|Summary sheet: MDMA|
|Common names||MDMA, Molly, Mandy, Emma, MD, Ecstasy, E, X, XTC, Rolls|
|Psychoactive class||Stimulant / Entactogen|
|Routes of Administration|
3,4-Methylenedioxymethamphetamine (also known as ecstasy, E, XTC, molly, mandy, and MDMA) is an entactogen substance of the amphetamine class. MDMA is considered to be the prototype entactogen and is part of a group that includes substances like MDA, methylone, and 6-APB. It acts primarily by increasing the activity of neurotransmitters serotonin, dopamine, and norepinephrine in the brain.
MDMA was first synthesized in 1912. It first saw use in underground psychotherapy circles in the 1970s. In the 1980s, MDMA spread into nightlife and rave culture and was subsequently banned. In 2014, MDMA was estimated to be one of the most popular recreational drugs used in the world, alongside cocaine and cannabis. Researchers are investigating whether MDMA may assist in treatment-resistant posttraumatic stress disorder (PTSD), social anxiety in autistic adults, and anxiety in those with life-threatening illness.
Typical effects of MDMA include anxiety relief, disinhibition, enhanced empathy and sociability, relaxation, and euphoria. MDMA is classified as an entactogen due to how it facilitates feelings of closeness with oneself and others. It is commonly associated with dance parties, raves, and electronic dance music. Tolerance to MDMA builds unusually quickly and many users report that it dramatically loses its effectiveness if used on a regular basis. It is commonly recommended to wait one to three months between uses to give the brain enough time to restore serotonin levels.
Acute adverse effects of MDMA are usually the result of high or multiple doses, although single dose toxicity can occur in susceptible individuals. The most serious short-term physical health risks of MDMA are overheating and dehydration, which has resulted in deaths. MDMA has also been shown to be neurotoxic at high doses. However, it is unclear if this risk applies to typical users. It is highly advised to use harm reduction practices if using this substance.
- 1 History and culture
- 2 Chemistry
- 3 Pharmacology
- 4 Subjective effects
- 5 Forms
- 6 Research
- 7 Toxicity and harm potential
- 8 Legal status
- 9 See also
- 10 External links
- 11 References
History and culture
MDMA was originally synthesized in 1912 by the Merck chemist Anton Köllisch. Köllisch was interested in developing substances that would help manage excess bleeding and was interested in the activity of MDMA, an intermediary in the production of hydrastinine, a hemostatic agent used at the time. In 1965, Alexander Shulgin synthesized MDMA while conducting experiments with methylenedioxy-substituted compounds but did not test the psychoactivity of the compound.
Around 1975, Shulgin heard about the effects of MDMA from a student. After hearing several more stories about the self-administration of MDMA, he decided to experiment with it. Shulgin was impressed with the effects of the substance and thought it could have therapeutic applications. Shulgin advertised the substance to therapists and psychiatrists for medical use, and it eventually became quite popular in the medical world for the treatment of various psychiatric disorders. During this time, the psychotherapist Dr. Leo Zeff came out of retirement and subsequently introduced the then-legal MDMA to over 4,000 patients. Then known as "Adam", from the mid-1970s to the mid-1980s there was a growth of clinicians using MDMA around California.
The recreational use of MDMA became popular at around the same time, particularly in nightclubs, and eventually caught the attention of the Drug Enforcement Administration. After several hearings, a US Federal Administrative Law Judge recommended that MDMA should be made a Schedule III controlled substance so that it could be used in the medical field. Despite this, the director of the DEA overruled this and classified MDMA as a Schedule I controlled substance.
In the United Kingdom, the 1971 Misuse of Drugs Act, which had already been altered in 1977 to include all ring-substituted amphetamines like MDMA, was further amended in 1985 to refer specifically to Ecstasy, placing it in the Class A category.
MDMA, or 3,4-methylenedioxy-N-methylamphetamine, is a synthetic molecule of the substituted amphetamine class. Molecules of the amphetamine class all contain a phenethylamine core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain, with an additional methyl substitution at Rα. In addition to this, MDMA contains a methyl substitution on RN, a feature it shares with methamphetamine. Critically, the MDMA molecule also contains substitutions at R3 and R4 of the phenyl ring with oxygen groups -- these oxygen groups are incorporated into a methylenedioxy ring through a methylene bridge. MDMA shares this methylenedioxy ring with other entactogens and stimulants like MDA, MDEA and MDAI.
MDMA acts primarily as a releasing agent of the three principal monoamine neurotransmitters serotonin, norepinephrine, and dopamine through its action at trace amine-associated receptor 1 (TAAR1) and vesicular monoamine transporter 2 (VMAT2). MDMA is a monoamine transporter substrate (i.e. a substrate for the transporters for dopamine (DAT), norepinephrine (NET), and serotonin (SERT), enabling it to enter monoaminergic neurons via these neuronal membrane transport proteins. By acting as a monoamine transporter substrate, MDMA produces competitive reuptake inhibition at the neuronal membrane transporters, competing for endogenous monoamines for reuptake.
MDMA inhibits both vesicular monoamine transporters (VMATs), the second of which (VMAT2) is highly expressed within monoamine neurons vesicular membranes. Once inside a monoamine neuron, MDMA acts as a VMAT2 inhibitor and a TAAR1 agonist. The inhibition of VMAT2 by MDMA results in increased concentrations of the aforementioned monoamine neurotransmitters in the cytosol of the neuron. Activation of TAAR1 by MDMA triggers protein kinase signaling events which then phosphorylates the associated monoamine transporters of the neuron.
Subsequently, these phosphorylated monoamine transporters either reverse transport direction – i.e. move neurotransmitters from inside the cell to the synaptic cleft – or withdraw into the neuron, respectively producing the inflow of neurotransmitters and noncompetitive reuptake inhibition at the neuronal membrane transporters. MDMA has ten times more affinity for uptake at serotonin transporters compared to dopamine and norepinephrine transporters and consequently has mainly serotonergic effects.
MDMA also has weak agonist activity at postsynaptic serotonin receptors 5-HT1 and 5-HT2 receptors, and its more efficacious metabolite MDA likely augments this action. Cortisol, prolactin, and oxytocin quantities in serum are increased by MDMA.
Additionally, MDMA is a ligand at both sigma receptor subtypes, though its efficacies at these receptors and the role that they play have yet to be elucidated.
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. These effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances of inducing a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.
- Stimulation & Sedation - MDMA is commonly regarded as being stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes MDMA a popular choice for musical events such as festivals and raves. The distinct style of stimulation which MDMA presents can be described as forced. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily body shakes and vibrations become present, resulting in an unsteadiness of the hands and a general lack of motor control. This can also paradoxically be accompanied by persistent or wave-like feelings of deep sedation and relaxation, typically at moderate to strong doses.
- Spontaneous bodily sensations - The "body high" of MDMA can be characterized as a moderate to extreme euphoric tingling sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
- Tactile enhancement
- Bodily control enhancement
- Stamina enhancement
- Abnormal heartbeat
- Increased blood pressure
- Increased heart rate
- Temperature regulation suppression
- Increased bodily temperature  - As MDMA is a serotonin releasing agent, a rise in core body temperature tends to be a significant and consistent part of the experience. Caution must be taken as too high of a dose in a dangerously hot environment can result in serotonin toxicity, which can be fatal if left untreated.
- Muscle contractions
- Increased perspiration
- Dehydration - Users may experience signs of dehydration such as dry mouth and sweating while dancing or in a hot environment. However, MDMA causes water retention and dilution of electrolytes. Consequently, overhydration has caused death from water intoxication. It is advised that users have hydration available, drink to thirst and never over-drink.
- Dry mouth
- Difficulty urinating - Higher doses of MDMA result in an overall difficulty when it comes to urination. This is caused by MDMA’s promotion of the release of anti-diuretic hormone (ADH); ADH is responsible for regulating urination. This effect can be lessened by relaxing, but can also be relieved by placing a hot flannel over the genitals to encourage blood flow.
- Vibrating vision - At high doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as nystagmus.
- Nausea - This effect is most commonly present during the come up phase of the experience, and at higher doses, but has been reported to occur spontaneously in those who seem to be susceptible to it.
- Appetite suppression
- Pain relief - This effect is generally not as powerful as it is with opioids.
- Excessive yawning
- Pupil dilation
- Orgasm suppression
- Temporary erectile dysfunction
- Teeth grinding - This effect when experienced alongside the cognitive and physical euphoria can often lead to users mildly or intensely clenching their jaw muscles, sometimes even to the point where the individual’s facial expression begins to change. This is sometimes colloquially called “gurning” and is typically only experienced in moderate to high dosages.
- Seizure - This is a rare effect but is thought to be able to occur in those predisposed to them, especially when taking higher doses or redosing while in physically taxing conditions such as being dehydrated, fatigued, undernourished, or overheated.
The visual effects of MDMA occur more selectively and less consistently than any of the traditional psychedelics. This has resulting in many people disregarding the psychedelic aspects of MDMA as a myth or rumor, despite a large body of anecdotal reports suggesting otherwise. The effects can not be guaranteed to manifest themselves, but are the most likely to occur with chemically pure MDMA at high doses, towards the end of the experience and particularly if the user has been smoking cannabis. They also seem more likely to occur if the user has prior experience with psychedelics.
MDMA presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctly present. These generally include:
The visual geometry produced by MDMA can be characterized as more similar in appearance to that of psilocin than LSD. It can be comprehensively described through its variations as primarily intricate in complexity, abstract in form, organic in style, structured in organization, dimly lit in lighting, mostly monotone in colour with blues and greys, glossy in shading, sharp in edges, small in size, fast in speed, smooth in motion, equal in round and angular corners, non-immersive in-depth and consistent in intensity. At higher doses, they are significantly more likely to give rise to states of level 8A visual geometry over level 8B. Many users report that MDMA geometry presents itself with dark and menacing emotional vibes with a synthetic and nerve-racking feel to them.
MDMA is capable of producing a unique range of low and high-level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of most other commonly used psychedelics. These effects are far more common during either the very peak or offset of the experience and commonly include:
- External hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - This effect shares many similarities to those produced by deliriant substances, but does not manifest itself consistently and usually happens only at heavy, likely toxic doses. It can be comprehensively described through its variations as delirious in believability, autonomous in controllability and solid in style. They usually follow themes of memory replays and semi-realistic or expected events. For example, people could be casually holding objects or performing actions which one would expect them to be in real life before disappearing and dissolving under further inspection. Common examples of this include seeing people wearing glasses, or hats when they are not and mistaking objects for human beings or animals.
- Internal hallucinations - The internal hallucinations which MDMA induces are only present as spontaneous breakthroughs at extremely high doses. This effect's variations are delirious in believability, interactive in style, new experiences in content, autonomous in controllability and solid in appearance. The most common way in which they manifest themselves is through hypnagogic scenarios which the user may experience as they are drifting off to sleep after a night of use; these can usually be described as memory replay from the previous several hours. These are brief and fleeting, but frequent and completely believable and convincing as they happen. In terms of the theme, they often are in the form of conversations with people or instead manifest as bizarre and extremely nonsensical plots.
- Peripheral information misinterpretation
The general head space of MDMA is described by many as one of pronounced mental stimulation, feelings of love, empathy, openness and a pronounced sense of rejuvenation and euphoria. It is capable of producing a large number of cognitive effects that are typically associated with entactogens and stimulants.
The most prominent of these effects include:
- Amnesia - Very high doses can sometimes cause partial amnesia.
- Anxiety suppression
- Empathy, affection, and sociability enhancement - This particular effect is usually more consistent, pronounced, powerful and therapeutic with MDMA than any other known substance. It is the most evident and noticeable effect within any MDMA experience and dominates the head space. With time and repeated use, however, this effect becomes severely diminished as the perspective it instills becomes fully grounded and already in place, making people feel merely stimulated and euphoric with no new found urges to communicate with others. Some users report that MDMA "loses its magic" with as few as ten experiences, while others have reported hundreds of uses before the empathic qualities disappear. This does not appear to be valid for all users, however, with many users reporting that they have not experienced any decrease in quality of the experience despite dozens or even hundreds of uses.
- Emotion enhancement
- Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within MDMA and are likely a direct result of a concerted mechanism of serotonin, norepinephrine, and dopamine release.
- Increased music appreciation
- Time compression - Strong feelings of time compression are commonly produced by MDMA and speed up the experience of time noticeably.
- Increased libido
- Creativity enhancement
- Motivation enhancement
- Focus enhancement - This component is most effective at low to moderate doses, as higher doses will usually impair attention and concentration, particularly during the "come down" phase of the experience.
- Immersion enhancement
- Ego inflation
- Increased sense of humor
- Compulsive redosing
- Thought acceleration
- Delirium & Confusion - This effect typically only occurs with overly high doses, and is associated with temperature dysregulation and overheating, particularly when MDMA is taken in crowded, physically strenuous environments that leaves the user unable to cool off, rest, or rehydrate adequately.
- Tinnitus - This effect is rare, but typically manifests as a muffled roaring in the ears, affected by whether the user is upright or laying down. It is most commonly reported when using in conjunction with other substances but can manifest on its own at higher doses. This may be accompanied by partial or total, yet highly temporary (on the order of a minute), hearing loss, especially when standing.
- Existential self-realization - Although this effect is present, it is not quite as pronounced or as consistent when compared to hallucinogens such as mescaline, psilocybin, LSD or MXE. This component is unique to MDMA in that it almost always comes about in the form of self-affirmation and a personal appreciation for one’s self as well as others.
- Unity and interconnectedness - Experiences of lower-level unity and interconnectedness are commonly produced by MDMA. This component most consistently manifests itself within large crowds at raves and musical events in the form of "becoming one with the crowd." Music is said to consistently intensify this effect as well.
The effects which occur during the offset of an entactogen or stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and is thought to occur because of neurotransmitter depletion. Its effects commonly include:
- Appetite suppression
- Brain zaps
- Cognitive fatigue
- Dream suppression or Dream potentiation - Although this substance have been known to suppress dreaming, some users note extremely strange and sometimes scary dreams for several nights after taking large doses of MDMA.
- Sleep paralysis - Some users report a higher incidence of experiencing sleep paralysis after consuming MDMA.
- Motivation suppression
- Thought deceleration
- Thought disorganization
- Suicidal ideation
Anecdotal reports which describe the effects of this compound within our experience index include:
- Experience:0.75g MDMA - Possibly some MDA through metabolisation?
- Experience:150mg MDMA + 20mg 2C-B - I designed it this way myself
- Experience:250mg MDA / 250mg MDMA - unnecessarily large dosage
- Experience:450mg MDMA - Quarter consumption through whole night
Additional experience reports can be found here:
Since the 1980s, MDMA has become widely known as "Ecstasy" (shortened to "E", "X", or "XTC"), usually referring to its street forms as illicitly pressed pills or tablets. The American term "Molly" and the British equivalent term "Mandy" originally referred to crystal or powder MDMA that was purported to be of high purity and free of adulteration. However, it has since evolved into a generic street term for any number of euphoric stimulants that are sold in powder or crystal form.
MDMA can be found in a number of forms:
- Pills are the most common form in which MDMA is sold, and are commonly referred to as Ecstasy. They often contain other substances or adulterants that range from anything from MDA, MDEA, amphetamine, methamphetamine, caffeine, 2C-B or mCPP to synthesis by-products such as MDP2P, MDDM or 2C-H. They can also contain an array random substances such as research chemicals, prescription drugs, over-the-counter drugs, poisons or nothing at all. It is strongly recommended to take harm reduction measures such as using a reagent testing kit when ingesting unknown pills.
- Crystals or Powder (commonly called Molly) is a white to brownish substance which can be dissolved, crushed, put into gel capsules or edible paper ("parachutes"). It can be administered orally, sublingually, buccally or via insufflation ("snorting" or "sniffing").
MDMA-assisted psychotherapy for PTSD
In 2011, a pilot study on 20 patients demonstrated promising results in the treatment of post-traumatic stress disorder (PTSD). After two or three MDMA-assisted psychotherapy sessions, 83% of the patients no longer met the criteria for PTSD, compared to only 25% in the control group where MDMA was replaced with a placebo. The results sustained at two and twelve months after the treatment. The MDMA and placebo group both received non-drug psychotherapy before and after the sessions. In the study, a dose of 125mg MDMA plus a 62.5mg supplemental dose after 2 hours have been administered. After completion of the study, the patients from the placebo group also received MDMA-assisted psychotherapy, and a long-term follow-up study of 19 patients published in 2013 shows that even after three years the positive results maintained.
In 2017, the FDA granted MDMA a breakthrough therapy designation for PTSD, meaning if studies show promise, a review for potential medical use could occur more quickly. Phase 3 clinical trials to look at effectiveness and safety expected to begin in 2018.
MDMA is typically produced and consumed in its racemic form (known as SR-MDMA) which consists of equal parts S-MDMA and R-MDMA. A 2017 study found that high doses of R-MDMA administered in mice increased prosocial behavior and facilitated fear-extinction learning but did not produce hyperthermia or signs of neurotoxicity. This is thought to owe itself to the lower dopamine release R-MDMA displays relative to SR-MDMA. This result suggests that R-MDMA may be a safer and more viable therapeutic than racemic MDMA.
Toxicity and harm potential
The short-term physical health risks of MDMA consumption include dehydration, insomnia, hyperthermia, and hyponatremia. Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further due to the excessive amounts of dehydration they may cause.
The exact toxic dosage is unknown, but considered to be far greater than its effective dose.
The neurotoxicity of MDMA use has long been the subject of debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDMA is most certainly neurotoxic in some form.
Administration of MDMA causes subsequent down-regulation of serotonin reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA. Other studies have suggested that the brain may recover from serotonergic damage.
It is thought that MDMA's metabolites play a large role in the in the uncertain levels of neurotoxicity. For example, a metabolite of MDMA called alpha-MethylDopamine (which is known to be toxic to dopamine neurons) was thought believed to be involved in the toxicity of MDMA to serotonin receptors. However, one study found this to not be the case as direct administration of aMD did not cause neurotoxicity. Additionally, MDMA injected directly into the brain was found to not be toxic, implying a metabolite is responsible for the toxicity when MDMA is administered via insufflation or oral consumption.
This study found that although aMD is involved, it is a further metabolite of aMD involving glutathione that is primarily responsible for the selective damage to 5-HT receptors triggered by MDMA/MDA.This metabolite forms in higher concentrations when core temperature is elevated. It is taken up into serotonin receptors by its transporters and metabolized by MAO-B into a reactive oxygen species which can cause neurological damage.
The long-term heavy use of MDMA has been shown to be cardiotoxic and may lead to valvulopathy (heart valve damage) through its actions on the 5-HT2B receptor. In one study, 28% of long-term users (2-3 doses per week for a mean of 6 years, mean of age 24.3 years) had developed clinically evident valvular heart disease.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
As with other stimulants, the chronic use of MDMA can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if one suddenly stops their usage.
Tolerance to many of the effects of MDMA develops with prolonged and repeated use. This results in users having to administer increasingly larger doses to achieve the same effects. Upon a single administration, it takes about 1 month for the tolerance to be reduced to half and 2.5 months to be back at baseline (in the absence of further consumption). MDMA presents cross-tolerance with all dopaminergic and serotonergic stimulants, meaning that after the consumption of MDMA all stimulants will have a reduced effect.
Although many psychoactive substances are safe to use on their own, they can become dangerous or even life-threatening when taken with other substances. The list below contains some potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses but still increase the possibility of injury of death. Independent research should always be conducted to ensure that a combination of two or more substances is safe before consumption.
- 25x-NBOMe/25x-NBOH - Members of the 25x family are highly stimulating and physically straining. Combinations with stimulants should be avoided due to the risk of excessive stimulation. This can result in panic attacks, thought loops, seizures, increased blood pressure, vasoconstriction, and heart failure in extreme cases.
- Alcohol - Alcohol can be dangerous to combine with stimulants due to the risk of accidental over-intoxication. Stimulants mask the sedative effects of alcohol, which is the main factor people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects of alcohol are left unopposed, which can result in blackouts and respiratory depression. If combined, one should strictly limit themselves to only drinking a certain amount of alcohol per hour.
- DXM - Combinations with DXM should be strictly avoided due to DXM's effects on serotonin and dopamine reuptake. This can lead to panic attacks, hypertensive crisis, or serotonin syndrome.
- MXE - Combinations with MXE may dangerously elevate blood pressure and increase the risk of psychosis.
- Tramadol - Tramadol lowers the seizure threshold. Combinations with stimulants may further increase this risk.
- Stimulants - The neurotoxic and cardiotoxic effects of MDMA may be increased when combined with other stimulants.
- Cocaine - This combination may increase strain on the heart to dangerous levels.
- Psychedelics - There is some evidence that the combination of MDMA and serotonergic psychedelics may increase the neurotoxicity of MDMA. 
Serotonin syndrome risk
Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.
- MAOIs such as syrian rue, banisteriopsis caapi, 2C-T-7, αMT, phenelzine, selegiline, and moclobemide
- Serotonin releasers such as MDMA, 4-FA, methamphetamine, methylone and αMT
- Selective serotonin re-uptake inhibitors (SSRIs)
- Serotonin-norepinephrine reuptake inhibitors (SNRIs) such as tramadol and DXM
There is an increased risk of serotonin syndrome when MDMA is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if MDMA is taken with SSRIs and SNRIs, it will be significantly less active or may not produce any distinguishable effects at all.
- Austria: MDMA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).
- Belgium: MDMA is illegal to possess, produce and sell in Belgium.
- Brazil: MDMA is illegal to possess, produce and sell in Brazil.
- Canada: MDMA is a Schedule I drug in Canada.
- Denmark: MDMA is illegal to possess, produce and sell in Denmark.
- Egypt: MDMA is a Schedule III drug in Egypt.
- Finland: MDMA is illegal to possess, produce and sell in Finland.
- Germany: MDMA is an Anlage I controlled drug in Germany.
- Latvia: MDMA is a Schedule I drug in Latvia.
- The Netherlands: MDMA is illegal to possess, produce and sell in the Netherlands.
- New Zealand: MDMA is a Class B1 drug in New Zealand.
- Norway: MDMA is illegal to possess, produce and sell in Norway.
- Sweden: MDMA is illegal to possess, produce and sell in Sweden.
- Switzerland: MDMA is illegal to possess, produce and sell in Switzerland.
- United Kingdom: MDMA is a Class A drug in the UK.
- United States: MDMA is a Schedule I drug in the US.
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