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Methylenedioxymethcathinone2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one
IUPAC name:
CAS number
Racemic Methylone: 186028-79-5; (S)-Methylone: 191916-41-3
ATC code
?
Chemical formula C11H13NO3
Molecular weight 207.23
Bioavailability ?
Metabolism ?
Elimination half life ?
Excretion ?
Pregnancy category ?
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Methylone is a designer drug that is a methcathinone analogue of MDMA (Ecstasy). It is also known as bk-MDMA, or MDMC. It is more properly known as methylenedioxymethcathinone. MDMC is related to methcathinone just as MDMA is related to methamphetamine, and as MDA is related to amphetamine.

Methylone is an empathogen and a mild stimulant, producing effects similar to yet less intense than MDMA. It is not explicitly scheduled in the United States, but possession may still result in prosecution under the Federal Analog Act as an MDMA analogue.

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 (herbal) 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. 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 MDMC) is the benzylic ketone analogue of 3,4-methylenedioxymethamphetamine (MDMA): it contains an additional oxygen atom at the benzylic position of the molecule ( Figure 1) (Cozzi et al., 1999). 3,4-Methylenedioxymethcathinone was first synthesized by Alexander Shulgin. Because of the similarity of effects between methamphetamine and its benzylic ketone methcathinone, he examined whether there was a comparable connection between MDMA and its benzylic analogue. He called the new substance methylone (Cognitiveliberty.org).

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 (Dal Cason et al., 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 (Cozzi et al., 1999).

In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs of abuse are not completely identical (Erowid.org). Shulgin wrote about the effects of this drug: ‘methylone has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA’ (Cognitiveliberty.org).

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 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.

See also


External links


Alkaloids | Entactogens and Empathogens

Methylone | Methylone

 

This article is licensed under the GNU Free Documentation License. It uses material from the "Methylenedioxymethcathinone".

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