MDMA

MDMA
The skeletal formula of MDMA
Chemical Nomenclature
Common names	MDMA, Ecstasy, Molly, Mandy
Substitutive name	E, X, XTC, Rolls
Systematic name	(RS)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Routes of Administration
Oral Dosage WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is a summary of data gathered from users and resources. It is NOT a recommendation and should be verified with other sources for accuracy. Threshold 30 mg Light 40 - 75 mg Common 75 - 150 mg Strong 150 - 200 mg Heavy 200 mg+ Duration Onset 20 - 70 minutes Peak 3 - 5 hours Afterglow 24 hours

Summary sheet: MDMA

MDMA (3,4-methylenedioxy-N-methylamphetamine) is a stimulant and entactogenic drug of the phenethylamine and amphetamine class. MDMA has become widely known as "ecstasy" (shortened to "E", "X", or "XTC"), usually referring to its street form (although this term may also include the presence of possible adulterants). The U.K. term "Mandy" and the U.S. term "Molly" colloquially refer to MDMA that is relatively free of adulterants and impurities, but is also commonly used as a term for MDMA in powder or crystal form.

MDMA was first synthesized in 1912 by the chemist Anton Köllisch as a potential medicine to stop abnormal bleeding. Over the following 65 years, MDMA was largely forgotten about with the first reports of it being used recreationally dating back to 1970. Chemist Alexander Shulgin is credited for popularizing the use of MDMA in psychotherapy in the late 1970s. It was finally scheduled as a controlled substance in 1985 when its use began to spread out to mainstream society and rave culture.

Chemistry

General formula of phenethylamine molecule

MDMA, also known as 3,4-methylenedioxy-N-methylamphetamine, is a synthetic molecule of the amphetamine family. Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at R_α. MDMA contains a methyl substitution on R_N, which it shares with methamphetamine. MDMA 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 chain. MDMA shares this methylenedioxy ring with MDAI.

Pharmacology

MDMA acts as a releasing agent of the neurotransmitters known as serotonin, dopamine and noradrenaline which are the neurotransmitters in charge of pleasure, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused and causing physically stimulating and euphoric effects.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

The physical effects of MDMA can be broken down into several components which progressively intensify proportional to dosage. These are described below and generally include:

• Spontaneous tactile sensations - The "body high" of MDMA can be described 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.
• Stimulation - In terms of its effects on the user's physical energy levels, MDMA is commonly considered to be extremely 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 particular 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 bodily shakes and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control.
• 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.
• Dehydration - Feelings of dry mouth and dehydration are a universal experience with MDMA; this effect is a product of an increased heart rate and an extreme motivation to engage in strenuous physical activities. While it is important to avoid becoming dehydrated (especially when out dancing in a hot environment) there have been a number of users suffering from water intoxication through over-drinking, so it is advised that users simply sip at water and never over-drink.
• Difficulty urinating - Higher doses of MDMA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is due to MDMA’s promotion of the release of anti-diuretic hormone (ADH); ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
• Tactile enhancement
• Increased perspiration
• Temporary erectile dysfunction
• Increased heart rate
• Increased blood pressure

Cognitive effects

The cognitive effects of MDMA can be broken down into several components which progressively intensify proportional to dosage. The general head space of MDMA is described by many as one of extreme mental stimulation, feelings of love or empathy and powerful euphoria. It contains a large number of typical psychedelic, entactogenic and stimulant cognitive effects.

The most prominent of these cognitive effects generally include:

• Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within MDMA and are likely a direct result of serotonin and dopamine release.
• Empathy, love and sociability enhancement - This particular effect is more pronounced, powerful and therapeutic with MDMA than any other known substance. It is the most obvious 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 instils 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 10 experiences, while others have reported hundreds of uses before the empathic qualities disappear. This does not appear to be true 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.
• Time distortion - Strong feelings of time compression are common within MDMA and speed up the experience of time quite noticeably.
• Unity and interconnectedness - Experiences of unity, oneness and interconnectedness between level 2 - 3 are common within MDMA. This component most consistently manifests itself at high doses within large crowds at raves and musical events in the form of "becoming one with the crowd."
• Thought acceleration
• Anxiety suppression
• Mindfulness
• Immersion enhancement
• Creativity enhancement

Visual effects

The visual effects of MDMA have an occurrence rating that is more selective and less consistent than any of the traditional psychedelics. This is to the point where many people disregard psychedelic experiences within MDMA as a "myth" or "rumour", but this is simply because they have not experienced it for themselves. The effects can never be guaranteed to manifest themselves, but are more likely to occur with chemically pure, high dose MDMA experiences, towards the end of the experience and if the user has been smoking marijuana. They are also more likely to occur if the user has prior experience with psychedelics, but also remain entirely possible within those who have never tried one for themselves.

Enhancements

MDMA presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctively present. These generally include:

• Colour enhancement
• Pattern recognition enhancement

Distortions

MDMA presents a single visual distortion:

• Tracers - This effect is rarely manifested beyond levels 1 - 3.

Geometry

The visual geometry that is present throughout this trip can be described 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 result in states of level 8A visual geometry over level 8B. Many users report that MDMA geometry presents itself with ominous and menacing emotional vibes with a synthetic and nerve-racking feel to them.

Hallucinatory states

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 many other commonly used psychedelics. These effects are far more common during the offset of the experience and commonly include:

• External hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - This effect is very similar to the same experience found within deliriants, but does not manifest itself consistently and usually happens only at high 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 when they are not and mistaking objects as human beings or animals.
• Internal hallucinations - The internal hallucinations which MDMA induces are generally 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 are 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 short and fleeting, but frequent and completely believable and convincing as they happen. In terms of the theme, they often take the form of conversations with the people who were with you or instead manifest themselves as bizarre and extremely nonsensical plots.
• Peripheral information misinterpretation

Auditory effects

The auditory effects of MDMA are common in their occurrence and exhibit a partial range of effects which commonly includes:

• Enhancements
• Hallucinations

Toxicity and harm potential

This radar plot shows relative physical harm, social harm, and dependence of MDMA.

Short-term health concerns

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.

Long-term health concerns

The neurotoxicity of MDMA use has long been debated. 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.

MDMA causes a 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 toxic to dopamine neurones) was previously 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 high. It is uptaken into serotonin receptors by its transporters and metabolized by MAO-B into a reactive oxygen species which can cause neurological damage.

Long-term heavy use of MDMA is cardiotoxic and leads to valvulopathy 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.

Dangerous interactions

Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

• 25x-NBOMe - Both the NBOMe series and MDMA induce powerful stimulation. Side effects such as thought loops, seizures, increased blood pressure, vasoconstriction, increased heart rate, and heart failure (in extreme cases) may occur.
• Alcohol - It is dangerous to combine alcohol, a depressant, with stimulants due to the risk of excessive intoxication. Stimulants decrease the sedative effect of alcohol which is the main factor most people consider when determining their level of intoxication. Once the stimulant wears off, the effects of alcohol will be significantly increased, leading to intensified disinhibition as well as other effects. If combined, one should strictly limit themselves to only drinking a certain amount of alcohol per hour.
• DXM - This combination may cause increased heart rate and panic attacks (in extreme cases).
• MXE - Increased heart rate and blood pressure may occur.
• Tramadol - This combination can increase the risk of seizures.
• MAOIs - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, 2C-T-2, 2C-T-7, αMT, and some antidepressants.
• Stimulants - The neurotoxic effects of MDMA may be increased when combined with other stimulants.
• Cocaine - This combination will increase strain on the heart.

Serotonin syndrome risk

Combinations in the list below may increase the amount of neurotransmitters such as serotonin and dopamine to dangerous or even fatal levels.

• MAOIs such as syrian rue, banisteriopsis caapi, 2C-T-2, 2C-T-7, αMT, and some antidepressants
• Serotonin releasers such as MDMA, 4-FA, MDAI and αMT
• Selective serotonin re-uptake inhibitors (SSRIs)
• 5-HTP

Lethal dosage

The median lethal dose of MDMA within humans is unknown, but considered to be far greater than its active dose.

Tolerance and addiction potential

The potential of MDMA to produce addiction is controversial. Some studies indicate that many users may be addicted, but this depends on the definition of addiction. While many MDMA users may take the drug regularly and develop significant tolerance to its effects, relatively few users exhibit cravings or physical symptoms of dependence or find it difficult to stop using the drug when they decide to do so.

Legal issues

• Austria: Possession, production and sale is illegal.
• Belgium: Possession, production and sale is illegal.
• Brazil: Possession, production and sale is illegal.
• Canada: MDMA is a Schedule I drug.
• Denmark: Possession, production and sale is illegal.
• Egypt: MDMA is a Schedule III drug.
• Finland: Possession, production and sale is illegal.
• Germany: MDMA is a Schedule I drug.
• Latvia: MDMA is a Schedule I drug.
• The Netherlands: Possession, production and sale is illegal.
• New Zealand: MDMA is a Class B1 drug.
• Norway: Possession, production and sale is illegal.
• Sweden: Possession, production and sale is illegal.
• UK: MDMA is a Class A drug.
• USA: MDMA is a Schedule I drug.

Experience reports

Anecdotal reports which describe 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

See also

• Responsible use
• Psychedelics
• Entactogens
• Stimulants
• Phenethylamines
• Amphetamines
• MDA
• MDAI
• MDMA (Wikipedia)
• MDMA (Erowid)