related deaths fell for the first time in four years, and fewer soldiers tested positive for cocaine in 2009 than in 2008. She suggested this may have been due to users switching to mephedrone from cocaine, but cautioned that before full figures are available for 2009 and 2010, it will be difficult to determine whether mephedrone saved lives, rather than cost them.<ref name=Laurance/><ref name=Bird/> Other supposedly legal drugs have filled the gap in the market since mephedrone was made illegal, including [[naphyrone]] (NRG-1) (since made illegal)<ref name=bbc1207/> and [[Ivory Wave]], which has been found to contain [[MDPV]], a compound made illegal at the same time as mephedrone. However, some products branded as Ivory Wave possibly do not contain MDPV.<ref name=jones/> When tested, some products sold six weeks after mephedrone was banned, advertised as NRG-1, NRG-2 and [[MDAI]], were found to be mephedrone.<ref name=brandt/> A ''Drugscope'' survey of drugs workers at the end of 2012 reported that mephedrone use was still widespread in the UK and that there increasing reports of problematic users. It was being taken as not only a "poor man's cocaine" but also amongst users of [[heroin]] and [[crack cocaine]]. Cases of intravenous use were also reported to be on the increase.<ref name=drugscope1212/>

==Society and culture==

===Legal status===

[[File:4mmc.png|thumb|250px|A sample of mephedrone that was confiscated in Oregon, US, 2009]]

When mephedrone was rediscovered in 2003, it was not specifically illegal to possess in any country. As its use has increased, many countries have passed legislation making its possession, sale and manufacture illegal. It was first made illegal in [[Israel]], where it had been found in products such as Neodoves pills, in January 2008.<ref name=Cumming/> After the death of a young woman in [[Sweden]] in December 2008 was linked to the use of mephedrone, it was classified as a hazardous substance a few days later, making it illegal to sell in Sweden. In June 2009, it was classified as a narcotic with the possession of 15&nbsp;grams or more resulting in a minimum of two years in prison—a longer sentence, gram for gram than given for the possession of cocaine or heroin.<ref name=sweden/><ref name=stigson/> In December 2008, [[Denmark]] also made it illegal<ref name=emcddadenmark/> and through the Medicines Act of [[Finland]], it was made illegal to possess without a prescription.<ref name=finland/> In November 2009, it was classified as a "narcotic or psychotropic" substance and added to the list of controlled substances in [[Estonia]]<ref name=estonia/> and made illegal to import into [[Guernsey]] along with other legal highs,<ref name=bbc0604/> before being classified as a Class B drug in April 2010.<ref name=bbc1304/> It was classified as a Class C drug in Jersey in December 2009.<ref name=bbc0403/>

In 2010, as its use became more prevalent, many countries passed legislation prohibiting mephedrone. It became illegal in Croatia<ref name=croatia/> and Germany<ref name=germany/> in January, followed by Romania<ref name=romania/> and the [[Isle of Man]] in February.<ref name=iom/> In March 2010, it was classified as an unregulated medicine in the [[Netherlands]], making the sale and distribution of it illegal.<ref>{{cite web|url=http://www.cbc.ca/news/technology/club-drug-mephedrone-faces-ban-in-u-k-1.881177 |title=Club drug mephedrone faces ban in U.K. |publisher=CBC News |date=29 March 2010 |access-date=18 March 2014}}</ref><ref>{{cite web |url=http://www.drugtext.org/EMCDDA-Report-on-the-risk-assessment-of-mephedrone/8-description-of-the-control-measures-that-are-applicable-to-mephedrone-in-the-member-states.html |title=8. Description of the control measures that are applicable to mephedrone in the Member States |publisher=Drugtext.org |access-date=18 March 2014 |archive-date=10 December 2014 |archive-url=https://web.archive.org/web/20141210015424/http://www.drugtext.org/EMCDDA-Report-on-the-risk-assessment-of-mephedrone/8-description-of-the-control-measures-that-are-applicable-to-mephedrone-in-the-member-states.html |url-status=dead }}</ref> The importation of mephedrone into the UK was banned on 29 March 2010.<ref name=police/> The next day, the ACMD in the UK published a report on the cathinones, including mephedrone, and recommended they be classified as [[List of controlled drugs in the United Kingdom|Class B drugs]]. On 7 April 2010, the Misuse of Drugs Act 1971 (Amendment) Order 2010 was passed by parliament, making mephedrone and other [[substituted cathinone]]s, Class B drugs from 16 April 2010.<ref name=bbc0704/><ref name=opsi.gov/> Prior to the ban taking effect, mephedrone was not covered by the [[Misuse of Drugs Act 1971]].<ref name=devlin/> It was, though, an offence under the [[Medicines Act 1968|Medicines Act]] to sell it for human consumption, so it was often sold as "[[plant food]]" or "[[bath salts]]", although it has no use as these products; this, too, was possibly illegal under the [[Trade Descriptions Act 1968]].<ref name=bbc2711/><ref name=reed1301/><ref name=acmdreport/> In the US, similar descriptions have been used to describe mephedrone, as well as [[methylenedioxypyrovalerone]] (MDPV).<ref>{{cite news|url=http://blog.al.com/breaking/2011/02/synthetic_form_of_cocaine_and.html|title=Synthetic form of cocaine and methamphetamine being packaged as bath salts|work=The Huntsville Times|author=Victoria Cumbow|date=6 February 2011|access-date=10 February 2011}}</ref> In May 2010, the [[Republic of Ireland]] made mephedrone illegal,<ref name=kelly/><ref name=ireland/><ref name=gartland/> followed by [[Belgium]],<ref name=belgium/> [[Italy]],<ref name=italy/> [[Lithuania]],<ref name=lithuania/> [[France]]<ref name=france/><ref name=francegov/> and [[Norway]]<ref name=norway/> in June and [[Russia]] in July.<ref name=russia/> In August 2010, [[Austria]]<ref name=austria/> and [[Poland]]<ref name=poland/> made it illegal and [[China]] announced it would be illegal as of 1 September 2010.<ref name=china/> Mephedrone had been reported to be used in Singapore in February 2010,<ref name=loh/> but it was made illegal in November 2010.<ref name=singapore/> In December 2010, following the advice of the EMCDDA, mephedrone was made illegal throughout the EU, a move [[Switzerland]] also made shortly afterwards.<ref name=swiss/><ref name=EU/> Countries which have not already banned it, such as the Netherlands, Greece and Portugal, will need to change legislation to comply with the EU ruling.<ref name=EU/> In [[Hungary]], a government advisory body recommended mephedrone should be made illegal in August 2010, which was followed, making it illegal in January 2011;<ref name=hungary/><ref name=hungary2/> Spain followed in February 2011.<ref>{{cite web|url=http://boe.es/diario_boe/txt.php?id=BOE-A-2011-2490 |title=Documento BOE-A-2011-2490 |pages=13595–13596 |publisher=BOE.es |access-date=18 March 2014}}</ref> Mexico, by [[Law of Mexico#Regulations|decree]],<ref>{{cite web|url=http://dof.gob.mx/nota_detalle.php?codigo=5329099&fecha=07/01/2014| title=DECRETO por el que se reforman las fracciones I y III del artículo 245 de la Ley General de Salud|website=Diario Oficial de la Federación|publisher=Secretaría de Gobernación|access-date=1 September 2014|language=Spanish|date=7 January 2014}}</ref> outlawed mephedrone as a substance "with low or no therapeutical use which pose a serious threat to public health"<ref>{{cite web|title=Mexico: mephedrone, TFMPP and synthetic cannabinoids placed under control|url=https://www.unodc.org/LSS/Announcement/Details/816ab930-efcf-4e92-a65c-404b022f25eb|website=United Nations Office on Drugs and Crime|publisher=United Nations|access-date=1 September 2014|date=January 2014}}</ref> in 2014.

In some countries, mephedrone is not specifically listed as illegal, but is controlled under legislation that makes compounds illegal if they are [[Structural analog|analogs]] of drugs already listed. In [[Australia]] during 2010, it was not specifically listed as prohibited,<ref name=Camilleri/> but the Australian Federal Police stated it is an analogue to [[methcathinone]] and therefore illegal. It is now listed as a Schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534</ref> A Schedule 9 substance is 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="Poisons Standard" /> In February 2010, 22 men were arrested in connection with importing mephedrone.<ref name=smh/> By January 2011, every state in Australia, other than [[Victoria (Australia)|Victoria]], had listed it as a controlled drug.<ref name=levy/>

In [[New Zealand]], it is not included in the [[Misuse of Drugs Act 1975]],<ref name=newzealand1/> but is illegal, as it is similar to controlled substances.<ref name=newzealand2/>

In [[Canada]], mephedrone is not explicitly listed in any schedule of the [[Controlled Drugs and Substances Act]], but "amphetamines, their salts, derivatives, isomers and analogues and salts of derivatives, isomers and analogues" are included in Section 19 of Schedule I of the act. [[Cathinone]] and [[methcathinone]] are listed in separate sections of Schedule III, while [[diethylpropion]] and [[pyrovalerone]] (also cathinones), are listed in separate sections of Schedule IV, each without language to capture analogues, isomers, etc.<ref name=canada/> Mephedrone is considered a controlled substance by [[Health Canada]].<ref name=tgab/> In a report by the [[Canadian Medical Association]] in 2010, one lawyer was quoted as suggesting that mephedrone was less popular in Canada than in the U.K. because "there's a provision in the substance act that says analogues of certain drugs and other similar drugs may be illegal too,"; on the other hand, the assistant director of the Centre for Addictions Research of British Columbia suggested there was a lack of "clear illegality".<ref name=cmaj/> There have been several media reports of the Canadian police seizing mephedrone,<ref name=cbcnews/><ref name=McCallum/><ref name=telegram/> but no reports of any successful prosecution of a Controlled Drugs and Substances Act offence implicating mephedrone.<!-- Please see the talk page before adding information saying that it is legal -->

Mephedrone is also currently [[Controlled Substances Act|scheduled in the United States as of 2011]]. The [[Drug Enforcement Administration]] (DEA) states, as an analogue of [[methcathinone]], possession of mephedrone can be controlled by the [[Federal Analog Act]], but according to the ''Los Angeles Times'', this only applies if it is sold for human consumption.<ref name=usdea/><ref name=deaconcern/><ref name=sewell/> Several cities and states, such as New York state,<ref name="nyhd"/> have passed legislation to specifically list mephedrone as illegal, but in most areas it remained legal, so long as it is not sold for human consumption, so retailers described it as 'bath salts'.<ref name=sewell/> In September 2011, The DEA began using its emergency scheduling authority to temporarily control mephedrone. Except as authorised by law, this action made possessing and selling mephedrone or the products that contain it illegal in the US for at least one year while the DEA and the United States Department of Health and Human Services conduct further study.<ref name=USADEA /> Control of these compounds became permanent on 9 July 2012, via passage of the Synthetic Drug Abuse Prevention Act of 2012.<ref>{{cite magazine| vauthors = Keim B |url=https://www.wired.com/wiredscience/2012/07/synthetic-drug-ban/ |title=New Federal Ban on Synthetic Drugs Already Obsolete |magazine=Wired |date=12 July 2012 |access-date=18 March 2014}}</ref>

===Usage===

A survey conducted in late 2009 by the National Addiction Centre (UK) found 41.3% of readers of ''[[Mixmag]]'' had used mephedrone in the last month, making it the fourth-most popular drug amongst clubbers. Of those, two-thirds snorted the drug and the average dosage per session was 0.9&nbsp;g; the length of sessions increased as the dosage increased. Users who snorted the drug reported using more per session than those who took it orally (0.97&nbsp;g compared to 0.74&nbsp;g) and also reported using it more often (five days per month compared to three days per month).<ref name=winstockaddiction/> An Irish study of people on a [[methadone]] treatment program for heroin addicts found 29 of 209 patients tested positive for mephedrone usage.<ref name=McNamara/>

===Harm assessment===

Professor [[David Nutt]], former chair of the [[Advisory Council on the Misuse of Drugs]] (ACMD) in the UK has said, "people are better off taking ecstasy or amphetamines than those [drugs] we know nothing about" and "Who knows what's in [mephedrone] when you buy it? We don't have a testing system. It could be very dangerous, we just don't know. These chemicals have never been put into animals, let alone humans."<ref name=Saner/> Les King, a former member of the ACMD, has stated mephedrone appears to be less potent than amphetamine and ecstasy, but that any benefit associated with this could be negated by users taking larger amounts. He also told the BBC, "all we can say is [mephedrone] is probably as harmful as ecstasy and amphetamines and wait until we have some better scientific evidence to support that."<ref name=reed1301what/>

== See also ==

{{columns-list|colwidth=15em|

* [[Bath salts (drug)|Bath salts]]

* [[4-Methylamphetamine]]

* [[4-Methylbuphedrone]]

* [[4-Methylcathinone]]

* [[4-Methylpentedrone]]

* [[4-Methylthioamphetamine]]

* [[Methylenedioxyamphetamine]]

* [[Methamphetamine]]

* [[para-Methoxyamphetamine|''para''-Methoxyamphetamine]]

}}

== Notes ==

{{notelist}}

== References ==

{{Reflist|colwidth=30em|refs=

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<ref name=EU>{{cite news|url=http://www.dw-world.de/dw/article/0,,6293967,00.html |title=EU bans 'meow meow' party drug |publisher=Deutsche Welle | vauthors = Impey J |date=3 December 2010 |access-date=19 December 2010 |archive-url=https://web.archive.org/web/20110209221322/http://www.dw-world.de/dw/article/0,,6293967,00.html |archive-date=9 February 2011 |url-status=dead }}</ref>

<ref name=Eye>''[[Private Eye]]'', "Street of Shame", No. 1259, 2–15 April 2010, p. 6: Way back in January 2009, not long after mephedrone first began to be sold online, members of the web forum attached to the now-defunct "[[headshop]]" Champagne Legals discussed what brand name they might attach to the new product, which has the chemical identity dimethylmethcathinone or MM-Cat.

"What shall we call this drug? It's called MM-CAT, so why not Miaow?" suggested one. The name did not catch on ... But on 1 November 2009, someone did add the name "Meow" to the Wikipedia entry for Mephedrone at the head of a list of "street names."

Three weeks later ... the ''[[The Sun (United Kingdom)|Sun]]'' declared the arrival of a "new party favourite called 'meow meow{{'"}} and the world went cat-call crazy.

Among a host of recent headlines the ''[[Sunday Times]]'' has reported on "the rise of Meow", the ''[[The Times|Times]]'' has heralded "Meow Meow arrests", the ''Sun'' shrieked about a "[[Harriet Harman|Harman]] snub for Meow Meow Ban" and the ''[[Daily Telegraph]]'' took a long hard look at the "Meow Meow Menace in Europe."

"No one ever called it Meow seriously till the papers picked up on the Wikipedia entry," one drugs expert tells the ''Eye''.</ref>

<ref name=finland>{{cite web|url=http://www.city.fi/artikkeli/Rapujuhlat+saaristossa+/2783/ |title=Rapujuhlat saaristossa|trans-title=Crayfish parties in the archipelago| language=Finnish |publisher=City Magazine |date=September 2009 |access-date=14 September 2010}}</ref>

<ref name=fleming1803>{{cite web|url = https://www.newscientist.com/article/dn18672-briefing-should-miaowmiaow-be-banned.html|title = Briefing: Should miaow-miaow be banned? | vauthors = Fleming N |date=18 March 2010 |publisher=New Scientist |access-date=16 September 2010}}</ref>

<ref name=fleming2903>{{Cite news|url=https://www.newscientist.com/article/dn18712-miaowmiaow-on-trial-truth-or-trumpedup-charges.html?full=true|title=Miaow-miaow on trial: Truth or trumped-up charges? | vauthors = Fleming N |date=29 March 2010 |publisher=New Scientist |access-date=1 April 2010}}</ref>

<ref name=fleming0504>{{cite news | vauthors = Fleming N |url=https://www.theguardian.com/media/2010/apr/05/mephedrone-drug-media-scare-newspapers |title=Mephedrone: the anatomy of a media drug scare |work=The Guardian|date=5 April 2010 |access-date=20 September 2010 | location=London}}</ref>

<ref name=france>{{cite web|author=AFP |url=http://www.france24.com/fr/20100611-classement-comme-stupefiant-mephedrone-derivee-khat |publisher=france24.com |date=11 June 2010 |title=Classement comme stupéfiant de la méphédrone, dérivée du khat |trans-title=Classification of mephedrone from khat as a narcotic |language=French |access-date=4 July 2010 |archive-url=https://web.archive.org/web/20100616003748/http://www.google.com/hostednews/afp/article/ALeqM5gJFLO__-o8qmTFgxe3dQx8aSR0Cg |archive-date= 16 June 2010 |url-status=dead }}</ref>

<ref name=francegov>{{cite web|url=http://www.sante-sports.gouv.fr/la-mephedrone-classee-comme-stupefiant.html |title=La méphédrone classée comme stupéfiant |trans-title=Mephedrone classified as a narcotic |language=French |publisher=French Ministry of Health and Sports |date=11 June 2010 |access-date=26 October 2010 |archive-url=https://web.archive.org/web/20101020080521/http://www.sante-sports.gouv.fr/la-mephedrone-classee-comme-stupefiant.html |archive-date=20 October 2010 |url-status=dead }}</ref>

<ref name=Gammell>{{cite news | vauthors = Gammell C |url=https://www.telegraph.co.uk/health/healthnews/4977750/Legal-online-drugs-providing-real-alternative-to-Class-A-substances.html |archive-url=https://web.archive.org/web/20090912135819/http://www.telegraph.co.uk/health/healthnews/4977750/Legal-online-drugs-providing-real-alternative-to-Class-A-substances.html |url-status=dead |archive-date=12 September 2009 |title= Legal online drugs providing real alternative to Class A substances |newspaper= The Daily Telegraph| date= 12 March 2009 |access-date=16 September 2010 | location=London}}</ref>

<ref name=garnett>{{cite news |vauthors = Garnett N |title=Mephedrone freely available on the internet despite ban|url=https://www.bbc.co.uk/news/uk-12389321|publisher=BBC Radio 5 Live|date=9 February 2011|access-date=17 February 2011}}</ref>

<ref name=Garrett>{{cite journal | vauthors = Garrett G, Sweeney M | title = The serotonin syndrome as a result of mephedrone toxicity | journal = BMJ Case Reports | volume = 2010 | pages = bcr0420102925 | date = September 2010 | pmid = 22778288 | pmc = 3029518 | doi = 10.1136/bcr.04.2010.2925 }}{{subscription required}}</ref>

<ref name=gartland>{{cite news | vauthors = Gartland F |url=http://www.irishtimes.com/newspaper/ireland/2009/1106/1224258193510.html |title=Irish youth are fourth highest cocaine users in Europe |newspaper=The Irish Times|date=6 November 2009 |access-date=21 September 2010 |archive-url=https://web.archive.org/web/20101023191544/http://www.irishtimes.com/newspaper/ireland/2009/1106/1224258193510.html |archive-date=23 October 2010 |url-status=dead }}</ref>

<ref name=germany>{{cite web|url=http://www.buzer.de/gesetz/9164/index.htm |title=Vierundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften |trans-title=24th Amendment of narcotics legislation |publisher=Selected laws in Germany – Buzer.de |date=22 January 2010|language=German |access-date=4 July 2010}}</ref>

<ref name=gibbons>{{cite journal | vauthors = Gibbons S, Zloh M | title = An analysis of the 'legal high' mephedrone | journal = Bioorganic & Medicinal Chemistry Letters | volume = 20 | issue = 14 | pages = 4135–9 | date = July 2010 | pmid = 20542690 | doi = 10.1016/j.bmcl.2010.05.065 }}{{subscription required}}</ref>

<ref name=greenslade>{{cite news|url=https://www.theguardian.com/media/greenslade/2010/dec/02/drugs-newspapers|title=New guide aims to bring sense to the media coverage of drugs.| vauthors = Greenslade R |work=The Guardian|date=2 December 2010|access-date=19 December 2010}}</ref>

<ref name=guppy>{{cite news |vauthors = Guppy D |url=http://www.cairns.com.au/article/2008/06/18/4685_local-news.html |title=Killer pills hit Cairns |publisher=Cairns.com.au |date=18 June 2008 |access-date=11 August 2009}}</ref>

<ref name=Gustavsson>{{cite journal | vauthors = Gustavsson D, Escher C |date=20 October 2009|title=Mefedron – Internetdrog som tycks ha kommit för att stanna|trans-title=Mephedrone – Internet drug that seems to have come to stay|journal=Läkartidningen|language=Swedish|url=http://www.lakartidningen.se/07engine.php?articleId=12986|access-date=21 February 2010|archive-url=https://web.archive.org/web/20091022230620/http://www.lakartidningen.se/07engine.php?articleId=12986|archive-date=22 October 2009|url-status=dead}}</ref>

<ref name=hamilton>{{cite web|url=https://www.vice.com/en_us/article/hamilton-s-pharmacopeia-455-v17n6 |title=Hamilton's Pharmacopeia. Mephedrone: the phantom menace | vauthors = Morris H |publisher=Vice Magazine |date=5 April 2010|access-date=4 July 2010}}</ref>

<ref name=herald>{{cite web|url=http://www.heraldscotland.com/comment/herald-view/a-joined-up-approach-to-drugs-is-needed-now-1.1014820 |title=A joined-up approach to drugs is needed now |publisher=Herald Scotland |date=21 March 2010 |access-date=15 September 2010}}</ref>

<ref name=hungary>{{cite web|url=http://index.hu/belfold/2010/09/02/eldolt_betiltjak_a_katit/|title=Eldőlt: betiltják a katit|trans-title=Decided: cathinones banned|language=Hungarian|date=2 September 2010|access-date=2 January 2011}}</ref>

<ref name=hungary2>{{cite web|url=http://www.kozlonyok.hu/nkonline/MKPDF/hiteles/MK10190.pdf|title=Magyar közlöny 2010. december 15. Kormányrendelet a Mephedrone listáravételéről.|trans-title=Hungarian Government bans Mephedrone|language=Hungarian|date=15 December 2010|access-date=24 January 2011}}</ref>

<ref name=incb>{{cite news|url=http://articles.nydailynews.com/2011-03-02/entertainment/28666749_1_designer-drugs-drug-abuse-mephedrone|title=Designer drug abuse out of control: U.N. drugs board; abuse of 4-methyl-methcathinone, or mephedrone|publisher=Reuters|date=2 March 2011|access-date=26 March 2012}}</ref>

<ref name=incbreport>{{cite report|url=http://www.incb.org/pdf/annual-report/2010/en/AR_2010_English.pdf|publisher=International Narcotics Control Board|title=INCB Annual Report 2010|date=March 2011|access-date=26 March 2012|url-status=dead|archive-url=https://web.archive.org/web/20120402104444/http://www.incb.org/pdf/annual-report/2010/en/AR_2010_English.pdf|archive-date=2 April 2012}}</ref>

<ref name=iom>{{cite web |url=http://www.iomtoday.co.im/news/Now-illegal-to-import-drug.6103144.jp |title=Now illegal to import drug 'plant food' to Isle of Man |publisher=Isle of Man Today |date=25 February 2010 |access-date=4 July 2010 |url-status=dead |archive-url=https://web.archive.org/web/20100228070359/http://www.iomtoday.co.im/news/Now-illegal-to-import-drug.6103144.jp |archive-date=28 February 2010 }}</ref>

<ref name=ireland>{{cite web |url=http://www.dohc.ie/press/releases/2010/20100511.html |title=Minister for Health and Children announces immediate criminal ban on list of head shop products |publisher=Irish Department of Health and Children |date=11 May 2010 |access-date=22 August 2010 |url-status=dead |archive-url=https://web.archive.org/web/20110221174712/http://www.dohc.ie/press/releases/2010/20100511.html |archive-date=21 February 2011 }}</ref>

<ref name=ISCoD>{{cite web |url=http://www.drugscience.org.uk/mephedroneadvice.html |title=Mephedrone: harm reduction advice |publisher=Independent Scientific Committee on Drugs |work=Drugscience.org.uk |year=2010 |access-date=15 September 2010 |archive-date=2 July 2012 |archive-url=https://web.archive.org/web/20120702211758/http://www.drugscience.org.uk/mephedroneadvice.html |url-status=dead }}</ref>

<ref name=italy>{{cite web|url=http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti|title=Tabelle sostanze stupefacenti e psicotrope|trans-title=Table of drugs and psychotropics|publisher=Italian Ministry of Health|language=Italian|date=10 June 2010|access-date=2 January 2011|url-status=dead|archive-url=https://web.archive.org/web/20110627153948/http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti|archive-date=27 June 2011}}</ref>

<ref name=james>{{cite journal | vauthors = James D, Adams RD, Spears R, Cooper G, Lupton DJ, Thompson JP, Thomas SH | title = Clinical characteristics of mephedrone toxicity reported to the U.K. National Poisons Information Service | journal = Emergency Medicine Journal | volume = 28 | issue = 8 | pages = 686–9 | date = August 2011 | pmid = 20798084 | pmc = 3143586 | doi = 10.1136/emj.2010.096636 | author8 = National Poisons Information Service }}</ref>

<ref name=jones>{{Cite news| vauthors = Jones S, Power M |url=https://www.theguardian.com/society/2010/aug/17/ivory-wave-drug-alleged-death |title=Ivory Wave drug implicated in death of 24-year-old man |work=The Guardian|date= 17 August 2010|access-date=23 August 2010|location=London}}</ref>

<ref name=kavanagh>{{cite web |vauthors=Kavanagh PV, McNamara S, Angelov D, McDermott S, Mullan D, Ryder SA |date=March 2010 |title=The Characterization of 'Legal Highs' Available from Head Shops in Dublin |publisher=The Drug Treatment Centre Board |url=http://addictionireland.com/_fileupload/publications/Legal_Highs_Poster.pdf |access-date=17 February 2011}}</ref>

<ref name=Kehr>{{cite journal | vauthors = Kehr J, Ichinose F, Yoshitake S, Goiny M, Sievertsson T, Nyberg F, Yoshitake T | title = Mephedrone, compared with MDMA (ecstasy) and amphetamine, rapidly increases both dopamine and 5-HT levels in nucleus accumbens of awake rats | journal = British Journal of Pharmacology | volume = 164 | issue = 8 | pages = 1949–58 | date = December 2011 | pmid = 21615721 | pmc = 3246659 | doi = 10.1111/j.1476-5381.2011.01499.x }}</ref>

<ref name=kelly>{{Cite news|url=http://www.independent.ie/national-news/head-shop-substances-to-be-banned-2086255.html|title=Head shop substances to be banned| vauthors = Kelly F |date=3 March 2010|work=Irish Independent|access-date=21 September 2010}}</ref>

<ref name=kmietowicz>{{cite journal | vauthors = Kmietowicz Z | title = Home secretary bans mephedrone after taking advice from depleted council | journal = BMJ | volume = 340 | pages = c1784 | date = March 2010 | pmid = 20356967 | doi = 10.1136/bmj.c1784 | s2cid = 8396924 }}</ref>

<ref name=lancet>{{cite journal | author = Anonymous editorial | title = A collapse in integrity of scientific advice in the UK | journal = Lancet | volume = 375 | issue = 9723 | pages = 1319 | date = April 2010 | pmid = 20399965 | doi = 10.1016/S0140-6736(10)60556-9 | s2cid = 39998854 | doi-access = free }}</ref>

<ref name=Laurance>{{cite news|url=https://www.independent.co.uk/life-style/health-and-families/health-news/mephedrone-ban-blamed-for-rise-in-cocaine-deaths-2142097.html |archive-url=https://ghostarchive.org/archive/20220512/https://www.independent.co.uk/life-style/health-and-families/health-news/mephedrone-ban-blamed-for-rise-in-cocaine-deaths-2142097.html |archive-date=12 May 2022 |url-access=subscription |url-status=live|title=Mephedrone ban blamed for rise in cocaine deaths| vauthors = Laurance J |work=The Independent|date=24 November 2010|access-date=20 December 2010}}</ref>

<ref name=levy>{{cite news|url=http://www.theage.com.au/victoria/judge-puts-users-of-new-drug-on-notice-20110121-1a02k.html|title=Judge puts users of new drug on notice | vauthors = Levy M |publisher=The Age|date=22 January 2011|access-date=17 February 2011}}</ref>

<ref name=lithuania>{{cite web|author=Ministry of Health of the Republic of Lithuania |url=http://www3.lrs.lt/pls/inter3/dokpaieska.showdoc_l?p_id=375830 |archive-url=https://web.archive.org/web/20201130102017/http://www3.lrs.lt/pls/inter3/dokpaieska.showdoc_l?p_id=375830 |archive-date=30 November 2020 |title=2000 m. sausio 6 d. įsakymo nr. 5 "dėl narkotinių ir psichotropinių medžiagų sąrašų patvirtinimo" pakeitimo |trans-title=6 January 2000 Order no. 5 of narcotic drugs and psychotropic substances list |language=Lithuanian |date=18 June 2010 |access-date=21 September 2010 |url-status=dead }}</ref>

<ref name=local>{{cite web|url=http://www.thelocal.se/16366/20081215/ |title=Teenager dies of 'net drug' overdose |publisher=The Local|date=15 December 2008 |access-date=20 September 2010}}</ref>

<ref name=loh>{{cite web| vauthors = Loh L |url=http://www.cnngo.com/singapore/play/mephedrone-party-drug-legal-singapore-535515 |title=Legal in Singapore – the party drug that's banned everywhere else |publisher=Cnngo.com |date=24 February 2010|access-date=4 July 2010}}</ref>

<ref name=lough>{{cite web |url=https://www.sciencedaily.com/releases/2010/07/100714104231.htm |title=Risks of banned drug mephedrone revealed in new research |publisher=Science Daily|date=15 July 2010|access-date=10 February 2011}}</ref>

<ref name=mann>{{cite web |vauthors=Mann J |url=http://www.rsc.org/chemistryworld/Issues/2010/April/CanWeHaltTheFlowOfNewDesignerDrugs.asp |title=Can we halt the flow of new designer drugs?|publisher=Chemistry World|date=April 2010|access-date=16 September 2010}}</ref>

<ref name=matthews>{{cite journal |vauthors=Matthews AJ, Bruno RB |title=Mephedrone use among regular ecstasy consumers in Australia |journal=Ecstasy and Related Drug Trends Bulletin |year=2010 |url=http://www.med.unsw.edu.au/ndarcweb.nsf/resources/BulletinsEDRS2010/$file/EDRS+December+2010.pdf |archive-url=https://www.webcitation.org/5wZFYyEx7?url=http://www.med.unsw.edu.au/ndarcweb.nsf/resources/BulletinsEDRS2010/%24file/EDRS%20December%202010.pdf |archive-date=17 February 2011 |url-status=dead}}</ref>

<ref name=McCallum>{{cite web| vauthors=McCallum J |url=https://montrealgazette.com/Legal+ecstasy+causing+concern+Quebec/3415148/story.html |title='Legal ecstasy' causing concern in Quebec |work=The Montreal Gazette |date=18 August 2010 |access-date=22 August 2010 |archive-url=https://web.archive.org/web/20100822131002/http://www.montrealgazette.com/Legal%2Becstasy%2Bcausing%2Bconcern%2BQuebec/3415148/story.html |archive-date=22 August 2010 |url-status=dead }}</ref>

<ref name=McElrath>{{cite journal | vauthors = McElrath K, O'Neill C | title = Experiences with mephedrone pre- and post-legislative controls: perceptions of safety and sources of supply | journal = The International Journal on Drug Policy | volume = 22 | issue = 2 | pages = 120–7 | date = March 2011 | pmid = 21242082 | doi = 10.1016/j.drugpo.2010.11.001 }}{{subscription required}}</ref>

<ref name=McNamara>{{cite journal | vauthors = McNamara S, Stokes S, Coleman N | title = Head shop compound abuse amongst attendees of the Drug Treatment Centre Board | journal = Irish Medical Journal | volume = 103 | issue = 5 | pages = 134, 136–7 | date = May 2010 | pmid = 20666082 | url = http://www.imj.ie/ViewArticleDetails.aspx?ArticleID=5909 | url-status = dead | archive-url = https://web.archive.org/web/20110721124903/http://www.imj.ie/ViewArticleDetails.aspx?ArticleID=5909 | archive-date = 21 July 2011 }}</ref>

<ref name=Measham>{{Cite journal| vauthors=Measham F, Moore K, Newcombe R, Welch Z |date=12 March 2010 |title=Tweaking, bombing, dabbing and stockpiling: the emergence of mephedrone and the perversity of prohibition |journal=Drugs and Alcohol Today |volume=10 |issue=1 |pages=14–21 |doi=10.5042/daat.2010.0123 |s2cid=56998007}}{{subscription required}}</ref>

<ref name=meyer2009>{{Cite journal | vauthors = Meyer MR, Peters FT, Maurer HH |title=Metabolism of the new designer drug mephedrone and toxicological detection of the beta keto designer drugs mephedrone, butylone and methylone in urine |journal=Annales de Toxicologie Analytique |year=2009 |volume=21 |issue=S1 |page=22 |url=http://www.ata-journal.org/articles/ata/pdf/2009/02/ata2009s102.pdf }}</ref>

<ref name=meyer2010>{{cite journal | vauthors = Meyer MR, Wilhelm J, Peters FT, Maurer HH | title = Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry | journal = Analytical and Bioanalytical Chemistry | volume = 397 | issue = 3 | pages = 1225–33 | date = June 2010 | pmid = 20333362 | doi = 10.1007/s00216-010-3636-5 | s2cid = 21471611 }}{{subscription required}}</ref>

<ref name=newzealand1>{{cite web|url=http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html |title=Misuse of Drugs Act 1975 No 116, Public Act – New Zealand Legislation |publisher=New Zealand Ministry of Health |date=1 December 2009 |access-date=4 July 2010 |archive-url=https://web.archive.org/web/20110519205338/http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html |archive-date=19 May 2011 |url-status=dead }}</ref>

<ref name=newzealand2>{{cite web | vauthors = Edens J |url=http://www.stuff.co.nz/national/health/4125151/Low-quality-drugs-prompt-risk-warning |title=Low-quality drugs prompt risk warning |work=The Southland Times|date=14 September 2010 |access-date=21 September 2010 |archive-url=https://web.archive.org/web/20100916055832/http://www.stuff.co.nz/national/health/4125151/Low-quality-drugs-prompt-risk-warning |archive-date=16 September 2010 |url-status=dead }}</ref>

<ref name=Nicholson>{{cite journal | vauthors = Nicholson PJ, Quinn MJ, Dodd JD | title = Headshop heartache: acute mephedrone 'meow' myocarditis | journal = Heart | volume = 96 | issue = 24 | pages = 2051–2 | date = December 2010 | pmid = 21062771 | doi = 10.1136/hrt.2010.209338 | s2cid = 36684597 }}{{subscription required}}</ref>

<ref name=nmsta>{{cite report|url=http://www.nta.nhs.uk/uploads/nta_annualreport_0910.pdf |title=Drug Treatment in 2009–10 |publisher=National Treatment Agency for Substance Misuse |date=October 2010 |access-date=27 October 2010 |archive-url=https://web.archive.org/web/20110301084748/http://www.nta.nhs.uk/uploads/nta_annualreport_0910.pdf |archive-date=1 March 2011 |url-status=dead }}</ref>

<ref name=Noorden>{{cite news|url=http://blogs.nature.com/news/thegreatbeyond/2010/12/science_advice_not_mandatory_o_1.html |title=Science advice not mandatory on drugs council, proposes UK government | vauthors = Van Noorden R |publisher=Nature News |date=6 December 2010 |access-date=20 December 2010 |archive-url=https://web.archive.org/web/20101228045506/http://blogs.nature.com/news/thegreatbeyond/2010/12/science_advice_not_mandatory_o_1.html |archive-date=28 December 2010 |url-status=dead }}</ref>

<ref name=norway>{{cite web|url=http://www.nrk.no/nyheter/norge/1.7163768 |title=Ti nye stoffer på narkotikalisten |trans-title=Ten new compounds for drug list |publisher=Norwegian Broadcasting Corporation (NRK) |date=11 June 2010 |language=Norwegian |access-date=31 August 2010 |archive-url=https://web.archive.org/web/20100614113201/http://www.nrk.no/nyheter/norge/1.7163768 |archive-date=14 June 2010 |url-status=dead }}</ref>

<ref name=npsad>{{cite web | vauthors = Ghodse H, Corkery J, Ahmed K, Naidoo V, Oyefeso A, Schifano F |title=Drug-related deaths in the UK: Annual Report 2010 |url=http://www.sgul.ac.uk/about-st-georges/divisions/faculty-of-medicine-and-biomedical-sciences/mental-health/icdp/website-pdfs/np-SAD%2011th%20annual%20report%20Final.pdf |publisher=International Centre for Drug Policy, St George's University of London |page=77 |date=July 2010 |access-date=2 January 2010 |archive-url=https://web.archive.org/web/20101229101541/http://www.sgul.ac.uk/about-st-georges/divisions/faculty-of-medicine-and-biomedical-sciences/mental-health/icdp/website-pdfs/np-SAD%2011th%20annual%20report%20Final.pdf |archive-date= 29 December 2010 |url-status=dead }}</ref>

<ref name=nutt11>{{cite journal | vauthors = Nutt D | title = Perverse effects of the precautionary principle: how banning mephedrone has unexpected implications for pharmaceutical discovery | journal = Therapeutic Advances in Psychopharmacology | volume = 1 | issue = 2 | pages = 35–6 | date = April 2011 | pmid = 23983925 | pmc = 3736901 | doi = 10.1177/2045125311406958 }}</ref>

<ref name=nyhd>{{cite web |title=New York State Health Commissioner Bans Sale and Distribution of Dangerous Substances Marketed as Bath Salts |url=http://www.health.state.ny.us/press/releases/2011/2011-05-23_bath_salts.htm |publisher=New York State Health Department|date=23 May 2011|access-date=22 June 2011}}</ref>

<ref name=opsi.gov>{{cite web|url=http://www.legislation.gov.uk/uksi/2010/1144/made |title=The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144 |publisher=Office of Public Sector Information |date=16 April 2010 |access-date=8 April 2010 |archive-url=https://web.archive.org/web/20110105053256/http://www.legislation.gov.uk/uksi/2010/1144/made |archive-date=5 January 2011 |url-status=dead }}</ref>

<!--unused<ref name=Osorio-Olivares>{{Cite journal | vauthors = Osorio-Olivares M, Rezende MC, Sepúlveda-Boza S, Cassels BK, Baggio RF, Muñoz-Acevedo JC | doi = 10.1016/S0957-4166(03)00317-3 | title = A two-step method for the preparation of homochiral cathinones | journal = Tetrahedron: Asymmetry | volume = 14 | pages = 1473–1477 | year = 2003 | issue = 11 }}{{subscription}}</ref>-->

<ref name=poland>{{cite web|url=http://isap.sejm.gov.pl/DetailsServlet?id=WDU20101430962 |title=Ustawa z dnia 10 czerwca 2010 r. o zmianie ustawy o przeciwdziałaniu narkomanii |trans-title=The Law of 10 June 2010 amending the Act on Counteracting Drug Addiction|language=Polish|publisher=Polish Internet Database System of Legal Acts |date=10 June 2010 |access-date=25 August 2010}}</ref>

<ref name=police>{{Cite news|url=http://www.policeprofessional.com/news.aspx?id=10163 |title=Mephedrone to be classified a Class B drug | vauthors = Ilston G |date=1 April 2010 |publisher=Police Professional |access-date=21 September 2010 |archive-url=https://web.archive.org/web/20110715102011/http://www.policeprofessional.com/news.aspx?id=10163 |archive-date=15 July 2011 |url-status=dead }}</ref>

<ref name=press0410>{{cite news|url=http://www.pressassociation.com/component/pafeeds/2010/10/04/inquiries_over_mephedrone_effects |title=Inquiries over mephedrone effects |publisher=Press Association |date=4 October 2010 |access-date=27 October 2010 |archive-url=https://web.archive.org/web/20110715112748/http://www.pressassociation.com/component/pafeeds/2010/10/04/inquiries_over_mephedrone_effects |archive-date=15 July 2011 |url-status=dead }}</ref>

<ref name=psycho>{{cite web|url=http://194.83.136.209/newsletters/n2.php |title=Psychonaut Web Mapping Project Newsletter |publisher=Psychonaut Web Mapping Project |date=June–September 2009 |access-date=19 December 2009 |archive-url=https://web.archive.org/web/20110216030557/http://194.83.136.209/newsletters/n2.php |archive-date=16 February 2011 |url-status=dead }}<!-- old link – http://www.p2002.sgul.ac.uk/newsletters/n2.php --></ref>

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<!-- <ref name=telegraph0104>{{Cite news|url=https://www.telegraph.co.uk/health/healthnews/7545261/Mephedrone-can-cause-impotence-warns-expert.html |archive-url=https://web.archive.org/web/20100404071617/http://www.telegraph.co.uk/health/healthnews/7545261/Mephedrone-can-cause-impotence-warns-expert.html |url-status=dead |archive-date=4 April 2010 |title=Mephedrone can cause impotence, warns expert |publisher=The Daily Telegraph |date=1 April 2010 |access-date=4 July 2010 |location=London}}</ref> -->

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<ref name=Torrance>{{cite journal | vauthors = Torrance H, Cooper G | title = The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland | journal = Forensic Science International | volume = 202 | issue = 1–3 | pages = e62-3 | date = October 2010 | pmid = 20685050 | doi = 10.1016/j.forsciint.2010.07.014 }}</ref>

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<ref name=USADEA>{{cite news|url=https://abcnews.go.com/Blotter/bath-salts-dea-announces-emergency-ban/story?id=14467134|title=DEA Announces Emergency Ban on 'Bath Salts'|publisher=ABC News|author=Ferran L.|date=7 September 2011 |access-date=8 September 2011}}</ref>

<ref name=winstock>{{cite journal |vauthors=Winstock AR, Marsden J, Mitcheson L |title=What should be done about mephedrone? |journal=BMJ |volume=340 |pages=c1605 |date=March 2010 |pmid=20332508 |doi=10.1136/bmj.c1605 |s2cid=5500659}}</ref>

<ref name=winstockaddiction>{{cite journal |vauthors=Winstock AR, Mitcheson LR, Deluca P, Davey Z, Corazza O, Schifano F |title=Mephedrone, new kid for the chop? |journal=Addiction |volume=106 |issue=1 |pages=154–61 |date=January 2011 |pmid=20735367 |doi=10.1111/j.1360-0443.2010.03130.x }}</ref>

<ref name=winstock1210>{{cite journal |vauthors=Winstock A, Mitcheson L, Marsden J |title=Mephedrone: still available and twice the price |journal=Lancet |volume=376 |issue=9752 |pages=1537 |date=November 2010 |pmid=21056754 |doi=10.1016/S0140-6736(10)62021-1 |s2cid=41708575}}</ref>

<ref name=wood>{{cite journal | vauthors = Wood DM, Greene SL, Dargan PI | title = Clinical pattern of toxicity associated with the novel synthetic cathinone mephedrone | journal = Emergency Medicine Journal | volume = 28 | issue = 4 | pages = 280–2 | date = April 2011 | pmid = 20581379 | doi = 10.1136/emj.2010.092288 | s2cid = 26029573 }}{{subscription required}}</ref>

<ref name=woodsubcataneous>{{cite journal | vauthors = Wood DM, Davies S, Puchnarewicz M, Button J, Archer R, Ovaska H, Ramsey J, Lee T, Holt DW, Dargan PI | display-authors = 6 | title = Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity | journal = Journal of Medical Toxicology | volume = 6 | issue = 3 | pages = 327–30 | date = September 2010 | pmid = 20358417 | pmc = 3550484 | doi = 10.1007/s13181-010-0018-5 }}{{subscription required}}</ref>

}}

== External links ==

* {{cite report | author = European Monitoring Center for Drugs and Drug Addiction | year = 2011 | title =Report on the risk assessment of mephedrone in the framework of the Council Decision on new psychoactive substances | issue = 9 | publisher = Publications Office | doi = 10.2810/40800 | url = http://www.emcdda.europa.eu/html.cfm/index116639EN.html }}

* [http://www.erowid.org/chemicals/4_methylmethcathinone/ Erowid 4-Methylmethcathinone Vault]

* [https://web.archive.org/web/20100331230043/http://www.lifeline.org.uk/docs/Meph%20faq.pdf Mephedrone – Frequently asked questions] www.lifeline.org.uk

* [https://www.theguardian.com/world/audio/2010/mar/19/guardian-daily-podcast-mephedrone-drug-meow Guardian Daily Podcast: How dangerous is mephedrone?]

* [http://chemsub.online.fr/name/mephedrone.html ChemSub Online: Mephedrone]

{{Drug use}}

{{Stimulants}}

{{Entactogens}}

{{Monoamine releasing agents}}

{{Phenethylamines}}

{{Good article}}

{{DEFAULTSORT:Methylmethcathinone, 4-}}

[[Category:Cathinones]]

[[Category:Euphoriants]]

[[Category:Phenethylamines]]

[[Category:Sympathomimetics]]

[[Category:Designer drugs]]

[[Category:Vasoconstrictors]]

[[Category:Serotonin-norepinephrine-dopamine releasing agents]]

[[Category:Substituted amphetamines]]

[[Category:Entactogens and empathogens]]