Methylenedioxymethamphetamine MDMA 1- ( benzo [ d ] [ 1 , 3 ] dioxol-5-yl ) - N -methylpropan-2-amine CAS number 42542-10-9 66142-89-0 69610-10-2 81262-70-6 Chemical formula C 11 H 15 N O 2 Molecular weight 193.25 g/mol SMILES CC ( NC ) CC1=CC=C ( OCO2 ) C2=C1 Elimination half life The half-life of MDMA is dose dependent , increasing with higher doses , but is around 6-10 hours at doses of 40-125 mg Legal status Schedule I ( USA ) Class A ( UK ) Schedule III ( Canada ) Delivery 75-120 mg tablets 100 mg sublingual Recreational uses : euphoria Other putative uses : Marriage counseling Anxiety PTSD End of Life Care 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 . Side effects : Endocrine : hyponatremia Eye : dilated pupils nystagmus Psychological : euphoria strong sense of empathy serotonin deficiency Skin : sweaty palms heavy sweating increased heart rate Increased body temperature Miscellaneous : restlessness chattering teeth muscle spasms MDMA ( 3 , 4-methylenedioxy-N-methylamphetamine ) , most commonly known by the street names Ecstasy or X , is a semisynthetic entactogen of the phenethylamine family , whose primary effect is believed to be the stimulation of secretion as well as inhibition of re-uptake of large amounts of serotonin as well as dopamine and norepinephrine in the brain , inducing a general sense of openness , empathy , energy , euphoria , and well-being . Tactile sensations are enhanced for some users , making general physical contact with others more pleasurable ; but , contrary to popular belief it generally does not have aphrodisiac effects . Its reported ability to facilitate self-examination with reduced fear may prove useful in some therapeutic settings , leading in 2001 to permission from the United States FDA for testing in patients with post-traumatic stress disorder in conjunction with psychotherapy . Acute dehydration is a risk among users who are highly physically active and forget to drink water , as the drug may mask one 's normal sense of exhaustion and thirst . Also the opposite , `` water intoxication , `` resulting in acute hyponatremia , has been reported as a consequence of use . Sometimes dangerous chemicals such as PMA or methamphetamine alone or in combination with MDMA are added to ecstasy tablets . Long-term effects in humans are largely unknown and the subject of much controversy - particularly with regard to the risks of severe long-term depression as a result of a reduction in the natural production of serotonin . History A patent for MDMA was originally filed on Christmas Eve 1912 by the German pharmaceutical company Merck , after being first synthesised for them by German chemist Anton Köllisch at Darmstadt earlier that year . The patent was granted two years later , though in 1916 , after two more additional years Köllisch died with no idea of the impact his synthesis would have . At the time , MDMA was not known to be a drug in its own right ; rather , it was patented as an intermediate chemical used in the synthesis of a styptic ( a drug intended to control bleeding from wounds. ) Over half a century would pass before the first recorded ingestion of MDMA by humans . The U.S. Army did , however , carry out lethal dose studies on MDMA and several other compounds in the mid-1950s . It was given the name EA-1475 , with the EA standing for Edgewood Arsenal . The results of these studies were not declassified until 1969 . MDMA was legal in the United States until May 31 , 1985 . Before then , it was used both as an adjunct to psychotherapy and as a recreational drug . MDMA began to be used therapeutically in the mid-1970s after the chemist Alexander Shulgin introduced it to psychotherapist Leo Zeff . As Zeff and others spread word about MDMA , it developed a reputation for enhancing communication , reducing psychological defenses , and increasing capacity for introspection . However , no formal measures of these putative effects were made and blinded or placebo -controlled trials were not conducted . A small number of therapists–including George Greer , Joseph Downing , and Philip Wolfson–used it in their practices until it was made illegal . MDMA appeared sporadically as a street drug in the early 1970s , but it came into prominence in the early 1980s in certain trendy yuppie bars in the Dallas area , then in gay dance clubs . From there use spread to rave clubs , and then to mainstream society . During the 1990s , along with the growing popularity of the rave subculture , MDMA use became increasingly widespread among young adults in universities and later in high schools . It rapidly became one of the four most widely used illegal drugs in the U.S. , along with cocaine , heroin and marijuana . In the late 1980s and early 1990s , ecstasy was widely used in the United Kingdom and other parts of Europe , becoming an integral element of rave culture . It has also been associated with other psychedelic/dancefloor-influenced music scenes , such as Madchester and Acid House . Recreational use The primary effects of MDMA include feelings of openness , euphoria , empathy , love , and heightened self-awareness . Its initial adoption by the dance club sub-culture is possibly due to the enhancement of the overall social and musical experience . Taking MDMA or ecstasy is commonly referred to as popping , rolling , pilling , boshing or dropping in the United Kingdom , `` pinging '' or `` peaking '' in Australia , `` flipping '' , `` getting chewed '' and/or `` murfing '' in Canada or `` thizzing '' in Northern California . Some term the rushing feeling of the drug as blowing up , coming up , flying , or zooming . MDMA use has increased markedly since the late 1980s , and spread beyond its original sub-cultures to mainstream use . Prices have also fallen since the 1980s . In countries where distribution is more extensive , such as in the Netherlands and other places in Europe , prices can sometimes be as low as €1 per tablet . In countries where distribution is more difficult , such as the US and Australia , prices are accordingly higher at up to US $ 10-20 and AUD $ 35-50 respectively per tablet . In the United Kingdom it is common to pay around £2 to £3 for a tablet on average . Prices are also usually higher when the drug is purchased in a club or at a rave . Supply and administration Ecstasy commonly appears in a tablet form , usually imprinted with a monogram . MDMA is usually ingested in pill form , although use of powder or crystal is increasing in popularity ( sometimes known as `` Mud , `` `` Molly , `` `` Mandy , `` `` M.D. '' or `` Madman '' ) . Pills come in a variety of `` brands '' , usually identified by the icons stamped on the pills . However the brands do not consistently designate the actual active compound within the pill , as it is possible for `` copycat '' manufacturers to make their own pills which replicate the features of a well-known brand . Although full and proper characterization of ecstasy pills requires advanced lab techniques such as gas chromatography-mass spectrometry and gas chromatography-infrared spectroscopy , it is also possible to use a less accurate presumptive alkaloid test known as the Marquis reagent . Many organizations sell testing kits containing this reagent . DanceSafe is one such company , and it includes an extensive database of photographs of different pills , along with the results of a laboratory analysis of their contents . EcstasyData.org is a non-profit site that tests the purity of street pills and compiles results . PillReports.com allows users to post reports of pills they 've purchased and share the experience , pictures , and testing results . Other users can then post what they think about the pill in question or even rate the report on the pill . Effects Pharmacokinetics MDMA reaches maximal concentrations in the blood between 1.5 and 3 hours after ingestion . It is then slowly metabolized and excreted , with levels decreasing to half their peak concentration over approximately 8 hrs . Metabolites of MDMA that have been identified in humans include 3 , 4-methylenedioxyamphetamine ( MDA ) , 4-hydroxy-3-methoxy-methamphetamine ( HMMA ) , 4-hydroxy-3-methoxyamphetamine ( HMA ) , 3 , 4-dihydroxyamphetamine ( DHA , also called alpha-methyldopamine ) , 3 , 4-methylenedioxyphenylacetone ( MDP2P ) , and N-hydroxy-3 , 4-methylenedioxyamphetamine ( MDOH ) . The contributions of these metabolites to the psychoactive and toxic effects of MDMA are an area of active research . MDMA is known to be metabolized via three pathways . One such pathway proceeds via N-demethylation ; byproducts of which include several active metabolites , including MDA. The metabolism may be primarily by the cytochrome P450 enzymes CYP2D6 ( in humans , but CYP2D1 in mice ) , and CYP3A4 . Complex , nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8 , resulting in zeroth order kinetics at higher doses . It is thought that this can result in sustained and higher drug concentrations if the user takes consecutive doses of the drug. 65% of MDMA is excreted unchanged in the urine ( additionally 7% is metabolised into MDA ) during 24 hours after usage . MDMA is a chiral compound and has been almost exclusively administered as a racemate . However , an early uncontrolled report suggests that the S-enantiomer is significantly more potent in humans than the R-enantiomer ( Anderson et al. 1978 ) . Studies in humans indicate that the disposition of MDMA is stereoselective , with the S-enantiomer having a shorter elimination half-life and greater excretion than the R-enantiomer . For example , Fallon et al. ( 1999 ) reported that the area under the plasma concentration versus time curve ( AUC ) was two to four times higher for the R-enantiomer than the S-enantiomer after a 40 mg oral dose in human volunteers . Similarly , the plasma half-life of ( R ) -MDMA was significantly longer than that of the S-enantiomer ( ( 5.8 ± 2.2 hours ) vs 3.6 ± 0.9 hours ) . However , because MDMA has dose dependent kinetics , it is likely that these half lives would be higher at more typical doses ( 100 mg is sometimes considered a typical dose ) . Given as the racemate , MDMA has a half-life of around 8 hours . Short-term neurochemical effects Serotonin is a neurotransmitter believed to play a role in the regulation of mood and pleasure . MDMA causes serotonin vesicles in the neurons to release quantities of serotonin into the synapses . Although popular press accounts focus on the role of serotonin release , the mechanism by which MDMA causes its unusual psychoactivity is largely unknown . In vitro and nonhuman animal studies have established that MDMA also induces dopamine , norepinephrine , and acetylcholine release and can act directly on a number of receptors , including a2-adrenergic ( adrenaline ) and 5HT2A ( serotonin ) receptors . MDMA promotes the release of several hormones including prolactin and the antidiuretic hormone vasopressin , which may be important in its occasional production of water intoxication or hyponatremia . Subjective effects Effects desired by users include : increased positive emotion and decreased negative emotion increased sense of well-being increased sociability and feelings of closeness or connection with other people reduced defensiveness and fear of emotional injury a sense of increased insightfulness and introspective ability MDMA , particularly with larger doses , is sometimes reported to cause visual distortions . In a review of studies in which 1.5 to 1.7 mg/kg oral MDMA was administered in their laboratory to 74 people , Vollenweider et al. reported that scenic hallucinations were reported only once , while simple patterns , distorted objects , and flashes of light were commonly reported . Other short-term effects Acute physiological effects include : Pupil dilation with attendant photosensitivity and color perception Nystagmus General restlessness Loss of appetite Increased heart rate and blood pressure Loss of sleep Dehydration Acute toxic/dangerous effects Apart from the dangers from impurities , the primary acute risks of taking MDMA resemble those of other stimulant amphetamines . The majority of fatalities and cases requiring emergency care involve hyperthermic syndromes . MDMA appears to decrease heat loss in the body by causing constriction of blood vessels near the skin . In addition , it may sometimes increase heat production by muscles and the brain . These effects may be amplified in people who become dehydrated and are unable to cool by sweating . MDMA can mask the body 's normal thirst and exhaustion responses , particularly if a user is dancing or is otherwise physically active for long periods of time without hydration . Because of these effects , MDMA can temporarily reduce the body 's ability to regulate its core temperature , and in high-temperature surroundings ( e.g. clubs ) combined with physical exertion this may lead to hyperpyrexia if precautions are not taken to remain cool . Sustained hyperpyrexia may lead to rhabdomyolysis ( muscle breakdown ) , which in turn can cause renal failure and death . It has been argued that `` the seriousness of the effects can be dependent on environmental factors other than the drug concentration , `` as blood concentrations of the drug spanned a large range in cases of death in MDMA users . This notwithstanding , `` most of the cases of serious toxicity or fatality have involved blood levels ... up to 40 times higher than the usual recreational range. '' ( Kalant H. , 2001 ) While dehydration is undesirable , there also have been a number of users suffering from water intoxication and associated hyponatremia ( dilution of the blood that can cause swelling of the brain ) . Although many cases of this clearly involved individuals drinking large amounts of water , there are cases where there is no evidence of excessive water consumption . Their cases may be caused by MDMA inducing release of the antiduretic hormone vasopressin by the pituitary gland . This causes one to retain water to a greater extent . The death of British teen Leah Betts may be the most widely publicised MDMA-related fatality , and resulted from her consuming too much water due to concerns over dehydration . Signs of hyponatremia include confusion , nausea , headache and loss of consciousness . Hyponatremia in MDMA users is a medical emergency and requires prompt treatment . In general , females are at greater risk of developing symptoms and dying from hyponatremia than males . MDMA users have also been recorded to demonstrate bruxism ( teeth grinding ) and trisma ( jaw clenching ) as a short-term effect from the drug Many users of MDMA alleviate this by using chewing gum , however this can result in temporary mouth ulcers through inadvertent biting of the mouth lining . Temporary jaw ache often results from jaw clenching or excessive chewing . Some users consume supplemental magnesium tablets to relax the jaw muscles and relieve clenching . While users sometimes report increased sexual desire , there are many reports of difficulty achieving orgasm and erection while on the drug . `` [ MDMA ] is a love drug but not a sex drug for most people. '' ( Beck & Rosenbaum , 1994 ) , , . This is the rationale behind the use of sextasy ( combining MDMA with Viagra ) . There are reported allergic reactions , which are extremely rare . Liver damage , which may have an immunological cause , has been seen in a small number of users . Animal studies suggest risk and extent of liver damage is increased by high body temperature . A UK parliamentary committee commissioned report found the use of `` Ecstasy '' to be less dangerous than tobacco and alcohol in social harms , physical harm and addiction While most MDMA is taken orally , some users resort to drug injection to achieve a faster , more intense effect . This entails the risks associated with injection of many illicit drugs , including the transmission of blood-borne viruses , bacterial infections , vein damage and increased chance of overdose . Addiction and Tolerance The potential of MDMA to produce addiction ( dependence ) is controversial . Some studies indicate that many users may be addicted . For example , Cottler et al ( 2001 ) interviewed 52 users and found that 43% met standard criteria for dependence . However , some of these people may have been inappropriately diagnosed with dependence because they reported tolerance or after effects from MDMA. Tolerance and after effects ( 'withdrawal ' effects ) are symptoms of dependence for many drugs , but seem to occur in some MDMA users who are actually not dependent . For example , studies in Switzerland in which MDMA was given to people who had never used it before documented after effects . When people are classified as addicted to MDMA , it is not clear if that indicates a difficulty in quitting the drug . In a prospective study in Germany , many who were initially categorized as addicted , spontaneously 'improved ' without any treatment for the alleged addiction . Given the complexities in classifying MDMA users as addicted , conclusions about the addictive potential of MDMA are less reliable than nicotine addiction . http : //www.nida.nih.gov/researchreports/nicotine/Nicotine.html Long-term adverse effects Long-term effects are still unknown and heavily debated among scientists . There are several reports of Hallucinogen Persisting Perception Disorder being induced by MDMA. In some cases , the disorder appears to be permanent . The disorder seems to occur in only a small fraction of a percentage of users , and its mechanism of causation is unknown . Some experiments indicate that use at very high doses may lead to the Synaptic Terminals of serotonin neurons being damaged . The precise mechanism of this action is unknown , but recent evidence ( Jones 2004 ; Miller 1997 ; Monks et al. 2004 ) suggests that the metabolic breakdown of MDMA includes the formation of reactive oxygen species ( ROS ) , chemicals known to cause oxidative cell damage when taken up into the releasing synapse . This effect has been demonstrated experimentally in the brains of rats , where the serotonin terminals of animals who are given extremely high doses of MDMA over a prolonged period of time ( usually ten to one hundred times greater than a typical human dose ) become withered and useless , although this is n't certain . This hypothesis is supported by the fact that the administration of selective serotonin reuptake inhibitors ( `` SSRIs '' , which bind to the serotonin cell 's reuptake transporters and thus block ROS from entering the serotonin cells ) along with or immediately following MDMA seems to block neuron damage in rats given MDMA . The mechanism proposed as a large part of this neurotoxicity and its functional consequences appear to involve the induction of oxidative stress . This stress results from an increase in free radicals and a decrease in antioxidants in the brain. ( Shankaran , 2001 ) Oxidation is part of the normal metabolic processes of the body . As the cell goes about its life , by-products called oxidative radicals are formed , also called free radicals . These molecules have an unpaired electron that makes them highly reactive . They pull strongly on the electrons of neighboring molecules and destabilize the electrical balance of those molecules , sometimes causing those molecules to fall apart . This can become a chain reaction . In normal functioning , there are antioxidants in the system that act as free radical scavengers . These are molecules with an extra electron that they are willing to give up to the free radicals , making both the free radical and the antioxidant more stable . MDMA rapidly increases the levels of free-radicals in the system and overwhelms the reserves of scavengers . The radicals then damage cell walls , reduce the flexibility of blood vessels , destroy enzymes , and cause other molecular damage in the neurological pathways. ( Erowid , 2001 ) It has been shown that MDMA-neurotoxic effects are increased by a hyperthermic environment and decreased by a hypothermic one. ( Yeh , 1997 ) Studies have suggested that the neurotoxic molecules are not hydroxyl free radicals , but superoxide free radicals . When rats are injected with salicylate , a molecule that scavenges hydroxyl free radicals , the neurotoxic effects of MDMA are not attenuated , but actually potentiated . Further evidence of this superoxide theory comes from the observation that CuZn-superoxide dismutase transgenic mice ( mice with excess human antioxidant enzyme ) demonstrate neuroprotective mechanisms that protect the mice from MDMA-induced depletion of 5-HT ( serotonin ) and 5-HIAA and lethal effects. ( Baggott , 2001 and Yeh , 1997 ) Studies giving animal species injections have shown that ascorbic acid , alpha lipoic acid , l-cysteine , and some other radical scavengers are effective in reducing oxidative stress caused by MDMA. ( Erowid , 2001 ) A combination of antioxidants , including Vitamin A , C , and E are recommended ; taking multivitamins including selenium , riboflavin , zinc , cartenoids , etc. should help reduce oxidative damage . Many of these vitamins , though , are water soluble , and are quickly excreted from the body . The typical MDMA user is psychoactive for 4-6 hours and may not have an appetite from the time of taking until the following sleep cycle or many hours later . These vitamins flush through the system in 3-4 hours . Damage occurs in the absence of these antioxidants . There are some fallacies in applying these animal studies to human use . Firstly , it is difficult to equate rat doses to human doses , rats metabolise MDMA twice as fast as humans and often larger doses or multiple doses are administered to simulate human plasma levels . The doses given in experiments are far greater than typical human use of 100-300 mg in order to notice the problems caused so that we may say that if this happens at large doses , then a lesser form should happen at low doses . There could be a threshold of nothing happening or a threshold of the worst problems at low doses . Secondly , the effective doses of antioxidants given to these animals are much higher than humans would ever take both in its method of administration ( injected vs. oral ) and in its dosage . Essentially both the neurotoxic and neuroprotective effects are exaggerated , but it is not possible to say if this scales down the same way . Some MDMA users administer an SSRI while , or shortly after taking MDMA , in an attempt to prevent possible neurotoxicity . These SSRIs are typically antidepressants such as fluoxetine or sertraline . However , administration of SSRIs before using MDMA is known to block the euphoric high from the drug , due to the regulation of serotonin . This blocking effect can last several weeks , depending on the half-life of the SSRI. The same effects are seen with recent cocaine use , which itself is an SSRI . However , MDMA use in conjunction with a different class of antidepressants , namely Monoamine oxidase inhibitors , is strongly contra-indicated due to danger of serotonin syndrome and the possibility of life-threatening hypertension . The safety of this practice has not been systematically evaluated . Many users also attempt to replenish the deficit of serotonin which follows the use of MDMA by administering 5-HTP , in an attempt to alleviate to a degree the depression and overall mental unsettlement in the days following MDMA usage ( including the immediate `` come-down '' and what is known as `` suicide Tuesday `` ) . The serotonin precursor 5-HTP , which is commercially available as a dietary supplement , reportedly supplies the user with more of the raw materials to synthesize the neurotransmitter , reducing the negative psychological effects of depleted serotonin . Pre-loading with 5-HTP has not been shown to increase the subjective effects of MDMA. Anecdotal reports seem to indicate this is largely placebo with some users reporting a moderate muting of the MDMA effect when 5-HTP is consumed within 24 hours prior to MDMA use . Because the neurotoxicity of MDMA is believed by some to be highly dependent on its metabolic disposition ( Jones 2004 ; de la Torre & Farré 2004 ) , it is unclear how to generalize to humans from experiments in rats and monkeys . Considerable research has been done into possible cognitive-behavioral deficits among ecstasy users but data have been largely inconclusive . At least two meta-analyses of these studies have been completed ( Morgan 2000 ; Sumnall & Cole 2005 ) . Morgan 's analysis of 17 studies showed that ecstasy users had a slight tendency to be more impulsive and depressed than controls . Sumnall and Cole 's analysis showed a slight increase in the prevalence of depressive symptoms in ecstasy users over controls . Of course , in retrospective studies like these we are always faced with a chicken-or-egg question : did these impulsive and depressed people use ecstasy to self-medicate or did otherwise normal people become depressed and impulsive after using ecstasy ? This question has not been answered . Although some experimental evidence exists indicating that long-term ecstasy users experience memory difficulties [ citation needed ] , a large study in 2002 ( Strote et al. ) showed that ecstasy users in 4-year colleges have GPAs which do not differ significantly from those of non-users . MDMA and Parkinson 's Research at the University of Manchester indicates that MDMA dramatically reduces tremors in patients receiving L-DOPA treatment for Parkinson 's disease . In a now-retracted study , a research team led by Dr. George A. Ricaurte at Johns Hopkins University implicated MDMA as a cause of Parkinson's-like brain abnormalities in monkeys , suggesting that a single use of MDMA caused permanent and serious brain damage . These claims were hotly disputed by physicians , therapists , and other experts in the field , including a team of scientists at New York University . Criticisms of the study included its use of injection rather than oral administration ; that this type and scale of damage ( > 20% mortality ) would translate to hundreds of thousands or millions of deaths which had not materialized in the real world amidst extremely broad global MDMA usage ; and , perhaps most important , that other research teams could not duplicate the study 's findings . On September 6 , 2003 , Dr. George A. Ricaurte and his team announced that they were retracting all results of their commonly cited and controversial study . The researchers said that the labels on the drugs had been somehow switched , and they had inadvertently injected their experimental monkeys and baboons with extremely high doses of methamphetamine instead of MDMA. The chemical supplier , Research Triangle Institute , has publicly claimed that the proper drug was supplied , and Ricaurte has yet to pursue them for their alleged error . Ricaurte had also come under fire for supplying PET scans to the U.S. Office of National Drug Control Policy that were used in anti-drug literature ( Plain Brain/Brain After Ecstasy ) that seemed to suggest MDMA created holes in human brains , an implication that critics called misleading . Ricaurte later asked the Agency to change the literature , citing the `` poor quality '' of the images . These images are still circulating in educational systems across the U.S. , however , and the myth that ecstasy users develop `` holes in their brains '' remains quite popular and government funded . Legal issues Use , supply and trafficking of ecstasy are currently illegal in most countries . In the United States , MDMA was legal and unregulated until May 31st 1985 , at which time it was added to DEA Schedule I , for drugs deemed to have no medical uses and a high potential for abuse . During DEA hearings to criminalize MDMA , most experts recommended DEA Schedule III prescription status for the drug , due to its beneficial usage in psychotherapy . The judge overseeing the hearings , Francis Young , also made this recommendation . Nonetheless , the DEA classified it as Schedule I . That same year , the World Health Organization 's Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the Convention on Psychotropic Substances . Unlike the Controlled Substances Act , the Convention has a provision ( in Article 7 ( a ) ) that allows use of Schedule I drugs for `` scientific and very limited medical purposes '' . The Committee 's report stated : The Expert Committee held extensive discussions concerning therapeutic usefulness of 3 , 4 Methylenedioxymethamphetamine . While the Expert Committee found the reports intriguing , it felt that the studies lacked the appropriate methodological design necessary to ascertain the reliability of the observations . There was , however , sufficient interest expressed to recommend that investigations be encouraged to follow up these preliminary findings . To that end , the Expert Committee urged countries to use the provisions of article 7 of the Convention on Psychotropic Substances to facilitate research on this interesting substance . In the United Kingdom , MDMA is Schedule I/Class A , making it illegal to sell , buy , or possess without a license . Penalties include a maximum of seven years and/or unlimited fine for possession ; life and/or unlimited fine for production or trafficking . A mandatory seven year sentence is now the penalty for a third conviction for trafficking . Medical use and clinical studies In 2001 , the FDA granted permission for experimental administration of MDMA to patients suffering from post-traumatic stress disorder . This research is being sponsored by the Multidisciplinary Association for Psychedelic Studies ( MAPS ) . For further information on this , see MAPS 's MDMA Research Information and the recent article from MSNBC/Newsweek . This research in patients builds on studies in which MDMA was given to healthy volunteers . The first of these healthy volunteer studies was conducted by Dr. Charles Grob , with other studies done by Dr. Franz Vollenweider in Switzerland , Drs . John Mendelson and Reese Jones at the University of California San Francisco , and Drs . Magi Faree and Rafael de la Torre in Spain . Safety and contraindications Some information in this article or section has not been verified and may not be reliable . Please check for any inaccuracies , and modify and cite sources as needed . The illegality of this drug in many countries makes exact study of its effects difficult . Some safety considerations to consider with the use of ecstasy , which may or may not be conclusive , are the following : Because of its illegality , the dose and purity of an ecstasy pill varies dramatically . The dose may be stronger than is advertised , may be adulterated , or might not even contain MDMA . Ecstasy affects the regulation of the body 's internal systems . Continuous dancing without sufficient breaks or drinks can lead to dangerous overheating and dehydration . Drinking too much water without consuming a corresponding amount of salt can lead to hyponatremia or Water intoxication . The use of ecstasy can exacerbate depression [ citation needed ] and may produce temporary depression as an after-effect for some users . Some individuals also might experience wild or unexpected mood swings the first couple of days following the use of MDMA. [ citation needed ] The use of ecstasy can be very dangerous when combined with other drugs ( particularly monoamine oxidase inhibitors ( MAOIs ) and antiretroviral drugs , in particular Ritonavir ) . Combining MDMA with MAOIs can precipitate a hypertensive crisis and can result in a near-fatal repercussion . In some cases , pills marketed as ecstasy do not contain only MDMA , but instead are substituted with various substances like ketamine , methamphetamine and caffeine . Some users purchase testing kits to verify that pills are actually MDMA. Organizations such as DanceSafe provide testing kits . One effect of this in Europe , and particularly the UK , has been to make pure MDMA powder ( known as `` Dabs '' ) and crystals ( known as `` Crystal '' , not to be confused with Methamphetamine , which is known as Crystal in the US ) increasingly popular . In some areas of the UK , pure forms of MDMA are easier to get hold of than Ecstacy pills . Long-term after-effects are greatly exacerbated by high doses and frequent use . A small percentage of users may be highly sensitive to MDMA ; this may make first-time use especially hazardous . This includes but is not limited to people with congenital heart defects . Some scientists have suggested that a small percentage of people lack the proper enzymes to break down the drug . One enzyme involved in MDMA 's breakdown is CYP2D6 , which is deficient or totally absent [ citation needed ] in 5-10% of the caucasian population and those of African descent and 1-2% of Asians . . However , there is no clear evidence linking lack of this enzyme to problems in users and the connection remains theoretical . See also Empathogen-entactogen Amphetamine Phenethylamines Alexander Shulgin ( Infamous Ecstasy Chemist ) Eleusis/Zoesis ( Famous Underground Ecstasy Chemist ) Otto Snow ( Author of Chemistry books concerning Ecstasy ) Psychedelic therapy Psychoactive drug Sextasy RAVE Act Retracted article on neurotoxicity of ecstasy Leah Betts & Anna Wood ( people who have died as a result of drinking too much water while on ecstasy ) Drug injection External links Media The title screen to Peter Jennings - Ecstasy Rising The title screen to The `` X '' Files - A Dateline Special Jennings , Peter . `` Primetime Special : Peter Jennings - Ecstasy Rising . '' ABC News , April 1 , 2004 . Conant , Eve . `` Ecstasy : A Possible New Role for a Banned Club Drug . '' Newsweek , May 2 , 2005 . Generation on X : An undercover look at the growing trend of teens using Ecstasy FOX News , April 26 , 2005 . Weiss , Rick . `` Use Studied to Ease Fear in Terminally Ill. '' The Washington Post , December 27 , 2004 . Philipkoski , Kristen . `` Long Trip for Psychedelic Drugs. '' Wired , September 27 , 2004 . Philipkoski , Kristen . `` DEA Approves Ecstasy Tests. '' Wired , March 2 , 2004 . Darman , Jonathan . `` Out of the Club , Onto the Couch Newsweek .com , December 5 , 2003 . - An interview with NYU 's Dr. Julie Holland Weiss , Rick . `` Results Retracted on Ecstasy Study . '' The Washington Post , September 6 , 2003 . Recer , Paul `` Ecstasy-Parkinson 's Connections ? . '' CBS News , September 26 , 2002 . Man found to have taken 40 , 000 tabs in 9 years - London. ; The Guardian , April 4 , 2006 . Wittlin , Maggie . `` Hitting a High E : Italian scientists find loud music intensifies and extends the brain’s response to MDMA , `` Seed Magazine ( 02/15/2006 ) Powers , Nicholas . New York journalist does ecstasy at Burning Man Academic The Multidisciplinary Association for Psychedelic Studies ( MAPS ) : MDMA project MAPS is at the forefront of human MDMA research , having obtained FDA permits for two studies administering MDMA to human volunteers in order to explore the drug 's potential psychiatric benefits ( one study is already underway . ) The DEA.org 's extensive critique/review of the evidence against MDMA ( 'ecstasy' ) causing brain damage at common recreational doses . This is your brain on Ecstasy - A slideshow that illustrates the neuropharmacokinetics of Ecstasy ( how the drug affects the brain. ) Some of the information on this page is at present ( July 2005 ) outdated . PiHKAL entry The MAPS research library , containing downloadable copies of most of the MDMA and LSD research ever done . Ecstasy news page - Alcohol and Drugs History Society General Multidisciplinary Association for Psychedelic Studies - A non-profit organization currently conducting FDA-approved studies with MDMA . EcstasyData.org A database of photos and lab-test results of over 1500 pills of `` Ecstasy '' . Pillreports A similar database to EcstasyData , but with user-contributed photos of pills and subjective `` pill reports '' and ratings . Over 1600 listings ( as of Jan. 2006 ) . DanceSafe - a risk reduction site with lots of information on Ecstasy . Includes a large database of photographs of different pill types , along with laboratory analysis of what was actually found in the pill . Erowid 's Ecstasy page - lots of information UK National Drugs Line factsheet on Ecstasy American Council for Drug Education factsheet on Ecstasy Congressional Research Service ( CRS ) Reports regarding Ecstasy Utopian Pharmacology . Detailed essay discussing the history and uses of MDMA TheDEA.org An ecstasy user 's guide with detailed discussions of risks and scientific research . MDMA , Personality and Human Nature : The Power to Transform People . Essay by Bruce Eisner , author of Ecstasy : The MDMA Story Ecstasy : a Nurses View . Website created to show the risks related to the use of MDMA . Asia & Pacific Amphetamine-Type Simulants Information Centre Chemical Link page to external chemical sources . References ^ Freudenmann , R.W. et al. ( 2006 ) . The origin of MDMA ( ecstasy ) revisited : the true story reconstructed from the original documents . Addiction 101 , 1241-1245 . PMID 16911722 PDF ^ Benzenhöfer , U. and Passie , T. ( 2006 ) . The early history of `` Ecstasy '' . Nervenarzt 77 , 95-99. ( Article in German ) PMID 16397805 PDF ^ The Ecstasy Testing Program ^ Science and Technology Committee Report ( page 176 ) , 2006 ) . ^ Baumann MH , Wang X , Rothman RB. ( 2006 ) . `` 3 , 4-Methylenedioxymethamphetamine ( MDMA ) neurotoxicity in rats : a reappraisal of past and present findings . `` . Psychopharmacology . ^ Saunders , Nicholas ( 1995 ) . Interviews with two foremost researchers into neurotoxicity who hold opposing views . ^ Schwartz , Richard H and Miller , Norman S ( 1997 ) . `` MDMA ( Ecstasy ) and the Rave : A Review `` . ^ Bluelight 5-HTP FAQ ^ MDMA and 5-HTP information and advice ^ MAPS. Documents from the DEA Scheduling Hearing of MDMA , 1984-1988 . Baggott , Matthew , and John Mendelson. “MDMA Neurotoxicity” . Ecstasy : The Complete Guide . Ed . Julie Holland . Spring 2001 from www.erowid.com . de la Torre , Rafael et al. ( 2000 ) , Non-linear pharmacokinetics of MDMA ( `ecstasy' ) in humans . Br J Clin Pharmacol , 2000 ; 49 ( 2 ) : 104-9 de la Torre , Rafael & Farré , Magí ( 2004 ) . Neurotoxicity of MDMA ( ecstasy ) : the limitations of scaling from animals to humans . Trends in Pharmacological Sciences 25 , 505-508 . Erowid , Earth. “Do Antioxidants Protect Against MDMA Hangover , Tolerance , and Neurotoxicity ? ” Erowid Extracts . Dec 2001 ; 2 : 6-11 . Jennings , Peter . Ecstasy Rising , ABC television documentary. 2004-01-04 . Adam , David . Truth about ecstacy 's unlikely trip from lab to dance floor : Pharmaceutical company unravels drug 's chequered past , Guardian Unlimited , 2006-08-18 . Jones , Douglas C. et al. ( 2004 ) . Thioether Metabolites of 3 , 4-Methylenedioxyamphetamine and 3 , 4-Methylenedioxymethamphetamine Inhibit Human Serotonin Transporter ( hSERT ) Function and Simultaneously Stimulate Dopamine Uptake into hSERT-Expressing SK-N-MC Cells . J Pharmacol Exp Ther 311 , 298-306 . Kalant H. ( 2001 ) The pharmacology and toxicology of `` ecstasy '' ( MDMA ) and related drugs . CMAJ . Oct 2 ; 165 ( 7 ) : 917-28 . Review . PMID 11599334 Full Text Miller , R.T. et al. ( 1997 ) . 2 , 5-Bis- ( glutathione-S-yl ) -alpha-methyldopamine , a putative metabolite of ( +/- ) -3 , 4-methylenedioxyamphetamine , decreases brain serotonin concentrations . Eur J Pharmaco. 323 ( 2-3 ) , 173-80 . Abstract retrieved Apr 17 , 2005 , from PubMed . Monks , T.J. et al. ( 2004 ) . The role of metabolism in 3 , 4- ( + ) -methylenedioxyamphetamine and 3 , 4- ( + ) -methylenedioxymethamphetamine ( ecstasy ) toxicity . Ther Drug Monit 26 ( 2 ) , 132-136 . Morgan , Michael John ( 2000 ) . Ecstasy ( MDMA ) : a review of its possible persistent psychological effects . Psychopharmacology 152 , 230-248 . Shankaran , Mahalakshmi , Bryan K. Yamamoto , and Gary A. Gudelsky. “Ascorbic Acid Prevents 3 , 4 , -Methylenedioxymethamphetamine ( MDMA ) - Induced Hydroxyl Radical Formation and the Behavioral and Neurochemical Consequences of the Depletion of Brain 5-HT” . Synapse. 2001 ; 40 : 55-64 . Strote , Jared et al. ( 2002 ) . Increasing MDMA use among college students : results of a national survey . Journal of Adolescent Health 30 , 64-72 . Sumnall , Harry R. & Cole , Jon C. ( 2005 ) . Self-reported depressive symptomatology in community samples of polysubstance misusers who report Ecstasy use : a meta-analysis . Journal of Psychopharmacology 19 ( 1 ) , 84-92 . Vollmer , Grit . `` Crossing the Barrier '' . Scientific American Mind . June/July 2006 , 34-39 . Yeh , S. Y. “Effects of Salicylate on 3 , 4-Methylenedioxymethamphetamine ( MDMA ) -Induced Neurotoxicity in Rats” . Pharmacology Biochemistry and Behavior. 1997 ; Vol. 58 , No. 3 : 701-708 . Empathogen-entactogens - edit α-ET | Bk-MBDB | Bk-MDEA | DMMDA-2 | IAP | Bk-MDMA | MBDB | MDEA | MDA | MDMA | MMDA Hallucinogenic phenethylamines edit 2C-B , 2C-B-FLY , 2C-C , 2C-D , 2C-E , 2C-G , 2C-I , 2C-N , 2C-O , 2C-O-4 , 2C-P , 2C-T , 2C-T-2 , 2C-T-4 , 2C-T-7 , 2C-T-8 , 2C-T-9 , 2C-T-21 , 2C-TFM , 3C-E , 3C-P , Br-DFLY , DESOXY , DMMDA-2 , DOB , DOC , DOET , DOI , DOM , DON , Escaline , Isoproscaline , Lophophine , MDA , MMDA , Macromerine , Mescaline , Proscaline , TMA Categories : Articles with unsourced statements | Wikipedia articles needing factual verification | Alkaloids | Entactogens and Empathogens | Class A drugs | Schedule I controlled substances | Psychedelic phenethylamines | Criminology topics | Amphetamines In other languages : Български | Česky | Dansk | Deutsch | Español | Esperanto | Français | 한국어 | Hrvatski | עברית | Italiano | Nederlands | 日本語 | Norsk ( bokmål ) | Polski | Português | Русский | Русский | Српски / Srpski | Suomi | Svenska | Tiếng Việt | اردو | 中文 Baumann MH , Wang X , Rothman RB. 3 , 4-Methylenedioxymethamphetamine ( MDMA ) neurotoxicity in rats : a reappraisal of past and present findings. 2006 http : //www.ncbi.nlm.nih.gov/entrez/query.fcgi ? cmd=Retrieve & db=pubmed & dopt=Abstract & list_uids=16541247 & query_hl=1 & itool=pubmed_docsum 16541247 Psychopharmacology Interviews with two foremost researchers into neurotoxicity who hold opposing views Saunders , Nicholas 1995 http : //ecstasy.org/info/interviews.html Schwartz , Richard H and Miller , Norman S MDMA ( Ecstasy ) and the Rave : A Review 1997 http : //pediatrics.aappublications.org/cgi/content/full/100/4/705 Documents from the DEA Scheduling Hearing of MDMA , 1984-1988 MAPS http : //www.maps.org/dea-mdma/ he 