MDMA

MDMA

MDMA

Psychedelics are drugs which cause profound changes in a one’s perceptions of reality, otherwise known as hallucinations. While under the influence of hallucinogens, users might see images, hear sounds or feel sensations. These chemicals offer some of the most intense psychological experiences and care should be taken when ingesting them.

This is a commonly used substance with well known and widely available human consumption data. This does not guarantee that the substance will be safe. The safety profile has been established based on usage data commonly available.

Disclaimer: Psychedelic drugs offer some of the most power and intense psychological experiences. Additionally these substances are illegal in many places. We understand that even though these substances are illegal, their use occurs frequently. We do not condone breaking of the law. By providing accurate information about these substances, we encourage the user to make responsible decisions and practice harm reduction.

Read the full disclaimer here.

Practice Harm Reduction. Proceed with Caution.

Description

MDMA

Also known as:

  • (±)-(3,4-Methylenedioxy)methamphetamine
  • (±)-3,4-METHYLENEDIOXYMETHAMPHETAMINE
  • (±)-N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane
  • (±)-N-Methyl-3,4-(methylenedioxy)amphetamine
  • (RS)-3,4-(methylenedioxy)methamphetamine
  • 1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamin[German][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine[ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-N-méthyl-2-propanamine[French][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine
  • 1,3-Benzodioxole-5-ethanamine, N,α-dimethyl-[ACD/Index Name]
  • 3,4-Methylenedioxymethamphetamine[Wiki]
  • 3,4-Methylenedioxy-N,a-dimethyl-b-phenylethylamine
  • DL-(3,4-Methylenedioxy)methamphetamine
  • methamphetamine, 3,4-methylenedioxy-
  • methylenedioxymethamphetamine[Wiki]
  • MFCD00287291[MDL number]
  • midomafetamina[Spanish][INN]
  • midomafétamine[French][INN]
  • midomafetaminum[Latin][INN]
  • N,a-Dimethyl-1,3-benzodioxole-5-ethanamine
  • N,a-Dimethyl-3,4-methylenedioxyphenethylamine
  • N,a-Dimethylhomopiperonylamine
  • N-Methyl-3,4-methylenedioxyphenylisopropylamine
  • мидомафетамин[Russian][INN]
  • ميدومافيتامين[Arabic][INN]
  • 米度非他明[Chinese][INN]
  • (±)-(3,4-Methylenedioxy)methamphetamine
  • [1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
  • 1-(1,3-benzodioxol-5-yl)-N-methyl-propan-2-amine
  • 1,3-Benzodioxole-5-ethanamine, N,α-dimethyl-
  • 1-BENZO[1,3]DIOXOL-5-YL-N-METHYL-PROPAN-2-AMINE
  • 3,4-methyl enedioxymethamphetamine
  • 3,4-METHYLENDIOXY METHAMPHETAMINE
  • 3,4-methylenedioxymethylamphetamine
  • 3,4-Methylenedioxy-N,α-dimethyl-β-phenylethylamine
  • 3,4-Methylenedioxy-N,α-dimethyl-β-phenylethylamine
  • Methamphetamine, 3,4-methylenedioxy
  • N,α-dimethyl-1,3-benzodioxole-5-ethanamine
  • N-Methyl-3,4-methylenedioxyamphetamine
  • Phenethylamine, N,α-dimethyl-3,4-methylenedioxy-
  • Phenethylamine, N,α-dimethyl-3,4-methylenedioxy-
  • rac-3,4-Methylenedioxymethamphetamine
  • rac-MDMA
  • XTC

The world’s most popular empathogen with powerful pro-social effects. Has been strongly linked to cognitive decline in excess. Popular at parties, it is often sold in powder or in pills, and may be adulterated with other similar chemicals.

Summary

It is considered to be the prototypical entactogen, a diverse group of substances that includes MDA, methylone, mephedrone, and 6-APB. It primarily acts by increasing the activity of the neurotransmitters serotonin, dopamine, and norepinephrine in the brain. MDMA was first developed in 1912 by the pharmaceutical company.

However, there is no evidence of human use prior to the 1970s, when it became known in underground psychotherapy circles in the United States. In the early 1980s, MDMA spread into nightlife and rave culture, eventually leading to its federal prohibition in 1985. By 2014, MDMA was estimated to be one of the most popular recreational drugs in the world, alongside cocaine and cannabis.

Recreational use is popularly associated with dance parties, electronic dance music, and the club and rave scene. Researchers are currently investigating whether MDMA may assist in treatment-resistant post-traumatic stress disorder (PTSD), social anxiety in autistic adults, and anxiety in those with life-threatening illness. Subjective effects include stimulation, anxiety suppression, disinhibition, enhanced empathy and sociability, relaxation, and euphoria.

MDMA is classified as an entactogen due to how it facilitates feelings of closeness with one’s self and others. Tolerance to MDMA builds unusually quickly and many users report that it dramatically loses its effectiveness if used on a frequent basis. It is commonly recommended to wait one to three months between each use to give the brain adequate time to restore serotonin levels and avoid toxicity.

Additionally, using excessively high doses and multiple redosing is highly discouraged as these are thought to significantly increase toxicity. 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 how much this risk applies to typical recreational usage. It has moderate to high abuse potential and can produce psychological dependence in some users. As a result, it is highly advised to use harm reduction practices if using this substance.

History

Anton Köllisch while employed at the pharmaceutical company Merck. Köllisch was in the process of developing agents that would help manage excess bleeding and was interested in MDMA synthesis because it was an intermediate in the production of methylhydrastinin, the methylated analogue of the hemostatic agent hydrastinine. There are no indications of interest in MDMA as an active agent itself. MDMA was not mentioned again until 1927, when Dr.

Max Oberlin conducted the first proven pharmalogical tests at Merck while searching for compounds with a similar action spectrum to adrenaline or ephetonine. Despite promising results, research was halted due to rising substance prices. In 1965, Alexander Shulgin synthesized MDMA as an academic exercise but did not test it for psychoactivity. Shulgin first heard about the effects of MDMA in 1967 from a student and decided to experiment with it. He was impressed with the effects of the substance and thought it could have therapeutic utility.

He advertised it to therapists and psychiatrists and it gained some popularity as an adjunct treatment for various psychological disorders. During this period, psychotherapist Dr. Leo Zeff came out of retirement and subsequently introduced the then-legal MDMA to over 4,000 patients.

From the mid-1970s to the mid-1980s there was a growth of clinicians using MDMA (then known as “Adam”) in California. The recreational use of MDMA became popular at around the same time, particularly in nightclubs, eventually catching 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 recommendation 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.

Chemistry

MDMA

MDMA

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.

Common NameMDMA
Systematic nameMDMA
FormulaC_{11}H_{15}NO_{2}
SMILESCC(Cc1ccc2c(c1)OCO2)NC
Std. InChiInChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
Std. InChiKeySHXWCVYOXRDMCX-UHFFFAOYSA-N
Avg. Mass193.2423 Da
Molecular Weight193.2423
Monoisotopic Mass193.110275 Da
Nominal Mass193
ChemSpider ID1556

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Dosing Guide

Oral
Light40-75mg
Common75-125mg
Strong125-175mg
Heavy175mg+
Insufflated/Rectal
Light30-70mg
Common70-120mg
Strong120-165mg
Heavy165mg+

Duration

MDMA Duration Data
Onset20-70 minutes
Duration3-5 hours
After-effects1-72 hours

Interactions and Synergies

Caution

  1. DOx
    • The combined stimulating effects of the two can be uncomfortable. Coming down on the MDMA while the DOx is still active can be quite anxiogenic.
  2. NBOMes
  3. 2C-T-x
  4. 5-MeO-xxT
    • Some of the 5-MeO tryptamines are a bit unpredictable and should be mixed with MDMA with care
  5. MXE
    • There have been reports of risky serotonergic interactions when the two are taken at the same time, but MXE taken to the end of an MDMA experience does not appear to cause the same issues.
  6. Cocaine
    • Cocaine blocks some of the desirable effects of MDMA while increasing the risk of heart attack.
  7. Caffeine
    • Caffiene is not really necessary with MDMA and increases any neurotoxic effects from MDMA
  8. Alcohol
    • Both MDMA and alcohol cause dehydration. Approach this combination with caution, moderation and sufficient hydration. More than a small amount of alcohol will dull the euphoria of MDMA
  9. GHB/GBL
    • Large amounts of GHB/GBL may overwhelm the effects of MDMA on the comedown.

Dangerous

  1. PCP
    • This combination can easily lead to hypermanic states

No Synergy

  1. Opioids

High Synergy

  1. Mushrooms
  2. LSD
  3. DMT
  4. Mescaline
  5. 2C-x
  6. Cannabis
    • Large amounts of cannabis may cause strong and somewhat unpredictable experiences in combination with MDMA. Cannabis should be saved for towards the end of the experience if possible.
  7. Ketamine
    • No unexpected interactions, though likely to increase blood pressure but not an issue with sensible doses. Moving around on high doses of this combination may be ill advised due to risk of physical injury.
  8. N2O
  9. Amphetamines
    • Amphetamines increase the neurotoxic effects of MDMA

General Information

Experiences
Oral
Vaporization
Come up
Dosage
Effects
After Effects
Avoid
Warning
Risks
Test Kits
Marguis Test ResultBlack (may have purple tint)
Tolerance
Detection1-3 days single use, 3-5 days heavy use
Half-life
Advice
Note
Note 2:
Note 3:

Effects

Pharmacological Effects

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.

Subjective Effects

Disclaimer: The effects listed below are cited from the Subjective Effect Index (SEI), which relies on assorted anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Physical Effects

  • Stimulation - MDMA is popularly known for 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. Unlike most other stimulants, however, the stimulating effects of MDMA 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. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
    • Physical euphoria - Physical euphoria is a prominent aspect of the MDMA experience and occurs reliably when MDMA is used responsibly (i.e. reasonable dosing and spacing between experiences) and can lead to profound feelings of social and physical disinhibition. However, euphoria is quick to fade as one builds tolerance to MDMA's effects, colloquially known as "losing the magic".
  • Tactile enhancement - MDMA produces distinct enhancements to tactile sensations. Users commonly report a sense of softness and fuzziness draping over their skin. Likewise, touching soft and fuzzy objects such as shag rugs can become irresistibly pleasurable and satisfying. MDMA-type tactile enhancement appears to be an effect unique to the entactogen class and may be a serotonin-related effect.
  • Bodily control enhancement
  • Stamina enhancement
  • Bronchodilation
  • 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 - Excessive yawning is thought to occur as a result of serotonergic activity (similar to psilocybin mushrooms) and is more likely to occur with higher doses or pure MDMA. It is sometimes used as an indicator of a batch's quality.
  • 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 - Seizures are rare but may occur in those who are susceptible to them, especially when taking higher doses or redosing while in physically taxing conditions such as being dehydrated, fatigued, undernourished, or overheated.

Psychological Effects

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:

Visual Effects

The visual effects of MDMA occur more selectively and less consistently than any of the traditional psychedelics. This has resulted 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.

Enhancements

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

Suppressions

Distortions

Geometry

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.

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 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

Auditory Effects

  • Enhancements
  • Hallucinations
  • Distortions
  • Tinnitus - Tinnitus is rarely reported, 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. Some users have reported acquiring permanent tinnitus after abuse.

Sensory Effects

Transpersonal Effects

  • Existential self-realization - Although present, this effect 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.

Legal Status

Internationally, MDMA was added to the UN Convention on Psychotropic Substances as a Schedule I controlled substance in February 1986.

  • 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 under Portaria SVS/MS nº 344.
  • 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 controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of August 1, 1986. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • 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.
  • Portugal: MDMA is illegal to produce, sell or trade in Portugal. However, since 2001, individuals found in possession of small quantities (up to 1 gram) are considered sick individuals instead of criminals. The drugs are confiscated and the suspects may be forced to attend a dissuasion session at the nearest CDT (Commission for the Dissuasion of Drug Addiction) or pay a fine, in most cases.
  • Russia: MDMA is classified as a Schedule I prohibited substance.
  • 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 classified as a Schedule I drug under the Controlled Substance Act. This means it is illegal to manufacture, buy, possess, process, or distribute without a license from the Drug Enforcement Administration (DEA).

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    Sources

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    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
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    5. Wikipedia

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