{{distinguish|text=MDA, EDMA or 2,3-MDMA}}{{pp-vandalism|small=yes}}{{short description|Psychoactive drug}}{{Use dmy dates|date=August 2017}}{{Drugbox| Watchedfields = changed| verifiedrevid = 632164040| drug_name = MDMA

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Ëˆ

i}}{{IPAc-en

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iË|n}}| ATC_prefix = none

parent|MDMA}}

correct|TOXNET}}| CAS_number = 42542-10-9

correct|chemspider}}| ChemSpiderID = 1556

correct|FDA}}| UNII = KE1SEN21RM

correct|drugbank}}| DrugBank = DB01454

correct|EBI}}| ChEBI = 1391

correct|EBI}}| ChEMBL = 43048| PubChem = 1615| IUPHAR_ligand = 4574| KEGG = D11172

correct|kegg}}

3,4-MDMA|3,4-Methylenedioxymethamphetamine}}; Ecstasy (E, X, XTC); Molly; Mandy| PDB_ligand = B41

H=15

O=2| SMILES = CC(NC)CC1=CC=C(OCO2)C2=C1

correct|chemspider}}| StdInChI = 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

correct|chemspider}}| StdInChIKey = SHXWCVYOXRDMCX-UHFFFAOYSA-N| density =| melting_point =| melting_notes =| boiling_point = 105| boiling_notes = at 0.4 mmHg (experimental)| legal_AU = S9| legal_BR = F| legal_CA = Schedule I| legal_DE = Anlage I| legal_NZ = Class B| legal_UK = Class A| legal_US = Schedule I| legal_UN = Psychotropic Schedule I| legal_status =| pregnancy_category = | pregnancy_US =| licence_US =| class = empathogenâ€“entactogen stimulant

Physical dependence>Physical: not typicalPALMER>FIRST1=ROBERT B.

TITLE=MEDICAL TOXICOLOGY OF DRUG ABUSE : SYNTHESIZED CHEMICALS AND PSYCHOACTIVE PLANTS

PUBLISHER=JOHN WILEY & SONS

ISBN=978-0-471-72760-6

URL=HTTPS://BOOKS.GOOGLE.COM/BOOKS?ID=OWFIVADZNKQC&PG=PA139, Psychological: moderate

TITLE = MOLECULAR NEUROPHARMACOLOGY: A FOUNDATION FOR CLINICAL NEUROSCIENCE

PUBLISHER = MCGRAW-HILL MEDICAL

ISBN = 978-0-07-148127-4

EDITION = 2ND

JOURNAL = THE EUROPEAN JOURNAL OF NEUROSCIENCE

ISSUE = 1

DATE = JANUARY 2017

DOI = 10.1111/EJN.13480

JOURNAL = CURRENT DRUG ABUSE REVIEWS

ISSUE = 1

DATE = MARCH 2013

DOI = 10.2174/18744737112059990005, Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders.,

R)-MDMA: 5.8 Â± 2.2 hours (variable)3,4-METHYLENEDIOXYMETHAMPHETAMINE

WEBSITE=HAZARDOUS SUBSTANCES DATA BANK

ACCESS-DATE=22 AUGUST 2014

QUOTE=, (S)-MDMA: 3.6 Â± 0.9 hours (variable)

Liver, Cytochrome P450 oxidase>CYP450 extensively involved, including CYP2D6

3,4-methylenedioxyamphetamine>MDA, 4-Hydroxy-3-methoxymethamphetamine

, 4-Hydroxy-3-methoxyamphetamine>HMA, Alpha-Methyldopamine

, MDP2P, Methylenedioxyhydroxyamphetamine>MDOHCARVALHO M, CARMO H, COSTA VM, CAPELA JP, PONTES H, REMIÃ£O F, CARVALHO F, BASTOS M > TITLE = TOXICITY OF AMPHETAMINES: AN UPDATE

VOLUME = 86

PAGES = 1167â€“231

PMID = 22392347, 10.1007/s00204-012-0815-5, | excretion = Kidney

oral route>by mouth Uncommon: insufflation (medicine)

, inhalation (vaporization), injection (medicine)>injection,METHYLENEDIOXYMETHAMPHETAMINE (MDMA OR 'ECSTASY')>URL=HTTP://WWW.EMCDDA.EUROPA.EU/PUBLICATIONS/DRUG-PROFILES/MDMA

PUBLISHER=EUROPEAN MONITORING CENTRE FOR DRUGS AND DRUG ADDICTION

REF=EMCDDA, METHYLENEDIOXYMETHAMPHETAMINE (MDMA, ECSTASY)>URL = HTTP://WWW.NHTSA.DOT.GOV/PEOPLE/INJURY/RESEARCH/JOB185DRUGS/METHYLENEDIOXYMETHAMPHETAMINE.HTM

PUBLISHER = NATIONAL HIGHWAY TRAFFIC SAFETY ADMINISTRATION

ARCHIVE-URL = HTTPS://WEB.ARCHIVE.ORG/WEB/20120503102427/HTTP://WWW.NHTSA.GOV/PEOPLE/INJURY/RESEARCH/JOB185DRUGS/METHYLENEDIOXYMETHAMPHETAMINE.HTM

DF = DMY-ALL, rectal| onset = 30â€“45 minutes (by mouth)| duration_of_action = 4â€“6 hours| bioavailability =| protein_bound =}}3,4-Methyl{{wbr}}enedioxy{{wbr}}methamphetamine (MDMA),{{#tag:ref|The term MDMA is a contraction of {{nowrap|3,4-methylenedioxy-methamphetamine}}; it is also known as ecstasy (shortened to "E", "X", or "XTC"), mandy, and molly.JOURNAL, Luciano RL, Perazella MA, Nephrotoxic effects of designer drugs: synthetic is not better!, Nature Reviews. Nephrology, 10, 6, 314â€“24, June 2014, 24662435, 10.1038/nrneph.2014.44, WEB, DrugFacts: MDMA (Ecstasy or Molly),weblink National Institute on Drug Abuse, 2 December 2014, no,weblink" title="web.archive.org/web/20141203115531weblink">weblink 3 December 2014, dmy-all, | group = "note"}} commonly known as ecstasy (E), is a psychoactive drug primarily used as a recreational drug.JOURNAL, Meyer JS, 3,4-methylenedioxymethamphetamine (MDMA): current perspectives, Substance Abuse and Rehabilitation, 4, 83â€“99, 2013, 24648791, 3931692, 10.2147/SAR.S37258, The desired effects include altered sensations and increased energy, empathy, and pleasure.WEB, MDMA,weblink 30 March 2016, Anderson, Leigh, vanc, Drugs.com, Drugsite Trust, 18 May 2014, no,weblink" title="web.archive.org/web/20160323161153weblink">weblink 23 March 2016, dmy-all, When taken by mouth, effects begin after 30â€“45 minutes and last 3â€“6 hours.BOOK, Freye, Enno, vanc, Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs, 28 July 2009, Springer Netherlands, 978-90-481-2448-0, 151â€“160, Pharmacological Effects of MDMA in Man, 10.1007/978-90-481-2448-0_24, Adverse effects include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating, and a rapid heartbeat. Deaths have been reported due to increased body temperature and dehydration. Following use people often feel depressed and tired. MDMA acts primarily by increasing the activity of the neurotransmitters serotonin, dopamine, and noradrenaline in parts of the brain.WEB, DrugFacts: MDMA (Ecstasy/Molly),weblink National Institute on Drug Abuse, 30 March 2016, February 2016, no,weblink 23 March 2016, dmy-all, It belongs to the substituted amphetamine classes of drugs and has stimulant and hallucinogenic effects.BOOK, Freye, Enno, vanc, Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs: A comprehensive review on their mode of action, treatment of abuse and intoxication, 2009, Springer Science & Business Media, 978-90-481-2448-0, 147,weblink en, MDMA is illegal in most countriesBOOK, Patel, Vikram, vanc, Mental and neurological public health a global perspective, 2010, Academic Press/Elsevier, San Diego, CA, 978-0-12-381527-9, 57, 1st,weblink no,weblink 10 September 2017, dmy-all, and, as of 2018, has no approved medical uses.NEWS, Philipps, Dave, vanc, Ecstasy as a Remedy for PTSD? You Probably Have Some Questions.,weblink 14 July 2018, The New York Times, 1 May 2018, en, Limited exceptions are sometimes made for research. Researchers are investigating whether MDMA may assist in treating severe, treatment-resistant posttraumatic stress disorder (PTSD) with phase 3 clinical trials to look at effectiveness and safety expected to begin in 2018.JOURNAL, Feduccia AA, Holland J, Mithoefer MC, Progress and promise for the MDMA drug development program, Psychopharmacology, 235, 2, 561â€“571, February 2018, 29152674, 10.1007/s00213-017-4779-2, In 2017 the FDA granted MDMA a breakthrough therapy designation{{#tag:ref|The FDA's "breakthrough therapy" designation is not intended to imply that a drug is actually a "breakthrough" or that there is high-quality evidence of treatment efficacy for a particular condition;NEWS, Schwitzer G, CBS proclaims 'cancer breakthrough' â€“ doesn't explain what FDA means by that term,weblink Health News Review, 13 May 2016, 9 October 2017, rather, it allows the FDA to grant priority review to drug candidates if preliminary clinical trials indicate that the therapy may offer substantial treatment advantages over existing options for patients with serious or life-threatening diseases.JOURNAL, Kepplinger EE, FDA's Expedited Approval Mechanisms for New Drug Products, Biotechnology Law Report, 34, 1, 15â€“37, February 2015, 25713472, 4326266, 10.1089/blr.2015.9999, WEB, Fact Sheet: Breakthrough Therapies, United States Food and Drug Administration,weblink no,weblink 10 December 2014, 9 October 2017, 9 October 2017, A breakthrough therapy is a drug:{{bull, intended alone or in combination with one or more other drugs to treat a serious or life threatening disease or condition and{{bull}}preliminary clinical evidence indicates that the drug may demonstrate substantial improvement over existing therapies on one or more clinically significant endpoints, such as substantial treatment effects observed early in clinical development.}}| group="note" | name="breakthrough therapy"}} for PTSD, meaning if studies show promise, a review for potential medical use could occur more quickly.NEWS, Wan, William, vanc, Ecstasy could be 'breakthrough' therapy for soldiers, others suffering from PTSD,weblink 29 August 2017, Washington Post, 26 August 2017, no,weblink 29 August 2017, dmy-all, MDMA was first developed in 1912 by Merck.JOURNAL, Freudenmann RW, Ã–xler F, Bernschneider-Reif S, The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents,weblink Addiction, 101, 9, 1241â€“1245, August 2006, 16911722, 10.1111/j.1360-0443.2006.01511.x, Although MDMA was, in fact, first synthesized at Merck in 1912, it was not tested pharmacologically because it was only an unimportant precursor in a new synthesis for haemostatic substances., It was used to improve psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music.BOOK, World Health Organization, Neuroscience of Psychoactive Substance Use and Dependence,weblink 2004, World Health Organization, 978-92-4-156235-5, 97â€“, no,weblink 28 April 2016, dmy-all, It is often sold mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).BOOK, World Drug Report 2018, June 2018, United Nations, 978-92-1-148304-8, 7, 14 July 2018,weblink This was broadly similar to the percentage of people who use cocaine or amphetamines, but fewer than for cannabis or opioids. In the United States, as of 2017, about 7% of people have used MDMA at some point in their life and 0.9% have used in the last year.WEB, MDMA (Ecstasy/Molly),weblink National Institute on Drug Abuse, 14 July 2018, {{TOC limit|3}}

Effects

In general, MDMA users report feeling the onset of subjective effects within 30â€“60 minutes of MDMA consumption and reaching the peak effect at 75â€“120 minutes, which then plateaus for about 3.5 hours.JOURNAL, Liechti ME, Gamma A, Vollenweider FX, Gender differences in the subjective effects of MDMA, Psychopharmacology, 154, 2, 161â€“8, March 2001, 11314678, 10.1007/s002130000648, The desired short-term psychoactive effects of MDMA have been reported to include:

Euphoria â€“ a sense of general well-being and happiness
Increased self-confidence, sociability and feelings of communication being easy or simple
Entactogenic effects â€“ increased empathy or feelings of closeness with others and oneself
Relaxation and reduced anxiety
Increased emotionality
A sense of inner peace
Mild hallucination
Enhanced sensation, perception, or sexuality
Altered sense of time

The experience elicited by MDMA depends on the dose, setting, and user. The variability of the induced altered state by MDMA is lower compared to other psychedelics. For example, MDMA used at parties is associated with high motor activity, reduced sense of self-identity as well as poor awareness of the background surroundings. Use of MDMA individually or in a small groups in a quiet environment and when concentrating, is associated with increased lucidity, capability of concentration, sensitivity of aesthetic aspects of the background and emotions, as well as greater capability of communication with others.JOURNAL, Landriscina F, MDMA and the states of Consciousness, Eleusis, 1995, 2, 3â€“9, In psychotherapeutic settings MDMA effects have been described by infantile ideas, alternating phases of mood, sometimes memories and moods connected with childhood experiences.JOURNAL, Baggott MJ, Kirkpatrick MG, Bedi G, de Wit H, Intimate insight: MDMA changes how people talk about significant others, Journal of Psychopharmacology, 29, 6, 669â€“77, June 2015, 25922420, 4698152, 10.1177/0269881115581962, Sometimes MDMA is labelled as an "empathogenic" drug, because of its empathy-producing effects.JOURNAL, Schmid Y, Hysek CM, Simmler LD, Crockett MJ, Quednow BB, Liechti ME, Differential effects of MDMA and methylphenidate on social cognition, Journal of Psychopharmacology, 28, 9, 847â€“56, September 2014, 25052243, 10.1177/0269881114542454,weblink JOURNAL, Wardle MC, de Wit H, MDMA alters emotional processing and facilitates positive social interaction, Psychopharmacology, 231, 21, 4219â€“29, October 2014, 24728603, 4194242, 10.1007/s00213-014-3570-x, Results of different studies show its effects of powerful empathy with others. When testing MDMA for medium and high dosage ranges it showed increase on hedonic as well as arousal continuum.BOOK, Bravo GL, Holland J, Ecstasy: The complete guide. A comprehensive look at the risks and benefits of MDMA., 2001, Park Street Press, Rochester, What does MDMA feel like?, BOOK, 2005, Oxford University, New York, Mind-Altering Drugs: The Science of Subjective Experience, Psychedelic, Psychoactive, and Addictive Drugs and States of Consciousness, Mitch, Earleywine, Ralph, Metzner, vanc,weblink The effect of MDMA increasing sociability is consistent, however effects on empathy have been more mixed.JOURNAL, Kamilar-Britt P, Bedi G, The prosocial effects of 3,4-methylenedioxymethamphetamine (MDMA): Controlled studies in humans and laboratory animals, Neuroscience and Biobehavioral Reviews, 57, 433â€“46, October 2015, 26408071, 4678620, 10.1016/j.neubiorev.2015.08.016,

Use

Recreational

MDMA is often considered the drug of choice within the rave culture and is also used at clubs, festivals and house parties. In the rave environment, the sensory effects from the music and lighting are often highly synergistic with the drug. The psychedelic amphetamine quality of MDMA offers multiple reasons for its appeal to users in the rave setting. Some users enjoy the feeling of mass communion from the inhibition-reducing effects of the drug, while others use it as party fuel because of the drug's stimulatory effects.BOOK, Reynolds, Simon, vanc, Generation Ecstasy: Into the World of Techno and Rave Culture, 1999, Routledge, 978-0-415-92373-6, 81,weblink MDMA is used less frequently than other stimulants, typically less than once per week.MDMA is sometimes taken in conjunction with other psychoactive drugs such as LSD, psilocybin mushrooms, and ketamine, an act called "candy-flipping".BOOK, Capuzzi, David, Gross, Douglas R., vanc, Youth at Risk: A Prevention Resource for Counselors, Teachers, and Parents, John Wiley & Sons, 978-1-119-02694-5, 379,weblink 2014-11-21,

Medical

{{See also|MDMA#Research}}{{As of|2017}}, MDMA has no accepted medical indications.JOURNAL, Sessa B, Nutt D, Making a medicine out of MDMA, The British Journal of Psychiatry, 206, 1, 4â€“6, January 2015, 25561485, 10.1192/bjp.bp.114.152751, JOURNAL, Ebrahimian Z, Karimi Z, Khoshnoud MJ, Namavar MR, Daraei B, Haidari MR, Behavioral and Stereological Analysis of the Effects of Intermittent Feeding Diet on the Orally Administrated MDMA ("ecstasy") in Mice, Innovations in Clinical Neuroscience, 14, 1â€“2, 40â€“52, 1 February 2017, 28386520, 5373794, MDMA is listed as a Schedule 1 drug by the United States Drug Enforcement Agency, meaning that currently there are no accepted medical uses for MDMA in the United States, there is a lack of accepted safety for use under medical supervision, and there is a high potential for abuse., Before it was widely banned, it saw limited use in therapy.JOURNAL, Climko RP, Roehrich H, Sweeney DR, Al-Razi J, Ecstacy: a review of MDMA and MDA, International Journal of Psychiatry in Medicine, 16, 4, 359â€“72, 1986, 2881902, 10.2190/dcrp-u22m-aumd-d84h, A small number of therapists continue to use MDMA in therapy despite its illegal status.BOOK, Enno, Freye, Joseph V., Levy, vanc, Pharmacology and abuse of cocaine, amphetamines, ecstasy and related designer drugs a comprehensive review on their mode of action, treatment of abuse and intoxication, 2009, Springer Netherlands, Dordrecht, 978-90-481-2448-0, 152, Online-Ausg.,

Other

Small doses of MDMA are used as an entheogen to enhance prayer or meditation by some religious practitioners.MDMA and Religion. CSP. Retrieved on 11 June 2011. MDMA has been used as an adjunct to New Age spiritual practices.JOURNAL, Watson L, Beck J, New age seekers: MDMA use as an adjunct to spiritual pursuit, Journal of Psychoactive Drugs, 23, 3, 261â€“70, 1991, 1685513, 10.1080/02791072.1991.10471587,

Forms

MDMA has become widely known as ecstasy (shortened "E", "X", or "XTC"), usually referring to its tablet form, although this term may also include the presence of possible adulterants or dilutants. The UK term "mandy" and the US term "molly" colloquially refer to MDMA in a crystalline powder form that is thought to be free of adulterants. MDMA is also sold in the form of the hydrochloride salt, either as loose crystals or in gelcaps.In part due to the global supply shortage of sassafras oil, substances that are sold as molly frequently contain no MDMA and instead contain methylone, ethylone, MDPV, mephedrone, or any other of the group of compounds commonly known as bath salts.AV MEDIA, 13 August 2014, Molly Madness, TV documentary, National Geographic Channel, Drugs, Inc., B00LIC368M, AV MEDIA, 10 December 2014, Manic Molly, TV documentary, National Geographic Channel, Drugs, Inc., B00LIC368M, Powdered MDMA ranges from pure MDMA to crushed tablets with 30â€“40% purity. MDMA tablets typically have low purity due to bulking agents that are added to dilute the drug and increase profits (e.g., lactose) and binding agents. Tablets sold as ecstasy sometimes contain 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxyethylamphetamine (MDEA), other amphetamine derivatives, caffeine, opiates, or painkillers. Some tablets contain little or no MDMA. The proportion of seized ecstasy tablets with MDMA-like impurities has varied annually and by country. The average content of MDMA in a preparation is 70 to 120 mg with the purity having increased since the 1990s.MDMA is usually consumed by mouth. It is also sometimes snorted.{{multiple image| align = center| direction = horizontal| total_width = 600| image1 = Ecstasy monogram.jpg| width1 = 434| height1 = 424| alt1 = Image of Ecstasy tablets| caption1 = Ecstasy tablets which may contain MDMA| image2 = Tan MDMA Crystals.jpg| width2 = 4032| height2 = 3024| alt2 = Image of a chunk of impure MDMA| caption2 = A salt of MDMA (typically white) with impurities, resulting in a tan discoloration| image3 = Crushed MDMA crystals.jpg| width3 = 4032| height3 = 3024| alt3 = 1 gram crushed MDMA crystals| caption3 = Crushed MDMA (1 gram) crystals| image4 = | width4 = 1632| height4 = 1224| alt4 = Image of highly pure MDMA in capsules| caption4 = High purity MDMA in capsules}}

Adverse effects

Short-term

Acute adverse effects 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 hyperthermia and dehydration. Cases of life-threatening or fatal hyponatremia (excessively low sodium concentration in the blood) have developed in MDMA users attempting to prevent dehydration by consuming excessive amounts of water without replenishing electrolytes.JOURNAL, White CM, How MDMA's pharmacology and pharmacokinetics drive desired effects and harms, Journal of Clinical Pharmacology, 54, 3, 245â€“52, March 2014, 24431106, 10.1002/jcph.266, The immediate adverse effects of MDMA use can include:{{div col|colwidth=22em}}

Dehydration
Hyperthermia
Bruxism (grinding and clenching of the teeth)
Increased wakefulness or insomnia
Increased perspiration and sweating
Increased heart rate and blood pressure
Increased psychomotor activity
Loss of appetite
Nausea and vomiting
Diarrhea
Erectile dysfunctionJOURNAL, Spauwen LW, Niekamp AM, Hoebe CJ, Dukers-Muijrers NH, Drug use, sexual risk behaviour and sexually transmitted infections among swingers: a cross-sectional study in The Netherlands, Sexually Transmitted Infections, 91, 1, 31â€“6, February 2015, 25342812, 10.1136/sextrans-2014-051626, It is known that some recreational drugs (eg, MDMA or GHB) may hamper the potential to ejaculate or maintain an erection.,
Visual and auditory hallucinations (rarely)
Mydriasis

{{div col end}}The adverse effects that last up to a week following cessation of moderate MDMA use include:

Physiological

Trismus
Loss of appetite
Insomnia
Tiredness or lethargyWEB,weblink MDMA Toxicity: Background, Pathophysiology, Epidemiology, Hahn, In-Hei, vanc, 25 March 2015, Medscape, 14 May 2016, BOOK,weblink Drug Abuse and Addiction in Medical Illness: Causes, Consequences and Treatment, Parrott AC, 2012, Springer Science & Business Media, 978-1-4614-3375-0, Verster, Joris, 179, 13. MDMA and LSD, Brady, Kathleen, Galanter, Marc, Conrod, Patricia, vanc,

Psychological

Anxiety or paranoiaWEB, 3,4-Methylenedioxymethamphetamine,weblink Hazardous Substances Data Bank, National Library of Medicine, 22 August 2014, 28 August 2008,
Depression
Irritability
Impulsiveness
Restlessness
Memory impairment
Anhedonia

Long-term

{{As of|2015}}, the long-term effects of MDMA on human brain structure and function have not been fully determined,JOURNAL, Garg A, Kapoor S, Goel M, Chopra S, Chopra M, Kapoor A, McCann UD, Behera C, Functional Magnetic Resonance Imaging in Abstinent MDMA Users: A Review, Current Drug Abuse Reviews, 8, 1, 15â€“25, 2015, 25731754, 10.2174/1874473708666150303115833, however, there is consistent evidence of structural and functional deficits in MDMA users with a high lifetime exposure. Additionally, MDMA use at high doses, as distinct from high lifetime exposure, has been shown to produce brain lesions, a form of brain damage, in the serotonergic neural pathways of humans and animals. There is no evidence of structural or functional changes in MDMA users with only a moderate (

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