Methylenedioxymethamphetamine
Systematic (IUPAC) name
(±)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Identifiers
CAS number	69610-10-2
ATC code	?
PubChem	1615
Chemical data
Formula	C11H15NO2
Mol. mass	193.25 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic, CYP extensively involved
Half life	The half-life of MDMA is dose dependent, increasing with higher doses, but is around 6–10 hours at doses of 40–125 mg
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C [1] Chemical structure of MDMA Selfmade by cacycle File links The following pages link to this file: Ecstasy (drug) Categories: GFDL images ... Image File history File links Size of this preview: 561 × 600 pixel Image in higher resolution (1100 × 1176 pixel, file size: 294 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Methylenedioxymethamphetamine ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element and its most stable form, or dioxygen. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is the largest internal organ in the human body, and is an organ present in vertebrates and some other animals. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Routes	Sublingual salla

MDMA (3,4-methylenedioxy-N-methylamphetamine), most commonly known today by the street name Ecstasy (often abbreviated E, X, or XTC), is a semisynthetic member of the phenethylamine class of psychoactive drugs. MDMA also falls under many other broad categories of substances, including amphetamines/stimulants, psychedelics, and the empathogenic-entactogens. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... A semisynthetic or partial chemical synthesis uses compounds isolated from natural sources (e. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... Amphetamine or Amfetamine(Alpha-Methyl-PHenEThylAMINE), also known as beta-phenyl-isopropylamine and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... A fractal pattern similar to the spiral patterns that may be seen as the result of some psychedelic drug experiences. ... The terms empathogen and entactogen are different terms used to describe one class of hallucinogens that function as serotonin releasers; most of these are phenethylamines. ...

The drug is considered unusual for its tendency to produce feelings of euphoria, a sense of intimacy with others, and diminished feelings of fear and anxiety. MDMA has more consistent emotional effects than most psychedelics and has a euphoria that appears to be different from most stimulants. Before it was made a controlled substance, MDMA was used to aid psychotherapy, often couples therapy, although results of this therapy are poorly documented. Euphoria (Greek ) is a medically recognized emotional state related to happiness. ...

MDMA is criminalized in most countries, and its possession, manufacture, or sale may result in criminal prosecution. Despite widespread illegality, MDMA is today one of the most commonly-used illicit drugs in the world and is taken in a variety of contexts far-removed from its roots in psychotherapeutic settings. It is commonly associated with the rave culture and its related genres of music. Main Entry: crim·i·nal·ize Pronunciation: kri-m&-n&l-Iz, krim-n&-lIz Function: transitive verb Inflected Form(s): -ized; -iz·ing to make illegal : OUTLAW; also : to turn into or treat as a criminal - crim·i·nal·i·za·tion /kri-m&-n&l-&-zA-sh&n... For other uses, see Rave (disambiguation). ... This is a list of electronic music genres, sub-genres and styles, though for the latter, not all possess their own article (in which case, see the main genre article). ...

Many within science, health care, and drug policy are concerned that MDMA may lead to neurotoxic damage of the central nervous system, the reversibility, extent and significance of which is yet to be fully determined^[2][3]. Based on these and other health concerns, some feel the risks of even single doses of MDMA outweigh its potential benefits^[4][5]. Others feel that these concerns are based on inconclusive evidence and that MDMA deserves further study^[6][7]. Studies have been initiated to examine the therapeutic potential of MDMA for posttraumatic stress disorder and anxiety associated with cancer. In addition, several research groups are using it in humans for basic scientific research.^[8] The term neurotoxic is used to describe a substance, condition or state that damages the nervous system and / or brain, usually by killing neurons. ... A diagram showing the CNS: 1. ... Posttraumatic stress disorder[1][2] (PTSD) is an anxiety disorder that can develop after exposure to one or more terrifying events in which grave physical harm occurred or was threatened. ...

History

At the end of the 19th century, the Merck company of Germany was interested in developing substances that stopped abnormal bleeding. One of the most important compounds was hydrastinine. The plant from which it was isolated became rarer, and they started looking for alternatives. The scientific reports from the laboratory from 1911 and 1912 show that they wanted to use 3-methyl-hydrastinine as an alternative. They believed that this methylated analog of hydrastinine might be similarly effective. Drs. Walther Beck, Otto Wolfes and Anton Köllisch started on the project. In the newly developed synthetic pathway to 3-methyl-hydrastinine, MDMA was mentioned as one of several key precursors under the name of Methylsafrylamin. In 1912 Dr. Anton Köllisch was requested to develop a patentable synthesis for 3-methyl-hydrastinine. The patent started on December 24, 1912. It is a procedural patent for compounds which are key precursors for therapeutics. MDMA was not the purpose of the patent. It was Dr. Max Oberlin (also at Merck) who in 1927 was the first person interested in the pharmacological properties of MDMA. Research on the substance was stopped for economic reasons, and the substance was buried in oblivion for some decades. In the 1950s the American and German armies were interested in psychotropic agents; MDMA was among the tested substances. Most probably for this reason, MDMA was re-synthesized at Merck. In his laboratory journal of 1952 Dr. Albert van Schoor describes how MDMA kills 6 flies in 30 minutes. In 1959 Dr. Fruhstorfer works on MDMA and similar psychotropics, his substance H671 was identified to be MDMA. The research on these substances led to the marketing of Reaktivin in 1960. Its chemical structure is not related to MDMA. The first scientific paper on MDMA appeared in 1960 and described a synthesis for MDMA. It is written in Polish by Biniecki and Krajewski and almost unknown. In 1978 Shulgin published the first scientific article on the drug’s psychotropic effect in humans.^[9]

The U.S. Army did, however, carry out lethal dose studies of MDMA and several other compounds on animals in the mid-1950s. It was given the name EA-1475, with the EA standing for either (accounts vary) "Experimental Agent" or "Edgewood Arsenal."^[10] The results of these studies were not declassified until 1969. The United States Army is the largest, and by some standards oldest, established branch of the armed forces of the United States and is one of seven uniformed services. ... A lethal dose (LD) is an indication of the lethality of a given substance or type of radiation. ... Aberdeen Proving Ground is a United States Army proving ground located in Harford County, Maryland. ...

MDMA appeared sporadically as a street drug in the late 1960s (when it was known as the "love drug").^{[citation needed]}

MDMA began to be used therapeutically in the late-1970s after the chemist Alexander Shulgin tried it himself, in 1977,^[11] and subsequently introduced it to psychotherapist Leo Zeff. As Zeff and others spread word about MDMA, it developed a reputation for enhancing communication during clinical sessions, reducing patients' psychological defenses, and increasing capacity for therapeutic introspection. However, no formal measures of these putative effects were made and blinded or placebo-controlled trials were not conducted. A small number of therapists, including George Greer, Joseph Downing, and Philip Wolfson, used it in their practices until it was made illegal. Other therapists continued to conduct therapy illegally and MDMA was not legally given to humans until Charles Grob initiated an ascending-dose safety study in healthy volunteers. Subsequent legally-approved MDMA studies in humans have taken place in Detroit, Chicago, San Francisco, and South Carolina, as well as in Switzerland, the Netherlands, and Spain.^[12] Image File history File links No higher resolution available. ... Alexander and Ann Shulgin, in a photo from their book TiHKAL, c. ... For other uses, see Placebo (disambiguation). ...

Due to the wording of the U.K's existing Misuse of Drugs Act of 1971, MDMA was automatically classified as a Class A drug in 1977. The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ...

In the early 1980s in the U.S, MDMA rose to prominence in trendy nightclubs in the Dallas area, then in gay dance clubs.^[13] From there use spread to rave clubs in major cities around the country, and then to mainstream society. The drug was first proposed for scheduling by the DEA in July 1984,^[14] and was classified as a Schedule I controlled substance in the United States from May 31, 1985.^[15] A nightclub (often dance club or club, particularly in the UK) is an entertainment venue which does its primary business after dark. ... Dallas redirects here. ... For the song Gay Bar by Electric Six, see Electric Six. ... For other uses, see Rave (disambiguation). ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... is the 151st day of the year (152nd in leap years) in the Gregorian calendar. ... This article is about the year. ...

In the late 1980s and early 1990s, ecstasy was widely used in the United Kingdom and other parts of Europe, becoming an integral element of rave culture and other psychedelic/dancefloor-influenced music scenes, such as Madchester and Acid House. Spreading along with rave culture, illicit MDMA use became increasingly widespread among young adults in universities and later in high schools, and it rapidly became one of the four most widely used illicit drugs in the U.S along with cocaine, heroin and cannabis.^{[citations needed]} Today in the U.S, according to some estimates, only cannabis will attract more first-time users.^[16] This article is about a form of party. ... An NME Originals issue covering the Madchester movement. ... For the 1994 novel by Irvine Welsh, see The Acid House. ... For the community in Florida, see University, Florida. ... For other uses, see High school (disambiguation). ... For other uses, see Cocaine (disambiguation). ... For other uses, see Heroin (disambiguation). ... Cannabis, also known as marijuana[1] or ganja (Hindi: गांजा),[2] is a psychoactive product of the plant Cannabis sativa. ...

Effects

Mode of action

For more details on this topic, see Effects of MDMA on the human body.

The mechanism of MDMA's unusual effects has yet to be fully understood. One of the primary characteristics leading to production of effects is the drug's higher affinity for SERTs than serotonin itself. SERTs are the part of the serotonergic neuron which remove serotonin from the synapse to be recycled or stored for later use. Not only does MDMA inhibit the reuptake of serotonin into this pump, but it reverses the action of the transporter so that it begins pumping serotonin into the synapse from inside the cell.^[17][18] In addition, MDMA induces release of norepinephrine through an analogous mechanism. as well as an affinity for blocking that of dopamine.^[19] MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... The serotonin transporter is a monoamine transporter protein. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ... Norepinephrine (INN)(abbr. ... For other uses, see Dopamine (disambiguation). ...

MDMA's unusual empathic/entactogenic effects have been hypothesized to be at least partly the result of the release of oxytocin,^[20] a hormone usually released following such events as orgasm and childbirth, which is thought to facilitate bonding and the establishment of trust. MDMA is thought to cause this release by indirectly stimulating 5-HT1A receptors. However, the evidence that oxytocin is involved in the effects of MDMA is derived from studies conducted on rats where the emotional effects can only be indirectly measured, in this case by the time animals spend in close proximity to one another. Controlled human studies have not yet been carried out, and it is not known conclusively if MDMA has oxytocinergic action in humans. The question of why other serotonergic drugs do not produce a similarly profound emotional state like MDMA also remains unanswered. Oxytocin (Greek: quick birth) is a mammalian hormone that also acts as a neurotransmitter in the brain. ...

Acute effects

For more details on this topic, see Effects of MDMA on the human body.

The primary effects attributable to MDMA consumption are predictable and fairly consistent amongst users.[3] [4] [5] The most common effects include: MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ...

• Euphoria
• Decreased hostility and insecurity
• Increased feelings of intimacy with others
• Feelings of empathy towards others
• Ability to discuss anxiety-provoking topics with markedly-increased ease
• A strong sense of inner peace and self-acceptance
• Feelings of insightfulness and mental clarity
• Intensification of sensory experience, particularly auditory and tactile
• Decreased appetite
• Urinary retention (also see hyponatremia)
• Mydriasis (abnormal pupil dilation)
• Increased physical energy
• Increased heart rate and blood pressure

Other effects may include: Euphoria (Greek ) is a medically recognized emotional state related to happiness. ... Inner peace (or peace of mind) is a colloquialism that refers to a state of being mentally or spiritually at peace, with enough knowledge and understanding to keep oneself strong in the face of discord or stress. ... The electrolyte disturbance hyponatremia or hyponatraemia exists in humans when the sodium level in the plasma falls below 135 mmol/l. ... Mydriasis is an excessive dilation of the pupil due to disease or drugs. ...

• Short-term memory lapses
• Trisma (lockjaw)
• Bruxia (involuntary teeth grinding)
• Nystagmus (rapid, uncontrollable eye movements)
• Several hours of restlessness following primary subjective effects, often accompanied by a peaceful, "glowing" feeling
• A period of general malaise following primary subjective effects, normally resolving within a few days
• Mildly-blurred vision following primary subjective effects, gradually resolving over a period of up to several days, also known as "plurring"

Serious complications increasing in likelihood with dose, environmental severity, degree of physical activity, and/or certain drug interactions include: It has been suggested that this article or section be merged into Trismus. ... Name for the involuntary teeth-grinding that you do after consuming ecstasy (XTC). ... Nystagmus is involuntary eye movement that can be part of the vestibulo-ocular reflex (VOR), with the eyes moving first in the direction of the lesioned side (slow phase) followed by a quick correction (fast phase) to the opposite side or away from the lesioned side. ...

• Hyperthermia (due to an intemperate environment and/or lack of hydration and/or rest from physical activity, usually dancing)
• Dehydration (due to an intemperate environment and/or lack of hydration and/or rest from physical activity, usually dancing)
• Hyponatremia (due to drug induced antidiuretic hormone release and/or excess compensatory intake of fluids, a rare complication)
• Serotonin syndrome (believed to be due to excess release of serotonin, sometimes triggered by coadministration of other serotonergic drugs)

Hyperthermia in its advanced state referred to as heat stroke or sunstroke, is an acute condition which occurs when the body produces or absorbs more heat than it can dissipate. ... Dehydration (hypohydration) is the removal of water (hydro in ancient Greek) from an object. ... The electrolyte disturbance hyponatremia or hyponatraemia exists in humans when the sodium level in the plasma falls below 135 mmol/l. ... Serotonin syndrome is a rare, but potentially life-threatening adverse drug reaction that results from intentional self-poisoning, therapeutic drug use, inadvertent interactions between drugs, or the recreational use of certain drugs. ...

Effects of chronic use

This section needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (April 2008)

For more details on this topic, see Effects of MDMA on the human body.

The long-term health effects of Ecstasy use are generally not well-known, and the research that has been devoted to addressing the relevant issues thus far has been largely inconclusive. The primary concern is generally that there may be negative long-term consequences that result from the drug's potential neurotoxic effects on serotonergic neurons. Some animal studies suggest that dancing or being in a warm environment may increase risk of neurotoxic damage due to the consequences of increased bodily temperature. However, this has not been established in humans. Image File history File links Question_book-3. ... MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... The term neurotoxic is used to describe a substance, condition or state that damages the nervous system and / or brain, usually by killing neurons. ...

Many factors, including total lifetime MDMA consumption, the duration of abstinence between uses, the environment of use, poly-drug use/abuse, quality of mental health, various lifestyle choices, and predispositions to develop clinical depression and other disorders may contribute to various possible health consequences.

Generally-speaking, less-frequent and more moderate use of MDMA is not associated with decreased long-term psychological wellness.^{[citation needed]} Those who consume the drug excessively/frequently are at greater risk of developing depression and other disorders, although according to one four-year study, the vast majority of those who go on to do so have been diagnosed with some disorder prior to ever trying Ecstasy. [6]^{[dubious – discuss]}

The effects of the drug on memory and cognition are less clear still. Although generally not considered to significantly affect long-term memory, MDMA may contribute to reductions in performance on short-term memory and some cognitive tasks. The degree of manifestation of these types of effects and their reversibility are still in question.^{[citation needed]}

MDMA use has been occasionally associated with liver damage^[21], excessive wear of teeth^[22], and Hallucinogen persisting perception disorder^[23]. Hallucinogen Persisting Perception Disorder or HPPD is a disorder characterized by a continual presence of visual disturbances that are reminiscent of those generated by the ingestion of hallucinogenic substances. ...

Recreational use

MDMA use has increased markedly since the late 1980s, and spread beyond its original subcultures to mainstream use, with prices generally falling, although there is still wide geographical variance, both regionally and between countries.

Please help improve this article or section by expanding it. Further information might be found on the talk page or at requests for expansion. (March 2008)

Image File history File links This is a lossless scalable vector image. ...

United Kingdom

In 1995 it was reported that the street price per pill in the U.K. was "about £15 each,"^[24] although two years later this had shifted to a range of £8 to £15 each.^[25] A 2001 Home Office study reported that the cost per pill to end-point consumer, "could be as little as £7.50, or as much as £10 to £15 when purchased in clubs."^[26] The modern concept of Small Office and Home Office or SoHo , or Small or Home Office deals with the category of business which can be from 1 to 10 workers. ...

In 2007 the Greater London Authority highlighted regional variations, reporting on the average street price per pill in five selected cities.^[27] They were: The Greater London Authority (GLA) is the city-wide governing body for London, England. ...

• Bristol £5
• London £3.50
• Manchester £3
• Nottingham £2
• Torquay £1.50

This article is about the English city. ... This article is about the capital of England and the United Kingdom. ... This article is about the City of Manchester in England. ... For other uses, see Nottingham (disambiguation). ... This article is about the English town. ...

Supply

This section does not cite any references or sources. (March 2008) Please help improve this section by adding citations to reliable sources. Unverifiable material may be challenged and removed.

Worldwide, almost all MDMA is supplied via clandestine routes. The synthesis of MDMA is more complex than that of analogues such as methamphetamine, but still well within the grasp of a university-level chemistry student. Arguably the most difficult part of the synthesis is obtaining the necessary chemical precursors, as although all have legitimate uses outside of clandestine drug production, their distribution is now heavily monitored by government agencies like the DEA. Image File history File links Question_book-3. ... This article is about the psychostimulant, d-methamphetamine. ... The DEAs enforcement activities may take agents anywhere from distant countries to suburban U.S. homes. ...

Ecstasy commonly appears in a tablet form, usually imprinted with a monogram.

Ecstacy pills from http://www. ... Ecstacy pills from http://www. ...

Ecstasy pills

Pills come in a variety of "brands or batches", usually identified by the icons stamped on the pills. The purpose of this is to help identify and providing an indicator as to the strength and quality of a particular tablet. Many popular icons are appropriated for this use; an example would be "Red Mercedes", which derives its name from its red color and imprinted Mercedes-Benz logo. However, the brands do not consistently designate the actual active compound(s) within the pill, as it is possible for copycat manufacturers to make their own pills which replicate the appearance of a well-known brand. For other uses, see Brand (disambiguation). ... This page is about the Mercedes-Benz brand of automobiles and trucks from the DaimlerChrysler automobile manufacturer. ...

MDMA hydrochloride crystals.

Image File history File linksMetadata Size of this preview: 800 × 600 pixel Image in higher resolution (1632 × 1224 pixel, file size: 286 KB, MIME type: image/jpeg) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Methylenedioxymethamphetamine Metadata This... Image File history File linksMetadata Size of this preview: 800 × 600 pixel Image in higher resolution (1632 × 1224 pixel, file size: 286 KB, MIME type: image/jpeg) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Methylenedioxymethamphetamine Metadata This...

MDMA powder/crystals

MDMA powder, usually the hydrochloride salt, is often simply called 'crystal' or 'molly', and 'mandy', and in the UK 'Muds', 'Mud' or 'madman' (a play on words- MaDMAn), a mutation of 'madman' 'mandy', and 'MD'. This powder is produced in MDMA labs and provided to the pill-manufacturers to press the tablets into their desired form. When pressed into pill tablets, MDMA powder is always mixed with pill binders because pure MDMA cannot be pressed.

In many parts of the world the usage of plain MDMA powder instead of pills is popular. One of the reasons for this is likely the superior control over dose and purity that the user is granted. This is because the powder form is less likely to be cut due to the greater ease of detecting impurities, and also because of MDMA's distinctive, intensely bitter taste. Because of this unpleasant taste, many users choose to 'bomb' or 'parachute' pure MDMA, whereby a dose is wrapped in cigarette papers or a small piece of toilet paper and then swallowed.

MDMA powder can also be insufflated, a route which leads to a quicker onset and dissipation of more intense effects, although users claim that this method of administration can be very unpleasant. This article or section does not cite its references or sources. ...

Use in psychotherapy

Some scientists^{[citation needed]} have suggested that MDMA may facilitate self-examination with reduced fear, which may prove useful in a therapeutic setting.

A small number of therapists, including George Greer, Joseph Downing, and Philip Wolfson, used it in their practices until it was made illegal. George Greer synthesized MDMA in the lab of Alexander Shulgin and administered it to about 80 of his clients over the course of the remaining years preceding MDMA's Schedule I placement in 1985. In a published summary of the effects,^[28] the authors reported patients felt improved in various, mild psychiatric disorders and other personal benefits, especially improved intimate communication with their significant others. In a subsequent publication on the treatment method, the authors reported that one patient with severe pain from terminal cancer experienced lasting pain relief and improved quality of life. ^[29] However, few of the results in this early MDMA psychotherapy were measured using methods considered reliable or convincing in scientific practice. For example, the questionnaires used might not have been sensitive to negative changes and it is not known to what extent similar patients might improve from chance or from psychotherapy.

An ongoing study by the Multidisciplinary Association for Psychedelic Studies is evaluating the efficacy of MDMA-assisted psychotherapy for treating those diagnosed with posttraumatic stress disorder. To participate, patients must have had the disorder for a number of years and tried other treatments without success. In a newspaper interview, the researchers report promising tendencies for some participants to have reduced disease severity after MDMA psychotherapy.^[30] However, despite the initially positive nature of the results, they are only the findings of a currently-unpublished Phase II study, and similar research by other scientists will need to be conducted in order to demonstrate the efficacy of MDMA as a psychotherapeutic agent. The Multidisciplinary Association for Psychedelic Studies (MAPS) is a non-profit organization that aims to assist scientists to design, fund, obtain approval for and report on studies into the risks and benefits of MDMA, psychedelic drugs and marijuana. ... Posttraumatic stress disorder[1][2] (PTSD) is an anxiety disorder that can develop after exposure to one or more terrifying events in which grave physical harm occurred or was threatened. ... In medicine, a clinical trial (synonyms: clinical studies, research protocols, medical research) is a research study. ...

Synthesis

Industrial scale methamphetamine/MDMA factory in Cikande, Indonesia

Safrole, a colorless or slightly yellow oil, extracted from the root-bark or the fruit of sassafras plants is the primary precursor for all manufacture of MDMA. There are numerous synthetic methods available in the literature to convert safrole into MDMA via different intermediates. One common route is via the MDP2P (3,4-methylenedioxyphenyl-2-propanone, also known as piperonyl acetone) intermediate. This intermediate can be produced in at least two different ways. One method is to isomerize safrole in the presence of a strong base to isosafrole and then oxidize isosafrole to MDP2P. Another, reportedly better method, is to make use of the Wacker process to oxidize safrole directly to the MDP2P (3,4-methylenedioxy phenyl-2-propanone) intermediate. This can be done with a palladium catalyst. Once the MDP2P intermediate has been produced it is then consumed via a reductive amination to form MDMA as the product. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Safrole Safrole (chemical formula: C10H10O2, IUPAC name: 5-(2-propenyl)-1,3-benzodioxole), also called shikimol, is a colorless or slightly yellow oily liquid. ... This article is about the Sassafras tree. ... MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone. ... Methylenedioxy in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the structural formula -O-CH2-O- which is connected to the rest of a molecule by two chemical bonds. ... In chemistry, isomerization is the transformation of a molecule into a different isomer. ... Chemical structure of trans-isosafrole. ... Chemical structure of trans-isosafrole. ... MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone. ... The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name) originally referred to the oxidation of ethylene to acetaldehyde by oxygen in the presence of a palladium(II) chloride catalyst. ... MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone. ... For other uses, see Palladium (disambiguation). ... MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone. ... Reductive amination (also known as reductive alkylation) is a chemical reaction which involves the conversion of a carbonyl group to an amine, via an intermediate imine. ...

According to DEA Microgram newsletters very little safrole is actually required to make MDMA.^[31] "Ocotea cymbarum is an essential oil... that typically contains between 80 and 94 percent safrole," "a 500-milliliter bottle of Ocotea cymbarum sells for $20 to more than $100," "An MDMA producer with access to the proper chemicals can use a 500-milliliter quantity of Ocotea cymbarum to produce an estimated 1,300 to 2,800 tablets containing 120 milligrams of MDMA." Binomial name Kunth Ocotea cymbarum is a species of plant in the Lauraceae family. ...

Legal issues

Use, supply and trafficking of ecstasy are currently illegal in most countries. Ecstasy is illegal in all countries belonging to the United Nations. In the United States, MDMA was legal and unregulated until May 31, 1985, at which time it was added to DEA Schedule I, for drugs deemed to have no medical uses and a high potential for abuse. During DEA hearings to criminalize MDMA, most experts recommended DEA Schedule III prescription status for the drug, due to its beneficial usage in psychotherapy. The judge overseeing the hearings, Francis Young, also made this recommendation. Nonetheless, the DEA classified it as Schedule I.^[32] UN redirects here. ... is the 151st day of the year (152nd in leap years) in the Gregorian calendar. ... This article is about the year. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... The DEAs enforcement activities may take agents anywhere from distant countries to suburban U.S. homes. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ...

That same year, the World Health Organization's Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the Convention on Psychotropic Substances. Unlike the Controlled Substances Act, the Convention has a provision in Article 7(a) that allows use of Schedule I drugs for "scientific and very limited medical purposes." The committee's report stated:^[33] WHO redirects here. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ...

The Expert Committee held extensive discussions concerning therapeutic usefulness of 3,4 Methylenedioxymethamphetamine. While the Expert Committee found the reports intriguing, it felt that the studies lacked the appropriate methodological design necessary to ascertain the reliability of the observations. There was, however, sufficient interest expressed to recommend that investigations be encouraged to follow up these preliminary findings. To that end, the Expert Committee urged countries to use the provisions of article 7 of the Convention on Psychotropic Substances to facilitate research on this interesting substance.

In the United Kingdom, MDMA is a Class A drug under the Misuse of Drugs Act 1971, making it illegal to sell, buy, or possess without a license. Penalties include a maximum of seven years and/or unlimited fine for possession; life and/or unlimited fine for production or trafficking. A mandatory seven year sentence is now the penalty for a third conviction for trafficking. The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ...

Health concerns

While the short-term adverse effects and contraindications of MDMA are fairly well known, there is significant debate within the scientific and medical communities possible regarding long-term physical and psychological effects of MDMA.

U.K. government assessment of overall harm

The chief executive of the U.K. Medical Research Council stated that MDMA is "on the bottom of the scale of harm," and was rated to be of lesser concern than alcohol, tobacco, and cannabis, as well as several classes of prescription medications, when examining the harmfulness of twenty popular recreational drugs. The U.K. study placed great weight on the risk for acute physical harm, the propensity for physical and psychological dependency on the drug, and the negative familial and societal impacts of the drug. Based on these factors, the study placed MDMA at number 18 in the list. [7] This article does not cite any references or sources. ... Shredded tobacco leaf for pipe smoking Tobacco can also be pressed into plugs and sliced into flakes Tobacco is an agricultural product processed from the fresh leaves of plants in the genus Nicotiana. ... Cannabis, also known as marijuana[1] or ganja (Hindi: गांजा),[2] is a psychoactive product of the plant Cannabis sativa. ...

Physical

This section does not cite any references or sources. (April 2008) Please help improve this section by adding citations to reliable sources. Unverifiable material may be challenged and removed.

For more details on this topic, see Effects of MDMA on the human body.

The short-term physical health risks of MDMA consumption include hyperthermia, and hyponatremia. These dangers usually manifest themselves within the context of the rave subculture, as dancing often occurs in untempered environments where hundreds or even thousands of people are gathered in close proximity, sometimes indoors. Continuous dancing 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 and caffeine, also a stimulant, may exacerbate these risks further. Image File history File links Question_book-3. ... MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... Hyperthermia in its advanced state referred to as heat stroke or sunstroke, is an acute condition which occurs when the body produces or absorbs more heat than it can dissipate. ... The electrolyte disturbance hyponatremia or hyponatraemia exists in humans when the sodium level in the plasma falls below 135 mmol/l. ... For other uses, see Rave (disambiguation). ... A diuretic is any drug that tends to increase the flow of urine from the body (diuresis). ...

Hyponatremia (abnormally low salts in the blood) has been reported in some MDMA users. It is not clear to what extent this is due to the known ability of MDMA to induce antidiruetic hormone release and/or whether these people inadvertently consumed excess fluids in an attempt to remain hydrated. MDMA on its own does not cause dehydration and there is no need to drink extra fluids unless one has extra fluid loss, such as from sweating. Premenopausal females experiencing rapidly developing hyponatremia are at risk of neurological complications including seizures, coma, and death because hyponatremia can cause neurons to swell and stop working. MDMA-releated hyponatremia is relatively uncommon.

Hypertension is a risk in some users due to the increase in heart rate and blood pressure, but this is normally well-tolerated in young, healthy individuals who do not have pre-existing cardiovascular vulnerabilities. For other forms of hypertension, see Hypertension (disambiguation). ...

Neurological overview

For more details on this topic, see Effects of MDMA on the human body.

MDMA causes a reduction in the concentration of serotonin transporters (SERTs) in the brain. The rate at which the brain recovers from serotonergic changes is unclear. A number of studies ^[34] including some performed by George Ricaurte at Johns Hopkins University, have demonstrated lasting serotonergic changes occurring due to MDMA exposure. Baboons who were given a neurotoxic dose of MDMA showed partial regrowth of SERTs when scanned a year later.^[35] Human users also show some recovery of serotonergic markers and, in some PET studies, have been indistinguishable from non-users. However, the same study also concluded that the reduction in memory performance due to heavy, prolonged MDMA use may be long-lasting.^[36] MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... The serotonin transporter is a monoamine transporter protein. ... The term neurotoxic is used to describe a substance, condition or state that damages the nervous system and / or brain, usually by killing neurons. ...

Although oxidative stress (see neurotoxicity theory below) may cause SERTs to degrade faster than they are able to be replaced, the serotonin axon itself seems to have been spared^{[dubious – discuss]}, which indicates that neurotoxicity may not be the means by which SERT count was reduced. It is possible that excess serotonin in the synapse due to MDMA, especially if uses occur within a short period, causes the serotonin cells to produce fewer SERTs, a phenomenon which has already been demonstrated with other serotonin-depleting drugs.^[37] MDMA use may also cause a decrease in the number of serotonin receptors on the dendrite of the neuron. (See down-regulation theory below.) An axon or nerve fiber, is a long, slender projection of a nerve cell, or neuron, that conducts electrical impulses away from the neurons cell body or soma. ...

For a detailed and comprehensive explanation of this topic, see TheDea.org's evaluation of studies.^[38]

Receptor down-regulation

For more details on this topic, see Effects of MDMA on the human body.

One theory of SERT-depletion arising out of long-term MDMA use is receptor down-regulation which is one form of synaptic plasticity. When any neurotransmitter is present in excess for prolonged periods of time, the brain responds in an attempt to reestablish its own natural neuro-electrical balance. Weekly use of MDMA over a prolonged period may actually cause serotonin receptors to retreat into the dendrite of serotonin nerve cells. ^[39] The change in synaptic serotonin concentration due to recreational MDMA use is at the extreme end of what is even possible in the brain and therefore, down-regulation could occur fairly easily with regular use.^{[citation needed]} MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... In neuroscience, synaptic plasticity is the ability of the connection, or synapse, between two neurons to change in strength. ... Dendrites (from Greek dendron, “tree”) are the branched projections of a neuron that act to conduct the electrical stimulation received from other neural cells to the cell body, or soma, of the neuron from which the dendrites project. ...

This process causes the brain to become desensitized to the neurotransmitters present in the synapses and therefore also to the effects of MDMA itself. Therefore, in addition to a generally decreased quality of mood between doses^{[citation needed]}, greater amounts of MDMA are required to achieve the same level of desired effects. It is this cycle that is often believed to be the cause of long-term emotional problems among regular ecstasy users^{[citation needed]}.

Neurotoxicity

For more details on this topic, see Effects of MDMA on the human body.

Under another theory, MDMA is considered neurotoxic in humans. While the method of this toxicity has not been definitively established, the current leading theory^{[dubious – discuss]} is that the metabolism of MDMA-induced dopamine release leads to the lipid peroxidation of the axons of serotonergic neurons. This occurs when MAO-B metabolizes dopamine into free radicals capable of damaging cells, leading to a reduction in SERT count and damaging or destroying the axon, thus interfering with the integrity of the brain's serotonin network.^[40][41] Neurotoxicity of serotonergic neurons would occur in selective areas of the human brain as serotonin cells are highly concentrated in certain areas such as the neocortex and hippocampus. MDMA is commonly ingested in a pill form // MDMA reaches maximal concentrations in the blood between 1. ... Neurotoxicity occurs when the exposure to natural or manmade toxic substances ,which are called neurotoxins, alters the normal activity of the nervous system. ... RNA expression pattern Orthologs Human Mouse Entrez Ensembl Uniprot Refseq Location Pubmed search Monoamine oxidase B, also known as MAOB, is a human gene. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ... The neocortex (Latin for new bark or new rind) is a part of the brain of mammals. ... For other uses, see Hippocampus (disambiguation). ...

Normally, the brain is able to protect itself from oxidative stress, but it is believed that the aforementioned damage can be partially attributed to MDMA's unique interaction with serotonin transporters. Not only does MDMA reverse the normal functioning of the transporter in which case serotonin is pumped out of the cell, but once the stored serotonin has been depleted, the transporter begins to take up dopamine which has been shown to be toxic to serotonin cells by itself. Once MAO oxidizes dopamine inside the serotonin cell, the damage is greatly magnified. Several studies have demonstrated that such damage in the brain is reversible after prolonged abstinence from the drug.^[42][43]

One now infamous study on the MDMA toxicity, which claimed that a single recreational dose of MDMA could cause Parkinson's Disease in later life due to severe dopaminergic stress, was actually retracted by Ricaurte himself after he discovered his lab had administered not MDMA but methamphetamine, which is known to cause dopaminergic changes similar to the serotonergic changes caused by MDMA.^[44] Ricaurte blamed this mistake on the chemical supply company that sold the material to his lab. Most studies have found that levels of the dopamine transporter (or other markers of dopamine function) in MDMA users are normal. Parkinsons disease (also known as Parkinson disease or PD) is a degenerative disorder of the central nervous system that often impairs the sufferers motor skills and speech, as well as other functions. ... Severe dopaminergic neurotoxicity in primates after a common recreational dose regimen of MDMA[1] (ecstasy) is the title of a paper by Dr. George Ricaurte which was published in the leading journal Science and was later retracted. ... This article is about the psychostimulant, d-methamphetamine. ...

For more details on this topic, see Retracted article on toxicity of MDMA on dopamine cells.

Antioxidants have been shown to prevent the neurotoxicity of MDMA in rats. In one study, intravenous administration of alpha lipoic acid completely blocked the neurotoxic effects of MDMA. No scientific experiment has been performed to date with human subjects, although some users report that taking various combinations of antioxidants before, during, and after using MDMA serves to moderate the subsequent mood-dip and improve recovery time.^[45] An antioxidant is a chemical that prevents the oxidation of other chemicals. ... This is an article about wild rats; for pet rats, see Fancy rat Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... Lipoic acid, also known as α-lipoic acid (alpha lipoic acid) or thioctic acid, has formula C8H14S2O2 and systematic name 5-(1,2-dithiolan-3-yl)pentanoic acid. ...

The administration of an SSRI in rats prior to the administration of MDMA has been shown to completely block neurotoxicity. This is due to the binding of such medications with SERTs. However, administering an SSRI prior to administration of MDMA also completely or partially blocks the desired effects of the latter, something a large number of users prescribed an SSRI have reported. As a compromise it has been shown that administration of an SSRI 3-4 hours after MDMA, at which time the primary effects will have tapered off significantly, markedly limits neurotoxicity overall despite some axonal damage having already occurred.^[46] Several studies have administered MDMA and SSRIs to humans, including paroxetine and citalopram, and these combinations have not cause obvious increases in risk or toxicity. However, the SSRI was always given before the MDMA and potential complications may still exist.^{[citation needed]} SSRI is an acronym that stands for several things: It is a class of antidepressants called selective serotonin reuptake inhibitor SSRI also is used as the stock symbol for Silver Standard Resources Inc. ... The Special Emergency Response Team (SERT) was the RCMP counter-terrorism unit which existed until 1993. ... SSRI is an acronym that stands for several things: It is a class of antidepressants called selective serotonin reuptake inhibitor SSRI also is used as the stock symbol for Silver Standard Resources Inc. ...

Psychological

MDMA use commonly results in a rebound period of poor mood commonly known as a "comedown", the length and severity of which depends on the user, the dose, time since previous usage, any polydrug use/abuse, and a host of other factors. It is sometimes claimed that heavy or frequent use may precipitate lasting depression and anxiety in vulnerable users, particularly those prone to depression or other mental disorders as well as anyone in a state of life crisis, although there is little published data on this.

"Redosing" in an attempt to extend MDMA's desired effects has been shown to substantially increase neurotoxicity in animals. Users also report increases in undesired physical side effects associated with MDMA use such as trisma and bruxia^{[citation needed]}. The longer MDMA is active and being metabolized in the brain, the greater the neurotoxic damage and the greater the risk of exacerbating pre-existing emotional problems.^{[dubious – discuss]} The more occasions MDMA is used, the greater the chances of long-term problems.^[47] Deficits in memory have been shown in long term MDMA users.^[48] It has been suggested that this article or section be merged into Trismus. ... Name for the involuntary teeth-grinding that you do after consuming ecstasy (XTC). ... For other uses, see Memory (disambiguation). ...

A recent University of Louisiana study found no significant relationship between depression and recreational ecstasy use.^[49][50] The preliminary results from an ongoing Dutch study also indicates that the very moderate use of Ecstasy was not associated with depression or decreased mental state. These users also appear to be free of neurological injury of any kind.^{[dubious – discuss][51]}

Drug interactions

Individuals who have stopped taking any type of SSRI after prolonged medication may not be able to experience the desired effects of MDMA for as long as several months following discontinuation of the medication. This is due to the fact that SSRIs decrease the brain's sensitivity to the presence of serotonin as the brain seeks to reestablish a normal neuro-electrical balance. SSRI is an acronym that stands for several things: It is a class of antidepressants called selective serotonin reuptake inhibitor SSRI also is used as the stock symbol for Silver Standard Resources Inc. ...

Most people who die while under the influence of MDMA have also consumed significant quantities of at least one other drug. The risk of MDMA-induced death overall is very low. ^[52]

The use of MDMA can be dangerous when combined with other drugs (particularly monoamine oxidase inhibitors (MAOIs) and antiretroviral drugs, in particular ritonavir). Combining MDMA with MAOIs can precipitate hypertensive crisis, as well as serotonin syndrome which can be fatal.^[53] MAO-B inhibitors such as deprenyl do not seem to carry these risks when taken at selective doses, and have been used to completely block neurotoxicity in rats. ^[54] Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Antiretroviral drugs are medications for the treatment of infection by the retrovirus HIV. Different antiretroviral drugs act at various stages of the HIV life cycle. ... Ritonavir is a drug from the protease inhibitor class used to treat AIDS. It is manufactured as Norvir® by Abbott Laboratories. ... Serotonin syndrome is a rare, but potentially life-threatening adverse drug reaction that results from intentional self-poisoning, therapeutic drug use, inadvertent interactions between drugs, or the recreational use of certain drugs. ... Selegiline/l-Deprenyl Selegiline (l-deprenyl, Eldepryl® or Anipryl® [veterinary]) is a drug used for the treatment of early-stage Parkinsons disease and senile dementia. ...

Purity

Due to its nearly-universal illegality, the purity of a substance sold as Ecstasy is unknown to the typical user. The MDMA content of tablets varies widely between regions and different brands of pills and fluctuates somewhat each year.^[55]

Pills may contain other active substances meant to stimulate in a way similar to MDMA.^{[citation needed]} These substances may include amphetamine, methamphetamine, ephedrine, and caffeine, all of which may be comparatively cheap to produce and can help to boost profit overall.^{[citation needed]} In some cases, tablets sold as Ecstasy do not even contain any MDMA, chemicals in the Ecstasy Family, or even any kind of stimulant drug. Instead they may c