Methylenedioxymethcathinone

{| id="synChemInfoBox" class="wikitable" width="300px" style="float: right; margin: 0 0 .5em .5em;"
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bgcolor="#ffffff" align="center" colspan="2"
"Methylenedioxymethcathinone"
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align="center" colspan="2" | IUPAC name:
"2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one"
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CAS number Racemic Methylone: 186028-79-5; (S)-Methylone: 191916-41-3
ATC code ?
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bgcolor="#eeeeee" | Chemical formula
C₁₁H₁₃NO₃
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bgcolor="#eeeeee" | Molecular weight
207.23
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bgcolor="#eeeeee" | Elimination half life
?
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bgcolor="#eeeeee" | Legal status
Unscheduled (USA)
Unscheduled (UK)
Unscheduled (CA)

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bgcolor="#eeeeee" | Delivery
150-200mg orally
50-150mg intravenously
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colspan="2"|Recreational uses: :*euphoria:*bonding
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colspan="2"|Other uses: :*Marriage counseling:*Anxiety:*PTSD:*End of Life Care
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colspan="2"|Contraindications: :*Not for use in combination with stimulants (amphetamines, large doses of caffeine, etc). :*Not for use in combination with diuretics (alcohol). :*Not for use in individuals with high blood pressure, hypertension, or blood clotting disorders. :*Not for use in individuals who have displayed allergies to amphetamine drugs. :*Must never be used in combination with MAOI (Monoamine Oxidase Inhibitor) drugs.
-!colspan="2"|Side effects:
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colspan="2"|"Endocrine:" :*hyponatremia
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colspan="2"|"Eye:" :*mydriasis
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colspan="2"|"Psychological:" :*euphoria:*strong sense of empathy:*serotonin deficiency
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colspan="2"|"Skin:" :*sweaty palms:*heavy sweating
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colspan="2"|"Miscellaneous:" :*restlessness:*chattering teeth
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Methylone, or properly 3,4-methylenedioxymethcathinone, is a beta-ketone analogue of MDMA. Also known as bk-MDMA, M1, or MDMCat, the abbreviation MDMC is not used as this designation was already given to another chemical by Alexander Shulgin.

In spite of some substantial pharmacokinetic differences (its dopaminergic activity is far more pronounced relative to its serotonergic activity), methylone is an empathogen-like drug and a mild stimulant, producing effects similar to, yet less intense than MDMA. Fact|date=August 2008

Explosion

At the end of 2004, a new designer drug called ‘Explosion’ appeared in the Netherlands. This new drug is sold as a liquid via the internet and in Dutch ‘smartshops’, stores selling non-scheduled psychoactive substances. The product is advertised as a ‘room odorizer’ and is sold in plastic tubes containing 5 ml of liquid. The tubes cost between €10 and €15 ($13–$20) and do not present any information about the composition of Explosion; they contain only a label saying ‘Room odorizer Vanilla. Do not ingest’ and ‘Keep away from children. Never use more than one bottle’. In spite of this label, users mention that they ingest the liquid to reach the intended psychoactive effect.Fact|date=February 2007 The text was probably put onto the label to circumvent Dutch regulations for illicit drugs and psychoactive substances.

Analyses of Explosion have demonstrated that the main ingredient of the liquid is the compound methylone (3,4-methylenedioxymethcathinone or 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one). 3,4-Methylenedioxymethcathinone (MDMCat or methylone) is the β-ketone analogue of 3,4-methylenedioxymethamphetamine (MDMA): it contains an additional oxygen atom at the beta position (in phenethylamines, the benzylic carbon) of the molecule (Figure 1). [NV Cozzi, MK Sievert, AT Shulgin, P Jacob III, AE Ruoho. Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines. "Eur. J. Pharmacol., 381", 63-69 (1999)] 3,4-Methylenedioxymethcathinone was first synthesized by Alexander Shulgin. Because of the similarity of effects between methamphetamine and its β-ketone methcathinone, he examined whether there was a comparable connection between MDMA and its β-ketone analogue. He called the new substance methylone.cite web |url=http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm |title=Cathinone | Ask Dr. Shulgin Online |format= |work= |accessdate=]

MDMA resemblance

Methylone resembles MDMA in its behavioural profile, as methylone substitutes for MDMA in rats trained to discriminate MDMA from saline. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline. [TA Dal Cason, R Young, RA Glennon. Cathinone: an investigationof several N-alkyl and methylenedioxy-substituted analogs."Pharmacol. Biochem. Behav. 58", 1109–1116 (1997)] Further, also in common with MDMA, methylone acts on monoaminergic systems. In vitro, methylone is threefold less potent than MDMA at inhibiting platelet serotonin accumulation and as potent as MDMA in its inhibiting effects on the dopamine and noradrenaline transporters. [NV Cozzi, MK Sievert, AT Shulgin, P Jacob III, AE Ruoho. Methcathinone and 2 methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters. "Soc. Neurosci. Abs., 24", 341.8 (1998)] [NV Cozzi, AT Shulgin, AE Ruoho. Methcathinone (MCAT) and 2-methylamino-1-(3,4 methylenedioxyphenyl)propan-1-one (MDMCAT) inhibit [³H] serotonin uptake into human platelets. "Amer. Chem. Soc. Div. Med. Chem. Abs., 215", 152 (1998)] [NV Cozzi, MK Sievert, AT Shulgin, P Jacob III, AE Ruoho. Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines. "Eur. J. Pharmacol., 381", 63-69 (1999)]

In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin wrote of the former:

Legal Status

In the Netherlands, methylone is not yet scheduled as a drug of abuse, but is considered to be a psychoactive medicine. Because methylone is not registered officially, as such, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group (CAM) to gather information about this substance, resulting possibly in an official risk assessment (van Amsterdam et al., 2004). Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug.

Methylone is not explicitly scheduled in the United States, but possession may still result in prosecution under the Federal Analog Act as an MDMA analogue. In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an "amphetamine analogue" in the Misuse of Drugs Act, it is considered to be "substantially similar" to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug.

Methylone is currently not specifically mentioned in UK law as the beta-ketone is not covered under the Misuse of Phenethylamines Law.

Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an Ecstasy substitute, under the brand name Ease. The product was withdrawn after legal disputes with the government.

Metabolites

The two major metabolic pathways in humans and rats are N-demethylation to methylenedioxycathinone (). When 5mg/kg of methylone HCl was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreated unchanged). [ [http://taylorandfrancis.metapress.com/link.asp?id=j777t92213l50m70 Xenobioica.] HT Kamata, N Shima, K Zaitsu, T Kamata, A Miki, M Nishikawa, M Katagi, H Tsuchihashi. (2006). Metabolism of methylone in humans and rats. Volume 36, Number 8 / August 2006.]

Combination with MBDB

MDMA has both serotonergic and dopaminergic actions. Methylone does as well, but the dopaminergic activity is much more pronounced. MBDB is another closely related chemical, but its activity is mostly serotonergic. Some people have interpreted this situation as meaning that methylone and MBDB are "split halves" of the effects of MDMA, and have taken the two chemicals together in an attempt to recreate the pharmacology of MDMA. Whether or not the pharmacology of this mixture is comparable to MDMA is unknown, as is the safety of such mixtures.

Naming problem

While Shulgin assigned the name Methylone to this chemical, and that name has become the standard nomenclature, it is a problematic name. The problem is that Methylone is a trademarked brand name for an injectible form of methylprednisolone, a corticosteroid hormone used to treat arthritis and severe allergic reactions. Aside from context, they can be distinguished by the fact that the name will always be capitalized when referring to the prescription drug.

References

ee also

* Methcathinone
* Cathinone
* MDMA
* MBDB
* Phenethylamine

External links

* [http://www.erowid.org/chemicals/methylone/methylone.shtml Erowid Methylone Vault]
* [http://www.erowid.org/psychoactives/chemistry/chemistry_compare.php?lm=methylone_2d&rm=mdma_2d Difference between Methylone and MDMA - 2d molecules]