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MDMA

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly or mandy (crystal form), is a potent empathogen–entactogen with stimulant and minor psychedelic properties. Investigational indications include as an adjunct to psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. It was used to enhance 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. Tablets sold as ecstasy may be 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). This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids. In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year. The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances.

Short-term adverse effects include grinding of the teeth, blurred vision, sweating and a rapid heartbeat, and extended use can also lead to addiction, memory problems, paranoia and difficulty sleeping. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel depressed and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration. MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine and noradrenaline in parts of the brain. It belongs to the substituted amphetamine classes of drugs. MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.

MDMA has limited approved medical uses in a small number of countries, but is illegal in most jurisdictions. In the United States, the Food and Drug Administration is evaluating the drug for clinical use. Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada. In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.

Effects
In general, MDMA users report feeling the onset of subjective effects within 30 to 60 minutes of oral consumption and reaching peak effect at 75 to 120 minutes, which then plateaus for about 3.5 hours. The desired short-term psychoactive effects of MDMA have been reported to include:
 * Euphoria – a sense of general well-being and happiness
 * Increased self-confidence, sociability, and perception of facilitated communication
 * Entactogenic effects—increased empathy or feelings of closeness with others and oneself
 * Dilated pupils
 * 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 is lower compared to other psychedelics. For example, MDMA used at parties is associated with high motor activity, reduced sense of identity, and poor awareness of surroundings. Use of MDMA individually or in small groups in a quiet environment and when concentrating, is associated with increased lucidity, concentration, sensitivity to aesthetic aspects of the environment, enhanced awareness of emotions, and improved capability of communication. In psychotherapeutic settings, MDMA effects have been characterized by infantile ideas, mood lability, and memories and moods connected with childhood experiences.

MDMA has been described as an "empathogenic" drug because of its empathy-producing effects. Results of several studies show the effects of increased empathy with others. When testing MDMA for medium and high doses, it showed increased hedonic and arousal continuum. The effect of MDMA increasing sociability is consistent, while its effects on empathy have been more mixed.

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 of music and lighting are often highly synergistic with the drug. The psychedelic amphetamine quality of MDMA offers multiple appealing aspects 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. MDMA is used less often than other stimulants, typically less than once per week.

MDMA is sometimes taken in conjunction with other psychoactive drugs such as LSD, psilocybin mushrooms, 2C-B, and ketamine. The combination with LSD is called "candy-flipping". The combination with 2C-B is called "nexus flipping". For this combination, most people take the MDMA first, wait until the peak is over, and then take the 2C-B.

MDMA is often co-administered with alcohol, methamphetamine, and prescription drugs such as SSRIs with which MDMA has several drug-drug interactions. Three life-threatening reports of MDMA co-administration with ritonavir have been reported; with ritonavir having severe and dangerous drug-drug interactions with a wide range of both psychoactive, anti-psychotic, and non-psychoactive drugs.

Medical
, MDMA has no accepted medical indications. Before it was widely banned, it saw limited use in psychotherapy. In 2017 the United States Food and Drug Administration (FDA) approved limited research on MDMA-assisted psychotherapy for post-traumatic stress disorder (PTSD), with some preliminary evidence that MDMA may facilitate psychotherapy efficacy for PTSD.

Other
Small doses of MDMA are used by some religious practitioners as an entheogen to enhance prayer or meditation. MDMA has been used as an adjunct to New Age spiritual practices.

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 diluents. 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. MDMA tablets can sometimes be found in a shaped form that may depict characters from popular culture, likely for deceptive reasons. These are sometimes collectively referred to as "fun tablets".

Partly due to the global supply shortage of sassafras oil—a problem largely assuaged by use of improved or alternative modern methods of synthesis—the purity of substances sold as molly have been found to vary widely. Some of these substances contain methylone, ethylone, MDPV, mephedrone, or any other of the group of compounds commonly known as bath salts, in addition to, or in place of, MDMA. Powdered MDMA ranges from pure MDMA to crushed tablets with 30–40% purity. MDMA tablets typically have low purity due to bulking agents that are added to dilute the drug and increase profits (notably 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.

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.

The immediate adverse effects of MDMA use can include:

 * Bruxism (grinding and clenching of the teeth)
 * Dehydration
 * Diarrhea
 * Erectile dysfunction
 * Hyperthermia
 * Increased wakefulness or insomnia
 * Increased perspiration and sweating
 * Increased heart rate and blood pressure
 * Increased psychomotor activity
 * Loss of appetite
 * Nausea and vomiting
 * Visual and auditory hallucinations (rarely)

Other adverse effects that may occur or persist for up to a week following cessation of moderate MDMA use include:

 * Physiological

 * Insomnia
 * Loss of appetite
 * Tiredness or lethargy
 * Trismus (lockjaw)

 * Psychological

 * Anhedonia
 * Anxiety or paranoia
 * Depression
 * Impulsiveness
 * Irritability
 * Memory impairment
 * Restlessness

Administration of MDMA to mice causes DNA damage in their brain, especially when the mice are sleep deprived. Even at the very low doses that are comparable to those self-administered by humans, MDMA causes oxidative stress and both single and double-strand breaks in the DNA of the hippocampus region of the mouse brain.

Long-term
, the long-term effects of MDMA on human brain structure and function have not been fully determined. However, there is consistent evidence of structural and functional deficits in MDMA users with high lifetime exposure. These structural or functional changes appear to be dose dependent and may be less prominent in MDMA users with only a moderate (typically <50 doses used and <100 tablets consumed) lifetime exposure. Nonetheless, moderate MDMA use may still be neurotoxic and what constitutes moderate use is not clearly established.

Furthermore, it is not clear yet whether "typical" recreational users of MDMA (1 to 2 pills of 75 to 125 mg MDMA or analogue every 1 to 4 weeks) will develop neurotoxic brain lesions. Long-term exposure to MDMA in humans has been shown to produce marked neurodegeneration in striatal, hippocampal, prefrontal, and occipital serotonergic axon terminals. Neurotoxic damage to serotonergic axon terminals has been shown to persist for more than two years. Elevations in brain temperature from MDMA use are positively correlated with MDMA-induced neurotoxicity. However, most studies on MDMA and serotonergic neurotoxicity in humans focus more on heavy users who consume as much as seven times or more the amount that most users report taking. The evidence for the presence of serotonergic neurotoxicity in casual users who take lower doses less frequently is not conclusive.

However, adverse neuroplastic changes to brain microvasculature and white matter have been observed to occur in humans using low doses of MDMA. Reduced gray matter density in certain brain structures has also been noted in human MDMA users. Global reductions in gray matter volume, thinning of the parietal and orbitofrontal cortices, and decreased hippocampal activity have been observed in long term users. The effects established so far for recreational use of ecstasy lie in the range of moderate to severe effects for serotonin transporter reduction.

Impairments in multiple aspects of cognition, including attention, learning, memory, visual processing, and sleep, have been found in regular MDMA users. The magnitude of these impairments is correlated with lifetime MDMA usage  and are partially reversible with abstinence. Several forms of memory are impaired by chronic ecstasy use; however, the effects for memory impairments in ecstasy users are generally small overall. MDMA use is also associated with increased impulsivity and depression.

Serotonin depletion following MDMA use can cause depression in subsequent days. In some cases, depressive symptoms persist for longer periods. Some studies indicate repeated recreational use of ecstasy is associated with depression and anxiety, even after quitting the drug. Depression is one of the main reasons for cessation of use.

At high doses, MDMA induces a neuroimmune response that, through several mechanisms, increases the permeability of the blood–brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens. In addition, MDMA has immunosuppressive effects in the peripheral nervous system and pro-inflammatory effects in the central nervous system.

MDMA may increase the risk of cardiac valvulopathy in heavy or long-term users due to activation of serotonin 5-HT2B receptors. MDMA induces cardiac epigenetic changes in DNA methylation, particularly hypermethylation changes.

Reinforcement disorders
Approximately 60% of MDMA users experience withdrawal symptoms when they stop taking MDMA. Some of these symptoms include fatigue, loss of appetite, depression, and trouble concentrating. Tolerance to some of the desired and adverse effects of MDMA is expected to occur with consistent MDMA use. A 2007 delphic analysis of a panel of experts in pharmacology, psychiatry, law, policing and others estimated MDMA to have a psychological dependence and physical dependence potential roughly three-fourths to four-fifths that of cannabis.

MDMA has been shown to induce ΔFosB in the nucleus accumbens. Because MDMA releases dopamine in the striatum, the mechanisms by which it induces ΔFosB in the nucleus accumbens are analogous to other dopaminergic psychostimulants. Therefore, chronic use of MDMA at high doses can result in altered brain structure and drug addiction that occur as a consequence of ΔFosB overexpression in the nucleus accumbens. MDMA is less addictive than other stimulants such as methamphetamine and cocaine. Compared with amphetamine, MDMA and its metabolite MDA are less reinforcing.

One study found approximately 15% of chronic MDMA users met the DSM-IV diagnostic criteria for substance dependence. However, there is little evidence for a specific diagnosable MDMA dependence syndrome because MDMA is typically used relatively infrequently.

There are currently no medications to treat MDMA addiction.

During pregnancy
MDMA is a moderately teratogenic drug (i.e., it is toxic to the fetus). In utero exposure to MDMA is associated with a neuro- and cardiotoxicity and impaired motor functioning. Motor delays may be temporary during infancy or long-term. The severity of these developmental delays increases with heavier MDMA use.

Overdose
MDMA overdose symptoms vary widely due to the involvement of multiple organ systems. Some of the more overt overdose symptoms are listed in the table below. The number of instances of fatal MDMA intoxication is low relative to its usage rates. In most fatalities, MDMA was not the only drug involved. Acute toxicity is mainly caused by serotonin syndrome and sympathomimetic effects. Sympathomimetic side effects can be managed with carvedilol. MDMA's toxicity in overdose may be exacerbated by caffeine, with which it is frequently cut in order to increase volume. A scheme for management of acute MDMA toxicity has been published focusing on treatment of hyperthermia, hyponatraemia, serotonin syndrome, and multiple organ failure.

Interactions
A number of drug interactions can occur between MDMA and other drugs, including serotonergic drugs. MDMA also interacts with drugs which inhibit CYP450 enzymes, like ritonavir (Norvir), particularly CYP2D6 inhibitors. Life-threatening reactions and death have occurred in people who took MDMA while on ritonavir. Concurrent use of MDMA high dosages with another serotonergic drug can result in a life-threatening condition called serotonin syndrome. Severe overdose resulting in death has also been reported in people who took MDMA in combination with certain monoamine oxidase inhibitors, such as phenelzine (Nardil), tranylcypromine (Parnate), or moclobemide (Aurorix, Manerix). Serotonin reuptake inhibitors such as citalopram (Celexa), duloxetine (Cymbalta), fluoxetine (Prozac), and paroxetine (Paxil) have been shown to block most of the subjective effects of MDMA. Norepinephrine reuptake inhibitors such as reboxetine (Edronax) have been found to reduce emotional excitation and feelings of stimulation with MDMA but do not appear to influence its entactogenic or mood-elevating effects.

Pharmacodynamics
MDMA is a substituted amphetamine structurally, and a monoamine-releasing agent mechanistically. Like other monoamine-releasing agents, MDMA enters monoaminergic neurons through monoamine transporters. MDMA has high affinity for dopamine, norepinephrine and serotonin transporters, with some preference for the latter. The methylenedioxy- substitution provides the serotonergic activity, as most other substituted amphetamines show negligible affinity for the serotonin transporter.

Neurotransmitter release induced by monoamine-releasing agents differs significantly from the regular, action potential-evoked neurotransmitter release. Inside the neuron, MDMA inhibits VMAT2 and activates TAAR1. TAAR1 agonism results in the phosphorylation of monoamine transporters by PKA and PKC, which either internalizes the transporter, or reverses its flux direction. VMAT2 inhibition prevents the packaging of the cytosolic monoamines into the synaptic vesicles, which allows them to instead be pumped out of the neuron by the phosphorylated transporters. The result is that the neuron constantly "leaks" neurotransmitters into the synapse, regardless of any signal received.

MDMA has two enantiomers, (S)-MDMA and (R)-MDMA. Recreationally used MDMA is the equimolar mixture of both. (S)-MDMA causes the entactogenic effects of the racemate, because it releases serotonin, norepinephrine and dopamine much more efficiently via monoamine transporters. It also has higher affinity towards 5-HT2CR. (R)-MDMA has notable agonism towards 5-HT2AR, which supposedly contributes to the mild psychedelic hallucinations induced by high doses of MDMA in humans.

Pharmacokinetics
The MDMA concentration in the blood stream starts to rise after about 30 minutes, and reaches its maximal concentration in the blood stream between 1.5 and 3 hours after ingestion. It is then slowly metabolized and excreted, with levels of MDMA and its metabolites decreasing to half their peak concentration over the next several hours. The duration of action of MDMA is usually four to six hours, after which serotonin levels in the brain are depleted. Serotonin levels typically return to normal within 24–48 hours.

Metabolites of MDMA that have been identified in humans include 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-dihydroxyamphetamine (DHA) (also called alpha-methyldopamine (α-Me-DA)), 3,4-methylenedioxyphenylacetone (MDP2P), and 3,4-methylenedioxy-N-hydroxyamphetamine (MDOH). The contributions of these metabolites to the psychoactive and toxic effects of MDMA are an area of active research. 80% of MDMA is metabolised in the liver, and about 20% is excreted unchanged in the urine.

MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 (CYP450) enzymes CYP2D6 and CYP3A4 and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.

MDMA and metabolites are primarily excreted as conjugates, such as sulfates and glucuronides. MDMA is a chiral compound and has been almost exclusively administered as a racemate. However, the two enantiomers have been shown to exhibit different kinetics. The disposition of MDMA may also be stereoselective, with the S-enantiomer having a shorter elimination half-life and greater excretion than the R-enantiomer. Evidence suggests that the area under the blood plasma concentration versus time curve (AUC) was two to four times higher for the (R)-enantiomer than the (S)-enantiomer after a 40 mg oral dose in human volunteers. Likewise, the plasma half-life of (R)-MDMA was significantly longer than that of the (S)-enantiomer (5.8 ± 2.2 hours vs 3.6 ± 0.9 hours). However, because MDMA excretion and metabolism have nonlinear kinetics, the half-lives would be higher at more typical doses (100 mg is sometimes considered a typical dose).

Chemistry
MDMA is in the substituted methylenedioxyphenethylamine and substituted amphetamine classes of chemicals. As a free base, MDMA is a colorless oil insoluble in water. The most common salt of MDMA is the hydrochloride salt; pure MDMA hydrochloride is water-soluble and appears as a white or off-white powder or crystal.

Synthesis
There are numerous methods available to synthesize MDMA via different intermediates. The original MDMA synthesis described in Merck's patent involves brominating safrole to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine. Most illicit MDMA is synthesized using MDP2P (3,4-methylenedioxyphenyl-2-propanone) as a precursor. MDP2P in turn is generally synthesized from piperonal, safrole or isosafrole. One method is to isomerize safrole to isosafrole in the presence of a strong base, and then oxidize isosafrole to MDP2P. Another method uses the Wacker process to oxidize safrole directly to the MDP2P intermediate with a palladium catalyst. Once the MDP2P intermediate has been prepared, a reductive amination leads to racemic MDMA (an equal parts mixture of (R)-MDMA and (S)-MDMA). Relatively small quantities of essential oil are required to make large amounts of MDMA. The essential oil of Ocotea cymbarum, for example, typically contains between 80 and 94% safrole. This allows 500 mL of the oil to produce between 150 and 340 grams of MDMA.

Detection in body fluids
MDMA and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDMA or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.

Early research and use
MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. At the time, Merck was interested in developing substances that stopped abnormal bleeding. Merck wanted to avoid an existing patent held by Bayer for one such compound: hydrastinine. Köllisch developed a preparation of a hydrastinine analogue, methylhydrastinine, at the request of fellow lab members, Walther Beckh and Otto Wolfes. MDMA (called methylsafrylamin, safrylmethylamin or N-Methyl-a-Methylhomopiperonylamin in Merck laboratory reports) was an intermediate compound in the synthesis of methylhydrastinine. Merck was not interested in MDMA itself at the time. On 24 December 1912, Merck filed two patent applications that described the synthesis and some chemical properties of MDMA and its subsequent conversion to methylhydrastinine.

Merck records indicate its researchers returned to the compound sporadically. A 1920 Merck patent describes a chemical modification to MDMA. In 1927, Max Oberlin studied the pharmacology of MDMA while searching for substances with effects similar to adrenaline or ephedrine, the latter being structurally similar to MDMA. Compared to ephedrine, Oberlin observed that it had similar effects on vascular smooth muscle tissue, stronger effects at the uterus, and no "local effect at the eye". MDMA was also found to have effects on blood sugar levels comparable to high doses of ephedrine. Oberlin concluded that the effects of MDMA were not limited to the sympathetic nervous system. Research was stopped "particularly due to a strong price increase of safrylmethylamine", which was still used as an intermediate in methylhydrastinine synthesis. Albert van Schoor performed simple toxicological tests with the drug in 1952, most likely while researching new stimulants or circulatory medications. After pharmacological studies, research on MDMA was not continued. In 1959, Wolfgang Fruhstorfer synthesized MDMA for pharmacological testing while researching stimulants. It is unclear if Fruhstorfer investigated the effects of MDMA in humans.

Outside of Merck, other researchers began to investigate MDMA. In 1953 and 1954, the United States Army commissioned a study of toxicity and behavioral effects in animals injected with mescaline and several analogues, including MDMA. Conducted at the University of Michigan in Ann Arbor, these investigations were declassified in October 1969 and published in 1973. A 1960 Polish paper by Biniecki and Krajewski describing the synthesis of MDMA as an intermediate was the first published scientific paper on the substance.

MDMA may have been in non-medical use in the western United States in 1968. An August 1970 report at a meeting of crime laboratory chemists indicates MDMA was being used recreationally in the Chicago area by 1970. MDMA likely emerged as a substitute for its analog 3,4-methylenedioxyamphetamine (MDA), a drug at the time popular among users of psychedelics which was made a Schedule 1 controlled substance in the United States in 1970.

Shulgin's research

American chemist and psychopharmacologist Alexander Shulgin reported he synthesized MDMA in 1965 while researching methylenedioxy compounds at Dow Chemical Company, but did not test the psychoactivity of the compound at this time. Around 1970, Shulgin sent instructions for N-methylated MDA (MDMA) synthesis to the founder of a Los Angeles chemical company who had requested them. This individual later provided these instructions to a client in the Midwest. Shulgin may have suspected he played a role in the emergence of MDMA in Chicago.

Shulgin first heard of the psychoactive effects of N-methylated MDA around 1975 from a young student who reported "amphetamine-like content". Around 30 May 1976, Shulgin again heard about the effects of N-methylated MDA, this time from a graduate student in a medicinal chemistry group he advised at San Francisco State University who directed him to the University of Michigan study. She and two close friends had consumed 100 mg of MDMA and reported positive emotional experiences. Following the self-trials of a colleague at the University of San Francisco, Shulgin synthesized MDMA and tried it himself in September and October 1976. Shulgin first reported on MDMA in a presentation at a conference in Bethesda, Maryland in December 1976. In 1978, he and David E. Nichols published a report on the drug's psychoactive effect in humans. They described MDMA as inducing "an easily controlled altered state of consciousness with emotional and sensual overtones" comparable "to marijuana, to psilocybin devoid of the hallucinatory component, or to low levels of MDA".

While not finding his own experiences with MDMA particularly powerful, Shulgin was impressed with the drug's disinhibiting effects and thought it could be useful in therapy. Believing MDMA allowed users to strip away habits and perceive the world clearly, Shulgin called the drug window. Shulgin occasionally used MDMA for relaxation, referring to it as "my low-calorie martini", and gave the drug to friends, researchers, and others who he thought could benefit from it. One such person was Leo Zeff, a psychotherapist who had been known to use psychedelic substances in his practice. When he tried the drug in 1977, Zeff was impressed with the effects of MDMA and came out of his semi-retirement to promote its use in therapy. Over the following years, Zeff traveled around the United States and occasionally to Europe, eventually training an estimated four thousand psychotherapists in the therapeutic use of MDMA. Zeff named the drug Adam, believing it put users in a state of primordial innocence.

Psychotherapists who used MDMA believed the drug eliminated the typical fear response and increased communication. Sessions were usually held in the home of the patient or the therapist. The role of the therapist was minimized in favor of patient self-discovery accompanied by MDMA induced feelings of empathy. Depression, substance use disorders, relationship problems, premenstrual syndrome, and autism were among several psychiatric disorders MDMA assisted therapy was reported to treat. According to psychiatrist George Greer, therapists who used MDMA in their practice were impressed by the results. Anecdotally, MDMA was said to greatly accelerate therapy. According to David Nutt, MDMA was widely used in the western US in couples counseling, and was called empathy. Only later was the term ecstasy used for it, coinciding with rising opposition to its use.

Rising recreational use
In the late 1970s and early 1980s, "Adam" spread through personal networks of psychotherapists, psychiatrists, users of psychedelics, and yuppies. Hoping MDMA could avoid criminalization like LSD and mescaline, psychotherapists and experimenters attempted to limit the spread of MDMA and information about it while conducting informal research. Early MDMA distributors were deterred from large scale operations by the threat of possible legislation. Between the 1970s and the mid-1980s, this network of MDMA users consumed an estimated 500,000 doses.

A small recreational market for MDMA developed by the late 1970s, consuming perhaps 10,000 doses in 1976. By the early 1980s MDMA was being used in Boston and New York City nightclubs such as Studio 54 and Paradise Garage. Into the early 1980s, as the recreational market slowly expanded, production of MDMA was dominated by a small group of therapeutically minded Boston chemists. Having commenced production in 1976, this "Boston Group" did not keep up with growing demand and shortages frequently occurred.

Perceiving a business opportunity, Michael Clegg, the Southwest distributor for the Boston Group, started his own "Texas Group" backed financially by Texas friends. In 1981, Clegg had coined "Ecstasy" as a slang term for MDMA to increase its marketability. Starting in 1983, the Texas Group mass-produced MDMA in a Texas lab or imported it from California and marketed tablets using pyramid sales structures and toll-free numbers. MDMA could be purchased via credit card and taxes were paid on sales. Under the brand name "Sassyfras", MDMA tablets were sold in brown bottles. The Texas Group advertised "Ecstasy parties" at bars and discos, describing MDMA as a "fun drug" and "good to dance to". MDMA was openly distributed in Austin and Dallas–Fort Worth area bars and nightclubs, becoming popular with yuppies, college students, and gays.

Recreational use also increased after several cocaine dealers switched to distributing MDMA following experiences with the drug. A California laboratory that analyzed confidentially submitted drug samples first detected MDMA in 1975. Over the following years the number of MDMA samples increased, eventually exceeding the number of MDA samples in the early 1980s. By the mid-1980s, MDMA use had spread to colleges around the United States.

United States

In an early media report on MDMA published in 1982, a Drug Enforcement Administration (DEA) spokesman stated the agency would ban the drug if enough evidence for abuse could be found. By mid-1984, MDMA use was becoming more noticed. Bill Mandel reported on "Adam" in a 10 June San Francisco Chronicle article, but misidentified the drug as methyloxymethylenedioxyamphetamine (MMDA). In the next month, the World Health Organization identified MDMA as the only substance out of twenty phenethylamines to be seized a significant number of times.

After a year of planning and data collection, MDMA was proposed for scheduling by the DEA on 27 July 1984 with a request for comments and objections. The DEA was surprised when a number of psychiatrists, psychotherapists, and researchers objected to the proposed scheduling and requested a hearing. In a Newsweek article published the next year, a DEA pharmacologist stated that the agency had been unaware of its use among psychiatrists. An initial hearing was held on 1 February 1985 at the DEA offices in Washington, D.C., with administrative law judge Francis L. Young presiding. It was decided there to hold three more hearings that year: Los Angeles on 10 June, Kansas City, Missouri on 10–11 July, and Washington, D.C., on 8–11 October.

Sensational media attention was given to the proposed criminalization and the reaction of MDMA proponents, effectively advertising the drug. In response to the proposed scheduling, the Texas Group increased production from 1985 estimates of 30,000 tablets a month to as many as 8,000 per day, potentially making two million ecstasy tablets in the months before MDMA was made illegal. By some estimates the Texas Group distributed 500,000 tablets per month in Dallas alone. According to one participant in an ethnographic study, the Texas Group produced more MDMA in eighteen months than all other distribution networks combined across their entire histories. By May 1985, MDMA use was widespread in California, Texas, southern Florida, and the northeastern United States. According to the DEA there was evidence of use in twenty-eight states and Canada. Urged by Senator Lloyd Bentsen, the DEA announced an emergency Schedule I classification of MDMA on 31 May 1985. The agency cited increased distribution in Texas, escalating street use, and new evidence of MDA (an analog of MDMA) neurotoxicity as reasons for the emergency measure. The ban took effect one month later on 1 July 1985 in the midst of Nancy Reagan's "Just Say No" campaign.

As a result of several expert witnesses testifying that MDMA had an accepted medical usage, the administrative law judge presiding over the hearings recommended that MDMA be classified as a Schedule III substance. Despite this, DEA administrator John C. Lawn overruled and classified the drug as Schedule I. Harvard psychiatrist Lester Grinspoon then sued the DEA, claiming that the DEA had ignored the medical uses of MDMA, and the federal court sided with Grinspoon, calling Lawn's argument "strained" and "unpersuasive", and vacated MDMA's Schedule I status. Despite this, less than a month later Lawn reviewed the evidence and reclassified MDMA as Schedule I again, claiming that the expert testimony of several psychiatrists claiming over 200 cases where MDMA had been used in a therapeutic context with positive results could be dismissed because they were not published in medical journals. In 2017, the FDA granted breakthrough therapy designation for its use with psychotherapy for PTSD. However, this designation has been questioned and problematized.

United Nations
While engaged in scheduling debates in the United States, the DEA also pushed for international scheduling. In 1985 the World Health Organization's Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the 1971 United Nations Convention on Psychotropic Substances. The committee made this recommendation on the basis of the pharmacological similarity of MDMA to previously scheduled drugs, reports of illicit trafficking in Canada, drug seizures in the United States, and lack of well-defined therapeutic use. While intrigued by reports of psychotherapeutic uses for the drug, the committee viewed the studies as lacking appropriate methodological design and encouraged further research. Committee chairman Paul Grof dissented, believing international control was not warranted at the time and a recommendation should await further therapeutic data. The Commission on Narcotic Drugs added MDMA to Schedule I of the convention on 11 February 1986.

Post-scheduling
The use of MDMA in Texas clubs declined rapidly after criminalization, although by 1991 the drug remained popular among young middle-class whites and in nightclubs. In 1985, MDMA use became associated with acid house on the Spanish island of Ibiza. Thereafter in the late 1980s, the drug spread alongside rave culture to the UK and then to other European and American cities. Illicit MDMA use became increasingly widespread among young adults in universities and later, in high schools. Since the mid-1990s, MDMA has become the most widely used amphetamine-type drug by college students and teenagers. MDMA became one of the four most widely used illicit drugs in the US, along with cocaine, heroin, and cannabis. According to some estimates as of 2004, only marijuana attracts more first time users in the US.

After MDMA was criminalized, most medical use stopped, although some therapists continued to prescribe the drug illegally. Later, Charles Grob initiated an ascending-dose safety study in healthy volunteers. Subsequent FDA-approved MDMA studies in humans have taken place in the United States in Detroit (Wayne State University), Chicago (University of Chicago), San Francisco (UCSF and California Pacific Medical Center), Baltimore (NIDA–NIH Intramural Program), and South Carolina. Studies have also been conducted in Switzerland (University Hospital of Psychiatry, Zürich), the Netherlands (Maastricht University), and Spain (Universitat Autònoma de Barcelona).

"Molly", short for 'molecule', was recognized as a slang term for crystalline or powder MDMA in the 2000s.

In 2010, the BBC reported that use of MDMA had decreased in the UK in previous years. This may be due to increased seizures during use and decreased production of the precursor chemicals used to manufacture MDMA. Unwitting substitution with other drugs, such as mephedrone and methamphetamine, as well as legal alternatives to MDMA, such as BZP, MDPV, and methylone, are also thought to have contributed to its decrease in popularity.

In 2017 it was found that some pills being sold as MDMA contained pentylone, which can cause very unpleasant agitation and paranoia.

According to David Nutt, when safrole was restricted by the United Nations in order to reduce the supply of MDMA, producers in China began using anethole instead, but this gives para-methoxyamphetamine (PMA, also known as "Dr Death"), which is much more toxic than MDMA and can cause overheating, muscle spasms, seizures, unconsciousness, and death. People wanting MDMA are sometimes sold PMA instead.

Legal status
MDMA is legally controlled in most of the world under the UN Convention on Psychotropic Substances and other international agreements, although exceptions exist for research and limited medical use. In general, the unlicensed use, sale or manufacture of MDMA are all criminal offences.

Australia
In Australia, MDMA was rescheduled on 1 July 2023 as a schedule 8 substance (available on prescription) when used in the treatment of PTSD, while remaining a schedule 9 substance (prohibited) for all other uses. For the treatment of PTSD, MDMA can only be prescribed by psychiatrists with specific training and authorisation. In 1986, MDMA was declared an illegal substance because of its allegedly harmful effects and potential for misuse. Any non-authorised sale, use or manufacture is strictly prohibited by law. Permits for research uses on humans must be approved by a recognized ethics committee on human research.

In Western Australia under the Misuse of Drugs Act 1981 4.0g of MDMA is the amount required determining a court of trial, 2.0g is considered a presumption with intent to sell or supply and 28.0g is considered trafficking under Australian law.

The Australian Capital Territory passed legislation to decriminalise the possession of small amounts of MDMA, which took effect in October 2023.

United Kingdom
In the United Kingdom, MDMA was made illegal in 1977 by a modification order to the existing Misuse of Drugs Act 1971. Although MDMA was not named explicitly in this legislation, the order extended the definition of Class A drugs to include various ring-substituted phenethylamines. The drug is therefore illegal to sell, buy, or possess without a licence in the UK. Penalties include a maximum of seven years and/or unlimited fine for possession; life and/or unlimited fine for production or trafficking.

Some researchers such as David Nutt have criticized the scheduling of MDMA, which he determined to be a relatively harmless drug. An editorial he wrote in the Journal of Psychopharmacology, where he compared the risk of harm for horse riding (1 adverse event in 350) to that of ecstasy (1 in 10,000) resulted in his dismissal as well as the resignation of his colleagues from the ACMD.

United States
In the United States, MDMA is listed in Schedule I of the Controlled Substances Act. In a 2011 federal court hearing, the American Civil Liberties Union successfully argued that the sentencing guideline for MDMA/ecstasy is based on outdated science, leading to excessive prison sentences. Other courts have upheld the sentencing guidelines. The United States District Court for the Eastern District of Tennessee explained its ruling by noting that "an individual federal district court judge simply cannot marshal resources akin to those available to the Commission for tackling the manifold issues involved with determining a proper drug equivalency."

Netherlands
In the Netherlands, the Expert Committee on the List (Expertcommissie Lijstensystematiek Opiumwet) issued a report in June 2011 which discussed the evidence for harm and the legal status of MDMA, arguing in favor of maintaining it on List I.

Canada
In Canada, MDMA is listed as a Schedule 1 as it is an analogue of amphetamine. The Controlled Drugs and Substances Act was updated as a result of the Safe Streets and Communities Act changing amphetamines from Schedule III to Schedule I in March 2012. In 2022, the federal government granted British Columbia a 3-year exemption, legalizing the possession of up to 2.5 g of MDMA in the province from February 2023 until February 2026.

Demographics
In 2014, 3.5% of 18 to 25 year-olds had used MDMA in the United States. In the European Union as of 2018, 4.1% of adults (15–64 years old) have used MDMA at least once in their life, and 0.8% had used it in the last year. Among young adults, 1.8% had used MDMA in the last year.

In Europe, an estimated 37% of regular club-goers aged 14 to 35 used MDMA in the past year according to the 2015 European Drug report. The highest one-year prevalence of MDMA use in Germany in 2012 was 1.7% among people aged 25 to 29 compared with a population average of 0.4%. Among adolescent users in the United States between 1999 and 2008, girls were more likely to use MDMA than boys.

Europe
In 2008 the European Monitoring Centre for Drugs and Drug Addiction noted that although there were some reports of tablets being sold for as little as €1, most countries in Europe then reported typical retail prices in the range of €3 to €9 per tablet, typically containing 25–65 mg of MDMA. By 2014 the EMCDDA reported that the range was more usually between €5 and €10 per tablet, typically containing 57–102 mg of MDMA, although MDMA in powder form was becoming more common.

North America
The United Nations Office on Drugs and Crime stated in its 2014 World Drug Report that US ecstasy retail prices range from US$1 to $70 per pill, or from $15,000 to $32,000 per kilogram. A new research area named Drug Intelligence aims to automatically monitor distribution networks based on image processing and machine learning techniques, in which an Ecstasy pill picture is analyzed to detect correlations among different production batches. These novel techniques allow police scientists to facilitate the monitoring of illicit distribution networks.

, most of the MDMA in the United States is produced in British Columbia, Canada and imported by Canada-based Asian transnational criminal organizations. The market for MDMA in the United States is relatively small compared to methamphetamine, cocaine, and heroin. In the United States, about 0.9 million people used ecstasy in 2010.

Australia
MDMA is particularly expensive in Australia, costing A$15–A$30 per tablet. In terms of purity data for Australian MDMA, the average is around 34%, ranging from less than 1% to about 85%. The majority of tablets contain 70–85 mg of MDMA. Most MDMA enters Australia from the Netherlands, the UK, Asia, and the US.

Corporate logos on pills
A number of ecstasy manufacturers brand their pills with a logo, often being the logo of an unrelated corporation. Some pills depict logos of products or media popular with children, such as Shaun the Sheep.

Research
In 2017, doctors in the UK began the first clinical study of MDMA in alcohol use disorder.

The potential for MDMA to be used as a rapid-acting antidepressant has been studied in clinical trials, but as of 2017, the evidence on efficacy and safety was insufficient to reach a conclusion. A 2014 review of the safety and efficacy of MDMA as a treatment for various disorders, particularly post-traumatic stress disorder (PTSD), indicated that MDMA has therapeutic efficacy in some patients; however, it emphasized that issues regarding the controllability of MDMA-induced experiences and neurochemical recovery must be addressed. The author noted that oxytocin and -cycloserine are potentially safer co-drugs in PTSD treatment, albeit with limited evidence of efficacy. This review and a second corroborating review by a different author both concluded that, because of MDMA's demonstrated potential to cause lasting harm in humans (e.g., serotonergic neurotoxicity and persistent memory impairment), "considerably more research must be performed" on its efficacy in PTSD treatment to determine if the potential treatment benefits outweigh its potential to harm a patient.

MDMA in combination with psychotherapy has been studied as a treatment for PTSD, and four clinical trials provide moderate evidence in support of this treatment. However, the lack of appropriate blinding of participants likely leads to overestimation of treatment effects due to high levels of response expectancy. In addition, there are no trials comparing MDMA-assisted psychotherapy for PTSD with existent evidence-based psychological treatments for PTSD, which seem to attain similar or better treatment effects compared with those achieved by MDMA-assisted psychotherapy.

In 2018, researchers identified MDMA as a psychoplastogen, which refers to a compound capable of promoting neuroplasticity and received the "breakthrough therapy" designation by the Food and Drug Administration for treating PTSD.

title: MDMA


text:
Flag of Europe

The flag of Europe or European flag consists of twelve golden stars forming a circle on a blue field. It is the official flag of the European Union. It was designed and adopted in 1955 by the Council of Europe (CoE) as a symbol for the whole of Europe.

Since 1985, the flag has also been a symbol of the European Union (EU), whose 27 member states are all also CoE members, although in that year the EU had not yet assumed its present name or constitutional form (which came in steps in 1993 and 2009). Adoption by the EU, or EC as it then was, reflected long-standing CoE desire to see the flag used by other European organisations. Official EU use widened greatly in the 1990s. Nevertheless the flag has to date received no status in any of the EU's treaties. Its adoption as an official symbol was planned as part of the 2004 European Constitution but this failed to be ratified. Mention of the flag was removed in 2007 from the text of the Treaty of Lisbon, which was ratified. On the other hand, 16 EU members that year, plus France in 2017, have officially affirmed (by Declaration No. 5224) their attachment to the flag as an EU symbol.

The flag is used by other European entities, such as unified sport teams under the rubric Team Europe.

Blazon
The blazon given by the EU in 1996 describe the design as: "On an azure field a circle of twelve golden mullets, their points not touching."

Symbolism
The flag used is the Flag of Europe, which consists of a circle of twelve golden stars on a blue background. Originally designed in 1955 for the Council of Europe, the flag was adopted by the European Communities, the predecessors of the present European Union, in 1986. The Council of Europe gave the flag a symbolic description in the following terms, though the official symbolic description adopted by the EU omits the reference to the "Western world": "Against the blue sky of the Western world, the stars symbolise the peoples of Europe in a form of a circle, a sign of union. Their number is invariably twelve, the figure twelve being the symbol of perfection and entirety."

Other symbolic interpretations have been offered based on the account of its design by Paul M. Levy. The five-pointed star is used on many national flags and represents aspiration and education. Their golden colour is that of the sun, which is said to symbolise glory and enlightenment.

Their arrangement in a circle represents the constellation of Corona Borealis and can be seen as a crown and the stability of government. The blue background resembles the sky and symbolises truth and the intellect. It is also the colour traditionally used to represent the Virgin Mary. In many paintings of the Virgin Mary as Stella Maris she is crowned with a circle of twelve stars.

Marian interpretation

In 1987, following the adoption of the flag by the EC, Arsène Heitz (1908–1989), one of the designers who had submitted proposals for the flag's design, suggested a religious inspiration for it. He stated that the circle of stars was based on the iconographic tradition of showing the Blessed Virgin Mary as the Woman of the Apocalypse, wearing a "crown of twelve stars".

Heitz also made a connection to the date of the flag's adoption, 8 December 1955, coinciding with the Feast of the Immaculate Conception of the Blessed Virgin Mary.

Paul M. G. Lévy, then Director of Information at the Council of Europe responsible for designing the flag, in a 1989 statement maintained that he had not been aware of any religious connotations.

In an interview given 26 February 1998, Lévy denied not only awareness of the Marian connection, but also denied that the final design of a circle of twelve stars was Heitz's. To the question "Who really designed the flag?" Lévy replied:

"I did, and I calculated the proportions to be used for the geometric design. Arsène Heitz, who was an employee in the mail service, put in all sorts of proposals, including the 15-star design. But he submitted too many designs. He wanted to do the European currencies with 15 stars in the corner. He wanted to do national flags incorporating the Council of Europe flag."

Carlo Curti Gialdino (2005) has reconstructed the design process to the effect that Heitz's proposal contained varying numbers of stars, from which the version with twelve stars was chosen by the Committee of Ministers meeting at Deputy level in January 1955 as one out of two remaining candidate designs.

Lévy's 1998 interview apparently gave rise to a new variant of the Marian anecdote. An article published in Die Welt in August 1998 alleged that it was Lévy himself who was inspired to introduce a Marian element as he walked past a statue of the Blessed Virgin Mary.

An article posted in La Raison in February 2000 further connected the donation of a stained glass window for Strasbourg Cathedral by the Council of Europe on 21 October 1956. This window, a work by Parisian master Max Ingrand, shows a blessing Madonna underneath a circle of 12 stars on dark blue ground. The overall design of the Madonna is inspired by the banner of the cathedral's Congrégation Mariale des Hommes, and the twelve stars are found on the statue venerated by this congregation inside the cathedral (twelve is also the number of members of the congregation's council). The Regional Office for Cultural Affairs describe this stained glass window called "Le vitrail de l'Europe de Max Ingrand" (The Glass Window of Europe of Max Ingrand).

Specifications
According to graphical specifications published online by the Council of Europe in 2004, the flag is rectangular with 2:3 proportions: its fly (width) is one and a half times the length of its hoist (height). Twelve yellow stars are centred in a circle (the radius of which is a third of the length of the hoist) upon a blue background. All the stars are upright (one point straight up), have five points and are spaced equally, like the hour positions on the face of a clock. The diameter of each star is equal to one-ninth of the height of the hoist.

The colours are regulated in the 1996 guide by the EC, and equivalently in the 2004 guide by the Council of Europe. The base colour of the flag is defined as Pantone "Reflex Blue", while the golden stars are portrayed in Pantone "Yellow":

The 2013 logo of the Council of Europe has the colours:

Adoption and usage
The twelve-star "flag of Europe" was designed in 1950 and officially adopted by the Council of Europe in 1955. The same flag was adopted by the European Parliament in 1983. The European Council adopted it as an "emblem" for the European Communities in 1985. Its status in the European Communities was inherited by the European Union upon its formation in 1993. The proposal to adopt it as official flag of the European Union failed with the ratification of the European Constitution in 2005, and mention of all emblems suggesting statehood was removed from the Treaty of Lisbon of 2007, although sixteen member states signed a declaration supporting the continued use of the flag. In 2007, the European Parliament officially adopted the flag for its own use.

1950–present: Council of Europe
The Council of Europe in 1950 appointed a committee to study the question of adopting a symbol. Numerous proposals were looked into.

Among the unsuccessful proposals was the flag of Richard von Coudenhove-Kalergi's International Paneuropean Union, which he had himself recently adopted for the European Parliamentary Union. The design was a blue field with a red cross inside an orange circle at the centre. Kalergi was very committed to defending the cross as "the great symbol of Europe's moral unity", the Red Cross in particular being "recognized by the whole world, by Christian and non-Christian nations[,] as a symbol of international charity and of the brotherhood of man", but the proposal was rejected by Turkey (a member of the Council of Europe since 1949) on grounds of its religious associations in spite of Kalergi's suggestion of adding a crescent alongside the cross to overcome the Muslim objections.

Other proposals included the flag was the European Movement, which had a large green E on a white background, a design was based on the Olympic rings, eight golden rings on a blue background, rejected due to the rings' similarity with "dial", "chain" and "zeros", or a large yellow star on a blue background, rejected due to its equality with the flag of the Belgian Congo.

The Consultative Assembly narrowed their choice to two designs. One was by Salvador de Madariaga, the founder of the College of Europe, who suggested a constellation of stars on a blue background (positioned according to capital cities, with a large star for Strasbourg, the seat of the council). He had circulated his flag round many European capitals and the concept had found favour. The second was a variant by Arsène Heitz, who worked for the council's postal service and had submitted dozens of designs, one of which was accepted by the Assembly. The design was similar to Salvador de Madariaga's, but rather than a constellation, the stars were arranged in a circle. Arsène Heitz was one of several people who proposed a circle of gold stars on a blue background. None of his proposals perfectly match the design that was adopted. Paul Levy claims that he was the one who designed the template for the flag, not Arsène Heitz. In 1987, Heitz would claim that his inspiration had been the crown of twelve stars of the Woman of the Apocalypse, often found in Marian iconography (see below).

On 25 September 1953, the Consultative Assembly of the Council of Europe recommended that a blue flag with fifteen gold stars be adopted as an emblem for the organisation, the number fifteen reflecting the number of states of the Council of Europe. West Germany objected to the fifteen-star design, as one of the members was Saar Protectorate, and to have its own star would imply sovereignty for the region. The Committee of Ministers (the council's main decision making body) agreed with the Assembly that the flag should be a circle of stars, but opted for a fixed number of twelve stars, "representing perfection and entirety". The Parliamentary Assembly of the Council of Europe on 25 October 1955 agreed to this. Paul M. G. Lévy drew up the exact design of the new flag. Officially adopted on 8 December 1955, the flag was unveiled at the Château de la Muette in Paris on 13 December 1955.

For the flag of the Council of Europe, many stylistic proposals were made in regards to colours and symbolism. These first proposals were made 19 January 1950 by Paul Levy in a letter to the Secretary-General. He proposed that the flag should contain a cross for several reasons. Firstly, the cross symbolizes roads crossing, and also represents the east, the west, the north, and the south with its arms. Furthermore, the cross appears in most of the European Council members' flags, and it is the oldest and most noble symbol in Europe. Moreover, the cross depicted Christianity. As far as the colours are concerned, he proposed them to be white and green, colours of the European Movement, which was of great significance since 1947. Green also depicted hope, and the green cross over a white background was a design that had not been used yet. Finally, Levy proposed that the arms of Strasbourg was an important element to be added as it represented where the council would be, and being located in the heart of the cross meant that the council was the point where the European roads met.

Shortly after this design considerations by Paul Levy, on 27 July 1950, Richard Coudenhove-Kalergi, president of the Pan-European movement wrote a memorandum which contained some rules that a flag for such union should follow. The rules he stated where:

 * It should be a symbol of our common civilisation.
 * It should present a European emblem.
 * It should not provoke any national rivalry.
 * It should represent tradition.
 * It should be beautiful and dignified.

After these statements, Coudenhove-Kalergi proposed that the Pan-European movement flag would be the perfect one to fit these criteria

15 July 1951, the consultative assembly put forward a final memorandum on the European flag. The symbols proposed where the following

 * A cross: Symbol of Christianity, Europe's crossroads, reminiscent of the crusades, and present in half of the member state's flags.
 * An "E": Used by the European Movement.
 * A white star in a circle: Symbol used in 1944–45 by the armies of liberation.
 * Multiple stars: Each star could represent a member. They could be green on a white background, white stars on a red background, or silver stars for associate members, and golden stars for full members.
 * Strasbourg's Coat of Arms: To symbolize the official seat of the Council of Europe.
 * A sun: It would represent dawning hope.
 * A triangle: It would represent culture.

Furthermore, several colours were also proposed:

 * Multi-coloured: It was proposed that the flag could contain all the colours the flags of the member states had.
 * Green and White: These were the colours of the European Movement.
 * Blue: Symbol of peace and neutrality, as other colours were already used for other movements such as black for mourning, red for bolshevism, or green for Islam.

In the end, the flag of Europe was chosen to have 12 five-pointed golden stars in a circle over a blue background, probably inspired by the Pan-European flag and other designs such as Salvador de Madariaga's and Arsène Heitz's proposals.

1983–present: From European Communities to European Union

Following Expo 58 in Brussels, the flag caught on and the Council of Europe lobbied for other European organisations to adopt the flag as a sign of European unity. The European Parliament took the initiative in seeking a flag to be adopted by the European Communities. Shortly after the first direct elections in 1979 a draft resolution was put forward on the issue. The resolution proposed that the Communities' flag should be that of the Council of Europe and it was adopted by the Parliament on 11 April 1983.

The June 1984 European Council (the Communities' leaders) summit in Fontainebleau stressed the importance of promoting a European image and identity to citizens and the world. The European Council appointed an ad hoc committee, named "Committee for 'a People's Europe'" (Adonnino Committee).

This committee submitted a substantial report, including wide-ranging suggestions, from organising a "European lottery" to campaigning for the introduction of local voting rights for foreign nationals throughout Europe. Under the header of "strengthening of the Community's image and identity", the Committee suggested the introduction of "a flag and an emblem", recommending a design based on the Council of Europe flag, but with the addition of "a gold letter E" in the center of the circle of stars. The European Council held in Milan on 28/29 June 1985 largely followed the recommendations of the Adonnino Committee. But as the adoption of a flag was strongly reminiscent of a national flag representing statehood and was extremely controversial with some member states (in particular the United Kingdom, as the proposed flag closely resembled the Queen's personal standard), the Council of Europe's "flag of Europe" design was adopted, without the letter E, only with the official status of a "logo". This compromise was widely disregarded from the beginning, and the "European logo", in spite of the explicit language of giving it the status of a "logo", was referred to as the "Community flag" or even "European flag" from the outset.

The Communities began to use the "emblem" as its de facto flag from 1986, raising it outside the Berlaymont building (the seat of the European Commission) for the first time on 29 May 1986.

The European Union, which was established by the Maastricht Treaty in 1992 to replace the European Communities and encompass its functions, has retained de facto use of the "Community logo" of the EC. Technically and officially, the "European flag" as used by the European Union remains not a "flag" but "a Community 'logo' — or 'emblem' — [...] eligible to be reproduced on rectangular pieces of fabric".

In 1997, the "Central and Eastern Eurobarometer" poll included a section intending to "discover the level of public awareness of the European Union" in what were then candidate countries in Central and Eastern Europe. Interviewees were shown "a sticker of the European flag" and asked to identify it. Responses considered correct were: the European Union, the European Community, the Common Market, and "Europe in general". 52% of those interviewed gave one of the correct answers, 15% gave a wrong answer (naming another institution, such as NATO or the United Nations), and 35% could or would not identify it.

In 2002, Dutch architect Rem Koolhaas designed a symbol, dubbed the "barcode", which displayed the colours of the national flags of the EU member states in vertical stripes. It was reported as a replacement for the European flag, which was not the intention. It was not adopted by the EU or any other organisation at the time, but an updated version was used in the visual identity of the Austrian EU Presidency in 2006.

The official status of the emblem as the flag of the European Union was to be formalised as part of the Treaty establishing a Constitution for Europe. However, as the proposed treaty failed ratification, the mention of all state-like emblems, including the flag, were not included in the replacement Treaty of Lisbon, which entered into force in 2009.

Instead, a separate declaration by sixteen Member States was included in the final act of the Treaty of Lisbon stating that the flag, the anthem, the motto and the currency and Europe Day "will for them continue as symbols to express the sense of community of the people in the European Union and their allegiance to it."

In reaction to the removal of the flag from the treaty, the European Parliament, which had supported the inclusion of such symbols, backed a proposal to use these symbols "more often" on behalf of the Parliament itself; Jo Leinen, MEP for Germany, suggested that the Parliament should take "an avant-garde role" in their use.

In September 2008, the Parliament's Committee on Constitutional Affairs proposed a formal change in the institution's rules of procedure to make "better use of the symbols". Specifically, the flag would be present in all meeting rooms (not just the hemicycle) and at all official events. The proposal was passed on 8 October 2008 by 503 votes to 96 (15 abstentions).

In 2015, a set of commemorative Euro coins was issued on the occasion of the 30th anniversary of the adoption of the emblem by the European Communities.

In April 2004, the European flag was flown on behalf of the European Space Agency, by Dutch astronaut André Kuipers while on board the International Space Station, in reference to the Framework Agreement establishing the legal basis for co-operation between the European Space Agency and the European Union.

Following the 2004 Summer Olympics, President Romano Prodi expressed his hope "to see the EU Member State teams in Beijing [viz., the 2008 games] carry the flag of the European Union alongside their own national flag as a symbol of our unity". Use of the flag has also been reported as representing the European team at the Ryder Cup golf competition in the early 2000s, although most European participants preferred to use their own national flags.

The flag has been widely used by advocates of European integration since the late 1990s or early 2000s. It is often displayed in the context of Europe Day, on 9 May. Outside the EU, it was used in the context of several of the "colour revolutions" during the 2000s. In Belarus, it was used on protest marches alongside the white-red-white flag and other flags of opposition movements, such as Zubr, during the protests of 2004–2006. The flag was used widely in a 2007 pro-EU march in Minsk. Similar uses were reported from Moldova in 2009.

In Georgia, the flag has been on most government buildings since the coming to power of Mikheil Saakashvili (2007), who used it during his inauguration, stating: "[the European] flag is Georgia's flag as well, as far as it embodies our civilisation, our culture, the essence of our history and perspective, and our vision for the future of Georgia."

It was used in 2008 by pro-western Serbian voters ahead of an election.

The flag became a symbol of European integration of Ukraine in the 2010s, particularly after Euromaidan. Ukraine is not a part of the EU but is a member of the Council of Europe. The flag is used by the Cabinet of Ukraine, Prime Minister of Ukraine, and MFA UA during official meetings. It was flown during the 2013 Euromaidan protests in Ukraine, and in 2016 by the pro-EU faction in the EU membership referendum campaigns in the United Kingdom.

The flag has also been adopted as a symbol for EU policies and expansionism by EU-sceptics. In an early instance, Macedonian protesters burned "the flag of the EU" in the context of EU involvement in the 2001 insurgency in the Republic of Macedonia. In the 2005 Islamic protests against the Jyllands-Posten Muhammad cartoons, the Danish flag was most frequently burned, but (as the cartoons were reprinted in many European countries), some protesters opted for burning "the EU flag" instead. Protesters during the Greek government-debt crisis of 2012 "burned the EU flag and shouted 'EU out' ". Burning of the EU flag has been reported from other anti-EU rallies since.

By the 2010s, the association of the emblem with the EU had become so strong that the Council of Europe saw it necessary to design a new logo, to "avoid confusion", officially adopted in 2013.

The EU emblem ("EU flag") is depicted on the euro banknotes. Euro coins also display a circle of twelve stars on both the national and common sides.

It is also depicted on many driving licences and vehicle registration plates issued in the Union. Diplomatic missions of EU member states fly the EU flag alongside their national flag. In October 2000, the then-new British Embassy in Berlin sparked controversy between the UK and Germany and the EU when the embassy did not have a second external flagpole for the EU flag. After diplomatic negotiations, it was agreed that the outside flagpole would have the diplomatic Union Flag while inside the embassy, the EU flag would accompany the UK flag. Some member states' national airlines such as Lufthansa have the EU flag alongside their national flags on aircraft as part of their aircraft registration codes, but this is not an EU-mandated directive.

A number of logos used by EU institutions, bodies and agencies are derived from the design and colours of the EU emblem.

Other emblems make reference to the European flag, such as the EU organic food label that uses the twelve stars but reorders them into the shape of a leaf on a green background. The original logo of the European Broadcasting Union used the twelve stars on a blue background adding ray beams to connect the countries.

There was a proposal in 2003 to deface national civil ensigns with the EU emblem. The proposal was rejected by Parliament in 2004.

The flag is usually flown by the government of the country holding the rotating presidency Council of Ministers. In 2009, Czech President Václav Klaus, a eurosceptic, refused to fly the flag from his castle. In response, Greenpeace projected an image of the flag onto the castle and attempted to fly the flag from the building themselves.

Extraordinary flying of the flag is common on Europe Day, celebrated annually on 9 May. On Europe Day 2008, the flag was flown for the first time above the German Reichstag.

The flag has also been displayed in the context of EU military operations (EUFOR Althea).

Sixteen out of twenty-seven member states in 2007 signed the declaration recognising "the flag with a circle of twelve golden stars on a blue background" as representing "the sense of community of the people in the European Union and their allegiance to it." In 2017, president of France Emmanuel Macron signed a declaration endorsing the 2007 statement, so that, as of 2018, 17 out of 27 member states have recognised the emblem as a flag representing "allegiance to the EU": Austria, Belgium, Bulgaria, Cyprus, France, Germany, Greece, Hungary, Italy, Lithuania, Luxembourg, Malta, Portugal, Romania, Slovakia, Slovenia and Spain.

Italy has incorporated the EU flag into its flag code. According to an Italian law passed in 2000, it is mandatory for most public offices and buildings to hoist the European Flag alongside the Italian national flag (Law 22/1998 and Presidential Decree 121/2000). Outside official use, the flag may not be used for "aims incompatible with European values". The 2000 Italian flag code expressly replaces the Italian flag with the European flag in precedence when dignitaries from other EU countries visit – for example the EU flag would be in the middle of a group of three flags rather than the Italian flag. In Germany, the federal flag code of 1996 is only concerned with the German flag, but some of the states have legislated additional provisions for the European flag, such as Bavaria in its flag regulation of 2001, which mandates that the European flag take the third order of precedence, after the federal and state flags, except on Europe Day, where it is to take the first order of precedence.

In Ireland on occasions of "European Union Events" (for example, at a European Council meeting), where the European flag is flown alongside all national flags of member states, the national flags are placed in alphabetical order (according to their name in the main language of that state) with the European flag either at the head, or the far-right, of the order of flags.

In most member states, use of the EU flag is only de facto and not regulated by legislation, and as such subject to ad hoc revision. In national usage, national protocol usually demands the national flag takes precedence over the European flag (which is usually displayed to the right of the national flag from the observer's perspective). In November 2014, the speaker of the Hungarian Parliament László Kövér ordered the removal of the EU flag from the parliament building, following an incident in which a member of parliament had "defenestrated" two EU flags from a fourth story window. In November 2015, the newly elected Polish government under Beata Szydło removed the EU flag from government press conferences.

British consent
In Oxford, after a post-Brexit law, consent is required for use of the EU flag

Derivative designs
The design of the European flag has been used in a variation, such as that of the Council of Europe mentioned above, and also to a greater extent such as the flag of the Western European Union (WEU; now defunct), which uses the same colours and the stars but has a number of stars based on membership and in a semicircle rather than a circle. It is also defaced with the initials of the former Western European Union in two languages.

The European Parliament used its own flag from 1973, but never formally adopted it. It fell out of use with the adoption of the twelve-star flag by the Parliament in 1983. The flag followed the yellow and blue colour scheme however instead of twelve stars there were the letters EP and PE (initials of the European Parliament in the six community languages at the time) surrounded by a wreath. Sometime later, the Parliament chose to use a logo consisting of a stylised hemicycle and the EU flag at the bottom right.

The flag of Bosnia and Herzegovina, imposed by High Representative Carlos Westendorp after the country's parliament failed to agree on a design, is reminiscent of the symbolism of the EU flag, using the same blue and yellow colours; also, the stars (although of a different number and colour) are a direct reference to those of the European flag.

Likewise, Kosovo uses blue, yellow and stars in its flag, which has been mocked as a "none too subtle nod to the flag of the European Union, which is about to become Kosovo's new best friend as it takes over protector status from the United Nations".

The flag of the Brussels-Capital Region (introduced in 2016) consists of a yellow iris with a white outline upon a blue background. Its colours are based on the colours of the Flag of Europe, because Brussels is considered the unofficial capital of the EU.

Heraldry
The coat of arms of the chairman of the European Union Military Committee (CEUMC), the highest-ranking officer within the EU's Common Security and Defence Policy (CSDP), depicts the European emblem as a coat of arms, i.e. emblazoned on an escutcheon. In heraldic terms, this makes the European flag is the banner of arms, i.e. the flag form of this coat of arms. In English blazon, the arms is Azure, a circle of 12 mullets or, their points not touching.

Several EU publications related to the CSDP generally, and its prospective development as a defence arm, have also displayed the European emblem in this manner, albeit as a graphical design element rather than an official symbol.

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: Flag of Europe


text:
Anthem of Europe

The Anthem of Europe or European Anthem, also known as Ode to Joy, is a piece of instrumental music adapted from the prelude of the final movement of Beethoven's 9th Symphony composed in 1823, originally set to words adapted from Friedrich Schiller's 1785 poem "Ode to Joy". In 1972, the Council of Europe adopted it as an anthem to represent Europe, and later in 1985 it was also adopted by the European Union.

Its purpose is to honour shared European values. The EU describes it as expressing the ideals of freedom, peace and solidarity. The anthem is played on official occasions such as political or civil events.

History
Friedrich Schiller wrote the poem "An die Freude" ("To Joy") in 1785 as a "celebration of the brotherhood of man". In later life, the poet was contemptuous of this popularity and dismissed the poem as typical of "the bad taste of the age" in which it had been written. After Schiller's death, the poem provided the words for the choral movement of Ludwig van Beethoven's 9th Symphony.

In 1971 the Parliamentary Assembly of the Council of Europe decided to propose adopting the prelude to the "Ode to Joy" from Beethoven's 9th Symphony as the anthem, taking up a suggestion made by Richard von Coudenhove-Kalergi in 1955. Beethoven was generally seen as the natural choice for a European anthem. The Committee of Ministers of the Council of Europe officially announced the European Anthem on 19 January 1972 at Strasbourg: the prelude to "Ode to Joy", 4th movement of Ludwig van Beethoven's 9th symphony.

Conductor Herbert von Karajan was asked to write three instrumental arrangements – for solo piano, for wind instruments and for symphony orchestra and he conducted the performance used to make the official recording. Karajan decided on a decidedly slower tempo, using crotchet (quarter note) = 120 whereas Beethoven had written minim (half note) = 80.

The anthem was launched via a major information campaign on Europe Day in 1972, without a public holiday, since it is close to May Day. In 1985, it was adopted by EU heads of state and government as the official anthem of the then European Community – since 1993 the European Union. It is not intended to replace the national anthems of the member states but rather to celebrate the values they all share and their unity in diversity. It expresses the ideals of a united Europe: freedom, peace, and solidarity.

It was to have been included in the European Constitution along with the other European symbols; however, the treaty failed ratification and was replaced by the Treaty of Lisbon, which does not include any symbols. A declaration was attached to the treaty, in which sixteen member states formally recognised the proposed symbols. In response, the European Parliament decided that it would make greater use of the anthem, for example at official occasions. In October 2008, the Parliament changed its rules of procedure to have the anthem played at the opening of Parliament after elections and at formal sittings.

Usage
"Ode to Joy" is the anthem of the Council of Europe (CoE) and the European Union (EU). In the context of the CoE, the anthem is used to represent all of Europe. In the context of the EU, the anthem is used to represent the union and its people. It is used on occasions such as Europe Day and formal events such as the signing of treaties. The European Parliament seeks to make greater use of the music; then-Parliament President Hans-Gert Pöttering stated he was moved when the anthem was played for him on his visit to Israel and ought to be used in Europe more often.

The German public radio station Deutschlandfunk has broadcast the anthem together with the Deutschlandlied shortly before midnight since New Year's Eve 2006. The two anthems were specially recorded by the Berlin Radio Symphony Orchestra in versions characterized by "modesty and intensity".

At the 2007 signing ceremony for the Treaty of Lisbon, the plenipotentiaries of the European Union's twenty-seven member states stood in attendance while the "Ode to Joy" was played and a choir of 26 Portuguese children sang the original German lyrics.

In 2008 it was used by Kosovo as its national anthem until it adopted its own, and it was played at its declaration of independence, as a nod to the EU's role in its independence from Serbia.

"Ode to Joy", automatically orchestrated in seven different styles, was used on 18 June 2015 during the ceremony celebrating the 5000th ERC grantee as anthem of the European Research Council to represent achievements of European research.

"Ode to Joy" is used as the theme song to the 2016 UEFA Euro qualifying and the European qualifying of the 2018 FIFA World Cup football competition at the introduction of every match.

In 2017, members of the Parliament of the United Kingdom from the Scottish National Party first whistled and then sang "Ode to Joy" during a vote at the House of Commons to protest against Brexit.

In 2018, the anthem of Japan and the anthem of the EU were performed in Tokyo during the official signing of the EU-Japan Economic Partnership Agreement. The European anthem is often played at the signing of official economic or political agreements with foreign governments. In 2023, it was played after the anthem of Ukraine during President of Ukraine Volodymyr Zelenskyy's visit to the EU parliament.

title: Anthem of Europe


text:
Talk:Educational perennialism

Great article! --Seb

Yes, very interesting article, a subject close to my heart.

Do you know who coined "educational perennialism"?

 * Perennialists believe that one should teach the things of everlasting importance to all people everywhere. ... Therefore, one should teach principles, not facts.

The above strikes me as a pretty obvious nonsequitur. (There are plenty of facts that everybody should know.) Is that actually what real perennialists say?

--Larry Sanger

Which educational philosophy is the most relevant today to Educational perennialism? --Turki Alomani — Preceding unsigned comment added by Talomani (talk • contribs) 02:42, 27 March 2023 (UTC)

Aquinas' De Magistro
Note that the link to the De Magistro of Aquinas is broken. I will try to find a good link.

De Magistro
The De Magistro of Aquinas is the same as Quaestio 11 of De veritate, which is found in the Quaestiones disputatae. Here is a link to the complete Latin text, which should probably be included in this article in place of the current broken link:

http://www.corpusthomisticum.org/qdv11.html

I am still looking for an online English translation of this quaestio. 24.128.21.135 16:01, 18 May 2006 (UTC)

I have provided a working link to the complete article, in English and Latin. TheDean (talk) 17:56, 8 January 2014 (UTC)

The link was again broken. I have replaced it with a working link to the Latin and English. TheDean (talk) 18:36, 22 April 2021 (UTC)

Lost Information in this Article
On November 21, due to an edit by 68.222.17.16, a significant amount of information was lost from this article: most of the Religious Perennialism section, and the entire list of Colleges Exemplifying This Philosophy. I cannot tell whether this was vandalism or an inadvertent deletion. Unless anyone objects, I will restore the previous content soon. TheDean 16:51, 16 December 2006 (UTC)

 * I don't see any reason to wait in reverting a large deletion with no edit comment and no discussion here. I've restored it. Dpbsmith (talk) 17:12, 16 December 2006 (UTC)

Is the article not too biased towards American thinkers in the 20th century?

 * Probably. The recent observation that some Muslims consider perennialism too pluralistic is not a great step forward, either, since the same could be said of many educational philosophies.  The note cites no sources, either; I propose deleting it, as it is not in keeping with the rest of the article.  A deeper history of perennialism would probably trace it back from Aquinas through Augustine to Greek philosophy.  It is hard to see that the distinction between secular perennialism and religious perennialism would remain so significant if a full historical treatment were attempted. TheDean 03:31, 3 December 2007 (UTC)

Definition of Perennialism 102.70.2.50 (talk) 20:09, 3 September 2023 (UTC)

title: Talk:Educational perennialism


text:
Timeline of the evolutionary history of life

The timeline of the evolutionary history of life represents the current scientific theory outlining the major events during the development of life on planet Earth. Dates in this article are consensus estimates based on scientific evidence, mainly fossils.

In biology, evolution is any change across successive generations in the heritable characteristics of biological populations. Evolutionary processes give rise to diversity at every level of biological organization, from kingdoms to species, and individual organisms and molecules, such as DNA and proteins. The similarities between all present day organisms imply a common ancestor from which all known species, living and extinct, have diverged. More than 99 percent of all species that ever lived (over five billion) are estimated to be extinct. Estimates on the number of Earth's current species range from 10 million to 14 million, with about 1.2 million or 14% documented, the rest not yet described. However, a 2016 report estimates an additional 1 trillion microbial species, with only 0.001% described.

There has been controversy between more traditional views of steadily increasing biodiversity, and a newer view of cycles of annihilation and diversification, so that certain past times, such as the Cambrian explosion, experienced maximums of diversity followed by sharp winnowing.

Extinction
Species go extinct constantly as environments change, as organisms compete for environmental niches, and as genetic mutation leads to the rise of new species from older ones. At long irregular intervals, Earth's biosphere suffers a catastrophic die-off, a mass extinction, often comprising an accumulation of smaller extinction events over a relatively brief period.

The first known mass extinction was the Great Oxidation Event 2.4 billion years ago, which killed most of the planet's obligate anaerobes. Researchers have identified five other major extinction events in Earth's history, with estimated losses below:

 * End Ordovician: 440 million years ago, 86% of all species lost, including graptolites
 * Late Devonian: 375 million years ago, 75% of species lost, including most trilobites
 * End Permian, The Great Dying: 251 million years ago, 96% of species lost, including tabulate corals, and most trees and synapsids
 * End Triassic: 200 million years ago, 80% of species lost, including all conodonts
 * End Cretaceous: 66 million years ago, 76% of species lost, including all ammonites, mosasaurs, plesiosaurs, pterosaurs, and nonavian dinosaurs

Smaller extinction events have occurred in the periods between, with some dividing geologic time periods and epochs. The Holocene extinction event is currently under way.

Factors in mass extinctions include continental drift, changes in atmospheric and marine chemistry, volcanism and other aspects of mountain formation, changes in glaciation, changes in sea level, and impact events.

Detailed timeline
In this timeline, Ma (for megaannum) means "million years ago," ka (for kiloannum) means "thousand years ago," and ya means "years ago."

Hadean Eon

4540 Ma – 4031 Ma

Archean Eon

4031 Ma – 2500 Ma

Proterozoic Eon

2500 Ma – 539 Ma. Contains the Palaeoproterozoic, Mesoproterozoic and Neoproterozoic eras.

Phanerozoic Eon
539 Ma – present

The Phanerozoic Eon (Greek: period of well-displayed life) marks the appearance in the fossil record of abundant, shell-forming and/or trace-making organisms. It is subdivided into three eras, the Paleozoic, Mesozoic and Cenozoic, with major mass extinctions at division points.

Palaeozoic Era
538.8 Ma – 251.9 Ma and contains the Cambrian, Ordovician, Silurian, Devonian, Carboniferous and Permian periods.

Mesozoic Era
From 251.9 Ma to 66 Ma and containing the Triassic, Jurassic and Cretaceous periods.

Cenozoic Era
66 Ma – present