Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

This is a commonly used substance with well known effects, but that does not guarantee the substance will be safe. The safety profile has been established based on usage data commonly reported by others.

Disclaimer: Psychedelic drugs offer some of the most powerful 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.

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

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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Dose Chart

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

Duration Chart

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

Interactions

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

Low Synergy

  1. Benzodiazepines
  2. SSRIs

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

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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    940. Royal Society of Chemistry b312336g
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    942. Royal Society of Chemistry B615669J
    943. Royal Society of Chemistry b817839a
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    947. Royal Society of Chemistry c0ib00083c
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    950. Royal Society of Chemistry c2ob25245g
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    957. The Merck Index Online cs000000011852
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    959. VulcanChem VC331859
    960. Wikidata Q69488
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    963. xPharm 8881

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