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MDMA

MDMA, or 3,4-methylenedioxy-N-methamphetamine is a unique psychedelic amphetamine with stimulant, euphoriant, and empathogenic/entactogenic effects. Unlike amphetamine or methamphetamine, MDMA has a much larger effect on serotonin as well as a marked effect on oxytocin and prolactin secretion. It is used recreationally for its ability to create intense euphoria, encourage social bonding, and amplify the senses, most especially sound and touch. It is often sold under the names "ecstasy" or "molly," although genuine pure MDMA is difficult to reliably obtain. In therapeutic settings, the drug has been used for couples therapy, depression, and the treatment of post traumatic stress disorder. The Multidisciplinary Association For Psychedelic Studies is currently studying MDMA as an adjunct to therapy in the treatment of PTSD in multiple countries around the world.

Contents




[top]Introduction to MDMA


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.


[top]Using MDMA


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.

[top]Administration of MDMA

[top]Routes of administration

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.

[top]Dosage

[top]Recreational


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:
MDMA Dosage  
Threshold 30mg
Light 40-75mg
Common (small or sensitive people) 60-90mg
Common (most people) 75-125mg
Common (large or less sensitive people) 110-150mg
Strong 150-200mg
Heavy 200mg and up

[top]Therapeutic


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).

[top]Effects of MDMA

[top]Subjective effects


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.

[top]Positive

  • mild to extreme mood lift, euphoria
  • increased willingness to communicate
  • increase in energy (stimulation)
  • ego softening
  • decreased fear, anxiety, and insecurities
  • feelings of comfort, belonging, and closeness to others
  • feelings of love and empathy
  • forgiveness of self and others
  • a sense of inner peace and acceptance of self, others, and the world
  • increased awareness & appreciation of music
  • increased awareness of senses (eating, drinking, smell)
  • increased pleasure from the sense of touch and being touched
  • life-changing spiritual experiences
  • sensations bright and intense
  • urge to hug and kiss people
  • analgesia, anti-nociception, decreased pain perception

[top]Neutral

  • appetite loss
  • visual distortion
  • rapid, involuntary eye jiggling (nystagmus)
  • mild visual hallucinations (uncommon)
  • moderately increased heart rate and blood pressure
  • restlessness, nervousness, shivering
  • change in body temperature regulation
  • upwellings of unexpected emotion, emotional liability
  • strong desire to do or want more when coming down

[top]Negative

  • inappropriate and/or unintended emotional bonding
  • anxiety or paranoia (less common than opposite)
  • agitation (less common than opposite)
  • xerostomia (dry mouth)
  • tendency to say things you might feel uncomfortable about later
  • mild to extreme jaw clenching (trismus), tongue and cheek chewing, teeth grinding (bruxism)
  • difficulty concentrating & problems with activities requiring linear focus
  • short-term memory scramble or loss & confusion
  • muscle tension
  • insomnia, inability to fall asleep when physically tired
  • erectile dysfunction and difficulty reaching orgasm
  • increase in body temperature, hyperthermia, dehydration
  • hyponatremia (sodium deficiency as a result of too much water)
  • nausea and vomiting
  • headaches, dizziness, loss of balance, and vertigo
  • sadness on coming down, sense of loss or immediate nostalgia
  • post-trip crash- unpleasantly harsh comedown from the peak effect
  • hangover the next day, lasting days to weeks
  • mild depression and fatigue for up to a week
  • severe depression and/or fatigue (uncommon)
  • possible strong urge to repeat the experience, though not physically addictive
  • possible psychological crisis requiring hospitalization (psychotic episodes, severe panic attacks, etc) (rare)
  • possible liver toxicity (rare)
  • possible neurotoxicity (controversial; very likely but has been exaggerated and can be combatted)
  • small risk of death; approximately 2 per 100,000 users have extreme negative reactions resulting in death (rare)

[top]Duration


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:
Duration
Total Duration 3-5 hrs
Onset 20-90 mins
Come up 5-20 mins
Plateau 2-3 hrs
Come down 1-2 hrs
After effects 2-24 hrs
Hangover 2-72+hrs

In graph form:

[top]Combinations with MDMA


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.

[top]MDMA and other stimulants

[top]Amphetamine


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.

[top]Methamphetamine

[top]Cocaine

[top]Caffeine


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.[REFERENCE NEEDED]

[top]MDMA and alcohol

[top]MDMA and depressants

[top]Benzodiazepines

[top]GHB/GBL

[top]Opiates/Opioids

[top]MDMA and cannabis


Combining MDMA and cannabis can have varying effects depending on the user. Generally the user will gain an enhanced high from the MDMA, this may alter depending how far on there trip they are. Quite often the user will be too affected to realize the high until reaching the comedown. In some cases it will remove the sensation achieved from the MDMA. People who experiment will feel more inclined to relax and cuddle up. Having water near handy is essential as dehydration becomes a major issue.

[top]MDMA and nitrous oxide

[top]MDMA and viagra

[top]MDMA and psychedelics

[top]LSD

[top]Psilocybin mushrooms

[top]DMT

[top]2C-B

[top]MDMA and antidepressants

[top]MAOI's


Serotonin syndrome can occur following concomitant use of MDMA and MAOI's.
[top]Moclobemide
Moclobemide is a monoamine oxidase inhibitor prescribed as an antidepressant. Four deaths have been reported from moclobemide and MDMA combination[1]. In both cases the cause of death couldn't be clearly identified at autopsy. The authors suggested that a serotonin syndrome might have occured as a result from this combination, as the clinical observations, althought limited, are consistent with a serotonin syndrome.

[top]SSRI's

[top]TCA's

[top]MDMA and antipsychotics

[top]MDMA and research chemicals

[top]Tryptamines

[top]Phenethylamines

[top]Cannabinoids

[top]Piperazines

[top]Other drugs

[top]Ritonavir


Ritonavir, a HIV-1 protease inhibitor, interacts with cytochrome P450 enzymes. In particular, Ritonavir inhibits CYP2D6, the main metabolization pathway of MDMA [GENREF]. Thus consumption of MDMA while under ritonavir treatment may lead to clinically significant effects:

- A patient infected with HIV-1 reported prolonged effect from a small dose of MDMA.
- A death has been reported[2]:

Quote:
A 32-year-old HIV-positive man, who added ritonavir 600 mg bd to his antiretroviral regimen of zidovudine and lamivudine, became unwell within hours after having taken two and a half tablets of ecstasy, estimated to contain 180 mg of MDMA. He was hypertonic, sweating profusely, tachypneic, tachycardic, and cyanosed. Shortly after he had a tonic clonic seizure and a cardiorespiratory arrest. Attempts at resuscitation were unsuccessful. Blood concentrations obtained post-mortem showed an MDMA concentration of 4.56 mg/L, in the range of that reported in a patient with a life threatening illness and symptoms similar to this patient after an overdose of 18 tablets of MDMA

[top]Different Uses of MDMA

[top]Recreational use

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.

[top]Therapeutic Use


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:

Quote:
What does MDMA do that could be beneficial to a patient? First, it powerfully suppresses emotional fear, to such an extent that people under the influence are often able to openly discuss deeply traumatic events, such as rape, suicide attempts, etc. MDMA produces complete emotional honesty with yourself. Second, it is a moderately powerful stimulant, not simply allowing the patient to sit there indifferently, but prodding them to examine and discuss their lives. Animal experiments also indicate that MDMA enhances learning, allowing what is discovered and experienced during the MDMA state to strongly affect and stay with the patient long after the session.

The net result is a patient who, for a few hours, is almost perfectly primed to grow as a person. Their fears are gone. They feel strong, at peace, and able to handle almost anything emotionally. They're also hyperactive and extremely talkative, eager to explore ideas and issues and share their thoughts. The 'hyper-focused' MDMA state can also allow the therapist to steer the conversation into otherwise highly charged topics...they don't have to tease the story out of them; the patient is truly ready to talk about what's on their mind. And finally, the experience seems to allow a high degree of incorporation of what they learn about themselves back into their normal lives.
It is important to keep in mind that while for some, MDMA alone can be enough to allow the alleviation of depression or to stimulate the reconnection between a husband and a wife, in the context of clinical therapy it is not viewed as a panacea. MDMA, like any other drug, will not automatically allow someone to come to terms with a traumatic incident, it can only make it easier to do so. It can put the patient in a more receptive, forgiving, or happier state, but it is just as necessary that the patient desire to get better and that the therapist continue to do whatever necessary to help them achieve their goal.


[top]Pharmacology of MDMA


LD50 (mg/kg) (as the hydrochloride)[3] :
Mice : 97 intraperitoneally
Rat : 49 intraperitoneally
Guinea pig : 98 intraperitoneally

[top]Bioavailability


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.


[top]The dangers of MDMA


This section concerns the medical problems associated with the use of MDMA. The pharmacological origin of a problem can be found in the pharmacology section.

[top]Neurotoxicity


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.

[top]Hepatoxicity


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.

[top]Prevention and treatment


Liver transplant is the only option in some cases. Althought some patients die after liver transplantation, a significant number recovers.

[top]Reported deaths


Some death have occured following severe hepatic damage. In particular, deaths occured in drug-naive subjects after consumming a low dose of MDMA. More than 70 deaths have been reported between 1990 and 1998.

[top]Cardiovascular risk


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.

[top]Dehydration


This condition is not directly caused by MDMA, but rather by behavioral and environmental causes like dancing for long periods in a hot environment. No deaths are reported due to dehydration at the date of 2015. Contrary to what is written and said in various websites, dehydration is not a dangerous condition and must not be confused with the frequently associated hyperthermia (a life threatening condition, see next section).

[top]Hyperthermia

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 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.

Hyperthermia generally result from a combination of causes rather than a definite behavior or toxic effect of MDMA. In a study[4]., the authors mentionned the possible implication of a genetic predisposition to defective metabolism of MDMA, especially CYP2D6 deficiency. Hyperthermia is very rarely associated with hyponatremia.


Symptoms include :
- Tonic-clonic seizure
- High body temperature (> 40C)
-

[top]Prevention and treatment


Simple cooling is a generally effective treatment.[5]

[top]Reported deaths


Some death cases have been reported from hyperthermia.

The following case was reported[4]:

Quote:
A 20 years-old woman was found unresponsive at a rave. She was as hot on the touch and on the way to hospital had a tonic-clonic seizure and became pulseless and apneic. Aggressive ressucitation was unsuccessful. An autopsy showed gross pulmonary congestion and edema. She had acute neural ischemia and mild hepatic steatosis, without the evidence of myocardiac damage. Her blood ecstasy concentration was 1.21 mg/L. Death was reported to have been secondary to ecstasy toxicity.

[top]Hyponatremia


Hyponatremia consecutive to a SIADH (Syndrome of Inappropriate AntiDiuretic Hormone secretion) has been reported. Excessive fluid intake is generally associated with hyponatremia. Association of hyponatremia and hyperthermia is extremely rare.

A review [6] analyzed 32 cases of hyponatremia. Only 4 of them were males subjects, suggesting that female subjects are more prone to hyponatremia than male subjects.

Symptoms include [6] :
- headache
- cerebral edema
- cardiac arrest
- hyperthermia
- hypotension
- respiratory arrest
- seizure
- respiratory depression
- pulmonary edema on chest X-ray
- electrocardiogram abnormalities
- altered mental status

[top]Prevention and treatment


Initial treatment of hyponatremia has an importance to reduce mortality. A treatment with an hypertonic saline solution is recommended. A higher risk of death is observed when other treatments, like diuretics and water restriction, are choosen.

Hyponatremia can be prevented by avoiding excess water ingestion. The ingestion of fruit juices or "sports" type drinks may help to prevent hyponatremia and counteract dehydration[NOT REFERENCED].

[top]Reported deaths


Some deaths resulting from hyponatremia have been reported[2][6].

The following case has been reported from new Zealand[2]:

Quote:
A 27 year-old woman was admitted to the intensive care unit with coma and respiratory arrest. She had been seen taking two ecstasy tablets while dancing at a nightclub 5 hours before admission. She had drunk copious amounts of water to cool herself. When she reached the hospital, her Glasgow score was 3 and she was in respiratory arrest with fixed dilated pupils. Her serum sodium concentration was 124 mmol/L with a low serum osmolarity (267 mmol/L) and normal renal function. Her toxicology screen was positive for ethanol, and MDMA was found in her serum. The electrocardiogram showed a sinus tachycardia without ischemia, and a chest X-ray showed gross pulmonary edema. A CT scan of the brain showed generalized cerebral edema, diffuse cerebral swelling, and significantly increased intracranial pressure; the basal cisterns and extracerebelar spaces were completely effaced. Brain death was confirmed by cerebellar angiography, which showed no intracranial flow in the carotid of vertebral arteries. The post-mortem report confirmed marked cerebral edema with signs of cerebellar tonsillar herniation.
Other famous cases include those of Leah Betts, Anna Woods and Sasha Rodriguez.

[top]Hyperkalemia


Hyperkalemia has been reported in a fatal case of MDMA toxicity. The authors suggested that the hyperkalemia could have been induced by an hypermetabolic state[2].

[top]Overdose


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 50 mg/kg, as the figures for mice is 97 mg/kg, rats 49 mg/kg and guinea pigs 98 mg/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.

[top]Hematologic problems


Transient anemia has been associated with anemia[X].

[top]Skin

[top]Urinary tract

[top]Mouth

Ulceration of oral mucosa from contact with MDMA has been reported[7]. Among regular (undefined) ecstasy users the occurrence of mouth ulcer seems to be rather frequent one or two days after MDMA ingestion (8.2% of 466 interviewed subjects 24-48h after ingestion). A few cases have also been recorded[7], where gingivitis probably resulted from prolonged contact of MDMA with oral mucosa.

MDMA-induced jaw clenching may lead to tooth wearing, especially in the molar region[7]. The condition is worsen by regular consumption of acidic soft drinks and sweet things and by the decreased saliva production.

[top]Attenuating toxicity

[top]Deaths

The question of whether a decease can be attributed to MDMA is complex, as in most cases other factors contribute to the death. Therefore, rates of death attributed to MDMA are very dependent on how ecstasy-related deaths are defined by the authors.

MDMA-related deaths data are available from np-SAD and GMR (General Mortality Register) registry databases. From 1993 to 2006 there was an average (in the UK) of 17 deaths per year involving only MDMA, and 33 for which co-drug use was reported [REFGMR].


[top]Chemistry of MDMA


Systematic (IUPAC) name:(RS)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Synonyms:()-1,3-benzodioxolyl-N-methyl-2-propanamine; ()-3,4-methylenedioxy-N-methyl-α-methyl-2-phenethylamine; DL-3,4-methylenedioxy-N-methylamphetamine; 3,4-methylenedioxymethamphetamine
Molecular Formula:C11H15NO2, C11H15NO2.HCl (hydrochloride), C11H15NO2.H3PO4 (phosphate)
Molar mass:193.24 g/mol, 229.70 g/mol (hydrochloride), 291.24 g/mol (phosphate) [8]
CAS Registry Number:42542-10-9, 64057-70-1 (hydrochloride)
Melting Point:Hydrochloride 147-148 C (crystals from isopropanol/n-hexane), 152-153C (crystals rfrom isopropanol/ether)[3]. Phosphate 184-185 C[9]
Boiling Point:100-110C @ 0.4 mmHg [3]
Flash Point:no data
Solubility:Freebase soluble in chloroform, ether, hexane, methanol; insoluble in water. Hydrochloride soluble in chloroform, ethanol, water; slightly soluble in acetone; insoluble in ether. Phosphate very soluble in water; soluble in methanol; insoluble in acetone, chloroform, ether, hexane[3][9]
Additionnal data:none
Notes:Frebase aspect : oil. Hydrochloride aspect : white powder or crystals; crystallized from isopropanol/n-hexane or isopropanol/ether

[top]General information


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 (see the pharmacology section for more information).

MDMA is usually found as a mixture of the two enantiomers.

Melting Point: (not referenced)
Freebase in vacuo: 155
C (@ 20 mm/Hg); 110-120C (0.4 mm/Hg)
MDMA-HCl: 147 153C
MDMA-HCl1/4H2O: soften 132C; m.p. 135C
MDMA-HCl1/2H2O: soften 92C; m.p. 138-145C
MDMA-HCl3/4H2O: soften 50C; m.p. 90-132C
MDMA-HClH2O: soften 80C; m.p. 107-133C
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)

Refractive index:
nD @ 19C: 1.5311 (Biniecki and Krajewski 1960)

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 a very 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

Structural properties:
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.






NMR, FT/IR, GC/MS and TLC analyses can be found here (MDMA monograph)

[top]Reagent test results of MDMA


While it is virtually impossible for the layman to determine the quantity of MDMA or other substances present in a pill or powder without access to advanced analysis techniques. It is still possible to qualitatively determine whether a pill contains MDMA and what other substances may be present.

Reagent color produced picture video
Marquis Purple to Black - -
Mandelin Purple to black - -
Mecke dark green/turquoise to dark blue/black - -
Simon's Positive (blue coloration) - -
Robadope Negative (pink coloration) - -

Simon's reagent is selective towards secondary amines, MDMA being a secondary amine.

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 Robadope reagent (see Simon's reagent) is a variant of Simon's reagent, but is selective towards primary amines, which MDMA is not. Thus MDMA should not react with the Robadope.

[top]Cleaning ecstasy


MDMA (hydrochloride, as this is the only form found in the streets) is almost insoluble in acetone. Some impurities may be soluble in acetone, therefore an acetone wash can be used to clean ecstasy to some extent. A procedure for acetone wash can be found here.

[top]Synthesis of MDMA


Various synthetic strategies have been developped to synthetize MDMA, generally depending of the chemicals available to the chemist.

[top]Starting from safrole


Safrole is often used as the aromatic precursor.

[top]Starting from piperonal


Piperonal is also used, althought less extensively, as the aromatic precursor.


[top]Forms of MDMA

[top]Freebase


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. Freebase MDMA is unstable and corrosive. MDMA is not found as freebase in the streets or over the internet.

[top]Salts


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-HCl powder


MDMA-HCl crystals

[top]Powder/crystalline MDMA


MDMA can be found as a powder or as a crystalline solid. It is often assumed than this form of MDMA is purer than ecstasy pills. However, there is no real evidence for a higher purity of this form of MDMA as compared to ecstasy pills.

[top]Ecstasy pills


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)

[top]Adulterants



[top]Legal status of MDMA

[top]United Nations

[top]USA

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:

Baseline Offense Level Mass of MDMA Months of Imprisonment
38 60kg or more Cell C
36 20kg up to 60kg Cell C
34 6kg up to 20kg Cell C
32 2kg up to 6kg Cell C
30 1.4kg up to 2kg Cell C
28 800g up to 1.4kg Cell C
26 200g up to 800g Cell C
24 160g up to 200g Cell C
22 120g up to 160g Cell C
20 80g up to 120g Cell C
18 40g up to 80g Cell C
16 20g up to 40g Cell C
14 10g up to 20g Cell C
12 5g up to 10g Cell C
10 2g up to 5g Cell C
8 500mg up to 2g Cell C
6 less than 500mg Cell C

[top]European Union

Country Class/Schedule Legal Status
Austria CSV V.1 Illegal to buy, sell, or possess without a license
Belgium PII.1a Illegal to buy, sell, or possess without a license
Croatia 2.1. Legal Status
Cyprus A Legal Status
Czech Republic 4 Legal Status
Denmark B Illegal to buy, sell, or possess without a license
Estonia I Legal Status
Germany I Illegal to buy, sell, or possess without a license
Greece A Legal Status
Finland PI Legal Status
France SIII Legal Status
Hungary PI Legal Status
Ireland 1 (1c) Legal Status
Italy I Legal Status
Latvia I Legal Status
Lithuania I Legal Status
Luxembourg P Legal Status
Malta A Legal Status
Netherlands I Legal Status
Norway Check Illegal to buy or possess without a license
Poland I-P Legal Status
Portugal IIA Illegal to buy or sell, but possession of less than 1g is not a criminal offense
Romania I Legal Status
Slovenia I Legal Status
Slovakia I Legal Status
Spain PI Legal Status
Sweden I Illegal to buy or possess without a license
UK A Illegal to sell, buy, or possess without a license


[top]History of MDMA


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:
Quote:
I feel absolutely clean inside, and there is nothing but pure euphoria. I have never felt so great, or believed this to be possible. The cleanliness, clarity, and marvelous feeling of solid inner strength continued throughout the rest of the day, and evening, and through the next day. I am overcome by the profundity of the experience, and how much more powerful it was than previous experiences, for no apparent reason, other than a continually improving state of being. All the next day I felt like 'a citizen of the universe' rather than a citizen of the planet, completely disconnecting time and flowing easily from one activity to the next.
Part of his research involved giving his substances to a small group of close friends he termed his "research group", and MDMA was no exception. In 1977, one of the people he introduced it to was psychotherapist and psychologist Leo Zeff--Shulgin thought "It didn't have the other visual and auditory imaginative things that you often get from psychedelics... it opened up a person, both to other people and inner thoughts, but didn't necessarily color it with pretty colors and strange noises", so it might be effective when used in therapy. Zeff was so impressed by the action of MDMA that he came out of retirement to introduce it to the psychotherapeutic community. It was he who dubbed MDMA "Adam", because it "stripped away neuroses and put users in a primordial state". Shulgin wrote:
Quote:
He phoned me a few days later to tell me he had abandoned his plans for a quiet retirement. I know none of the details of the increasingly complex network which he proceeded to develop over the following decade, but I do know that he traveled across the country introducing MDMA to other therapists and teaching then how to use it in their therapy. They had all began, of course, by taking the drug themselves. He believed (as I do) that no therapist has the right to give a psychoactive drug to another person unless and until he is thoroughly familiar with its effects on his own mind. Many of the psychologists and psychiatrists whom Leo instructed developed small groups or enclaves of professionals who had been similarly taught, and the information and techniques he had introduced spread widely and, in time, internationally...

I asked an old friend of his whether she had a guess at the number of people he had introduced to this incredible tool, either directly or indirectly. She was silent for a moment, then said, 'Well, I've thought about that, and I think probably around four thousand, give or take a few.' Those first psychotherapists to use MDMA were keenly aware that they had found a valuable new tool. As one put it [Shulgin's wife, Ann Shulgin], "MDMA is penicillin for the soul, and you don't give up prescribing penicillin, once you've seen what it can do".
Inevitably, MDMA became a popular "street drug" (although it wasn't exactly a street drug for a long time whilst it was totally legal). A group of chemists known as the "Boston Group" were mass producing MDMA in the early 1980's. It could be bought at bars, convenience stores, and via toll free telephone lines. It began to show up at nightclubs, raves, etc. and eventually became mainstream; unfortunately, the DEA noticed and announced in 1984 that they would move to have MDMA scheduled, citing that it "had no legitimate medical use or manufacturer in the USA, was responsible for an undisclosed number of trips to emergency rooms, and had a high potential for abuse".

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.

[top]Popularity of MDMA over time



[top]More MDMA Sections

MDMA Experiences - Post & read experiences with MDMA.

MDMA File Archive] Upload and read research & articles on MDMA.

MDMA Forum Post and read about MDMA.

MDMA Image Gallery - Post and view pictures of MDMA.


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[top]References

  1. ^ Vuori E, Henry JA, Ojanpera I, Nieminen R, Savolainen T, Wahlsten P, Jantti M. Death following ingestion of MDMA (ecstasy) and moclobemide. Addiction 2003;08:365-8
  2. ^ a b c d Meyler's Side Effects of Psychiatric Drugs, J.K. Aronson, Elsevier, 2009
  3. ^ a b c d Merck Index, fifteenth edition (2013)
  4. ^ a b Patel MM, Belson MG, Longwater AB, Olson KR, Miller MA. MDMA (ecstasy)-related hyperthermia. J. Emerg. Med. 2005; 29(4): 451-4
  5. ^ Bordo DJ, Dorfman MA. Ecstasy overdose: rapid cooling leads to successive outcome. Am. J. Emerg. Med. 2004; 22(4): 326-327
  6. ^ a b c Campbell GA, Rosner MH. The Agony of Ecstasy: MDMA (3,4-Methylenedioxymethamphetamine) and the Kidney. Clin J Am Soc Nephrol 3: 18521860, 2008.
  7. ^ a b c Brand H.S., Dun S.N., Nieuw Amerongen A.V. Ecstasy (MDMA) and oral health. Br. Dent. J. 204, 77 - 81 (2008).
  8. ^ Calculated from Atomic Weights of the Elements, 2007
  9. ^ a b MDMA monograph


[HYPONATREMIA2] Farah R, Farah R. Ecstasy (3,4-methylenedioxymethamphetamine)-induced inappropriate antidiuretic hormone secretion (2008) Paediatric Emergency Care 2008 Sep;24(9):615-7
[REFGMR]


Created by NeuroChi, 24-01-2009 at 17:05
Last edited by John_bob, 23-06-2015 at 19:56
Last comment by John_bob on 22-10-2014 at 22:05
17 Comments, 473,294 Views

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