View source for Mephedrone

{{Redirect|Meow Meow||Meow (disambiguation)}}
{{Distinguish|methedrine|methedrone|methadone|methylone}}
{{Drugbox
| drug_name = Mephedrone
| IUPAC_name = (RS)-2-methylamino-1-(4-methylphenyl)propan-1-one<ref name=emcdda/>{{rp|5}}
| image = Mephedrone-2D-skeletal.png
| imagename = 1 : 1 mixture (racemate)<br />
| image2 = 4-MMC_3D.gif
| CAS_number = 1189805-46-6 
| CAS_supplemental = <br />1189726-22-4 ([[hydrochloride|HCl]])<ref name=emcdda/>{{rp|5}}
| ATC_prefix = none
| ATC_suffix =
| PubChem = 29982893
| ChemSpiderID = 21485694r
| DrugBank =
| C = 11|H = 15|N = 1|O = 1
| molecular_weight = 177.242 g/mol
| 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 = See [[mephedrone#Legal status|legal status section]]
| routes_of_administration = [[Oral]], [[Insufflation (medicine)|Insufflation]], [[Intravenous|IV]], [[Suppository|rectal]]<ref name=winstockaddiction/>}}

'''Mephedrone''', also known as '''4-methylmethcathinone''' ('''4-MMC'''), or '''4-methylephedrone''', is a [[Organic_compound#Synthetic_compounds|synthetic]] [[stimulant]] and [[entactogen]] [[drug]] of the [[substituted amphetamine|amphetamine]] and [[substituted cathinone|cathinone]] classes. Slang names include '''meph''',<ref name=lifeline/> '''drone'''<ref name=Cumming/> and '''MCAT'''.<ref name=bbc0803/> It is reportedly manufactured in China and is chemically based on the cathinone compounds found in the [[khat]] plant of [[eastern Africa]]. It comes in the form of tablets or a powder, which users can swallow, snort or inject, producing similar effects to [[MDMA]], [[amphetamine]]s and [[cocaine]]. It was first synthesised in 1929 but did not become widely known until it was rediscovered in 2003. By 2007 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, being particularly prevalent in the United Kingdom.

As well as producing the intended stimulant effects, negative [[side effects]] occur when mephedrone is used, with [[bruxism|teeth grinding]] being the most common. The [[drug metabolism|metabolism]] of mephedrone has been studied in rats and humans, with the metabolites being able to be detected in urine after usage. Nothing is known about the potential [[neurotoxicity]] of mephedrone, but scientists have suggested possible dangers associated with its use based on its similarity to other drugs. Several people have died after consuming mephedrone, but some deaths that the media attributed to the drug were later determined to have been caused by other factors. 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, but remains legal in others. In Australia, New Zealand, the USA and Canada it is considered illegal as an [[structural analog|analog]] of other illegal drugs and is controlled by laws similar to the [[Federal Analog Act]].

==History==
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=Sanchez1929/><ref name=emcdda/>{{rp|17}} but the compound remained an obscure product of academia until 2003, when it was "re-discovered" and publicised by an [[clandestine chemistry|underground chemist]] on [[The Hive (website)|The Hive]] website, 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 taking it he had a "fantastic sense of well-being that I haven’t got from any drug before except my beloved Ecstasy."<ref name=druglink0110/> A drug similar to mephedrone, containing [[cathinone]]s was sold in Israel from around 2004, under the name [[hagigat]]. When this was made illegal, the chemicals were modified so that they where no longer illegal.<ref name=druglink0309/> The Psychonaut Research Project, an EU organisation that searches the internet for information regarding new drugs, first identified mephedrone in 2008. Their research suggests that the drug first became available to purchase on the internet in 2007.<ref name=psycho/> Mephedrone was first seized in France in May 2007 after police sent a tablet that they assumed to be ecstasy to be analysed.<ref name=roussel/> The drug was used in early products, such as Neodoves pills, by the legal high company Neorganics,<ref name="Camilleri" /><ref name=davies09/> but the range was discontinued in January 2008 after the government of Israel, where the company is based, made mephedrone illegal.<ref name=Cumming/> 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/> [[Europol]] noted that they became aware of it in 2008, after it was found in Denmark, Finland and the UK.<ref name=emcdda08/> The [[Drug Enforcement Agency]] noted it was present in the United States in July 2009.<ref name=dea/> By May 2010, mephedrone had been detected in every one of the 22 [[EU member states]] that reported to Europol, as well as in Croatia and Norway.<ref name=emcdda/>{{rp|21}} It was reportedly manufactured in [[China]], but it has since been made illegal there.<ref name=devlin/> In March 2009, ''Druglink'' magazine reported that it only cost a "couple hundred pounds" to synthesise a kilogram of mephedrone.<ref name=druglink0309/> ''The Daily Telegraph'' reported that manufacturers were making "huge amounts of money" from selling the drug.<ref name=Gammell/> In January 2010 ''Druglink'' magazine reported that 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=druglink0110/><ref name=Campbell1701/> A later report, in March 2010, stated that the wholesale price of mephedrone was £4000 per kilogram.<ref name=fleming1803/>

===In the United Kingdom===
Between the summer of 2009 and March 2010 the use of mephedrone grew rapidly in the UK, with it being readily available at [[music festival]]s, [[head shop]]s and on the internet.<ref name=Measham/> A survey of ''[[Mixmag]]'' readers in 2009, found that 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 is used by a diverse range of social groups. Whilst the evidence is anecdotal, researchers, charity workers, teachers and users have reported widespread and increasing use of the drug. The drug's rapid growth in popularity was believed to be related to both its availability and legality.<ref name=Measham/> Fiona Measham, a criminologist at [[The University of Lancaster]], believes that the emergence of mephedrone was also related to the decreasing purity of ecstasy and cocaine on sale in the UK.<ref name=Measham/> 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 pills seized in the UK, contained no MDMA.<ref name=Reed2006/> A similar pattern was observed in the Netherlands, with the number of ecstacy tablets containing no MDMA rising from 10% in mid 2008 to 60% by mid 2009 and with mephedrone being detected in 20% of ecstacy tablets by mid 2009.<ref name=brunt/> The decrease of MDMA was thought in part, to be due to the seizure of 33 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=druglink0110/> According to John Ramsey, a [[toxicologist]] at [[St George's, University of London|St George’s University]] London, the emergence of mephedrone was also related to the UK government banning the [[benzylpiperazine]] class of drugs.<ref name=druglink0309/> Mephedrone was available on at least 31 websites based in the UK in December 2009; 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}} Between July 2009 and February 2010, UK health professionals accessed the National Poisons Information Service's entry on mephedrone 1664 times and made 157 telephone enquiries; 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/>

Media organisations including the [[BBC]] and ''[[The Guardian]]'', as well as a news section in the ''[[Annals of Botany]]'',<ref name=Chaffey/> incorrectly reported that 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, ''[[The Sun (United Kingdom)|The Sun]]'' published a story stating that a man had ripped off his own [[scrotum]] whilst using mephedrone,<ref name=soodin/> but this story was later shown to be an online [[hoax]].<ref name=davey/> The [[Advisory Council on the Misuse of Drugs]] (ACMD) have suggested that the media coverage of the drug lead to increased usage of it.<ref name=lancet/>

A survey of 1000 secondary school pupils and university students in [[Tayside]], conducted in February 2010, found that 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 that it was easy or very easy to obtain. Around 50% of users reported at least one negative effect associated with the use of mephedrone, with [[bruxism|teeth grinding]] being the most common.<ref name=dargan/>

On 30 March 2010, [[Alan Johnson]], then the [[Home Secretary]], announced that mephedrone would be made illegal "within weeks" after the ACMD sent him a report on the use of cathinones.<ref name=bbc2903/><ref name=acmdreport/> Prior to the ban being announced, Dr Polly Taylor, a member of the ACMD 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 that mephedrone would be made illegal. He said that 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 ex-members of the ACMD, and various charity groups have expressed concern regarding the banning of the drug, arguing it will inevitably criminalise users, particularly young people.<ref name=TDPF/> Others have expressed concern that the drug will now be left in the hands of [[black market]] dealers, who will only compound the problem.<ref name=doward/> 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]] 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/> Eric Carlin's resignation was specifically linked to the criminalisation of mephedrone, and 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/> An editorial in the April 2010 edition of ''[[The Lancet]]'' questioned the decision to ban mephedrone, saying that 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 can be influenced to not take it.<ref name=lancet/> In ''[[Chemistry World]]'', John Mann professor of chemistry at [[Queen's University Belfast]], suggested that 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/>

According to the [[Independent Scientific Committee on Drugs]], since mephedrone was made illegal a street trade in the drug has emerged, with prices around double that of before the ban, at £20-£25 per gram.<ref name=ISCoD/> Other supposedly legal drugs have also 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 it is possible that some products branded as Ivory Wave 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/>

==Effects==
There have been no formal published studies into the effects of mephedrone psychological and behavioural effects of mephedrone on humans, nor on animals from which the potential effects could be extrapolated. As a result the only information available comes from users themselves and clinical reports of acute mephedrone toxicity.<ref name=emcdda/>{{rp|12}} Psychologists at [[Liverpool John Moores University]] were to conduct research into the effects of mephedrone on up to 50 students already using the drug, when it was still legal in the UK.<ref name=bbc2303test/> At the time the study was proposed, Les Iversen, the chair of the [[Advisory Council on the Misuse of Drugs]] called the experiments "pretty unethical".<ref name=bbc2303iversen/> The study was discontinued in August 2010, following the change in the legal status of the drug.<ref name=faulkner/>

===Intended effects===
Users have reported that mephedrone causes [[euphoria]], [[stimulation]], an enhanced appreciation for [[music]], an elevated [[mood]], decreased [[hostility]], improved [[mental function]] and mild [[sexual stimulation]]; which are similar to the effects of cocaine, amphetamines and MDMA. These effects last different amounts of time, depending on the way the drug is taken. When taken orally, users report they can feel the effects within 15-45 minutes, when snorted the effects are felt within minutes. 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}} Out of 70 Dutch users of mephedrone, 58 described it as an overall pleasant experience and 12 described it as being an unpleasant experience.<ref name=brunt/> A survey of UK users, who had previously taken cocaine, found that most users found it produced a better quality and longer lasting high, was less addictive and carried the same risk to using cocaine.<ref name=winstockaddiction/>

===Side effects===
According to drugs counsellors on [[Teesside]], UK, mephedrone can cause [[hallucinations]], nausea, vomiting, blood circulation problems, [[rash]]es, [[anxiety]], [[paranoia]], [[convulsion|fits]] and delusions.<ref name=bbc2711/> According to the drugs advice charity, Crew2000, other [[acute|side effects]] may include poor [[concentration]], poor [[short-term memory]], [[tachycardia|increased heart rate]], [[palpitations|abnormal heart beats]], [[anxiety]], [[depression (mood)|depression]], [[hyperhidrosis|increased sweating]], [[mydriasis|dilated pupils]], [[trismus|the inability to normally open the mouth]], and [[bruxism|teeth grinding]].<ref name=crew/> When snorted it can also cause [[nose bleed]]s and nose burns.<ref name=bbc2711/> A survey conducted by the National Addiction Centre, UK found that 51% of mephedrone users said they suffered from headaches, 43% from heart palpitations, 27% from nausea and 15% from cold or blue fingers.<ref name=reed1301/> Doctors at [[Guy's Hospital]], London reported that of 15 patients they treated after taking mephedrone in 2009, 53.3% were agitated, 40% [[tachycardia|tachycardic]], 20% had [[systolic hypertension]] and 20% had seizures; three required treatment with [[benzodiazepines]], predominantly to control their agitation. They reported that none of their patients suffered from cold or blue peripheries, as other reports have done. Nine out of the 15 of patients had a [[Glasgow Coma Scale]] (GCS) of 15 or above, 4 had a GCS below 8, but these patients all reported using a [[central nervous system]] depressant, most commonly [[GHB]], with mephedrone. The patients also reported [[polydrug use]] of a variety of compounds.<ref name=wood/>

===Long-term effects===
Almost nothing is known about the long-term effects of the drug due to the short history of its use.<ref name=reed1301/> ''[[BBC News]]'' reported that one person who used the drug for 18 months became [[substance dependence|dependent]] on the drug, in the end using it twice a week, had to be admitted to a psychiatric unit after he started experiencing hallucinations, agitation, excitability and mania.<ref name=bbc3004/><ref name=emcdda/>{{rp|13}} Because of its similarity to [[cathinone]], John Mann, has posited that mephedrone may cause [[impotence]] with long-term use.<ref name=telegraph0104/>

==Typical use and consumption==
Mephedrone can come in the form of capsules, tablets or white powder that users may swallow, snort or inject.<ref name=nhs/> 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}} ''[[The Guardian]]'' reported that some users compulsively redose, consuming their whole supply when they are only meant to use a small dose<ref name=campbell1203/> and there have been other similar reports of users craving mephedrone, suggesting that it may be addictive.<ref name=brunt/><ref name=emcdda/>{{rp|13}} 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 0.9g; 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 (5 days per month compared to 3 days per month).<ref name=winstockaddiction/> An Irish study of people on a [[methadone]] treatment program for heroin addicts found that 29 out of 209 patients tested positive for mephedrone usage.<ref name=McNamara/>

===Harm reduction===
{{also|Responsible drug use}}
The drugs advice charity Lifeline recommends that to reduce the potential harm caused by using mephedrone, users should only use mephedrone occasionally (less than weekly), use less than 0.5g per session, dose orally rather than snorting the drug and avoid mixing it with alcohol and other drugs. Users should also drink plenty of water whilst taking the drug as it causes dehydration.<ref name=lifeline/>

==Pharmacology==
Writing in the ''[[British Medical Journal]]'', psychiatrists stated that given its chemical structure, "mephedrone is likely to stimulate the release of, and then inhibit the reuptake of [[monoamine neurotransmitters]]".<ref name=winstock/> 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 that 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/> Molecular modelling of mephedrone suggests it is more [[hydrophilic]] than [[methyl-amphetamine]]s 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}}<ref name=gibbons/>

===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 I pathways]]. It can be demethylated to the primary amine (producing compounds 2,3 and 4) the [[ketone]] group can be [[redox|reduced]] (producing 3) or the [[tolyl]] group can be oxidised (producing 5 and 6). It is thought that 5 and 6 are 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 cause 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 based on the analysis of rat and human urine after ingesting mephedrone<ref name=meyer2010/>]]

===Toxicity===
As of March 2010, nothing is known about the potential [[neurotoxicity]] of mephedrone<ref name=winstock/> nor is the [[median lethal dose]] known.<ref name=winstockaddiction/> 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 3.8&nbsp;g [[subcutaneous injection|subcutaneously]]. The patient was treated with 1&nbsp;mg of [[lorazepam]] and the sympathomimetic features decreased within 6 hours of treatment.<ref name=woodsubcataneous/> Reported side effects suggest mephedrone may cause pronounced peripheral [[vasoconstriction]], and consequently it has been speculated that some metabolites may be potent vasoconstrictors, as the compound 4-methylephedrine which is closely related to some mephedrone metabolites, is known to be a vasoconstrictor with significantly more cardiovascular toxicity than [[ephedrine]] itself.<ref name=meyer2009/><ref name=hartung/> The Swedish medical journal ''[[Läkartidningen]]'' reported that mephedrone could theoretically cause the [[cardiovascular]] problems associated with the use of cocaine and amphetamines and [[serotonin syndrome]] associated with the use of ecstasy and LSD.<ref name=Gustavsson/> 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 that based on the chemical similarities between methcathinone and mephedrone, "it is highly likely that mephedrone will display neurotoxicity".<ref name=gibbons/> However, Brunt ''et'' al. stated that "extreme caution" should be used when inferring the toxicity of mephedrone from methcathinone, noting that some of the toxicity associated with methcathinone is due to managanese impurities related to its synthesis, rather than the compound itself. They concluded that experimental research is needed to investigate the toxicity of mephedrone.<ref name=brunt/>

====Deaths====
=====Sweden=====
In 2008, an 18-year-old Swedish woman died in [[Stockholm]] after taking mephedrone allegedly in combination with cannabis. ''[[Svenska Dagbladet]]'' reported that the woman went into convulsions and turned blue in the face.<ref name=local/> Doctors reported that she was comatose and suffering from [[hyponatremia]] and severe hypokalemia; the women 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 girl's death at [[Karolinska University Hospital]] on Sunday, 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/>

=====UK=====
In 2010, there were unconfirmed reports speculating about the role mephedrone has played in the deaths of several young people in the UK.<ref name=nwpho/> 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 where caused directly by mephedrone.<ref name=npsad/> The first death reported to be caused by mephedrone use was that of 46 year old, Stirling Smith, who had underlying health problems and repeatedly injected the drug.<ref name=bbc2805/> A report in ''[[Forensic Science International]]'' in August 2010 stated that 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 that she died from natural causes.<ref name=fleming0504/> Toxicology reports following the deaths of two teenagers (Louis Wainwright, 18, and Nicholas Smith, 19) that were widely reported by the media to be caused by mephedrone, and which led to a ban on the substance in April 2010, showed that the teenagers had in fact not taken any mephedrone.<ref name=bbc2805/> 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"/>

=====USA=====
Mephedrone has been implicated in the death of a 22 year old male, 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/>

==Chemistry==
===Appearance===
[[Image:4mmc.png|thumb|right|250px|A sample of mephedrone that was confiscated in Oregon, USA, 2009]]
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=roussel/><ref name=reed1301what/> It can have a distinctive odour, reported to range from a synthetic [[fish]]y smell<ref name=power/> to the smell of [[vanilla]] and [[bleach]], stale [[urine]], electric [[circuit board]]s.<ref name=psychoreport/>

===Synthesis===
Mephedrone can be synthesised in several ways. The simplest method, due to the availability of the compounds,<ref name=emcdda/>{{rp|17}} is to add [[4-methylpropiophenone]] dissolved in [[glacial acetic acid]] to [[bromine]] to create an oil fraction of 4'-methyl-2-bromopropiophenone. This is then dissolved in CH<sub>2</sub>Cl<sub>2</sub> and drops of the solution are added to another solution of CH<sub>2</sub>Cl<sub>2</sub> containing methylamine hydrochloride and [[triethylamine]]. [[Hydrochloric acid]] is then added and the aqueous layer is removed and turned alkaline using [[sodium hydroxide]] before the amine is extracted using CH<sub>2</sub>Cl<sub>2</sub>. The CH<sub>2</sub>Cl<sub>2</sub> is then evaporated using a vacuum, creating an oil which is then dissolved in a non-aqueous [[ether]]. HCl gas is then 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}}

[[File:Mephedrone-synthesis-scheme-2D-skeletal-B.png|800px|Mephedrone synthesis scheme]]

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

==Legal status==
[[File:Map_of_european_countries_where_mephedrone_is_illegal.svg|thumb|Map of Europe showing countries where mephedrone is illegal, correct as of August 2010]]
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 the possession, sale and manufacturing of mephedrone 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 women 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 name=bbc2711/><ref name="kelly" /> On 30 March 2010, the ACMD in the UK published a report on mephedrone and recommended it being classifed as a Class B drug. On 7 April 2010 the Misuse of Drugs Act 1971 (Amendment) Order 2010 was passed by parliament, making mephedrone and other [[substituted cathinone]]s [[List of controlled drugs in the United Kingdom|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 however 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, as it has no use as such products, this too was possibly illegal under the [[Trade Descriptions Act 1968]].<ref name=bbc2711/><ref name=acmdreport/><ref name=reed1301/> The importation of mephedrone into the UK was banned on 29 March 2010.<ref name=police/> In May 2010 the [[Republic of Ireland]] made it illegal,<ref name=kelly/><ref name=ireland/><ref name=gartland/> followed by [[Belgium]],<ref name=belgium/> [[France]],<ref name=france/> [[Italy]],<ref name=italy/> [[Lithuania]]<ref name=lithuania/> and [[Norway]]<ref name=norway/> in June. In August 2010, [[Austria]]<ref name=austria/> and [[Poland]]<ref name=poland/> made mephedrone illegal and [[China]] announced that it would be illegal as of 1 September 2010.<ref name=china/>

In some countries, mephedrone is not specifically listed as illegal but is controlled under legislation that makes compounds illegal if they are [[Structural analog|analog]]s of drugs already listed. In [[Australia]] it is not specifically listed as prohibited,<ref name=Camilleri/> but Federal Police have stated that it is an analogue to [[methcathinone]] and therefore illegal. In February 2010, 22 men were arrested in conjunction with importing mephedrone.<ref name=smh/> Similarly in [[New Zealand]] it is not included in the [[Misuse of Drugs Act 1975]],<ref name=newzealand1/> but is illegal as it similar to controlled substances.<ref name=newzealand2/> In [[Canada]], mephedrone is not explicitly listed in any Schedule of the [[Controlled Drugs and Substances Act]], "amphetamines, their salts, derivatives, isomers and analogues and salts of derivatives, isomers and analogues" are included in Section I of Schedule III 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/> According to ''[[The Globe and Mail]]'', mephedrone is considered a controlled substance by [[Health Canada]].<ref name=tgab/> According to the [[Canadian Medical Association]], mephedrone is grouped with other amphetamines as Schedule III controlled substances.<ref name=cmaj/> There have been several media reports of the Canadian police seizing mephedrone.<ref name=cbcnews/><ref name=McCallum/><ref name=telegram/><!-- Please see the talk page before adding information saying that it is legal --> Mephedrone is also [[Controlled Substances Act|unscheduled in the United States]]<ref name=usdea/> but has been made illegal in [[North Dakota]].<ref name=michael/> Those selling the drug for human consumption may however, be prosecuted under the [[Federal Analog Act]] due to its similarity to [[methcathinone]].<ref name=deaconcern/>

As of April 2010 mephedrone is legal in [[Singapore]],<ref name=Sudderuddin/> in February 2010, 'CNN Go' reported that it was ordered over the internet and exported from the UK.<ref name=loh/> In August 2010, a government advisory body in [[Hungary]] recommended that mephedrone be made illegal, but it has yet to be controlled by parliament.<ref name=hungary/> As of August 2010, mephedrone is still legal in [[Switzerland]].<ref name=swiss/>

==See also==
*[[4-Methylamphetamine]]
*[[4-Methylthioamphetamine]]
*[[Methamphetamine]]
*[[para-Methoxyamphetamine]]

==References==

{{Reflist|colwidth=30em|refs=

<ref name=acmdreport>{{cite web|url=http://drugs.homeoffice.gov.uk/publication-search/acmd/ACMD-cathinones-report.pdf|title=Consideration of the cathinones|date=31 March 2010|publisher=Advisory Council on the Misuse of Drugs|page=25|accessdate=1 April 2010}}</ref>

<ref name=abcnews>{{cite news|url=http://www.abc.net.au/news/stories/2008/06/17/2277735.htm |title=Police warn of potentially fatal 'fake ecstasy' |publisher=Abc.net.au |date=17 June 2008 |accessdate=2009-08-11}}</ref>

<ref name=austria>{{Cite news|url=http://diepresse.com/home/panorama/589205/index.do?_vl_backlink=/home/index.do|title=Mode-Droge Mephedron in Österreich verboten|date=22 August 2010|publisher=DiePresse|accessdate=22 August 2010}}</ref>

<ref name=bbc2711>{{Cite news|url=http://news.bbc.co.uk/1/hi/england/tees/8370130.stm|title=Police warning over 'bubble' drug |date=20 November 2009|publisher=BBC News|accessdate=27 November 2009}}</ref>

<ref name=bbc0403>{{Cite news|url=http://news.bbc.co.uk/newsbeat/hi/health/newsid_10050000/newsid_10059100/10059133.stm|title= Call to ban legal high mephedrone test change|last=Campbell|first=Adina |date=4 March 2010|publisher=BBC Newsbeat|accessdate=17 March 2010}}</ref>

<ref name=bbc0803>{{Cite news|url=http://news.bbc.co.uk/1/hi/scotland/north_east/8555872.stm |title=Drugs crackdown hailed a success |publisher=BBC News |date=8 March 2010|accessdate=2010-03-31}}</ref>

<ref name=bbc2303test>{{Cite news|url=http://news.bbc.co.uk/1/hi/education/8582472.stm|title=Students test mephedrone drug |date=23 March 2010|publisher=BBC News|accessdate=23 March 2010}}</ref>

<ref name=bbc2303iversen>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/8582999.stm|title=Mephedrone may be banned, chief drug adviser indicates |date=23 March 2010|publisher=BBC News|accessdate=23 March 2010}}</ref>

<ref name=bbc2903>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/8592103.stm |title=Mephedrone to be made Class B drug 'within weeks' |publisher=BBC News |date= 29 March 2010|accessdate=2010-03-31}}</ref>

<ref name=bbc2903letter>{{cite web|url=http://news.bbc.co.uk/1/hi/uk/8592157.stm |title=Drug adviser Dr Polly Taylor's full resignation letter |publisher=BBC News |date=2010-03-29 |accessdate=2010-09-15}}</ref>

<ref name=bbc2903polly>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/8592103.stm |title=Resignation 'threatens drug ban' |publisher=BBC News |date= 29 March 2010|accessdate=2010-03-29}}</ref>

<ref name=bbc0204>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/8601315.stm|title=Government adviser Eric Carlin resigns over mephedrone |date=2 April 2010|publisher=BBC News|accessdate=2 April 2010}}</ref>

<ref name=bbc0204letter>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/8600929.stm|title=Eric Carlin's letter of resignation from the ACMD|date=2 April 2010|author=Carlin, Eric|accessdate=13 April 2010}}</ref>

<ref name=bbc0604>{{cite news|url=http://news.bbc.co.uk/1/hi/world/europe/guernsey/8604784.stm |title=Guernsey mephedrone ban 'only weeks away' |publisher=BBC News |date=2010-04-06 |accessdate=2010-09-14}}</ref>

<ref name=bbc0704>{{Cite news|url=http://news.bbc.co.uk/democracylive/hi/house_of_commons/newsid_8605000/8605939.stm |title=BBC - Democracy Live - MPs move to ban mephedrone |publisher=BBC News |date= 7 April 2010|accessdate=2010-04-08}}</ref>

<ref name=bbc1304>{{cite news|url=http://news.bbc.co.uk/1/hi/world/europe/guernsey/8618651.stm |title=Guernsey makes Mephedrone class B drug |publisher=BBC News |date=2010-04-13 |accessdate=2010-09-14}}</ref>

<ref name=bbc3004>http://news.bbc.co.uk/1/hi/health/8023451.stm</ref>

<ref name=bbc2805>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/10184803.stm|title=Teenagers' deaths 'not caused by mephedrone'|date=28 May 2010|publisher=BBC News}}</ref>

<ref name=bbc1207>{{Cite news|url=http://news.bbc.co.uk/1/hi/uk/10602398.stm |title=NRG-1 'legal high' drug is banned |publisher=BBC News |date=12 July 2010|accessdate=2010-08-23}}</ref>

<ref name=belgium>{{cite web|url=http://www.ejustice.just.fgov.be/cgi/article_body.pl?numac=2010018212&caller=list&pub_date=2010-06-21&language=fr |title=Arrêté royal du 13 Juin 2010 portant modification de l'arrêté royal du 22 janvier 1998 réglementant certaines substances psychotropes, et relatif à la réduction des risques et à l'avis thérapeutique |publisher=just.fgov.be |date= 13 June 2010|accessdate=2010-07-05}}</ref>

<ref name=brandt>{{Cite journal|last1=Brandt|first1=S. D.|last2=Sumnall|first2=H. R.|last3=Measham|first3=F.|last4=Cole|first4=J.|title=The confusing case of NRG-1|journal=BMJ|volume=341|pages=c3564|year=2010|doi=10.1136/bmj.c3564}}</ref>

<ref name=brunt>{{cite doi|10.1177/0269881110378370}}</ref>

<ref name=Camilleri>{{Cite journal |last1=Camilleri |first1=A |last2=Johnston |first2=MR |last3=Brennan |first3=M |last4=Davis |first4=S |last5=Caldicott |first5=DG |title=Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone |journal=Forensic Science International |volume=197 |issue=1–3 |pages=59–66 |year=2010 |pmid=20074881 |doi=10.1016/j.forsciint.2009.12.048}}</ref>

<ref name=canada>{{cite web|url=http://laws.justice.gc.ca/eng/C-38.8/page-6.html#anchorsc:2 |title=Controlled Drugs and Substances Act (1996, c. 19) |publisher=Canadian Department of Justice}}</ref>

<ref name=Campbell1701>{{Cite news|url=http://www.guardian.co.uk/politics/2010/jan/17/drug-legal-methedrone-high|title=Fears grow over safety of 'legal high' mephedrone|last=Campbell|first=Denis |date=17 January 2010 |publisher=The Observer|accessdate=9 March 2010|location=London}}</ref>

<ref name=campbell1203>{{cite news|first=Duncan |last=Campbell |url=http://www.guardian.co.uk/society/2009/mar/12/online-legal-drugs-stimulants |title= Online sales of legal alternatives to class A drugs raise safety fears |publisher=The Guardian  |date=12 March 2009}}</ref>

<ref name=cbcnews>{{Cite news|url=http://www.cbc.ca/canada/newfoundland-labrador/story/2010/06/25/newfoundland-police-make-mephedrone-bust-625.html |title=U.K. party drug hits St. John's streets |publisher=CBC News |date=25 June 2010|accessdate=2010-08-22}}</ref>

<ref name=Chaffey>{{Cite journal |last1=Chaffey |first1=Nigel |title=Plant Cuttings |journal=Annals of Botany |volume=105 |issue=6 |pages=v–viii |year=2010 |doi=10.1093/aob/mcq112}}</ref>

<ref name=china>[http://eng.sfda.gov.cn/cmsweb/webportal/W43879541/A64031541.html Mephedrone regulated as psychotropic substances] State Food and Drug Administration, 2 August 2010</ref>

<ref name=cmaj>{{cite web|url=http://www.cmaj.ca/cgi/rapidpdf/cmaj.109-3245v1.pdf |title=Britain moves to curtail new drug craze |format=PDF |date=26 April 2010 |accessdate=2010-07-04}}</ref>

<ref name=crew>{{cite web|url=http://www.crew2000.org.uk/|title= Crew 2000 - Drugs - Information, Advice and Support - Home|accessdate=2009-11-26}} Direct link to PDF file: [http://www.crew2000.org.uk/index.php?mact=Uploads,cntnt01,default,0&cntnt01mode=single&cntnt01upload_id=69&cntnt01category=Miscellaneous%20&cntnt01returnid=95]</ref>

<ref name=croatia>{{cite web|url=http://narodne-novine.nn.hr/clanci/sluzbeni/2010_01_2_12.html |title=Dopuna popisa opojnih droga, psihotropnih tvari i biljaka iz kojih se može dobiti opojna droga te tvari koje se mogu uporabiti za izradu opojnih droga, Narodne novine br.: 2, 04.01.2010 |publisher=Narodne-novine.nn.hr |date=28 December 2009|language=Croatian |accessdate=2010-07-04}}</ref>

<ref name=Cumming>{{cite web|last=Cumming |first=Ed |url=http://www.telegraph.co.uk/health/7614099/Mephedrone-Chemistry-lessons.html |title=Mephedrone: Chemistry lessons |publisher=The Daily Telegraph |date=2010-04-22 |accessdate=2010-09-14}}</ref>

<ref name=dargan>{{Cite journal|last1=Dargan|first1=P. I.|last2=Albert|first2=S.|last3=Wood|first3=D. M.|title=Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change|journal=QJM|year=2010|doi=10.1093/qjmed/hcq134}}</ref>

<ref name=darke>{{Cite journal| author=Shane Darke, Deborah Zador|title=Fatal Heroin 'Overdose': a Review|url=http://www.lindesmith.org/library/darke2.cfm|journal=[[Addiction (journal)|Addiction]]|year=1996|volume = 91|issue =12|pages= 1765–1772|doi=10.1046/j.1360-0443.1996.911217652.x }}</ref>

<ref name=davey>{{cite doi|10.5042/daat.2010.0467}}</ref>

<ref name=davies09>{{cite web|url=http://www.ltg.uk.net/admin/files/Methcathinones.pdf |title=Analytical profiles of Methcathinone Related Compounds |last=Davies |first=Susannah |coauthors=John Ramsey and Roland Archer |date=November 2009 |publisher=London Toxicology Group |accessdate=22 March 2010}}</ref>

<ref name=dea>{{cite web|url=http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0709/mg0709.pdf|title=DEA Microgram Bulletin |publisher=The Drug Enforcement Administration |date=July 2009}}</ref>

<ref name=deaconcern>{{cite web|url=http://www.deadiversion.usdoj.gov/drugs_concern/mephedrone.htm |title=Drugs and Chemicals of Concern - 4-Methylmethcathinone|publisher=United States Drug Enforcement Agency|date=July 2010|accessdate=2010-09-09}}</ref>

<ref name=devlin>{{cite news| last=Devlin |first=Kate |url=http://www.telegraph.co.uk/science/science-news/5244428/Psychiatrists-call-for-legal-high-drug-4-MMC-to-be-banned.html |title=Psychiatrists call for 'legal high' drug 4-MMC to be banned |publisher=''The Daily Telegraph'' |date=30 April 2009 |accessdate=2010-09-16}}</ref>

<ref name=dickson>{{Cite journal|url=http://www.jatox.com/index.php/Articles/Case-Report-Multiple-Drug-Toxicity-Caused-by-the-Coadministration-of-4-Methylmethcathinone-Mephedrone-and-Heroin.html |title=Case Report: Multiple-Drug Toxicity Caused by the Coadministration of 4-Methylmethcathinone (Mephedrone) and Heroin |journal=Journal of Analytical Toxicology |year=2010|volume=34|issue=3|pages=162–168|author=Dickson, Amber J. '' et al.''|pmid=20406541}}</ref>

<ref name=doward>{{cite web|author=Jamie Doward |url=http://www.guardian.co.uk/society/2010/apr/04/eric-carlin-mephedrone-classification |title=Mephedrone row grows as seventh member of drugs panel quits &#124; Society &#124; |publisher=The Observer |date=2010-04-04 |accessdate=2010-09-15}}</ref>

<ref name=druglink0309>{{cite web|url=http://www.drugscope.org.uk/Resources/Drugscope/Documents/PDF/Good%20Practice/Druglink_March_09_mephedrone.pdf |title=Mephedrone: the future of drug dealing?| publisher= Druglink| date= March 2009 |accessdate=2010-09-16}}</ref>

<ref name=druglink0110>[http://www.drugscope.org.uk/Resources/Drugscope/Documents/PDF/Good%20Practice/DruglinkJanFeb10.pdf How mephedrone shook the drug world] January/February 2010 issue of ''Druglink''</ref>

<ref name=emcdda>{{cite web|url=http://www.emcdda.europa.eu/attachements.cfm/att_102496_EN_Europol-EMCDDA_Joint_Report_Mephedrone.pdf|title=Europol–EMCDDA Joint Report on a new psychoactive substance: 4-methylmethcathinone (mephedrone)|publisher=European Monitoring Centre for Drugs and Drug Addiction |date=27 May 2010}}</ref>

<ref name=emcdda08>{{cite web|url=http://www.emcdda.europa.eu/attachements.cfm/att_77265_EN_Annex%202_New%20psychoactive%20substances%20reported%202008.pdf |title= EMCDDA 2008 Annual Report |publisher=European Monitoring Centre for Drugs and Drug Addiction |accessdate=2009-11-26}}</ref>

<ref name=emcddadenmark>{{cite report|url=http://www.emcdda.europa.eu/attachements.cfm/att_112008_EN_NR_2009_DK.pdf |title=2009 National Report (2008 data) To the EMCDDA by the Reitox National Focal Point - Denmark |format=PDF |date=2009 |accessdate=2010-09-14}}</ref>

<ref name=estonia>[http://www.estlex.ee/tasuta/?id=8&aktid=118262&fd=1&asutus=&grupp=3&leht=2 Sotsiaalministri 27.11.2009 määrus number 87] [Minister of Social Affairs Regulation Number 87] (in Estonian)</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=faulkner>{{cite web|first=Adam |last=Faulkner |url=http://www.clickliverpool.com/news/national-news/1210293-mephedrone-drugs-study-scrapped-by-a-liverpool-university.html |title=Mephedrone drugs study scrapped by Liverpool university |publisher=Click Liverpool |date=16 August 2010|accessdate=2010-08-30}}</ref>

<ref name=finland>{{cite web|url=http://www.city.fi/artikkeli/Rapujuhlat+saaristossa+/2783/ |title=Rapujuhlat saaristossa |publisher=City.fi |date= |accessdate=2010-09-14}}</ref>

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

<ref name=fleming2903>{{Cite news|url=http://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? |last=Fleming |first=Nic |date=29 March 2010 |publisher=New Scientist |accessdate=1 April 2010}}</ref>

<ref name=fleming0504>{{cite web|author=Nic Fleming |url=http://www.guardian.co.uk/media/2010/apr/05/mephedrone-drug-media-scare-newspapers |title=Mephedrone: the anatomy of a media drug scare |publisher=The Guardian |date=5 April 2010 |accessdate=2010-09-15}}</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|language=French |accessdate=2010-07-04}}</ref>

<ref name=Gammell>{{cite news|first=Caroline |last=Gammell |url=http://www.telegraph.co.uk/health/healthnews/4977750/Legal-online-drugs-providing-real-alternative-to-Class-A-substances.html |title= Legal online drugs providing real alternative to Class A substances |publisher= ''The Daily Telegraph''| date= 12 March 2009 |accessdate=2010-09-16}}</ref>

<ref name=gartland>[http://www.irishtimes.com/newspaper/ireland/2009/1106/1224258193510.html Irish youth are fourth highest cocaine users in Europe] Fiona Gartland The Irish Times, 6 November 2009 [http://www.webcitation.org/5nZOG07Dt archived]</ref>

<ref name=germany>{{cite web|url=http://www.buzer.de/gesetz/9164/index.htm |title=Vierundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften (24. BtMÄndV) |publisher=Buzer.de |date=22 January 2010|language=German |accessdate=2010-07-04}}</ref>

<ref name=gibbons>{{Cite journal|last1=Gibbons|first1=Simon|last2=Zloh|first2=Mire|title=An analysis of the ‘legal high’ mephedrone|journal=Bioorganic & Medicinal Chemistry Letters|volume=20|page=4135|year=2010|doi=10.1016/j.bmcl.2010.05.065}}</ref>

<ref name=guppy>{{cite news |first=Damon |last=Guppy |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 |accessdate=2009-08-11}}</ref>

<ref name=Gustavsson>{{Cite journal|last=Gustavsson|first=David|coauthors= Escher, Cecilia|date=20 October 2009|title=Mefedron – Internetdrog som tycks ha kommit för att stanna| journal=Lakartidningen |language=Swedish |url=http://www.lakartidningen.se/07engine.php?articleId=12986}}</ref>

<ref name=hamilton>{{cite web|url=http://www.viceland.com/int/v17n6/htdocs/hamilton-s-pharmacopeia-455.php |title=Hamilton’s Pharmacopeia |publisher=Vice Magazine |date=5 April 2003|accessdate=2010-07-04}}</ref>

<ref name=hartung>{{Cite journal|author = Hartung WH, Munch JC, Deckart WA, Crossley F|title = Amino-alcohols. ii. homologs and analogs of phenylpropanolamine|journal = Journal of the American Chemical Society|year = 1930|month = August|volume = 52|issue = 8|pages = 3317–3322|doi = 10.1021/ja01371a046}}</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 - Herald Scotland |publisher=Herald Scotland |date=2010-03-21 |accessdate=2010-09-15}}</ref>

<ref name=hungary>{{cite web|language=Hungarian|url=http://index.hu/belfold/2010/09/02/eldolt_betiltjak_a_katit/|title=Eldőlt: betiltják a katit|date=2 September 2010}}</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=Iomtoday.co.im |date=25 February 2010  |accessdate=2010-07-04}}</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=Dohc.ie |date=11 May 2010|accessdate=2010-08-22}}</ref>

<ref name=ISCoD>{{cite web|url=http://www.drugscience.org.uk/mephedroneadvice.html |title=Mephedrone: harm reduction advice - Independent Scientific Committee on Drugs |publisher=Drugscience.org.uk |date= |accessdate=2010-09-15}}</ref>

<ref name=italy>[http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti Tabelle sostanze stupefacenti e psicotrope] Ministero della Salute (Italian)</ref>

<ref name=james>{{cite doi|10.1136/emj.2010.096636}}</ref>

<ref name=jones>{{Cite news|author=Jones, Sam and Power, Mike|url=http://www.guardian.co.uk/society/2010/aug/17/ivory-wave-drug-alleged-death |title=Ivory Wave drug implicated in death of 24-year-old man &#124; Society &#124; guardian.co.uk |publisher=Guardian |date= 17 August 2010|accessdate=2010-08-23|location=London}}</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|last=Kelly|first=Fiack|date=3 March 2010|publisher=Irish Independent|accessdate=27 March 2010}}</ref>

<ref name=lancet>{{cite doi|10.1016/S0140-6736(10)60556-9}}</ref>

<ref name=lifeline>{{cite web |url=http://www.lifeline.org.uk/docs/Meph%20faq.pdf |title=Mephedrone - Frequently asked questions |author= |date= |format=PDF |publisher=Lifeline publications |accessdate=September 17, 2010}}</ref>

<ref name=lithuania>{{cite web|url=http://www3.lrs.lt/pls/inter3/dokpaieska.showdoc_l?p_id=375830|title=Ministry of Health of the Republic of Lithuania (Lithuanian)}}</ref>

<ref name=local>{{cite web|url=http://www.thelocal.se/16366/20081215/ |title=Teenager dies of 'net drug' overdose |publisher=Thelocal.se |date=15 December 2008 |accessdate=3 September 2010}}</ref>

<ref name=loh>{{cite web|last=Loh |first=Larry |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|accessdate=2010-07-04}}</ref>

<ref name=lifeline>{{cite web|url=http://www.lifelineproject.co.uk/docs/M-cat%20report%20small.pdf|title=The Use of Mephedrone (M-cat, Meow) in Middlesbrough|last=Newcombe|first=Russell|date=December 2009|publisher=Lifeline Publications and Research|accessdate=17 March 2010}}</ref>

<ref name=mann>{{cite web|first=John|last=Mann|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|accessdate=2010-09-16}}</ref>

<ref name=McCallum>{{cite web|last=McCallum |first=Jamie |url=http://www.montrealgazette.com/Legal+ecstasy+causing+concern+Quebec/3415148/story.html |title='Legal ecstasy' causing concern in Quebec |publisher=Montrealgazette.com |date=18 August 2010|accessdate=2010-08-22}}</ref>

<ref name=McNamara>{{Cite journal|url=http://www.imj.ie/ViewArticleDetails.aspx?ArticleID=5909 |title=Head Shop Compound abuse amongst attendees of The Drug Treatment Centre Board|author=McNamara, S; Stokes, S and Coleman, N|journal=The Irish Medical Journal|volume=102|issue=5|year=2009}}</ref>

<ref name=Measham>{{Cite journal|last=Measham|first=Fiona|coauthors=Karenza Moore, Russell Newcombe and Zoe Smith|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}} <!-- [http://pierprofessional.metapress.com/index/4NQ6X3502770322J.pdf Free pdf]{{dead link|date=August 2010}} --></ref>

<ref name=meyer2009>{{Cite journal|author = 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|last1=Meyer|first1=Markus R.|last2=Wilhelm|first2=Jens|last3=Peters|first3=Frank T.|last4=Maurer|first4=Hans H.|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|page=1225|year=2010|doi=10.1007/s00216-010-3636-5}}</ref>

<ref name=michael>{{cite web| first=jenny |last=michael |url=http://www.bismarcktribune.com/news/local/crime-and-courts/article_88821b32-2362-11df-8be9-001cc4c03286.html |title=Substances producing ‘legal highs’ no longer legal |publisher=Bismarcktribune.com |date=27 February 2010|accessdate=2010-07-04}}</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=Legislation.govt.nz |date=1 December 2009|accessdate=2010-07-04}}</ref>

<ref name=newzealand2>{{cite web|author=By JOHN EDENS - The Southland Times |url=http://www.stuff.co.nz/national/health/4125151/Low-quality-drugs-prompt-risk-warning |title=Low-quality drugs prompt risk warning |publisher=Stuff.co.nz |date= |accessdate=2010-09-14}}</ref>

<ref name=nhs>[http://www.nhs.uk/news/2010/03March/Pages/legal-high-drug-meow-mephedrone-death.aspx Legal drug 'meow meow' probed] NHS Choices 17 March 2010</ref>

<ref name=norway>{{cite web|url=http://www.nrk.no/nyheter/norge/1.7163768 |title=Ti nye stoffer på narkotikalisten |publisher=Nrk.no |date=11 June 2010|language=Norwegian |accessdate=2010-08-31}}</ref>

<ref name=npsad>{{cite web|title=Drug-related deaths in the UK|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=National Programme on Substance Abuse Deaths|coauthors=Hamid Ghodse, John Corkery, Kapil Ahmed, Vinesha Naidoo, Adenekan Oyefeso and Fabrizio Schifano|page=77|format=PDF|date=July 2010}}</ref>

<ref name=nwpho>{{cite web|url=http://www.cph.org.uk/showPublication.aspx?pubid=614|title=Mephedrone Briefing|first=Harry |last=Sumnall |coauthors=Olivia Wooding|publisher=North West Public Health Observatory|accessdate=18 March 2010}}</ref>

<ref name=opsi.gov>{{cite web|url=http://www.opsi.gov.uk/si/si2010/uksi_20101144_en_1 |title=The Misuse of Drugs (Amendment) (England, Wales and Scotland) Regulations 2010 No. 1144 |publisher=Opsi.gov.uk |date=16 April 2010 |accessdate=2010-04-08}}</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|date=10 June 2010 |accessdate=2010-08-25}}</ref>

<ref name=police>{{Cite news|url=http://www.policeprofessional.com/news.aspx?id=10163|title=Mephedrone to be classified a Class B drug|date=1 April 2010|publisher=Police Professional|accessdate=2 April 2010}}</ref>

<ref name=power>{{Cite news|last=Power|first=Mike|title=The Chinese laboratories where scientists are already at work on the new 'meow meow'|url=http://www.dailymail.co.uk/home/moslive/article-1267582/The-Chinese-laboratories-scientists-work-new-meow-meow.html|accessdate=13 September 2010|newspaper=Daily Mail|date=24 April 2010}}</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|accessdate=19 December 2009}}<!-- old link - http://www.p2002.sgul.ac.uk/newsletters/n2.php --></ref>

<ref name=psychoreport>{{cite web|title=Mephedrone Report|url=http://194.83.136.209/documents/reports/Mephedrone.pdf|publisher=Psychonaut Web Mapping Project|date=March 2010}}</ref>

<ref name=reed1301>{{Cite news|last=Reed |first=Jim |url=http://news.bbc.co.uk/newsbeat/hi/health/newsid_10000000/newsid_10004300/10004366.stm |title=Clubbers are 'turning to new legal high mephedrone'|publisher=BBC News |date=13 January 2010|accessdate=2010-07-04}}</ref>

<ref name=reed1301what>{{Cite news|url=http://news.bbc.co.uk/newsbeat/hi/health/newsid_10000000/newsid_10004300/10004383.stm|title= What is legal high mephedrone? |last=Reed|first=Jim|date=13 January 2010|publisher=BBC Newsbeat|accessdate=13 February 2010}}</ref>

<ref name=Reed2006>{{cite web|last=Reed |first=Jim |url=http://www.bbc.co.uk/newsbeat/10353130 |title=Newsbeat - Ecstasy 'disappearing' from British clubs |publisher=BBC |date=20 June 2010|accessdate=2010-08-30}}</ref>

<ref name=roussel>{{Cite journal|url = http://www.ata-journal.org/index.php?option=article&access=standard&Itemid=129&url=/articles/ata/pdf/first/ata09028.pdf|author = Roussel O, Perrin M, Herard P, Chevance M, Arpino P|title = La 4-méthyléphédrone sera-t-elle une "Ecstasy" du XXIème siècle |trans_title=Is 4-methylephedrone, an “Ecstasy” of the twenty first century?|language = French|journal = Annales de Toxicologie Analytique|year = 2009|doi = 10.1051/ata/2009048}}</ref>

<ref name=romania>[http://www.financiarul.ro/2010/02/11/salvia-divinorum-psilocybe-mushrooms-are-among-hallucinogenic-herbs-banned-by-govt/ Salvia divinorum, psilocybe mushrooms are among hallucinogenic herbs banned by gov’t] Financiarul 11 February 2010 [http://www.webcitation.org/5nZOId46i archived]</ref>

<ref name=Sanchez1929>{{cite journal |author=Saem de Burnaga Sanchez, J. |year=1929 |title=Sur un homologue de l’éphédrine |trans_title=On an analogue of ephedrine |journal=Bulletin de la Societé Chimique de France |volume=45 |pages=284–286}}</ref>

<ref name=Saner>{{Cite news|url=http://www.guardian.co.uk/society/2009/dec/05/mephedrone-problem-legal-highs|title=Mephedrone and the problem with 'legal highs'|last=Saner|first=Emine|date=5 December 2009|publisher=The Guardian|accessdate=24 December 2009|location=London}}</ref>

<ref name=smh>{{Cite news|url=http://www.smh.com.au/national/miaow-drug-seized-in-mail-busts-20100212-nwad.html|title='Miaow' drug seized in mail busts|date=12 February 2010|publisher=Sydney Morning Herald|accessdate=12 February 2010}}</ref>

<ref name=soodin>{{cite web|last=Soodin |first=Vince |url=http://www.thesun.co.uk/sol/homepage/news/2747979/Lad-ripped-his-scrotum-off.html |title='Meow meow' drug teen ripped his scrotum off |publisher=The Sun |date=2009-11-26 |accessdate=2010-09-15}}</ref>

<ref name=stigson>{{cite web|first=Gubb Jan |last= Stigson |url=http://www.dalademokraten.se/sida/id/124262 |title=15 gram narkotika ger två års fängelse  |publisher=Dala Demokraten|date=9 June 2010|accessdate=2010-07-04}}</ref>

<ref name=Sudderuddin>{{cite web|first= Shuli |last=Sudderuddin |url=http://www.asiaone.com/print/News/Education/Story/A1Story20100412-209857.html |title=Youths abusing drugs |publisher=The Straits Times |date=13 April 2010|accessdate=2010-08-30}}</ref>

<ref name=sweden>[http://62.95.69.3/SFSDOC/08/080908.PDF Svensk författningssamling] (in Swedish) 25 November 2008</ref>

<ref name=swiss>http://www.bz-berlin.de/aktuell/berlin/ich-verfiel-der-partydroge-meow-article961726.html</ref>

<ref name=TDPF>{{Cite news|url=http://transform-drugs.blogspot.com/2010/03/mephedrone-and-acmd-lessons-from-bzp.html |title=Mephredone and the ACMD: lessons from BZP and New Zealand's "Class D' experiment? |date=18 March 2010 |publisher=Transform Drug Policy Foundation |accessdate=13 April 2010}}</ref>

<ref name=telegram>{{cite web|url=http://www.thetelegram.com/Justice/2010-06-25/article-1448526/RNC-seizes-designer-drug/1|title=RNC seizes designer drug - Justice - News |publisher=The Telegram |date=25 June 2010 |accessdate=2010-08-22}}</ref>

<ref name=telegraph0104>{{Cite news|url=http://www.telegraph.co.uk/health/healthnews/7545261/Mephedrone-can-cause-impotence-warns-expert.html |title=Mephedrone can cause impotence, warns expert|publisher=The Daily Telegraph |date=1 April 2010|accessdate=2010-07-04|location=London}}</ref>

<ref name=tgab>{{Cite news|url=http://www.theglobeandmail.com/news/world/mephedrone-from-plant-food-to-britains-party-drug/article1504199/|title=Mephedrone: From plant food to Britain’s party drug |last=Chan|first=Kevin|date=18 March 2010|publisher=Globe and Mail |accessdate=23 March 2010}}</ref>

<ref name=Torrance>{{Cite journal|last1=Torrance|first1=Hazel|last2=Cooper|first2=Gail|title=The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland|journal=Forensic Science International|year=2010|doi=10.1016/j.forsciint.2010.07.014}}</ref>

<ref name=usdea>{{cite web|url=http://www.justice.gov/dea/pubs/scheduling.html |title=United States Drug Enforcement Agency Drug Scheduling|accessdate=11 January 2010 |publisher=Justice.gov |accessdate=2010-07-04}}</ref>

<ref name=winstock>{{Cite journal|last=Winstock|first=Adam|coauthors=John Marsden and Luke Mitcheson|date=23 March 2010|title=What should be done about mephedrone?|journal=British Medical Journal|pmid=20332508|doi=10.1136/bmj.c1605|volume=340|pages=c1605}}</ref>

<ref name=winstockaddiction>{{cite doi|10.1111/j.1360-0443.2010.03130.x}}</ref>

<ref name=wood>{{Cite journal| pmid = 20581379| year = 2010| last1 = Wood|first1 = D.| last2 = Greene|first2 = S.| last3 = Dargan|first3 = P.| title = Clinical pattern of toxicity associated with the novel synthetic cathinone mephedrone| journal = Emergency medicine journal : EMJ| doi = 10.1136/emj.2010.092288}}</ref>

<ref name=woodsubcataneous>{{Cite journal|url=http://www.eapcct.org/publicfile.php?folder=congress&file=Abstracts_SanAntonio.pdf|title=153. Recreational Use of 4-Methylmethcathinone (4-MMC) Presenting with Sympathomimetic Toxicity and Confirmed by Toxicological Screening|last=Wood|first=DM|journal=Clinical Toxicology|doi=10.1080/15563650903076924| volume= 47 |issue=7|page=702|year= 2009|accessdate=17 March 2010}}</ref>}}

==External links==
*[http://www.erowid.org/chemicals/4_methylmethcathinone/ Erowid 4-Methylmethcathinone Vault]
*[http://www.lifeline.org.uk/docs/Meph%20faq.pdf Mephedrone - Frequently asked questions] www.lifeline.org.uk
*[http://www.guardian.co.uk/world/audio/2010/mar/19/guardian-daily-podcast-mephedrone-drug-meow Guardian Daily Podcast: How dangerous is mephedrone?]
*[http://www.rivmixx.com/interview/feature-mephedrone/11619 Mephedrone: A Musical Movement Or The Latest Fad?]

{{Drug use}}
{{Stimulants}}
{{Entactogens}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Phenethylamines}}

{{Use dmy dates|date=September 2010}}

{{DEFAULTSORT:Methylmethcathinone, 4-}}
[[Category:Dopamine agonists]]
[[Category:Serotonin receptor agonists]]
[[Category:Cathinones]]
[[Category:Drugs acting on the nervous system]]
[[Category:Drugs acting on the cardiovascular system]]
[[Category:Euphoriants]]
[[Category:Phenethylamines]]
[[Category:Sympathomimetic amines]]

[[zh-min-nan:Mephedrone]]
[[ca:Mefedrona]]
[[cs:Mefedron]]
[[de:Mephedron]]
[[es:Mefedrona]]
[[fr:Méphédrone]]
[[hu:Mefedron]]
[[nl:Mephedrone]]
[[pl:Mefedron]]
[[ru:Мефедрон]]
[[sv:4-metylmetkatinon]]
[[Category:2Fix]]