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MDMA, some times referred to by its most common name 'Ecstasy' or 'Molly', is an entactogen, stimulant, and recreation drug. It was first proposed as a treatment to be used in psychotherapy. It has recently been shown to be safe in doses from 50 to 75mg, but has also been shown to cause neurotoxic effects in high doses. It is one of the most popular recreational substances used by thousands of people each year.
MDMA is undoubtedly one of the most famous recreational drugs of all time. It is the poster child of the class of substances called entactogens (from the Latin tactus meaning "touch", the Greek en meaning "in" and gen meaning "produce"; "producing a touch within") or empathogens (from the Greek en meaning "in", pathos meaning "feeling" or "emotion", and gen meaning "produce"; "producing an emotion within"), and, hence its name, is known for its ability to make the user empathize with others. It also can produce a characteristic euphoria to which few other drugs can compare.
MDMA is used by millions for a host of reasons. Some use it purely for fun, as MDMA produces intense euphoria, music appreciation, increased pleasure, openness, etc. (among a host of other effects which can be seen in the EFFECTS SECTION). Others use it for spiritual reasons; MDMA has the ability to induce a profound sense of well-being that can continue after the experience is over, as well as the ability to diminish insecurities, soften the ego, and induce a feeling of acceptance and/or belonging. It has the potential to produce life-changing experiences. In addition, its ability to diminish fear and anxiety, induce forgiveness, etc. make it an excellent candidate in a therapeutic setting (hence the outrage in the psychiatric community when it was outlawed)--whether that therapy be in a clinical setting or not.
MDMA can be administered orally, sublingually, intravenously, rectally, or can be insufflated. It is inadvisable to attempt IV administration if the product is bought on the street, i.e. the user does not know exactly what might be present in the pill or the powder. The other methods are much more safe aside from insufflating which is incredibly painful as MDMA. In addition, snorting anything (especially unknown substances) causes damage to the nasal lining if done frequently.
MDMA bioavailability in humans has not been concluded. It is known that when taken orally, MDMA's pharmacokinetics are non-linear. This is related to the dose-response curve--small increases in dose induce disproportionately higher plasma concentrations.
120 mg of MDMA is a dose which will induce a full-on experience in the majority of users. However, smaller users or those who are more sensitive can have the same experience at 80 mg and sometimes even a bit less. Less sensitive users might need 150 mg or so. Tolerance builds quickly, and in order to experience the same effects, recreational users will need to up the dosage if MDMA is being taken frequently.
Some users also double dose in order to prolong the experience. With 120mg, 40mg after about an hour can increase the length of the plateau. It is not necessary to take the same amount twice as the brain has a limited amount of serotonin and therefore there is a limit to how high a user can get. Too much will merely increase the adverse side effects.
Dose is dependent on huge number of variables. 120mg is enough for most, and weight or gender is generally a good guideline, but it also depends on what the user has eaten beforehand, how often one takes MDMA, genetic variance, and a multitude of other factors. 120mg after a huge meal might not produce the desired experience, or it might be way too much for a 170lb man. It is important to start low and experiment to find a dose that works. 100-120mg is generally a good starting dose for most because the negative side effects will be minimal and there is virtually no risk of overdose or a severely adverse reaction.
MDMA also has a non-linear dose-response relationship (i.e. a steep dose-response curve). What this means is that small increases will not necessarily mean small changes. A dose-response curve is a measure of magnitude of stressor (mg of MDMA) vs response of the receptor (subjective experience). 240mg will not be twice as enjoyable as 120mg. Similarly, 150mg is not five quarters as fun as 120mg. This is why double-dosing the same amount is inadvisable (and for other reasons) and why it is important to start low. It is incredibly unlikely that 200mg is necessary for a first timer or even for a 50th timer (provided use is not heavy), and often that amount can be uncomfortable or overwhelming for the user, not to mention physiologically unsafe.
Erowid provides an excellent recommended dose table:
In a therapeutic setting, or if one desires to use MDMA for therapeutic reasons but does not require or desire euphoria, stimulation, etc., 120mg is not necessary. A lighter dose is enough to induce the sorts of changes in consciousness or feelings that make MDMA a valuable therapeutic tool. There is not enough published literature to make a definitive statement, but one study [mdmatherapy.pdf] administered 50-75mg of MDMA to a small sample of women being treated for PTSD. Again, doses are not set in stone. 50mg may not be enough to be helpful and 75mg might be more than enough (although this is quite unlikely).
MDMA can produce a variety of effects. Most marked are euphoria (physical and mental), openness, empathy, increased sensory awareness (notably visual and aural), and a sense of belonging. Many others are quite common but the aforementioned are the effects that most users desire when taking MDMA. Contrary to popular belief, MDMA does not commonly increase one's libido, and in addition it actually makes sexual intercourse quite difficult as many users report a physical shrinking of the penis and difficulty achieving erection and/or orgasm. It is more of a sensual rather than a sexual drug, although the fact that it increases tactile pleasure can make intimacy extremely enjoyable.
Dose is important to the experience because negative effects tend to become more prominent if the dose is too high. Excessive stimulation, nystagmus, muscle tension (especially in the jaw) anxiety, etc. are more likely at higher doses. Higher doses are also more dangerous physiologically. MDMA has stimulant properties, therefore it can increase blood pressure, heart rate, body temperature, and dehydration. This will become more of a worry and/or an issue if the dose is too high.
The MDMA experience, from the time of ingestion until the user is completely back to "baseline" is usually about 4-6 hours (give or take a few). MDMA has a relatively quick onset, anywhere from 20-90 minutes. After this, the user will begin to notice a definite in perception and the experience will begin extremely quickly, with a come-up of about 5-20 minutes. For 2-3 hours after the come-up, the effects will remain at a plateau. A helper dose an hour after the original can extend this plateau by an hour or so. After the plateau, the effects will begin to diminish over an hour or two until they are not noticeable. This come down can be accompanied by physical exhaustion or other undesirable feelings, especially if the dose was excessive. Residual after effects, for example an afterglow or feeling a bit tired, can last for a day or so after the experience. Excessive doses will likely result in a "hangover" the day after wherein the user crashes due physical and mental overexertion. Using a safe amount of MDMA and staying hydrated does not often result in an unpleasant comedown or crash.
Erowid provides an organized table of the timeline of the MDMA experience:
In graph form:
It is inadvisable to combine MDMA, which has stimulant properties with other substances that influence cardiovascular function, for example stimulants or depressants. It is also extremely important to keep in mind how MDMA gets into and out of the brain--inhibiting or inducing the enzyme that breaks it down in the liver can make it more effective or less effective at the same dose as well as perhaps increase neurotoxicity, and inhibiting monoamine oxidase, which breaks serotonin down in neurons can have fatal consequences--when combining MDMA with other substances.
This is a common mix in Ecstasy pills, that may produce an intense empathy, pleasure and increase in energy. But this can be dangerous because it can lead to excessively high blood pressure and dangerous increases in body temperature (severe hyperthermia). It has been also showed that this combination will increase neurotoxic damage. This is because Amphetamine is mainly a dopaminergic drug, and dopamine is toxic to serotonin cells and endings when serotonin is depleted under MDMA.
In a recent study of the acute and chronic effects of MDMA, the possible interactions of caffeine and MDMA were examined. Caffeine exacerbated the acute hyperthermic response to MDMA and tended to increase the loss of serotonin (forebrain 5-HT or hydroxytryptamine) and 5-HIAA (5-hydroxyindoleacetic acid). Thus, caffeine may aggravate the hyperthermic and neurotoxic effects of MDMA, possibly through a mechanism involving dopamine release. It was also found that higher doses of caffeine (10 and 20 mg.kg-1 body mass) when co-administered with MDMA (20 mg.kg-1 body mass) had lethal effects in experimental animals.
These results suggest that caffeine enhances the effects of MDMA and could possibly exacerbate dehydration due to separate diuretic effects.
MDMA is used recreationally by millions. It is often prevalent at music-related events (especially dance, electronic, or house music) because it produces an increased appreciation and awareness of music and can provide the user with the energy to dance for hours on end. It is popular in nightclubs, raves, and the like because many find fast, upbeat music with lots of bass to be extremely pleasurable while under the influence, however this is not always the case. Different people find a variety of genres to be enjoyable. Some only enjoy listening to dance music, others only metal or jazz, some enjoy both, some, all, or none. It depends on the person, although its association with the rave culture is justified.
It is also used because it is undoubtedly one of the most emotionally and physically pleasurable/enjoyable drugs in existence. MDMA produces intense physical euphoria, unrivaled mood lift, astounding empathy, and much more. Many people use it at concerts, but just as many use it in the comfort of their own home or with a group or alone in any situation, whether it be just a quiet night watching a movie with a lover, a dinner party with a group of friends, or alone in a warm bath; it tends to make nearly everything more enjoyable.
MDMA's therapeutic value is vastly underestimated, partly because though nearly all of the evidence is anecdotal due to it becoming illegal before its use in therapy was properly documented. Its properties allow it to be a suitable adjunct to all kinds of therapy--increased willingness to communicate, openness, empathy/love and forgiveness can be beneficial in couples or family therapy; diminished fear and anxiety, and acceptance make it extremely valuable in treating anxiety disorders (it was recently approved for a trial involving patients with Post Traumatic Stress Disorder--the study concluded in 2008 with promising results; a study involving anxiety in cancer patients is currently underway); increased pleasure and awareness, forgiveness of self or others, diminished insecurities and feelings of comfort and well being can help those who suffer from mood disorders.
Alexander Shulgin wrote in PIHKAL about MDMA's value as a therapeutic tool:
It is possible to take advantage of our understanding of chemistry in order to test a pill or powder to determine whether it contains MDMA and what other substances may be present. Unfortunately, it is still virtually impossible for the layman to determine the quantity of MDMA or other substances present in a pill or powder without access to expensive and advanced analysis machines or materials or without the aptitude to employ a technique. Even the simpler techniques, while reliable, can produce false results.
Testing kits that contain certain chemicals that will react with MDMA or other substances to indicate their presence are available. The most common are the Marquis, Mandelin, and Mecke reagents. There are also two simple reagents called the Simons and Robadope reagents. The reagents differ in the types and number of substances for which they can be used to test.
All reagent tests are similar in how they are performed. A drop of a reagent is added to a small amount of powder or a scraping from a pill. Depending on the substances present, the solution will change color and the color change can be compared to a chart that indicates which color corresponds to which substance.
The testing kits are available on the internet. Each test comes with the reagent, a color chart, and an explanation of how to perform the procedure. The website and the description of the kits indicates for which substances the reagents can be used to test, but they will also react with other substances not indicated on the website.
The Marquis, Mandelin, and Mecke reagents will all turn dark purple/blue/black when they react with MDxx compounds. They cannot distinguish between the MDxx compounds. The Mandelin and Marquis reagents will both react with (meth)amphetamine as these two chemicals are very similar in structure to that of MDxx compounds, but they cannot distinguish between the two. They reagents differ in the other chemicals with which they will react.
It is also important to consider that if more than one substance is present the reaction may be different colors, therefore it is important to perform multiple tests and to use different reagents.
The Marquis reagent is a mix of formaldehyde (1 part) and sulfuric acid (9 parts). Sometimes it is mixed with methanol to slow the reactions. It is probably the most versatile reagent (i.e. can test for the most substances). Its advantage is that it can test for other phenethylamines like 2C-x and DXM.
Tests for: MDxx, (meth)amphetamine, 2C-x, DOx, DXM. It will also react with aspirin, some opiates, LSD, mescaline, methylphenidate and sugar.
MDxx: purple to black
(meth)amphetamine: orange to brown (final color reddish-orange to dark reddish brown)
2C-x: bright yellow to green
2C-T-xx: orange to red
DXM: gray to black with smoke (reaction is slow)
DOx: green to yellow
LSD: olive black (final color)
Mescaline: orange (final color)
Methylphenidate: orange-yellow (final color)
Aspirin: deep red
The Mandelin reagent is a mixture of sulfuric acid and ammonium vanadate. Its advantage is that it can test for PMA which has a behavioral profile similar to that of MDMA but is extremely dangerous at the same dose as that of a common MDMA dose. It can also test for ketamine.
Tests for: MDxx, (meth)amphetamine, PMA, and ketamine. It will also react with
MDxx: purple to black
(meth)amphetamine: green to dark green
PMA: green to red to brown
Ketamine: effervescence, orange to dark orange
The Mecke reagent is a mixture of selenous acid and sulfuric acid. Its advantage is that it can test for 2C-T-xx compounds (e.g. 2C-T-7 or 2C-T-21), DXM and opiates.
Tests for: MDxx, DXM, opiates, and 2C-T-xx.
MDxx: dark green/turquoise to dark blue/black
2C-T-xx: reddish-orange to reddish-purple
The Simon's and Robadope reagents can be used to distinguish between substances in a family, for example between MDA and MDMA. They should be used in conjunction with another more versatile reagent if one does not know what substances are present in the powder or pill, but they are sufficient if e.g. one knows that the substance is either MDE or MDMA.
If a pill or powder reacts with both Simon's reagent and the Robadope reagent, it is an indication that multiple substances are present one of which is definitely not MDMA.
The Simon's reagent is a mixture of sodium nitroprusside, acetaldehyde and sodium carbonate. Its advantage is that it indicates the presence of secondary amines, which include MDMA, MDE(A) and methamphetamine.
Tests for: secondary amines (MDMA, MBDB, MDE(A), methamphetamine)
Secondary amines: dark blue
The Robadope reagent is . Its advantage is that it indicates the presence of primary amines, which include MDA, amphetamine, PMA, and 2C-x or DOx compounds.
Tests for: primary amines (MDA, amphetamine, PMA, 2C-x, DOx)
Primary amines: reddish/purple
MDMA has neurotoxic effects on the serotonergic endings of the CNS. Indeed, MDMA reduces the cerebral rates of serotonin and its metabolite, 5-HIAA, in the long term, beyond week. All other biochemical parameters of the serotonergic transmission are also decreased, as the activity of the tryptophan hydroxylase or the density of the serotonin recapture sites. These data suggest strongly a destruction of serotonergic nerve endings.
Regular consumers of MDMA may present a hepatic problem which can evolve to the hepatocellular incapacity and require a liver transplant.
The mechanism of this hepatic problem is not clarified. However several hypotheses can be advanced:
The existence of the population at risk, presenting a Cytochrome Oxydase deficiency resulting in decreased production of the cytochrome P450 2D6 or CYP2D6 enzyme, which affects 5 to 10 % of the Caucasian, and would favor the formation of metabolic toxins.
Regular consumption of MDMA, the presence of eosinophils and mononuclear cells in the histology and the efficiency of corticoids could evoke an immunological mechanism responsible for the development of the hepatic problems.
Besides its capacity to release serotonin and dopamine, MDMA also increases the release of noradrenaline (norepinephrine), with a high affinity for the alpha-2 adrenergic receivers. The cardiovascular effects of MDMA could result from its complex influences on the noradrenergic transmission at the level of the heart and of the sympathetic nervous system. So a sinusal or supraventricular palpitation is frequent, it often comes along with a light arterial low blood pressure.
The regulation of the body temperature is under the dependence of the serotonergic system. According to numerous scientific studies, hyperthermia provoked by MDMA do not result from an increase of the locomotor activity (dancing for example), but depend essentially on the ambient temperature (this is a significant risk factor for those who use MDMA at "rave" parties where the ambient temperature is elevated from the large active crowds and inadequate ventilation facilities). The increase of the 5-HT neurotransmission would induce hyperthermia provoked by the stimulation of the 5-HT2 receivers. Finally, a limited access to the water increases the hyperthermal effect of MDMA without modifying the locomotor activity. The neurotoxicity (damage seen in serotonergic neurons) of MDMA seems also linked to the rise of the body temperature.
Cases of massive ingestion of MDMA with documented elevated serum levels have been reported. All cases experienced minimal toxicity, including slumber, confusion, hallucinations and tachycardia. Without malignant hyperthermia or hyponatremia, these cases are similar to a moderate Amphetamine overdose.
Severe cases can lead to coma, cerebral edema, malignant hyperthermia, seizures and serotonin syndrome.
LD50 figures for MDMA by human should be somewhere around 50mg/kg, as the figures for mice is 97mg/kg, rats 49mg/kg and guinea pigs 98mg/kg. This would translate to lethal dose varying between 2-5 grams depending on the persons weight and other dimensions, 1g and above should be considered very dangerous doses if taken at once.
MDMA: 193.2457 g/mol
MDMA-HCl: 229.7 g/mol
Freebase in vacuo: 155°C (@ 20 mm/Hg); 110-120°C (0.4 mm/Hg)
MDMA-HCl: 147 – 153°C
MDMA-HCl•1/4H2O: soften 132°C; m.p. 135°C
MDMA-HCl•1/2H2O: soften 92°C; m.p. 138-145°C
MDMA-HCl•3/4H2O: soften 50°C; m.p. 90-132°C
MDMA-HCl•H2O: soften 80°C; m.p. 107-133°C
The hydrochloride salt can be hydrated so the melting point is not necessarily an accurate indication of the identity of substance thought to be MDMA. (background and chemistry)
nD @ 19°C: 1.5311 (Biniecki and Krajewski 1960)
Synonyms: ±-1,3-benzodioxolyl-N-methyl-2-propanamine; ±-3,4-methylenedioxy-N-methyl-a-methyl-2-phenethylamine; DL-3,4-methylenedioxy-N-methylamphetamine; 3,4-methylenedioxymethamphetamine
Appearance: Pure MDMA is a white, crystalline solid. It can be found in a variety of colors on the black market due to quality, production method, dyes, etc.
Stability: MDMA is an EXTREMELY stable molecule. Alexander Shulgin, the "step-father" of MDMA once said something along the lines of "if they had put some in the pyramids with the pharaohs it would still be good today." As long as it is kept in a cool, dark, dry place it will be perfectly stable for a lifetime and more. One of the only studies published on its stability showed degradation after 21 weeks at -20 degrees, 4 degrees, and 20 degrees in the dark.
MDMA Material Safety Data Sheet
MDMA is a ring-substituted derivative of amphetamine, ergo also a derivative of phenethylamine. Here is a breakdown of how the name defines its structure and how it is related to these chemicals:
Its similarity to the monoamine neurotransmitters, serotonin, dopamine, and norepinephrine are responsible for its supposed mechanism of action which involves acting as a substrate for proteins to which the monoamines normally bind. In effect, this modulates the way the neurotransmitter systems work and is responsible for MDMA's subjective effects; its effect on the serotonin system, for example, is responsible for its characteristic euphoria, appetite suppression, and openness. This mechanism is explained in detail in the Pharmacology section.
Another important point is that MDMA is a chiral molecule. This means that the mirror image of molecule is not superimposable upon the original molecule. This is due to the fact that one of its carbons is bound to four different groups. No amount of turning or bending the molecule will allow the two molecules to be congruent; bonds must be broken in order to create the other molecule. The (R) enantiomer is more potent in vivo than the (S) enantiomer, but MDMA is usually found as the racemate, a 50-50 mixture of the two stereoisomers.
Freebase (the basic, pure form of an amine, sans counterions) MDMA is a white, musty smelling oil. It has a searing taste, is insoluble in water and soluble in most organic solvents.
MDMA is almost always encountered as a salt, specifically the hydrochloride salt (MDMA-HCl). Often at the end of a synthesis, an acid is bubbled through freebase MDMA to form the salt that exists usually as a white solid or oil that is extremely bitter, and soluble in water. MDMA can also exist as several other salts, for example MDMA-H2PO4 (the dihydrophosphate salt) but HCl is the most common. MDMA-HCl is found as a white to off-white powder or as a translucent crystal.
MDMA is found commonly in pill form (pressed powder, usually combined with fillers, binders, and/or other adulterants), and is notorious for being pressed into in a variety of different shapes, colors, and sizes (some "famous" pills include "Pink Dolphins" or "Red Playboys") as well as being adulterated. It is impossible to know whether a pill contains MDMA, how much it contains, or what other substances it may contain from any of its physical properties. It is possible to know, for example that a pill 5 mm in diameter is not going to contain a razor blade or a block of cheese, but even if the pill is a solid color and weighs somewhere in the range of common MDMA doses, it could contain any of literally thousands of different substances. The only way to know what is present in a pill (or a powder for that matter) is to analyze it chemically (CHEMICAL ANALYSIS SECTION)
In the United States of America, MDMA is a Schedule I drug, making it illegal to manufacture, buy, possess, or distribute (sell, trade or give) without a DEA license. Federal sentencing guidelines do not include MDMA specifically, but the drug equivalency table states that in terms of sentencing, 1g MDMA = 500g marijuana. The highest "Baseline Offense Level" (Level 38) in the sentencing guidelines includes 30,000 kg (30 million grams) or more of marijuana, which would equal 60 kg or more of MDMA. Here is a table for the amount of MDMA in question and related information:
MDMA was first synthesized in 1912 by the pharmaceutical giant, Merck, in the search for an antihemorraghing drug. Merck wanted to circumvent a patent for the drug hydrastinine, which was patented by Bayer at the time, so the chemists created an analogue, methylhydrastinine. MDMA was an intermediate in the synthesis, and was therefore documented when the synthesis was patented. At the time, Merck was not interested in the drug so it was not extensively studied, if at all.
In 1953, the US Army tested MDMA on various animals to study its toxicity. It was determined to be less toxic than MDA. There is no evidence to support that it was tested as a "truth serum". These studies were unknown until they were declassified in 1973.
Some years later, in 1965, MDMA was resynthesized by the aptly named "stepfather of MDMA", Alexander Shulgin, during his rather infamous work developing novel psychedelics. For a few years he toyed with synthesizing drugs with the phenethylamine backbone. He synthesized and tested MDA, but ignored MDMA for a few years due to its presumed lack of activity (many psychedelic drugs lose potency when N-methylated). Only after a "tip-off" in 1968 by a chemistry student he was advising did he investigate it further. Initially he was unimpressed, but as he tested the substance and slowly increased the dose, eventually he reported a wonderful experience in PIHKAL (Phenethylamines I Have Known And Loved) with 120mg:
Upon hearing word of this, many therapists wrote to the DEA of their work with MDMA and how beneficial it was in the field of therapy. These letters were effective in that in 1985 the DEA held hearings on the issue of MDMA's placement into Schedule I (meaning even licensed therapists couldn't use it with patients). Unfortunately, even though many psychiatrists and other people testified that MDMA was safe and valuable, the DEA pointed out that all of the evidence was anecdotal (which happened to be true).
Here is where the MDMA situation became dire. A new DEA administrator, John Lawn, was appointed by Reagan. Despite the fact that hearings were not over, Lawn used his power as an administrator to emergency schedule MDMA and declare it a Schedule I drug on July 1st, 1985, indicating that it had a high potential for abuse, no currently accepted medical use, and was not safe for use even under medical supervision. Judge Francis Young, who had lead the hearings, reviewed all of the evidence and on May 22, 1986, wrote that he felt it didn't meet any of the criteria for being placed in Schedule I. He recommended it be placed in Schedule III wherein it could still be prescribed and used in therapy.
Lawn ignored the recommendation and decreed that on November 13, 1986, MDMA would be placed permanently into Schedule I, on the basis that as it was not approved by the FDA, this meant it had no currently accepted medical use. The DEA was sued by Lester Grinspoon, a psychiatry professor at Harvard, in attempt to combat this decision; he interpreted accepted medical value as acceptance by the medical community. The federal court sided with Grinspoon and returned the case to the DEA so Lawn could not schedule the drug, however, slapping almost everyone involved in the ordeal in the face, less than a month later Lawn had "reconsidered the evidence" and came to the same conclusion. On March 23, 1988, MDMA was placed into Schedule I where it remains to this day.
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