Ecstasy (drug) Chemistry History Ecstasy As A Recreational Drug

MDMA, more commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. Tactile sensations are enhanced for some users, making general physical contact with others more pleasurable, but contrary to popular mythology it generally does not have aphrodisiac effects. Its ability to facilitate self-examination with reduced fear has proven useful in some therapeutic settings, leading to its 2001 approval by the United States FDA for use in patients with post-traumatic stress disorder.

There have been several fatal overdoses of MDMA, resulting in hyperthermia and serotonin syndrome. Acute dehydration is a risk among users who are highly physically active and forget to drink water, as the drug may mask one's normal sense of exhaustion and thirst. Also the opposite, Water intoxication resulting in acute hyponatremiaThe electrolyte disturbance hyponatremia exists when sodium levels in the blood are below 135mmol/l. Hyponatremia may lead to dehydration. Hyponatremia is mainly caused by solute loss, such as vomiting or diarrhea. Water retention resulting in hyponatremi has been reported. By far the biggest danger comes from the fact that other, more dangerous chemicals (such as PMAPMA (p-methoxyamphetamine) is a dangerous synthetic drug, psycho stimulant and hallucinogen. PMA in form of pills is sometimes passed off as MDMA ( Ecstasy) and can cause death, because it is more active and more toxic., DXM or methamphetamineMethamphetamine is a synthetic stimulant drug which induces a strong feeling of euphoria and is highly addictive. Pure methamphetamine is a colorless crystalline solid, sold on the streets as glass ice or crystal . It is also sold as less pure crystalline) are either added to ecstasy tablets, or more often simply sold as "ecstacy". Long-term effects in humans are largely unknown and the subject of much controversy.

MDMA is also known by many other street names, including Adam, Beans, Disco Biscuits, Eccies, M&Ms, Pills, Rolls, Smarties, Tabs, Yokes, X, XTC, Vitamin E, and E.

1 Chemistry

MDMA
Chemical nameIUPAC nomenclature is a systematic way of naming organic chemical compounds. Ideally, every organic compound should have a name from which an unambiguous structural formula can be drawn. In IUPAC nomenclature, a number of prefixes, suffixes and infixes ar	3,4-Methylenedioxymethamphetamine or 1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Chemical formulaA chemical formula (also called molecular formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. It identifies each type of element by its chemical symbol and identifies the number of atoms of su	C₁₁H₁₅NO₂
Molecular massThe molecular mass of a substance (less accurately called molecular weight and abbreviated as MW is the mass of one molecule of that substance, relative to the molecular mass unit u (equal to 1/12 the mass of one atom of carbon-12). Thus it is a dimension	193.25 g/mol
Melting pointThe melting point of a solid is the temperature at which it changes state from solid to liquid. When considered as the temperature of the reverse change, it is referred to as the freezing point . For example, the melting point of the element mercury is 23	148 - 153 °C ( hydrochloride)
CAS numbers	42542-10-9, 66142-89-0, 69610-10-2, 81262-70-6
SMILES	CC(NC)CC1=CC=C(OCO2)C2=C1

2 History

MDMA was first patented on Christmas eve 1914 by the German pharmaceutical company Merck, two years after its first synthesis. At the time, Merck was systematically synthesizing and patenting a wide variety of chemically related compounds which could be potentially used in human health, and MDMA remained largely forgotten for many years.

Contrary to many rumours, the drug was never used as an appetite suppressant or as a stimulant for armed forces during wartime. MDMA was first brought to public attention through Dr. Alexander Shulgin in the 1960s who recommended it for use in certain therapy sessions, naming the drug 'window' (he discovered it while searching for compounds that might have a similar psychoactive effect as other compounds contained in nutmeg). It was widely used therapeutically by US psychotherapists (especially on the West Coast) because of its empathogenic effects until its criminalization in the late 1980s, and a small number of therapists continue to use it in their practices today. (See below for 2001 FDA approval and DEA licensing for use in patients with post-traumatic stress disorder.)

Until the mid 1980s, MDMA was not illegal in the United States. Recreationally, it first came into prominence in certain trendy yuppie bars in the Dallas area, then in gay dance clubs. From there, use spread to rave clubs, and then to mainstream society. During the 1990s, along with the growing popularity of the rave subculture, MDMA use became increasingly popular among young adults in universities and later in high schools. It rapidly became one of the four most widely used illegal drugs in the US, along with cocaine, heroin and marijuana.

3 Ecstasy as a recreational drug

The primary effects of MDMA include openness, euphoria, empathy, love, and an appreciation of the repetitive rhythms of dance music. Its initial adoption by the dance club sub-culture is probably due to the enhancement of the dancing experience.

Taking MDMA or Ecstasy is referred to as rolling or dropping. Known in its related subcultures as E, "Eccies", X, pills, tabs, disco biscuits or beans, MDMA use has increased markedly since the late 1980s and spread beyond the original sub-cultures to mainstream use. Prices have also been falling since its introduction, with an evening's drug use often costing less than an equivalent evening drinking alcohol.

4 Supply and administration

MDMA is usually ingested in pill form. Pills come in a variety of "brands", usually identified by the icons stamped on the pills. The brands never consistently designate the actual active compound within the pill, as anyone can make their own pills which copy the features of a well-known brand.

Pills sold illegally on the street don't always have MDMA as the only active ingredient. Black market pills have been found to contain cheaper variants such as MDEA, MDA (which in most processes has to be created anyway to create MDMA) and MBDB , and occasionally other unrelated psychoactive additives such as amphetamines (speed), DXM, ephedrine, PMA, capheine , ketamine (Special K), and others.

While overdose from MDMA itself is rare, many more toxic substances are often sold as Ecstasy, and overdose or other adverse reaction to adulterants is not uncommon. MDMA appears to be one of the most commonly adulterated drugs. However, it is less likely that it is mixed, or "cut", with another substance than that it has simply been replaced by another substance which is sold as MDMA.

Although proper characterization of Ecstasy pills requires advanced lab facilities such as GCMS, it is also possible to use a less accurate presumptive alkaloid test known as the Marquis reagent. DanceSafe sells testing kits, and includes an extensive database of photographs of different pills, along with the results of a laboratory analysis of their contents.

5 Effects

5.1 Neurological effects

Serotonin is one of the chemicals responsible for mood and pleasure. MDMA's main action is believed to cause serotonin stores in the brain to dump abnormally large amounts of serotonin into the synapses during the 4 to 6 hour high, which is responsible for the primary subjective effects. MDMA also raises dopamine and norepinephrine levels. These effects are primarily due to MDMA's action on the monoamine transporters, SERT (serotonin transporter), DAT (dopamine transporter) and NET (norepinephrine transporter).

Apart from the dangers from impurities, the primary acute risks of taking Ecstasy are allergic reaction, which is extremely rare, and dehydration. Like many amphetamines, MDMA can mask the body's normal thirst and exhaustion responses, so dehydration is a risk, especially if a user is dancing or otherwise physically active for long periods of time without hydration. In sedentary therapeutic use, incidence of dehydration is not statistically significant. Experts do warn regular users of the drug in more physically active social settings to be cognizant of water intake. While dehydration is undesirable, there also have been a very small number of users overly concerned about hydration drinking excessive water and suffering from water intoxication and associated hyponatremia (dilution of the blood that can cause swelling of the brain). In fact, this is what caused the death of British teen Leah Betts, which may be the world's most widely-publicised MDMA-related fatality.

5.2 Systemic effects

Other effects include:

Pupil dilation with attendant photo-sensitivity, color perception
Jaw clenching or bruxism (" gurning or grinding")
Juddery vision ( nystagmus)
General restlessness
Loss of appetite/taste sensation
Impotence in men
Lack of focus / concentration
Tingling
Sweaty palms

Most users experience a coming down period afterwards that lasts between several hours and a day. During this time they feel uncommunicative, listless and depressed. This is thought to be due to depletion of serotonin in the brain, so some users take supplements in an attempt to boost serotonin levels. Tryptophan or 5-HTP, which are precursors to serotonin, are common choices. Because users generally do not eat while experiencing ecstasy's acute effects, vitamin supplements and antioxidants are also often used in an attempt to restore essential nutrients which have been depleted.

5.3 Long-term effects

Long-term effects are still unknown and heavily debated among scientists. Some experiments indicate that continuous use at very high doses may lead to the serotonin cells in the brain becoming damaged, probably through the uptake of dopamine into serotonin cells, where it is then metabolized into hydrogen peroxide, which causes oxidation damage to the interior of the serotonin cell.

This effect has been observed in the brains of rats, where serotonin cells of animals given extremely high doses of MDMA, usually one to two orders of magnitude greater than a typical human dose, over a prolonged period of time become withered and useless. This hypothesis is supported by the fact that the administration of selective serotonin reuptake inhibitors ("SSRIs", which bind to the serotonin cell's reuptake ports and thus block dopamine, and everything else, from entering the serotonin cells) along with or immediately following MDMA seems to completely block neuron damage in rats given MDMA.

For this reason many users self-administer an SSRI while, or shortly after taking MDMA, in an attempt to prevent possible neurotoxicity. These SSRIs are typically antidepressants such as Prozac or Zoloft. It should be noted, however, that MDMA use in conjunction with a different class of antidepressants, namely Monoamine oxidase inhibitors, is strongly contra-indicated due to danger of Serotonin syndrome

There is also some experimental evidence indicating that long-term ecstasy users experience memory difficulties. However, such research is problematic as ecstasy users are much more likely than control subjects to have taken other drugs in addition to ecstasy, or even abused various chemicals. This makes it difficult for researchers to establish a direct cause for these difficulties.

5.4 Ecstasy and Parkinson's

Research at the University of Manchester indicates that Ecstasy dramatically reduces tremors in patients receiving L-DOPA treatment for Parkinson's Disease.

A research team led by Dr. George A. Ricaurte at Johns Hopkins University implicated MDMA as a cause of Parkinson's-like brain abnormalities in monkeys, and suggested that a single use of MDMA caused permanent and serious brain damage. These claims were hotly disputed by physicians, therapists, and other experts - including a team of scientists at New York University. Criticisms of the study included that it used injection rather than oral administration; that this type and scale of damage (>20% mortality) would translate to hundreds of thousands or millions of deaths which had not materialized in the real world amidst extremely broad global MDMA usage; and, perhaps most important, that other research teams could not duplicate the study's findings.

On September 6, 2003, Dr. George A. Ricaurte and his team announced that they were retracting all results of their commonly cited and controversial study. The researchers said that the labels on the drugs had been somehow switched, and they had inadvertently injected their experimental monkeys and baboons with methamphetamine instead of MDMA. The chemical supplier, Research Triangle Institute, has publicly claimed that the proper drug was supplied, and Ricaurte has yet to pursue them for their alleged error.

Ricaurte had also come under fire for supplying PET scans to the US Office of National Drug Control Policy that were used in anti-drug literature (Plain Brain/Brain After Ecstasy) that seemed to suggest MDMA created holes in human brains, an implication that critics called misleading. Ricaurte later asked the Agency to change the literature, citing the "poor quality" of the images.

See the CBS News article linked below for more information.

6 Ecstasy and the law

Use, supply and trafficking of ecstasy are currently illegal in most countries. In the United States, MDMA was legal and unregulated until July 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 also made this recommendation. Nonetheless, DEA classified it as Schedule I.

In 2001, however, the FDA approved MDMA for research with patients suffering from post-traumatic stress disorder. In March of 2004, the DEA issued its first Schedule I possession licenses for those conducting research under the FDA approval. For further information on this, visit the MAPS website

7 Safety

Note: Wikipedia does not give medical advice

The illegality of this drug in many countries makes exact study of its effects difficult. Some of the effects ascribed to ecstasy, which may or may not be conclusive, are the following:

Because of its illegality, the dose and purity of a pill advertised as ecstacy may be stronger than is desired or may be unsafe.
Ecstasy affects the regulation of the body's internal systems. Continuous dancing without sufficent breaks or drinks can lead to dangerous overheating and dehydration. Drinking too much water without consuming a corresponding amount of salt can lead to hyponatremia or Water intoxication.
The use of ecstasy can exacerbate depression and produces temporary depression as an after-effect of its use.
The use of ecstasy can be very dangerous when combined with other drugs.
Because it substantially affects perception, concentration, and motor skills, it is dangerous to operate heavy machinery or motor vehicles when using ecstasy.
Long-term after-effects are greatly exacerbated by high doses and frequent use.
A small percentage of users may be highly sensitive to MDMA; this may make first-time use especially hazardous. This includes but is not limited to people with congenital heart defects, and a small percentage of people who lack the proper enzymes to break down the drug.

8 See also

9 External links

TiHKAL entry
"Wired News: Long Trip for Psychedelics" Wired, September 27, 2004
"DEA Approves Ecstasy Tests" Wired, March 2, 2004
"Out of the Club, Onto the Couch" Newsweek, December 5, 2003 - Interview with NYU's Dr. Julie Holland
Pillreports - The definitive Ecstasy database that is updated with "trip" reports and pictures daily.
Good Drugs Guide - Basic information
DanceSafe - a risk reduction site with lots of information on Ecstasy. Includes a large database of photographs of different pill types, along with laboratory analysis of what was actually found in the pill.
This is your brain on Ecstasy - A slideshow that illustrates the neuropharmacokinetics of Ecstasy (how the drug affects the brain)
Erowid's Ecstasy page - lots of information
UK National Drugs Line factsheet on Ecstasy
Multidisciplinary Association for Psychedelic Studies
American Council for Drug Education factsheet on Ecstasy
http://www.ecstasy.org
CBS News article on Ecstasy-Parkinson's Connections outlining some of the current scientific controversy
Utopian Pharmacology. Detailed essay discussing the history and uses of MDMA
Results Retracted on Ecstasy Study The Washington Post, September 6, 2003
[1] A paper on MDMA including long history section
TheDEA.org An ecstasy user's guide with detailed discussions of risks and scientific research.

10 References

Jennings, Peter. Ecstasy Rising, ABC television documentary. 2004-01-04.

11 Categorization

Entactogens
{ AET} { MBDB } { MDEA} { MDA} { MDMA}

Amphetamines Empathogens Entactogens

<Hide>

Home > Ecstasy (drug)