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Mephedrone

Mephedrone (4-methylmethcathinone, 4-MMC) is a research chemical drug of the beta-ketone family, first reported in Israel during the mid-2000's. It is a substituted cathinone and structurally related to both methcathinone and methamphetamine. It is usually taken orally or insufflated with a typical active oral dose ranging from 100 - 250mg. It has euphoric and stimulant properties. A boom in the popularity of this chemical as a recreational drug across the UK, Republic of Ireland and mainland Europe during 2009 attracted substantial media and political interest, and in many nations resulted in possession and distribution of mephedrone being criminalized.

Contents




[top]Introduction


Mephedrone (1-(4-methylphenyl)-2-methylaminopropan-1-one) is a phenethylamine, structurally comparable to cathinone ((S)-2-amino-1-phenyl-1-propanone) and methylone ((±) 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one). The name "mephedrone" was logical (methyl-ephedrone, ephedrone being a name for methcathinone) and probably not just coined to resemble "methylone". While MCat is a name for MethCathinone, the media often mislabels Mephedrone as such. Very little is known about the pharmacology or toxicity of mephedrone, as no studies have been published that establish such characteristics. We’re currently awaiting access to a recently-conducted study that may elucidate such properties.


[top]Using Mephedrone

The compound appears to typically be used analogously to other recreational stimulants in a wide variety of settings - from large social groups to isolation. Though reports exist for a number of different methods of administration, mephedrone appears to be most commonly ingested orally and intranasally. Some individuals consider the compound to be strictly stimulant in effect, while many observe pseudo-psychedelic visual and auditory distortion.

[top]Routes of administration

[top]Oral

Taking a fixed amount orally can help limit the common urge to redose and prevent excess use.
Oral doses can be taken in a variety of ways; the easiest being either mixed with water, or wrapped in a rizzla paper and swallowed.
First time doses should range between 100mg and 150mg and users are advised to try to avoid eating for a few hours before administration as this can dampen the effects.
"250mg is a good oral dose, but the tail end effects will last a lot longer and sleep will be difficult."
A dose of 150mg-250mg is the average, giving a duration of around 2 hours.
Oral doses last longer but also take longer at onset; it is important not to redose early even if users feel it has not affected them. When using a gel capsule, onset of effects can take up to 45 minutes to be felt.
Side-effects from oral dosages can be nausea, stomach cramps and vomiting (especially in larger 250mg+ dosages).

[top]Insufflation

Insufflating mephedrone can dramatically increase the urge to redose, therefore it is important users set out a maximum amount for the night and stick to it.
First time doses should range between 25-75mg and can take up to 15 minutes to start working. Crushing/chopping the powder as finely as possible and placing a straw well inside the nostril before snorting can greatly increase the effects.
Many people consider snorting to be a dangerous method of administration; especially for drugs which are active when taken orally, due to increased risk of nose damage. Side-effects from snorting seem to be worse when compared to taking the same total dose orally - it's "harsh" on the body.
It's recommended to not share straws/notes with other people as this can increase the risk of infection. This is particularly important with mephedrone, as nose bleeds and nasal sores are a common complaint compared with many other drugs taken via this route.

[top]Intravenous

Administering intravenous mephedrone is extremely dangerous, and highly enhances the potential for dangerous side-effects. Both sample purity and handling are important factors to consider. Additionally, the drug is observed to be quite addictive by individuals favoring oral and intranasal routes; the addictive components of the effects of the drug are likely to be quite higher, and may compel users to pursue dangerously high levels.
Doses for IV administration of 4-MMC range widely, and have been observed to range from 40mg to approximately 500mg.

[top]Rectal

Rectal administration, otherwise referred to as 'plugging', is characterized by a faster onset relative to oral dosing, requires lower doses, and has been suggested to be characterized as having a more rapid termination of activity relative to oral doses. A dose of 100 mg has been observed to last approximately 20 minutes, but this is quite likely variable between individuals.

Two general methods include the use of a syringe (needle removed) with 200 mg in fewer than 10 mL of water (approaching 5 mL) inserted while lying prone, allowing the solution to absorb over 3-5 min - as well as the use of gelatin caps as a vehicle for the compound to be inserted.

Rectal (plugging) administration of mephedrone
Mephedrone capsule...inserted anally?

[top]Effects of Mephedrone

The primary effects tend to reflect those of sympathomimetic stimulants such as amphetamines, cocaine, or MDMA. There appears to be a distinct euphoria and sociability inspired by the compound, as well as a strong urge to ingest large quantities subsequent to initial administration. Recreational doses induce transient anorexia, and appear to affect cardiac activity in typical CNS stimulant patterns.

The after-effects, or 'come-down' associated with mephedrone - occurring immediately subsequent to the duration of effects of the compound - is highly variable, but commonly consists of overall behavioral sedation and a desire to ingest more. There indeed appears to be an effect upon mood that reflects those of other recreational psychomotor stimulants such as cocaine or methamphetamine; individuals report 'come-downs' along a range of severity, from mild depression and languid disposition to intense depression. There is discussion of a transient suppression of immune system function, as many observe short periods of illness subsequent to ingestions of over 500 mg.

Side-effects are similarly variable, and include reactions as mild as persistently raised heart rate to severe - such as seizures and a bluing, or apparent bruising, of extremities. Other side-effects include difficulties with memory, persistently low body-temperature, anhedonia, and chest pain.

Mephedrone Experiences & Side-Effects Database

Very grumpy when mephedrone wears off?

Mephedrone comedown or just from sleep deprivation?

Cross Tolerance Mephedrone, Methylone and Ecstasy

[top]Combinations with Mephedrone


While there are reports of combining mephedrone with other compounds, it is important to maintain that none of this information suggests that any of the following combinations are safe.

There are reports of combining mephedrone with the following compounds to no significant side-effect:
Metefepramone
Pthalimidoprodiophenone
Venlafaxine
Cannabis
Metoprolol
Hydrochlorothiazide
Simvastatin
Buproprion
Depatoke
Lisinopril
Niaspan
Opium
Propanolol
Citalopram
Amitriptyline

There are reports of combining mephedrone with the following compounds, observed to generate deleterious or dangerous side-effects:
Imipramine
Amphetamine
Synthetic Cannabinoids

Mephedrone and pharmaceutical combination reports
MDMA & Mephedrone


[top]Pharmacology and Pharmacokinetics of Mephedrone

Pharmacology: 4-Methylmethcathinone is sympathomimetic stimulant. From proposed SAR modelling, 4-methylmethcathinone is expected to have similar pharmacological properties to methcathinone, but with increased activity on the serotonin neurotransmitter systems. Methcathinone is suggested as being more potent than its parent cathinone, and methamphetamine [1].

Methcathinone is a drug with a high abuse potential, with prolonged, high dosages known to cause psychosis and withdrawal tremors. Methcathinone is regarded as being similar in profile to methamphetamine in relation to neurotoxicity, with marked decreases in DA levels noted among abstinent users. While generally below levels associated with Parkinsons Disease, this is considered to be demonstrative of permanent, or semi-permanent neurological damage [2]. The compound is considered by some to be more potent than cathinone and methamphetamine. High doses of mephedrone have consistently generated convulsions, addictive tendencies, and symptoms of withdrawal.

Ethcathinone is closely related to mephedrone and causes many side effects: Stroke, Psychosis, Pulmonary hypertension, Tachycardia, hypertension, arrhythmia, chest pain, Bone marrow depression, agranulocytosis, leukopenia, Rash, hives, alopecia, ecchymosis, impotence, dizziness, anxiety, headache, mental depression, seizures, Nausea/vomiting, constipation, abdominal cramps, diarrhea. (From drug info thread)

[top]Enzyme Inhibition

According to M.R. Meyer, F.T. Peters, H.H. Maurer [3] a number of metabolites are possible, however the n-demethyl metabolite of Mephedrone will be 4-Methylcathinone (compound number 18 in table 1). This metabolite appears to be nearly inactive as a Monoamine Oxydase Inhibitor (table1,- [4]).


On further metabolism of this metabolite one of the possible metabolites is 4-Methylnorephedrine (compound number 31 in table 3 [4]), caused by the reduction of the Keto. This metabolite has almost the same level of MAO-A inhibition as that of Amphetamine (table 1).



Amphetamine's IC50 is 11, while the 4-Methylnorephedrine metabolite's is 12.

It is currently unclear as to the significance of this in normal recreational doses.

[top]Mephedrone receptor binding

Awaiting cellular/molecular studies.

[top]Tolerance

Mephedrone exhibits a strong desensitization effect upon repeated dosing, reminiscent of other traditionally addictive psychomotor stimulants. This compound in particular, however, appears to compel users to ingest higher subsequent doses as well as ‘booster-doses’. Physiological desensitization appears to be associated with long-term complications.

[top]Interactions

No conclusive studies have been preformed. Discussion of drug combinations.


[top]The health risks of Mephedrone

[top]Cardiovascular

Mephedrone has been observed to cause cardiovascular abnormalities when administered at doses above 200mg, though this isn’t ubiquitous. These abnormalities include heart palpitations, vasoconstrictive sensations, numbing as well as ‘bluing’ of limbs reminiscent of posturally dependent bruising.

Your BPM on Mephedrone

[top]Overdose

Mephedrone presents a very real danger of overdose; the most commonly-reported symptoms of overdose include: bluing limbs at doses above 300mg, numbing limbs at doses above 500mg, paranoia & anxiety at doses above 200mg, tinnitus at doses above 250mg, buccal blisters from insufflated doses, and chest pain at doses above 500mg. However, it’s been noted that overdose symptoms aren’t expressed by many individuals at much higher doses.

Mephedrone Side-Effects Database

Images of bluing
Meph_Knees_4_.jpg


Heart & Breathing Problems
How to reduce side-effects of mephedrone

[top]Cytotoxicity

Awaiting studies that may elucidate such characteristics

[top]Carcinogenic/Mutagenic Properties

Awaiting studies to further elucidate this dynamic


[top]Producing Mephedrone



[top]Chemical Characteristics



IUPAC: 1-(4-methylphenyl)-2-methylaminopropan-1-one
CAS#: Awaiting information
Formula: C11H15NO
Mol. Weight: 177.242
Solubility: Awaiting information
Stability: stability of the mephedrone molecule

[top]Marquis Reagent

The Marquis reagent is a test to facilitate identification of alkaloids, composed of formaldehyde and sulfuric acid. Compounds will produce signature colors characterizing their reactions.
Taken by Viscis:

[top]Mecke & Mandelin

The Mecke reagent consists of selenous acid in sulfuric acid, and purportedly offers enhanced capabilities at detecting MDMA. The Mandelin reagent is a 1% solution of ammonium vanadate in sulfuric acid, and similar to both the Marquis and Mecke, different compounds will generate different color reactions.

[top]Simons & Robadope


The Simons reagent is sodium nitroprusside in 50 mL distilled water, with 2 mL acetaldehyde added.

[top]Appearance

Mephedrone samples have been observed to vary in physical appearance.



[top]Legal status of Mephedrone

[top]United Kingdom

Mephedrone is a Class B controlled substance, effective 16th April 2010. This came into effect due to an amendment to the Misuse of Drugs Act 1971, which controls a number of synthetic derivatives of cathinone. The penalties for possession and supply of mephedrone are therefore in line with other class B controlled substances. The maximum penalty in a Crown prosecution for possession and supply of mephedrone are 5 years and 14 years imprisonment respectively (plus an unlimited fine in both cases). The maximum penalty for a Magistrates prosecution is 3 months imprisonment plus a fine up to £2,500 for possession of mephedrone, and 6 months imprisonment plus a fine up to £5,000 for supply of mephedrone. Any proceeds from the illicit sale of mephedrone may also be seized under the Proceeds of Crime Act 2002.

Which drugs will likely be outlawed by the cathinone ban?
Call for ban on 'legal high' drug: Mephedrone
UK Mephedrone vendor arrested & charged with harm to public health.

[top]USA

Remains unscheduled

[top]EU

[top]Ireland

Purported to remain legal, but there is discussion that this isn't to be assumed.

[top]Denmark

[top]Romania

While some claim the compound remains legal, methcathinone is explicitly prohibited - and so the compound may potentially be considered illegal.

Mephedrone legality in Romania

[top]Israel

Banned in December 2007

[top]Sweden

Banned on December 15, 2008, classified as a narcotic on June 15, 2009.

[top]Norway

Illegal under an act similar to the Analog Act

[top]Germany

From 22nd January 2010 it will be a controlled substance

Germany Bans Mephedrone

[top]Finland

Illegal to manufacture, import, possess, sell, or transfer without prescriptions.

[top]Poland

Remains legal (due to be banned soon, it's inclusion in an amendment to a narcotics bill is confirmed - June 2010).

[top]Australia

Though not explicitly identified, it's likely to be considered an illegal analogue of methcathinone.

Australia Mephedrone News Thread

[top]Related News Threads



[top]Mephedrone History

4-methylmethcathinone is structurally related to other beta-ketone compounds, and differs from methcathinone by an additional methyl group on the phenyl ring.

Posted by Benga, 05-10-2009, 05:00: History of bath salts
Quote:
A new Israeli company came up, and pretty much singlehandedly opened the way by introducing cathinone derivatives and other RC's in commercially marketed legal highs.
RC's, real R.C.'s in pill form, some of them quite obscure / untested, most cathinone derivatives this coming after the hagigat trend in which had become quite popular in Israel, especially in the rave/clubbing world.

After a little suspense, the mystery ingredients were soon revealed following an analysis partly funded by a new-zealand piperazine pill vendor, and their leading product identified as mephedrone, 4-MMC. The pills were first sold from Israel directly, then banned in Israel, then quickly distributed by other outlets in the U.K. and Europe. A new line was created after the Israeli ban, but never got as popular as the mephedrone pills.

Mephedrone sales, however, actually expanded, stimulating Chinese production, first in the R.C. market across Europe, with new R.C. vendors popping, up, some almost exclusively focusing business on mephedrone / betaketone / novel stimulant sales.

these stores were increasingly crossing the boundary between "proper" R.C. outlets, which traditionnally also offered psychedelic R.C.'s and rare chemicals over to the legal high market, and the legal high / party pill world.
new hybrid shops appeared, in the U.K. and Ireland specifically, specialised in betaketone and stimulant R.C.'s, mephedrone, methylone and a few others.

Then new legal high mephedrone pill lines came out, sold by head/smart shops.
Fueled by the headshop associated-legal high forum buzz, ear to mouth and either increasingly specialised R.C. outlet or legal high outlets sales, openly identified and packaged as such (snuffs, pills rather than pured powder); mephedrone use expanded, and still is. It then started to hit the media, with an increasing buzz, and governmental attention.

Increasingly, alarming reports started coming in, with vasoconstriction and potentially mephedrone related deaths- yet such negative reports are actually quite ancient, actually starting with the original Israeli pill range.
More recently some of these outlets have remarketed their products as plant feeders / hormones for more "discretion".

The (Irish?) bathsalts represent the last evolution of this movement, with the possible introduction of another untested R.C., (as was mephedrone in the first place). This new R.C. is thought to be "local synth" rather than a import from China, and particularly potent, long lasting and inducing severe near psychotic episodes in quite a few users...


[top]More Mephedrone Sections

Mephedrone Experiences Post & read experiences with mephedrone.

Mephedrone File Archive Upload and read research & articles on mephedrone.

Mephedrone Forum Post and read about mephedrone.

Mephedrone Image Gallery Post and view pictures of mephedrone.

Addiction Calculator Do this small test to calculate your dependency.


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[top]References

  1. ^ Martin D Schechter; Drug-Drug Discrimination: Stimulus Properties of Drugs of Abuse Upon a Serotonergic-Dopaminergic Continuum; Pharmacology Biochemistry and Behavior Volume 56, Issue 1, January 1997, Pages 89-96
  2. ^ Una D. McCann, Dean F. Wong, Fuji Yokoi, Victor Villemagne, Robert F. Dannals, and George A. Ricaurte; Reduced Striatal Dopamine Transporter Density in Abstinent Methamphetamine and Methcathinone Users: Evidence from Positron Emission Tomography Studies with [11C]WIN-35,428; The Journal of Neuroscience, October 15, 1998, 120):8417–8422.
  3. ^ Meyer M.R., Peters F.T., Maurer H.H.: Metabolism of the new designer drug mephedrone and toxicological detection of the beta keto designer drugs mephedrone, butylone and methylone in urine Annales De Toxicologie Analytique, Volume 21, Number Suppl. 1, 2009, The International Association of Forensic Toxicologists - TIAFT - 47th International Meeting, S1 22-S1 23
  4. ^ a b Mauricio Osorio-Olivares, Marcos Caroli Rezende, Silvia Sepulveda-Boza, Bruce K. Casselsc and Angelica Fierro: MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the b-position Bioorganic & Medicinal Chemistry, 12 (2004), 4055–4066


Created by Gradient, 03-01-2010 at 03:50
Last edited by Synesthesiac, 30-11-2011 at 20:35
Last comment by Phenoxide on 10-04-2012 at 01:41
57 Comments, 192,668 Views

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