MDMA

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Summary sheet: MDMA
MDMA
MDMA.svg
Chemical Nomenclature
Common names MDMA, Molly, Mandy, Emma, MD, Ecstasy, E, X, XTC, Rolls, Beans
Substitutive name 3,4-Methylenedioxy-N-methylamphetamine
Systematic name (RS)-1-(Benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Class Membership
Psychoactive class Stimulant / Entactogen
Chemical class Amphetamine / MDxx
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold 25 mg
Light 45 - 75 mg
Common 75 - 140 mg
Strong 140 - 180 mg
Heavy 180 mg +
Duration
Total 3 - 6 hours
Onset 30 - 60 minutes
Come up 15 - 30 minutes
Peak 1.5 - 2.5 hours
Offset 1 - 1.5 hours
After effects 12 - 48 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
5-MeO-xxT
Alcohol
Cocaine
DOx
GHB
GBL
MXE
ΑMT
Array5x-NBOMe
PCP
Serotonin releasers
ArrayC-T-x
5-HTP
Tramadol
MAOIs
DXM

3,4-Methylenedioxymethamphetamine (also known as ecstasy, E, XTC, emma, molly, mandy, and MDMA) is a classical entactogen substance of the amphetamine class. 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 Merck.[1] However, there is no evidence of human use prior to the 1970s, when it became known in underground psychotherapy circles in the United States.[2] In the early 1980s, MDMA spread into nightlife and rave culture, eventually leading to its federal prohibition in 1985.[3] By 2014, MDMA was estimated to be one of the most popular recreational drugs in the world, alongside cocaine and cannabis.[4] Recreational use is popularly associated with dance parties, electronic dance music, and the club and rave scene.[5] Researchers are currently investigating whether MDMA may assist in treatment-resistant post-traumatic stress disorder (PTSD), social anxiety in autistic adults,[6] and anxiety in those with life-threatening illness.[7][8][9]

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.[10] The most serious short-term physical health risks of MDMA are overheating and dehydration, which has resulted in deaths.[11] MDMA has also been shown to be neurotoxic at high doses;[12] however, it is unclear how much this risk applies to typical recreational usage.[13] 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 and culture

Patent Certificate for Merck's synthesis of MDMA, dated 1912

MDMA was first synthesized in 1912 by the German chemist Dr. 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.[1] 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.[1]

In 1965, Alexander Shulgin synthesized MDMA as an academic exercise but did not test it for psychoactivity.[14][2] 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.[2] 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.[15]

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.[16][14]

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.[15]

Chemistry

MDMA, or 3,4-methylenedioxy-N-methylamphetamine, is a synthetic molecule of the substituted amphetamine class. Molecules of the amphetamine class all contain a phenethylamine core comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain, with an additional methyl substitution at Rα. In addition to this, MDMA contains a methyl substitution on RN, a feature it shares with methamphetamine. Critically, the MDMA molecule also contains substitutions at R3 and R4 of the phenyl ring with oxygen groups -- these oxygen groups are incorporated into a methylenedioxy ring through a methylene bridge. MDMA shares this methylenedioxy ring with other entactogens and stimulants like MDA, MDEA and MDAI.

Pharmacology

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).[17][18][19] 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.[18] By acting as a monoamine transporter substrate, MDMA produces competitive reuptake inhibition at the neuronal membrane transporters, competing for endogenous monoamines for reuptake.[18][20]

MDMA inhibits both vesicular monoamine transporters (VMATs), the second of which (VMAT2) is highly expressed within monoamine neurons vesicular membranes.[19] Once inside a monoamine neuron, MDMA acts as a VMAT2 inhibitor and a TAAR1 agonist.[18][21] The inhibition of VMAT2 by MDMA results in increased concentrations of the aforementioned monoamine neurotransmitters in the cytosol of the neuron.[19][22] Activation of TAAR1 by MDMA triggers protein kinase signaling events which then phosphorylates the associated monoamine transporters of the neuron.[18]

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.[18] MDMA has ten times more affinity for uptake at serotonin transporters compared to dopamine and norepinephrine transporters and consequently has mainly serotonergic effects.[23]

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.[24][25][26][27] Cortisol, prolactin, and oxytocin quantities in serum are increased by MDMA.[28]

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.[29]

Subjective effects

Disclaimer: The effects listed below are cited from the subjective effect index, which is based on anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be treated with a healthy degree of skepticism. It is worth noting that these effects will rarely (if ever) occur all at once, although higher doses will increase the chances of inducing a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Physical effects
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Visual effects
Eye.svg

Cognitive effects
User.svg

Auditory effects
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Transpersonal effects
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After effects
Aftereffects (3).svg

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Names and forms

Names

MDMA Pills, commonly called Ecstasy
Off-white MDMA crystals, commonly called Molly

Since the 1980s, MDMA has become widely known as "Ecstasy" (shortened to "E", "X", or "XTC"), usually referring to its street forms as illicitly pressed pills or tablets.[43] The American term "Molly" and the British equivalent term "Mandy" originally referred to crystal or powder MDMA that was purported to be of high purity and free of adulteration.[44] However, it has since evolved into a generic street term for any number of euphoric stimulants that are sold in powder or crystal form.[citation needed]

Forms

MDMA can be found in the following forms:

  • Pills are the most common form in which MDMA is sold, and are commonly referred to as Ecstasy. They often contain other substances or adulterants that range from anything from MDA, MDEA, amphetamine, methamphetamine, caffeine, 2C-B or mCPP to synthesis by-products such as MDP2P, MDDM or 2C-H. They can also contain an array random substances such as research chemicals, prescription drugs, over-the-counter drugs, poisons or nothing at all. It is strongly recommended to take harm reduction measures such as using a reagent testing kit when ingesting unknown pills.
  • Crystals or powder (commonly called Molly) is a white to brownish substance which can be dissolved, crushed, put into gel capsules or edible paper ("parachutes"). It can be administered orally, sublingually, buccally or via insufflation ("snorting" or "sniffing").

Research

MDMA-assisted psychotherapy for PTSD

In 2011, a pilot study on 20 patients demonstrated promising results in the treatment of post-traumatic stress disorder (PTSD). After two or three MDMA-assisted psychotherapy sessions, 83% of the patients no longer met the criteria for PTSD, compared to only 25% in the control group where MDMA was replaced with a placebo. The results sustained at two and twelve months after the treatment. The MDMA and placebo group both received non-drug psychotherapy before and after the sessions. In the study, a dose of 125mg MDMA plus a 62.5mg supplemental dose after 2 hours have been administered.[45] After completion of the study, the patients from the placebo group also received MDMA-assisted psychotherapy, and a long-term follow-up study of 19 patients published in 2013 shows that even after three years the positive results maintained.[46]

In 2017, the FDA granted MDMA a breakthrough therapy designation for PTSD, meaning if studies show promise, a review for potential medical use could occur more quickly.[47] Phase 3 clinical trials to look at effectiveness and safety expected to begin in 2018.[48]

R-MDMA

MDMA is typically produced and consumed in its racemic form (known as SR-MDMA) which consists of equal parts S-MDMA and R-MDMA. A 2017 study found that high doses of R-MDMA administered in mice increased prosocial behavior and facilitated fear-extinction learning but did not produce hyperthermia or signs of neurotoxicity. This is thought to owe itself to the lower dopamine release R-MDMA displays relative to SR-MDMA. This result suggests that R-MDMA may be a safer and more viable therapeutic than racemic MDMA.[49] However, more research is needed to validate this finding.

Toxicity and harm potential

Radar plot showing relative physical harm, social harm, and dependence of MDMA[50]

Short term risks

The short-term physical health risks of MDMA consumption include dehydration, bruxism, insomnia, hyperthermia,[51][52] and hyponatremia.[53] Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further due to causing excessive amounts of dehydration.

Toxic dose

The exact toxic dosage is unknown, but considered to be far greater than its effective dose.[citation needed]

Neurotoxicity

The neurotoxicity of MDMA use is the subject of considerable debate. Scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of MDMA is most certainly neurotoxic in some form.

Administration of MDMA causes subsequent down-regulation of serotonin reuptake transporters in the brain. The rate at which the brain recovers from serotonergic changes is unclear. One study demonstrated lasting serotonergic changes in some animals exposed to MDMA.[54] Other studies have suggested that the brain may recover from serotonergic damage.[55][56][57]

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 (α-Me-DA, which is known to be toxic to dopamine neurons[58][59]) was thought believed to be involved in the toxicity of MDMA to serotonin receptors. However, one study found this to not be the case as direct administration of α-Me-DA did not cause neurotoxicity.[59] 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.[59]

This study found that although α-Me-DA is involved, it is a further metabolite of α-Me-DA involving glutathione that is primarily responsible for the selective damage to 5-HT receptors triggered by MDMA/MDA.[59]This metabolite forms in higher concentrations when core temperature is elevated. It is taken up into serotonin receptors by its transporters and metabolized by MAO-B into a reactive oxygen species which can cause neurological damage.[59][60]

Cardiotoxicity

The long-term heavy use of MDMA has been shown to be cardiotoxic and may lead to valvulopathy (heart valve damage) through its actions on the 5-HT2B receptor.[61][62] 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.[63]

It is strongly recommended that one use harm reduction practices when using this substance.

Dependence and abuse potential

As with other stimulants, the chronic use of MDMA can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if one suddenly stops their usage.

Tolerance to many of the effects of MDMA develops with prolonged and repeated use. This results in users having to administer increasingly larger doses to achieve the same effects. Upon a single administration, it takes about 1 month for the tolerance to be reduced to half and 2.5 months to be back at baseline (in the absence of further consumption). MDMA presents cross-tolerance with all dopaminergic and serotonergic stimulants, meaning that after the consumption of MDMA all stimulants will have a reduced effect.

Dangerous interactions

Although many psychoactive substances are reasonably safe to use on their own, they can quickly become dangerous or even life-threatening when taken with other substances. The following lists some known dangerous combinations, but cannot be guaranteed to include all of them. Independent research should always be conducted to ensure that a combination of two or more substances is safe to consume. Some interactions listed have been sourced from TripSit.

  • 25x-NBOMe - Due to the highly unpredictable and physically straining effects of 25x-NBOMe, combinations with MDMA are strongly discouraged.
  • 5-MeO-xxT - 5-MeO tryptamines are considered to be unpredictable and should be mixed with MDMA with care.
  • Alcohol - Both MDMA and alcohol cause dehydration and bodily strain. Approach this combination with caution, moderation and sufficient hydration. More than a small amount of alcohol will dull the euphoria of MDMA.
  • Cocaine - Cocaine blocks some of the desirable effects of MDMA while increasing the risk of heart attack.[citation needed]
  • DOx - The combined stimulating effects of DOx and MDMA can become overbearing, particularly during the come up phase. Additionally, coming down on the MDMA while the DOx is still active can produce significant anxiety and bodily discomfort.
  • GHB/GBL - Large amounts of GHB/GBL may overwhelm the effects of MDMA on the comedown and place the user at risk of sudden loss of consciousness.
  • MXE - There have been reports of concerning 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.
  • PCP - PCP with MDMA can easily lead to hypermanic states.
  • Tramadol - Tramadol and stimulants both increase the risk of seizures and this risk is especially elevated when tramadol is taken with MDMA.

Serotonin syndrome risk

Combinations with the following substances can lead to dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.

  • MAOIs such as syrian rue, banisteriopsis caapi, phenelzine, selegiline, and moclobemide[64] - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably. MAO-A inhibitors with MDMA will lead to hypertensive crises.
  • Serotonin releasers such as MDMA, 4-FA, methamphetamine, methylone and αMT
  • AMT
  • 2C-T-x
  • DXM
  • 5-HTP - 5-HTP is a supplement that acts as a precursor for serotonin. It is sometimes recommended to be used after MDMA experiences to try to restore depleted serotonin reserves. However, taking 5-HTP shortly before or with MDMA may cause excessive serotonin levels in the brain, which can lead to serotonin syndrome. As a result, it is advised to wait until the day after the MDMA has been used before consuming 5-HTP.

Legal status

Internationally, MDMA was added to the UN Convention on Psychotropic Substances as a Schedule I controlled substance in February 1986.[65]

  • Austria: MDMA is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).[66]
  • Belgium: MDMA is illegal to possess, produce and sell in Belgium.[67]
  • Brazil: MDMA is illegal to possess, produce and sell under Portaria SVS/MS nº 344.[68]
  • Canada: MDMA is a Schedule I drug in Canada.[69]
  • Denmark: MDMA is illegal to possess, produce and sell in Denmark.[70]
  • Egypt: MDMA is a Schedule III drug in Egypt.[citation needed]
  • Finland: MDMA is illegal to possess, produce and sell in Finland.[citation needed]
  • Germany: MDMA is controlled under BtMG Anlage I, making it illegal to manufacture, import, possess, sell, or transfer it without a license.[71]
  • Latvia: MDMA is a Schedule I drug in Latvia.[72]
  • The Netherlands: MDMA is illegal to possess, produce and sell in the Netherlands.[73]
  • New Zealand: MDMA is a Class B1 drug in New Zealand.[74]
  • Norway: MDMA is illegal to possess, produce and sell in Norway.[citation needed]
  • 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.[75]
  • Russia: MDMA is classified as a Schedule I prohibited substance.[76]
  • Sweden: MDMA is illegal to possess, produce and sell in Sweden.[citation needed]
  • Switzerland: MDMA is illegal to possess, produce and sell in Switzerland.[77]
  • United Kingdom: MDMA is a Class A drug in the UK.[78]
  • 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).[79]

See also

External links

Harm reduction

References

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