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org/wiki/Mephedrone
Mephedrone
Mephedrone
Systematic (IUPAC) name
(RS)-2-Methylamino-1-(4-methylphenyl)propan-1-one
[1]:5
Clinical data
Legal status
Routes
Oral, insufflation, IV, rectal,
[2]

smoking
[3]
Identifiers
CAS number
1189805-46-6

1189726-22-4 (HCl)
[1]:5
ATC code None
PubChem CID 29982893
ChemSpider
21485694

ChEBI
CHEBI:59331

Synonyms
4-methyl-N-methylcathinone; 2-methylamino-1-p-tolylpropan-1-one
[4]
Chemical data
Formula
C
11
H
15
NO

Mol. mass 177.242 g/mol
SMILES[show]
InChI[show]
(what is this?) (verify)
Mephedrone, also known as 4-methylmethcathinone (4-MMC) or 4-methylephedrone, is a synthetic stimulant drug
of the amphetamine and cathinone classes. Slang names include drone,
[5]
M-CAT,
[6]
and meow meow.
[7]
It is
chemically similar to 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, amphetamines and cocaine.
In addition to its stimulant effects, mephedrone produces side effects, of which teeth grinding is the most common.
The metabolism of mephedrone has been studied in rats and humans and the metabolites can be detected in urine
after usage. Despite similarities to known neurotoxins such as methamphetamine and cathinone derivatives,
mephedrone does not appear to produce neurotoxic effects in the dopamine system of mice.
[8]
Mephedrone 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, 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 USA, it is considered an analog of other illegal drugs and can be controlled by laws similar to the
Federal Analog Act . In September 2011, the USA temporarily classified mephedrone as illegal, in effect from October
2011.
Contents
[hide]
History[edit]
Mephedrone is one of hundreds of designer drugs 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.
[9]
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 Socit Chimique de
France, under the name "toluyl-alpha-monomethylaminoethylcetone",
[1]:17[10]
but the compound remained an obscure
product of academia until 2003, when it was "re-discovered" and publicised by an underground chemist on The Hive
website, working under the pseudonym "Kinetic".
[11]
Kinetic posted on the site, "Ive been bored over the last couple of
days and had a few fun reagents lying around, so I thought Id try and make some 1-(4-methylphenyl)-2-
methylaminopropanone hydrochloride, or 4-methylmethcathinone." before going on to describe that after taking it, the
user had a "fantastic sense of well-being that I havent got from any drug before except my beloved Ecstasy."
[12]
In
interviews Kinetic was described as "a mathematician who used to design sleeping pills for a major pharmaceutical
company" and he stated that he was based in Israel when he rediscovered mephedrone.
[13][14]
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.
[15][16][17]
The products had names such as Neodoves pills, but the range was discontinued in
January 2008 after the Israeli government made mephedrone illegal.
[5][18][19]
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, when it was also
discussed on internet forums.
[9][20]
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?"
[21]
Mephedrone was reported as having been sold as ecstasy in the Australian
city of Cairns, along with ethylcathinone, in 2008.
[22][23]
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 A$16 to $320.
[3]
Europol noted they became aware of it in 2008, after it was found in Denmark, Finland and the UK.
[24]
The Drug
Enforcement Administration noted it was present in the United States in July 2009.
[25]
By May 2010, mephedrone had
been detected in all 22 EU member states that reported to Europol, as well as in Croatia and Norway.
[1]:21
The Daily
Telegraph reported in April 2009 that it was manufactured in China, but it has since been made illegal there.
[26][27]
In
March 2009, Druglink magazine reported it only cost a "couple of hundred pounds" to synthesise a kilogram of
mephedrone,
[15]
the same month, The Daily Telegraph reported manufacturers were making "huge amounts of
money" from selling it.
[28]
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.
[12][29]
A later report, in March 2010,
stated the wholesale price of mephedrone was 4000 per kilogram.
[30]
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.
[31][32]
In the UK[edit]
Between the summer of 2009 and March 2010, the use of mephedrone grew rapidly in the UK, with it becoming readily
available at music festivals, head shops and on the internet.
[34]
A survey of Mixmag readers in 2009, found it was the
fourth most popular street drug in the United Kingdom, behind cannabis, cocaine, and ecstasy.
[30]
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.
[34]
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,
[34]
a view reinforced in a report by the
National Treatment Agency for Substance Misuse.
[35]
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,
[36]
and by June 2010 almost all ecstasy pills seized
in the UK contained no MDMA.
[37]
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.
[38]
The decrease of MDMA was thought to be partly 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.
[12]
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.
[15][39]
gamma-Butyrolactone (GBL), another previously "legal high", was also banned in August 2009
despite concerns it would be replaced by other drugs.
[40]
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 grams and half that also sold bulk quantities. The
price per gram varied from 9.50 to 14.
[1]:11
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.
[41]
After mephedrone was made illegal
the number of inquiries to the NPIS fell substantially, to only 19 in June 2010.
[42]
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.
[36]
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.
[43]
In
November 2009, the tabloid newspaper, The Sun published a story stating that a man had ripped off his own scrotum
whilst using mephedrone.
[44]
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.
[45][46]
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.
[47]
Parallels were drawn between the media coverage of mephedrone and a piece of satire by Chris
Morris in 1997 on Brass Eye when he tricked public figures into talking of the dangers of taking the fictional legal drug
"cake".
[46]
The Advisory Council on the Misuse of Drugs (ACMD) have suggested that the media coverage of the drug
led to its increased usage.
[48]
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.
[40][49]
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 teeth grinding is the most common.
[50]
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.
[9]
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.
[51][52]
The legislation would make all cathinones
illegal, which Johnson said would "stop unscrupulous manufacturers and others peddling different but similarly harmful
drugs".
[53]
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 ecstasy and cannabis, culminating in the dismissal of
the ACMD chairman, David Nutt, after he reiterated the ACMD's findings in an academic lecture.
[54]
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.
[55]
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."
[56]
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.
[57]
Others expressed concern that the drug would be left in the hands of black market dealers, who will only
compound the problem.
[58]
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 countrys drug problems. We need to stop harming
people who need help and support".
[59]
The parliamentary debate was held on 8 April, one day after the 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.
[60]
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.
[40]
In January 2011, however, Johnson told the
Scunthorpe Telegraph that the decision was based only on information from the ACMD.
[61]
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.
[48]
Evan Harris, then the Liberal
Democrat science spokesman, stated the ACMD "was not 'legally constituted'" as required by the Misuse of Drugs Act,
when the report on cathinones was published, since after Taylor resigned, it lacked a veterinary surgeon.
[53]
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.
[62]
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.
[63]
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.
[64][65][66]
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 2025 per gram.
[67]
In September 2010, Druglink
reported the ban had had a mixed effect on mephedrone use, with it decreasing in some areas, remaining similar in
others and becoming more prevalent in some areas.
[68]
In an online survey of 150 users after the ban, 63% said they
were continuing to use mephedrone, half of those used the same amount and half said they used less. 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.
[69]
The 2010 Mixmag survey of 2500 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 cut with other substances.
[70]
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.
[71]
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.
[9]
Professor Shiela Bird, a statistician at the 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.
[72][73]
Other supposedly
legal drugs have filled the gap in the market since mephedrone was made illegal, including naphyrone (NRG-1) (since
made illegal)
[74]
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.
[75]
When tested,
some products sold six weeks after mephedrone was banned, advertised as NRG-1, NRG-2 and MDAI, were found to
be mephedrone.
[76]
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.
[77]
Effects[edit]
No formal published studies have been conducted into the psychological and/or behavioural effects of mephedrone on
humans, nor on animals (from which the potential effects might be extrapolated). As a result, the only information
available comes from users themselves and clinical reports of acute mephedrone toxicity.
[1]: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.
[78]
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".
[79]
The study was
discontinued in August 2010, following the change in the legal status of the drug.
[80]
Intended effects[edit]
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; these effects are similar to the effects
of cocaine, amphetamines and MDMA, and last different amounts of time, depending on the way the drug is taken.
When taken orally, users reported they could feel the effects within 1545 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.
[1]:12
Of 70 Dutch users of mephedrone, 58 described it as an
overall pleasant experience and 12 described it as an unpleasant experience.
[38]
In a survey of UK users who had
previously taken cocaine, most users found it produced a better-quality and longer-lasting high, was less addictive and
carried the same risk as using cocaine.
[2]
Side effects[edit]
The ECMDDA reported mephedrone can cause various unintended side effects including: dilated pupils,
[81]
poor
concentration, teeth grinding, problems focusing visually, poor short-term memory, hallucinations, delusions, and
erratic behaviour.
[1]:13
They noted the most severe effects appear anecdotally to be linked with high doses or
prolonged usage, 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, increased heart rate, breathing difficulties, loss of
appetite, increased sweating, discolouration of extremities, anxiety, paranoia and depression.
[1]:13
When snorted, it
can also cause nose bleeds and nose burns.
[1]:13[82]
A survey conducted by the National Addiction Centre, UK, 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,
[83]
indicative of vasoconstriction occurring.
[41]
Doctors at Guy's
Hospital, London reported, 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 GHB, with mephedrone. The patients also reported polydrug use of a
variety of compounds.
[84]
Long-term effects[edit]
Almost nothing is known about the long-term effects of the drug due to the short history of its use.
[83]
BBC News
reported one person who used the drug for 18 months became dependent on the drug, in the end using it twice a
week, and had to be admitted to a psychiatric unit after he started experiencing hallucinations, agitation, excitability
and mania.
[1]:13[85]
Typical use and consumption[edit]
Mephedrone can come in the form of capsules, tablets or white powder that users may swallow, snort, inject, smoke or
use rectally.
[1]:12[2][3]
It is sometimes sold mixed with methylone in a product called bubbles in the UK
[86]
and also
mixed with other cathinones, including ethcathinone, butylone, fluoromethcathinone and methedrone.
[1]:9
The
Guardian reported some users compulsively redose, consuming their whole supply when they only meant to use a
small dose,
[87]
and there have been other similar reports of users craving mephedrone, suggesting it may be
addictive.
[1]:13[38]
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 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 g
compared to 0.74 g) and also reported using it more often (five days per month compared to three days per month).
[2]
An Irish study of people on a methadone treatment program for heroin addicts found 29 of 209 patients tested positive
for mephedrone usage.
[88]
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.
[9]
Harm reduction[edit]
See also: Harm reduction and 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 0.5 g 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 at sensible
The two enantiomers of mephedrone: The
potentially more potent S form is above the R
form
intervals while taking the drug, as it causes dehydration.
[89]
Pharmacology[edit]
The pharmacology and toxicology of mephedrone had not been studied in
detail until well after its sale as a designer drug and its addition to controlled
drug lists in many countries.
[90][91]
Writing in the British Medical Journal,
psychiatrists stated, given its chemical structure, "mephedrone is likely to
stimulate the release of, and then inhibit the reuptake of monoamine
neurotransmitters".
[81]
The cathinone derivatives methcathinone and
methylone act in a similar way to amphetamines, mainly acting on
catecholamine transporters, so mephedrone is expected also to act in this
way. The actions of amphetamines and cathinones are determined by the
differences in how they bind to noradrenalin, dopamine and serotonin
transporters.
[90]
Molecular modelling of mephedrone suggests it is more
hydrophilic than methyl-amphetamines, which may account for the higher
doses required to achieve a similar effect, because mephedrone is less
able to cross the bloodbrain barrier.
[1]:12[92]
Mephedrone has a chiral
centre, so exists in two forms, called enantiomers; the S form is thought to
be more potent than the R form, because this applies to cathinone.
[90]
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."
[93]
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."
[94]
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.
[95][96]
Metabolism[edit]
Based on the analysis of rat and human urine by gas chromatography and mass spectrometry, mephedrone is thought
to be metabolised by three phase 1 pathways. It can be demethylated to the primary amine (producing compounds 2,
3 and 5), the ketone group can be 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 tests, as well as more
accurate determination of the causes of side effects and potential for toxicity.
[97]
Proposed scheme for the metabolism of mephedrone (1) based on the analysis of rat and human urine
[97]
Toxicity[edit]
As of March 2010, no studies on the potential neurotoxicity of mephedrone have been reported,
[81]
nor is the median
lethal dose known.
[2]
In 2009, one case of sympathomimetic toxicity was reported in the UK after a person took 0.2 g
of mephedrone orally, and after this did not achieve the desired effect, subcutaneously injected 3.8 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 mg of lorazepam and the sympathomimetic features decreased and the user
was discharged within six hours of arrival.
[98]
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.
[99]
Both enantiomers 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".
[92]
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.
[38]
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.
[100]
In another case, a 19-year-old male was admitted to hospital suffering
from 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.
[101]
One
case of 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.
[102]
Detection in biological specimens[edit]
Mephedrone may be quantitated in blood, plasma or urine by gas chromatography-mass spectrometry to confirm a
diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or
plasma mephedrone concentrations are expected to be in a range of 50100 g/l in persons using the drug
recreationally, >100 g/l in intoxicated patients and >500 g/l in victims of acute overdosage.
[103]
Deaths[edit]
Sweden[edit]
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.
[104]
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.
[105]
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.
[104]
UK[edit]
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.
[106]
The
first death reported to be caused by mephedrone use was that of 46-year-old, John Sterling Smith,
[107]
who had
underlying health problems and repeatedly injected the drug.
[108]
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 mg/l in one case and 3.3 mg/l in the
other.
[109]
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.
[46]
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 heroin substitute
methadone.
[108][110]
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.
[34]
USA[edit]
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 mg/l and in his urine at a concentration of 198 mg/l. The
blood concentration of morphine, a metabolite of heroin, was 0.06 mg/l.
[111]
For comparison, the average blood
morphine concentration resulting from deadly overdoses involving only heroin is around 0.34 mg/l.
[112]
Chemistry[edit]
Appearance[edit]
Mephedrone is a white substance. It is sold most commonly as crystals or a powder, but also in the form of capsules or
pills.
[21][94]
It can have a distinctive odour, reported to range from a synthetic fishy smell
[113]
to the smell of vanilla and
bleach, stale urine, or electric circuit boards.
[114]
Synthesis[edit]
Mephedrone can be synthesised in several ways. The simplest method, due to the availability of the compounds,
[1]:17
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 (CH
2
Cl
2
) and drops of the solution
added to another solution of CH
2
Cl
2
-containing methylamine hydrochloride and triethylamine. Hydrochloric acid (HCl)
is then added and the aqueous layer is removed and turned alkaline using sodium hydroxide before the amine is
extracted using CH
2
Cl
2
. The CH
2
Cl
2
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.
[18]
This method produces a mixture of both enantiomers and requires similar knowledge to that required
A sample of mephedrone that was confiscated in
Oregon, USA, 2009
to synthesise amphetamines and MDMA.
[1]:17
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.
[1]:17
A stereospecific form of ( S)-mephedrone could be prepared via FriedelCrafts acylation. The first step in the synthesis
would be to react toluene and (S)-N-trifluoroacetylalanoyl chloride in the presence of aluminium chloride, then
deprotect the intermediate with hydrochloric acid-propyl alcohol. This would produce ( S)-4-methylcathinone, which
could then be methylated to produce mephedrone.
[90][115]
Purity[edit]
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.
[92]
An unpublished study of six samples also ordered off
the internet in the UK in 2010 found they contained very few organic impurities.
[116]
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.
[117]
Legal status[edit]
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.
[5]
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 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.
[118][119]
In December 2008, Denmark also made it illegal
[120]
and through the Medicines Act of Finland, it was made illegal to
possess without a prescription.
[121]
In November 2009, it was
classified as a "narcotic or psychotropic" substance and added to the
list of controlled substances in Estonia
[122]
and made illegal to import
into Guernsey along with other legal highs,
[123]
before being classified as a Class B drug in April 2010.
[124]
It was
classified as a Class C drug in Jersey in December 2009.
[125]
In 2010, as its use became more prevalent, many countries passed legislation prohibiting mephedrone. It became
illegal in Croatia
[126]
and Germany
[127]
in January, followed by Romania
[128]
and the Isle of Man in February.
[129]
In
March 2010, it was classified as an unregulated medicine in the Netherlands, making the sale and distribution of it
illegal.
[130][131]
The importation of mephedrone into the UK was banned on 29 March 2010.
[132]
The next day, the
ACMD in the UK published a report on the cathinones, including mephedrone, and recommended they be classified as
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 cathinones, Class B drugs from 16 April 2010.
[133][134]
Prior to the ban
taking effect, mephedrone was not covered by the Misuse of Drugs Act 1971.
[26]
It was, though, an offence under the
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.
[52][82][83]
In the USA,
similar descriptions have been used to describe mephedrone, as well as methylenedioxypyrovalerone (MDPV).
[135]
In
May 2010, the Republic of Ireland made mephedrone illegal,
[136][137][138]
followed by Belgium,
[139]
Italy,
[140]
Lithuania,
[141]
France
[142][143]
and Norway
[144]
in June and Russia in July.
[145]
In August 2010, Austria
[146]
and
Poland
[147]
made it illegal and China announced it would be illegal as of 1 September 2010.
[27]
Mephedrone had been
reported to be used in Singapore in February 2010,
[148]
but it was made illegal in November 2010.
[149]
In December
2010, following the advice of the EMCDDA, mephedrone was made illegal throughout the EU, a move Switzerland also
made shortly afterwards.
[150][151]
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.
[151]
In Hungary, a government advisory body
recommended mephedrone should be made illegal in August 2010, which was followed, making it illegal in January
2011;
[152][153]
Spain followed in February 2011.
[154]
Mexico, by Decree,
[155]
outlawed mephedrone as a substance
"with low or no therapeutical use which pose a serious threat to public health"
[156]
in 2014.
In some countries, mephedrone is not specifically listed as illegal, but is controlled under legislation that makes
compounds illegal if they are analogs of drugs already listed. In Australia during 2010, it was not specifically listed as
prohibited,
[18]
but the Australian Federal Police stated it is an analogue to methcathinone and therefore illegal. In
February 2010, 22 men were arrested in connection with importing mephedrone.
[157]
By January 2011, every state in
Australia, other than Victoria, had listed it as a controlled drug.
[158]
In New Zealand, it is not included in the Misuse of
Drugs Act 1975,
[159]
but is illegal, as it is similar to controlled substances.
[160]
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.
[161]
Mephedrone is considered a controlled substance by Health Canada.
[162]
According to
the Canadian Medical Association, mephedrone is grouped with other amphetamines as Schedule I controlled
substances.
[163]
There have been several media reports of the Canadian police seizing mephedrone.
[164][165][166]
Mephedrone is also currently 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.
[167][168][169]
Several cities
and states, such as New York,
[170]
have passed legislation to specifically list mephedrone as illegal, but in most areas
it was legal, so long as it is not sold for human consumption, so retailers described it as 'bath salts'.
[169]
In September
2011, The DEA began using its emergency scheduling authority to temporarily control mephedrone. Except as
authorized by law, this action made possessing and selling mephedrone or the products that contain it illegal in the
USA for at least one year while the DEA and the United States Department of Health and Human Services conduct
further study.
[171]
Control of these compounds became permanent on 9 July 2012, via passage of the Synthetic Drug
Abuse Prevention Act of 2012.
[172]
See also[edit]
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External links[edit]