Providing straightforward information pertaining to drugs, drug use & drug policy. The Grey Pages promotes drug-related literacy and advocates a system of viable and tolerant drug policies. This is my personal collection of commentaries, essays, tid-bits, and other such writings on everything ranging from drug use, drug policy and drug-myths, to drug-science, addiction, human behavior, and the workings of the human brain. I started this blog with a particular focus on opioids, and over the past year have found my interest gravitate toward the intriguing, ever-changing world of designer intoxicants (i.e. "research chemicals" or "designer drugs").

Wednesday, October 19, 2011

MDMA (Ecstasy) Vault


MDMA is one of the most widely popular recreational drugs in the world. It is an amphetamine derivative with stimulant and enactogen properties.


MDMA was origninally synthesized in 1912 by Merck, the German pharmaceutical firm. The pharmacological properties of MDMA were initially overlooked, as it had been specifically patented as an intermediate in the production of a haemostatic drug called methylhydrastinine.

In the 1920's it was observed that MDMA had effects on blood sugar and smooth muscle tissue that were similar to those of ephedrine, while in the 1950's, the US Army conducted toxicity and behavioral studies on animals injected with mescaline and MDMA.

The US government experimented with MDMA, among other drugs (including LSD) and sensory deprivation techniques, as an interrogation tool in Project MKUltra. The findings of these investigations were eventually declassified and made public in 1973.

In the US, MDMA was being taken recreationally in the early 1970's. In the mid 1970's, psychopharmacologist and drug chemist Alexander Shulgin synthesized MDMA and used the drug himself. He later published a paper with David E. Nichols documenting the psychoactive effects of the drug in humans.

In his process of advocating for the use of MDMA, Alexander Shulgin introduced the drug to a psychotherapist colleague named Leo Zeff. Zeff was intrigued with the tendency of the drug to promote open communication and empathy in patients during therapy sessions, and later came to popularize its use as a psychotherapy tool.

It was in the 1980's that MDMA became a popular drug in the nightclub scene and rave culture. It was sometimes referred to as "Adam", while its N-ethyl substituted homologue MDEA (methylenedioxyethylamphetamine) was referred to as "Eve". By the mid 1980's its casual use had become mainstream - the DEA responded by proposing its inclusion among other illicit drugs as a schedule I controlled substance, with no exception for clinical use.

The BBC reported in 2010 that MDMA use in the United Kingdom had declined in recent years. This could be due to substitution with other substances misrepresented as MDMA, or also due to the availability of newer analogous chemicals such as methylone, mephedrone, and 2C-I.


MDMA is a shortened abbreviation for the chemical name methylenedioxymethamphetamine. MDMA is closely related to methamphetamine. MDMA differs from methamphetamine at the molecular level with the presence of 2 oxygen atoms (conncected to positions 3 and 4 of the benzene ring) which are bound together by a methylene bridge (a carbon atom bount with 2 hydrogen atoms and connected by two single bonds with two distinct atoms, in this case being oxygen atoms).

A popular method of MDMA manufacture utilizes a compound called safrole as a precursor - safrole is derived from the root-bark or the fruit of sassafras plants, and contains the methylenedioxyphenyl backbone used as a starting point to produce MDMA.

Most available MDMA is the racemic mixture containing both dextrorotatory and laevorotatory enantiomers. The dextrorotatory enantiomer is slightly less active than the laevorotatory enantiomer; showing a weaker effect on dopamine release, but with a somewhat longer half life. 

Most MDMA is supplied through illicit channels and has been manufactured in the clandestine setting. Illicit
MDMA is often sold as a pill or powder. The compressed, tablet form of the drug is often referred to as ecstasy, X, or E. When in the form of a pure powder or capsulized powder, it is often referred to as molly, or M.

MDMA remains one of the more frequently used recreational drugs in the US (and in the rest of the world). A 2008 survey by the UN estimated a similar number of past year MDMA users as cocaine and opioid users, however this number was dwarfed by that for past-year marijuana users.

MDMA is taken in the casual setting as well as the social setting, and is often distributed at music festivals and raves alongside other enactogens, psychedelics, or dissociatives, which may include 2C-I, LSD, and ketamine.

MDMA is criminalized in many countries, under the UN's Convention on Psychotropic Substances. It is also, in most cases, illegal even for clinical use. However, there are some private therapists who administer MDMA to their patients in a clandestine setting (such as their office at home). Also, MDMA is being investigated for clinical use as a treatment for post traumatic stress disorder and other anxious conditions.

In the recreational setting, MDMA is usually available in tablet, encapsulized powder, or free powder form. It is usually taken by the oral route. It is less commonly adinistered by intranasal, rectal, and intravenous routes.

Effects are apparent around 30-90 minutes after oral administration and last a few hours to several hours, with after-effects lasting up to 24 hours. Typical doses range from 100-200mg when the drug is taken orally. Erowid.org lists a threshold dose of about 30mg, with a "heavy" dose being 200mg or higher.

Mode of Action:

Effects of MDMA are most likely due to increases in synaptic dopamine, norepinephrine and serotonin activity. MDMA promotes the "release" of these neurotransmitters and inhibits their reuptake by reversing the flow of monoamine transporters (i.e. reuptake pumps) - this reversal of transporter function is a process known as phosphorylation. MDMA elicits weak agonist activity at serotonin receptors and also at the Trace Amine-Associated (TAAR-1) Receptor; which is involved in monoamine transporter regulation. The major active metabolite MDA contributes to the effects of MDMA, particularly as a serotonin (subtype 1 and 2) receptor agonist.

Its empathogenic properties are aossociated with its action as a serotonin-releasing agent, and have been hypothesized to be linked in part with 5HT-induced oxytocin release, the latter of which serves as a hormone involved in the hard-wiring of emotional attatchments between a mother and fetus during pregnancy & childbirth.

Racemic MDMA has a half life of about 8-hours.


Psychological effects include a euphoric state or mood lift, enhanced tactile perception (i.e. perception of touch), altered visual perception (i.e. enhanced sense of color, etc), CNS stimulation (feeling "speedy"), social disinhibition, stronger empathetic tendencies, changes in ego, enhanced appreciation for music, increased motivation, grandiosity, analgesia (i.e. reduced pain perception).

Physiological effects include increased heart rate, thermal dysregulation, involuntary eye movements, dilated pupils, jaw clenching or grinding, perspiration, dehydration, nausea & vomiting, headache, dizziness, shortness of breath, erectile dysfunction, and trouble acheiving orgasm.

Adverse side effects may include depression, anxiety, paranoia or fear, amphetamine-psychosis, serotonin syndrome, neurotoxicity, cardiac arrhythmias, cardiac arrest, and seizures.

Related Compounds:

MDMA is just one compound of a larger series of methylenedioxy substituted amphetamines and cathinones which have been sold as grey market research chemicals and designer drugs. Drugs of this series include MDEA ("Eve"), methylone, ethylone, butylone, and MDPV.


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