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MDMA is a synthetic substance commonly known as ecstasy, although the latter term has now been generalised to cover a wide range of other substances. Originally developed in 1912 by the Merck chemical company, it was never marketed as such. Although proposed as an aid to psychiatric counselling, therapeutic use is extremely limited. Illicit MDMA is normally seen as tablets, many of which are manufactured in Europe. It acts as a central nervous system (CNS) stimulant and has a weak hallucinogenic property more accurately described as increased sensory awareness. MDMA is under international control.
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MDMA Chemistry
Molecular structure
Molecular formula: C11H15NO2
Molecular weight: 193.2
MDMA is an abbreviation for methylenedioxy-methylamphetamine. The formal (IUPAC) name is N-methyl-1-(3,4-methylenedioxyphenyl)propan-2-amine, but MDMA (CAS-42542-10-09) is commonly known as 3,4-methylenedioxymethamphetamine or methylenedioxy-methylamfetamine. Other chemical names include N,α-dimethyl-3,4-methylenedioxyphenethylamine or, less usually, N-methyl-1-(1,3-benzodioxol-5-yl)-2-propanamine. is a member of the larger group of ring-substituted phenethylamines. As with other phenethylamines, and like its close relative methamphetamine, MDMA also exists in two enantiomeric forms (R and S).
 Physical form
The most common salt is the hydrochloride (CAS-64057-70-1) which occurs as a white or off-white powder or as crystals soluble in water. The phosphate salt is also encountered. Illicit products are seen principally as white tablets with a characteristic impression (logo), less commonly as white powders or capsules. MDMA base is a colourless oil insoluble in water.
 Pharmacology
Whereas phenethylamines without ring substitution usually behave as stimulants, ring substitution leads to a modification in the pharmacological properties. Ingestion of this drugs causes euphoria, increased sensory awareness and mild central stimulation. It is less hallucinogenic than its lower homologue, methylenedioxyamphetamine (MDA). The terms empathogenic and entactogenic have been coined to describe the socialising effects of this drugs. Following ingestion, most of the dose of this drugs is excreted in the urine unchanged. Major metabolites are 3,4-methylenedioxyamphetamine (MDA) and O-demethylated compounds. Following a dose of 75 mg, the maximum plasma concentration of around 0.13 mg/L is reached within two hours. The plasma half-life is 6–7 hours.
In animals, this drugs causes neurotoxicity, as evidenced by anatomical changes in axon structure and a persisting reduction in brain serotonin levels. The significance of these findings to human users is still unclear, although cognitive impairment is associated with MDMA use. Some of the pharmacodynamic and toxic effects of this drugs vary, depending on which enantiomer is used. However, almost all illicit of this drugs exists as a racemic mixture. Fatalities following a dose of 300 mg have been noted, but toxicity depends on many factors, including individual susceptibility and the circumstances in which this drug is used.
Synthesis and precursors
There are four principal precursors which can be used in the manufacture of MDMA and related drugs: safrole, isosafrole, piperonal and 3,4-methylenedioxyphenyl-2-propanone (PMK). Safrole is the key starting material in so far as the other three can be synthesised from it. In the original Merck patent of 1914, safrole was reacted with hydrobromic acid to form bromosafrole, which was converted to this drugs using methylamine. Many illicit syntheses start with PMK and use either the Leuckart route or various reductive aminations including the aluminium foil method. All of these methods produce racemic of this drug. The four precursors noted above are listed in Table I of the United Nations 1988 Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. The corresponding EU legislation is set out in Council Regulation (EEC) No 3677/90 (as later amended), which governs trade between the EU and third countries.
Mode of use
MDMA in tablet form is almost always used orally (ingested), but the powdered form could also be snorted, inhaled or injected, although the latter route is rarely observed in the context of recreational ecstasy use.
Other names
As some of the above names suggest,this drug is a derivative of amphetamine and a member of the phenethylamine family. A number of homologous compounds with broadly similar effects, e.g. MDA (methylenedioxyamphetamine), MDEA (methylenedioxyethylamphetamine) and MBDB (N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine), have appeared, but have proved less popular. These and many other more distant relatives of MDMA have now been subsumed by the generic term ecstasy. Street terms for MDMA include Adam and XTC, but often reflect the imprinted logo, e.g. Mitsubishis, Love Doves and many others.
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