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MDMA

Systematic (IUPAC) name
(RS)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Clinical data
Pregnancy cat.	C[1]
Legal status	Prohibited (S9) (AU) Schedule III (CA) CD Lic (UK) Schedule I (US)
Routes	Oral, sublingual, insufflation, inhalation (vaporization), injection,[2] rectal
Pharmacokinetic data
Metabolism	Hepatic, CYP450 extensively involved, especially CYP2D6
Half-life	6–10 hours (though duration of effects is typically actually 3–5 hours)
Excretion	Renal
Identifiers
CAS number	42542-10-9 N
ATC code	N/A
PubChem	CID 1615
DrugBank	DB01454
ChemSpider	1556 Y
UNII	KE1SEN21RM Y
ChEBI	CHEBI:1391 Y
ChEMBL	CHEMBL43048 Y
Synonyms	(±)-1,3-benzodioxolyl-N-methyl-2-propanamine; (±)-3,4-methylenedioxy-N-methyl-α-methyl-2-phenethylamine; DL-3,4-methylenedioxy-N-methylamphetamine; methylenedioxymethamphetamine
Chemical data
Formula	C11H15NO2
Mol. mass	193.25 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3 Y Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N Y
N (what is this?)  (verify)

MDMA (3,4-methylenedioxy-N-methylamphetamine; methylenedioxymethamphetamine) is an entactogenic drug of the phenethylamine and amphetamine classes of drugs. In popular culture, MDMA has become widely known as "ecstasy", usually referring to its street pill form, although this term may also include the presence of possible adulterants. The terms "molly" (allegedly derived from "molecule") and "mandy" (a corruption of "MDMA") colloquially refer to MDMA in crystalline and/or powder form, usually implying purity.

MDMA can induce euphoria, a sense of intimacy with others, and diminished anxiety. Many studies, particularly in the fields of psychology and cognitive therapy, have suggested that MDMA has therapeutic benefits and facilitates therapy sessions in certain individuals, a practice for which it had formally been used in the past. Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer.^[3][4]

MDMA is criminalized in most countries, though some important civil society initiatives, such as the Global Commission on Drug Policy, are not concerned with putting a stop to it, but with educating the public about the drug,^[5] and its possession, manufacture, or sale may result in criminal prosecution, although some limited exceptions exist for scientific and medical research. For 2008 the UN estimated between 10–25 million people globally used ecstasy at least once in the past year. This was broadly similar to the number of cocaine, amphetamine and opiate users, but far fewer than the global number of cannabis users.^[6] It is taken in a variety of contexts far removed from its roots in psychotherapeutic settings and is commonly associated with dance parties (or "raves") and electronic dance music.^[7]

Regulatory authorities in several locations around the world have approved scientific studies administering MDMA to humans to examine its therapeutic potential and its effects.^[8]

Medical use[link]

There have long been suggestions that MDMA might be useful in psychotherapy, facilitating self-examination with reduced fear.^[9][10][11] Indeed, some therapists, including Leo Zeff, Claudio Naranjo, George Greer, Joseph Downing, and Philip Wolfson, used MDMA in their practices until it was made illegal. George Greer synthesized MDMA in the lab of Alexander Shulgin and administered it to about 80 of his clients over the course of the remaining years preceding MDMA's Schedule I placement in 1985. In a published summary of the effects,^[12] the authors reported patients felt improved in various, mild psychiatric disorders and experienced other personal benefits, especially improved intimate communication with their significant others. In a subsequent publication on the treatment method, the authors reported that one patient with severe pain from terminal cancer experienced lasting pain relief and improved quality of life.^[13]

Three neurobiological mechanisms for the therapeutic effects of MDMA have been suggested: "1) MDMA increases oxytocin levels, which may strengthen the therapeutic alliance; 2) MDMA increases ventromedial prefrontal activity and decreases amygdala activity, which may improve emotional regulation and decrease avoidance, and 3) MDMA increases norepinephrine (NE) release and circulating cortisol levels, which may facilitate emotional engagement and enhance extinction of learned fear associations."^[14]

The first phase-II double-blind randomized controlled clinical trial into the potential therapeutic benefits of using the drug as an augment to psychotherapy showed that most patients in the trial given psychotherapy treatment along with doses of MDMA experienced statistically significant reductions in the severity of their condition after two months, compared with a control group receiving psychotherapy and a placebo.^[15] The authors concludes "MDMA-assisted psychotherapy can be administered to posttraumatic stress disorder patients without evidence of harm, and it may be useful in patients refractory to other treatments."^[15]

The possible therapeutic potential of MDMA is being tested in several ongoing studies, some sponsored by the Multidisciplinary Association for Psychedelic Studies (MAPS). Studies in the U.S., Switzerland, and Israel are evaluating the efficacy of MDMA-assisted psychotherapy for treating those diagnosed with post-traumatic stress disorder (PTSD) or anxiety related to cancer.

Small doses of MDMA are used as an entheogen to enhance meditation by some Buddhist Monks.^[16]

Recreational use[link]

Tablets containing MDMA

MDMA capsules and pressed tablets

Prices are from cited sources, they may differ in reality.

The European Monitoring Centre for Drugs and Drug Addiction notes that, although there are some reports of tablets being sold for as little as €1, most countries in Europe now report typical retail prices in the range of €3 to €9 per tablet.^[17] The United Nations Office on Drugs and Crime claimed in its 2008 World Drug Report that typical U.S. retail prices are lower, costing 20 to 25 per tablet, or from 3 to 10 per tablet if bought in batches^[18] MDMA is expensive in Australia, costing A$20–A,0 per tablet, but in the Asian community it is A 0–30, depending on the size. In terms of purity data for Australian MDMA, the average is around 34%, ranging from less than 1% to about 85%. The majority of tablets contain 70–85 mg of MDMA. Most MDMA enters Australia from different markets, the Netherlands, the UK, Asia, and the U.S.^[19]

MDMA is occasionally known for being taken in conjunction with psychedelic drugs, such as LSD or psilocybin mushrooms, or even common drugs such as cannabis. As this practice has become more prevalent, most of the more common combinations have been given nicknames, such as "candy flipping", for MDMA combined with LSD, "MX Missile" (or "Hippy Flipping" in some circles) for MDMA with psilocybin, or "kitty flipping" for MDMA with ketamine.^[20] The term "flipping" may come from the subjective effects of using MDMA with a psychedelic in which the user may shift rapidly between a more lucid state and a more psychedelic state several times during the course of their experience. Many users use mentholated products while taking MDMA for its cooling sensation while experiencing the drug's effects. Examples include menthol cigarettes, Vick's Vapo Rub, NyQuil,^[21] and lozenges.

Subjective effects[link]

The primary effects attributable to MDMA consumption are predictable and fairly consistent among users. In general, users report feeling effects within 45 minutes to an hour of consumption, hitting a peak at approximately 2 1/2 to 3 hours, reaching a plateau that lasts about 2–3 hours, followed by a comedown of a few hours. After the drug has run its course, many users report feeling fatigue; other, more long-lasting effects such as diminished mental capacity, permanent sensitivity to light, paranoia, and impaired cognitive ability have also been reported.

The most common effects reported by users include:^[22]

• A general and subjective alteration in consciousness
• A strong sense of inner peace and self-acceptance
• Diminished aggression, hostility, and jealousy
• Diminished fear, anxiety, and insecurity
• Extreme mood lift with accompanying euphoria
• Feelings of empathy, compassion, and forgiveness toward others
• Feelings of intimacy and even love for others
• Improved self-confidence
• The ability to discuss normally anxiety-provoking topics with marked ease
• An intensification of all of the bodily senses (hearing, touch, smell, vision, taste)
• Substantial enhancement of the appreciation of music quality
• Mild psychedelia, consisting of mental imagery and auditory and visual distortions
• Stimulation, arousal, and hyperactivity (e.g., many users get an "uncontrollable urge to dance" while under the influence)
• Increased energy and endurance
• Increased alertness, awareness, and wakefulness
• Increased desire, drive, and motivation
• Analgesia or decreased pain sensitivity

Adverse effects[link]

In January 2001, an overview of the subjective side-effects of MDMA was published by Liechti, Gamma, and Vollenweider in the journal Psychopharmacology. Their paper was based on clinical research conducted over several years involving 74 healthy volunteers. The researchers found that there were a number of common side-effects and that many of the effects seemed to occur in different amounts based on gender. The top side-effects reported were difficulty concentrating, jaw clenching, grinding of the teeth during sleep, lack of appetite, and dry mouth/thirst (all occurring in more than 50% of the 74 volunteers). Liechti, et al. also measured some of the test subjects for blood pressure, heart rate, and body temperature against a placebo control but no statistically significant changes were seen.^[23][24]

A 2011 study carried out by Harvard Medical School and published in the journal Addiction found no signs of cognitive impairment due to ecstasy use, and that it did not decrease mental ability. The report also raised concerns that previous methods used to conduct that research on ecstasy had been flawed, and the experiments overstated the cognitive differences between ecstasy users and nonusers.^[25]

However, a study from John Hopkins Medical School in 2008 found a slight, but significant correlation of cognitive deficiency in MDMA users, but admitted that this data may be confounded by other illicit drug use. The significant finding of the article was the serotonergic neurotoxicity in stacked doses and a lasting decrease in serotonin reuptake (SERT) binding. In rats, high doses and in high temperatures, serotonergic neurotoxicity is limited and dopaminergic neurotoxicity occurs. However, rats may not be a generalizable model for human neurotoxicity studies. ^[26]

After-effects[link]

Effects reported by some users once the acute effects of MDMA have worn off include:

• Psychological
  • Anxiety and paranoia^[27]
  • Depression^{[27][28][29][30][31][32]}
  • Irritability^[30]
  • Fatigue^[31][32]
  • Impaired attention, focus, and concentration,^[29] as well as drive and motivation (due to depleted serotonin levels)^[28]
  • Residual feelings of empathy, emotional sensitivity, and a sense of closeness to others (afterglow)

• Physiological
  • Dizziness, lightheadedness, or vertigo^[32]
  • Loss of appetite^[28][29]
  • Gastrointestinal disturbances, such as diarrhea or constipation^[27]
  • Insomnia^[27][28][29]
  • Aches and pains, usually from excessive physical activity (e.g., dancing)^[28][29][31]
  • Exhaustion^[30][32]
  • Jaw soreness, from bruxism^[32][33][34]

A slang term given to the depressive period following MDMA consumption is Tuesday Blues (or "Suicide Tuesday"), referring to the low mood that can be experienced midweek by depleted serotonin levels following weekend MDMA use. Some users report that consuming 5-HTP, L-Tryptophan and vitamins the day after use can reduce the depressive effect by replenishing serotonin levels (magnesium supplements are also used prior to or during use).^[35]

Overdose[link]

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Upon overdose, the potentially serious serotonin syndrome, stimulant psychosis, and/or hypertensive crisis, among other dangerous adverse reactions, may come to prominence, the symptoms of which can include the following:

• Psychological
  • Disorientation and/or confusion
  • Anxiety, paranoia, and/or panic attacks
  • Hypervigilance or increased sensitivity to perceptual stimuli, accompanied by significantly increased threat detection
  • Hypomania or full-blown mania
  • Derealization and/or depersonalization
  • Hallucinations and/or delusions^[36]
  • Thought disorder or disorganized thinking
  • Cognitive and memory impairment potentially to the point of retrograde or anterograde amnesia^[37]
  • Acute delirium