Table of Contents: ==================
. I. Introduction - Disclaimer - Credits
. II. General - Dosing - Contraindications and overdose information - Effects - Notes on having a rewarding time - Note on using MDMA many times
. III. Safety & Neurotoxicity Discussion - Behavioral Safety Concerns - Neurotoxicity? - Immune System - Preventive Measures - Conclusion
. IV. Chemistry
. V. Miscellany - Rumor Control - Analogues and related compounds - Related Reading - Organizations ===============================================================================
. I. Introduction =============== Disclaimer: ----------- This file is an attempt to collect some of the information about MDMA that is floating around on the net in various stages of organization into one easy-to-read document.
. Ideally, everything that anyone would want to know about MDMA would be included in this document. In practice, there will always be some useful bit of information that haven't made it in yet.. If you find anything that you feel should be added, changed, deleted, or properly credited, please let the maintainer know (address given above).
. This FAQ is provided for informational purposes ONLY. The authors, contributors, and editors do not advocate the use of anything described in this document, and accept NO responsibility for any harm that might occur as a result of acting on any of the information contained here.
. Although good faith effort has been made to ensure the validity of the information contained in this document, no guarantees or assurances of accuracy are provided by anyone. Read at your own risk, act at your own risk. MDMA (also commonly known as Ecstacy, X, E, XTC, Adam, etc.) is a semi-synthetic chemical compound. In its pure form, it is a white crystalline powder.
. It usually seen in capsule form, in pressed pills, or as loose powder. Average cost ranges from $10-$30 (U.S.) a dose. Common routes of administration are swallowing or snorting, although it can be smoked or injected as well.
. Currently, MDMA is on the U.S. Schedule I of controlled substances, and is illegal to manufacture, possess, or sell in the United States.
. Most other countries have similar laws. According to Nicholas Saunders (1993), "MDMA was patented as long ago as 1913 by the German company Merck. [...] The patent doesn't mention uses.
. " See PIHKAL (Shulgin & Shulgin 1991) or Shulgin 1986 for more history, including how Alexander Shulgin brought the drug to the attention of psychotherapists in the 1970s.
. Dosing: ------- Usual doses of MDMA range from around 80 to 160 milligrams (orally), though monks have used lower doses (40-60 mg) to assist meditation, and therapists have sometimes taken similarly low doses to become more in tune with clients.
. A benchmark standard dose is often considered to be 2 mg of MDMA per kilogram of body weight (though response to the drug is not strictly proportional to body weight).
. When MDMA is taken by mouth, the effects manifest about 30-45 minutes later; snorting, smoking or injecting produces much quicker onset. The primary effects usually reach a plateau at T+1:00 (one hour after taking the dose) to T+1:30, stay there for some two hours, then start tapering gradually.
. The primary effects are pretty much over by T+4:00 to T+6:00. Secondary effects (afterglow) may be felt for days, and tertiary psychological effects (e.g. improved outlook) may last indefinitely.
. Supplemental dosing: If you have taken an ordinary dose of MDMA (say 2 mg/kg), you like where you are at about T+1:30 (you will have reached plateau by then), and would like to prolong your stay there, take a supplement equal to about 1/3 to 1/2 the initial dose.
. Taking much more than this is likely to induce or increase unwanted side effects without providing additional benefit in return.
. Contraindications and overdose information: ------------------------------------------- MDMA causes an increase in blood pressure and pulse rate, modest in most people, similar to moderate exercise. Because of this, and because a few people may have a more pronounced cardiac response to MDMA, people with a history of high blood pressure, heart trouble, or stroke are advised not to use MDMA, or at the very least are advised to start with a much lower than average dose. The same warning applies to people who are hypersensitive to drugs.
. Liver or kidney problems may also contraindicate MDMA use. It is, of course, desirable to hear from your physician that you're in good overall health before ingesting any powerful substance.
. Deaths have been reported of some MDMA users who were also taking Monoamine Oxidase Inhibitors (MAOIs are often prescribed as antidepressants). MDMA is *not* recommended to anyone taking any MAOI. Ask your doctor or pharmacist if you're unsure whether a drug you are taking is an MAOI.
. Also be aware that some antidepressants (e.g. Prozac and Zoloft) may inhibit some of the effects of MDMA.
MDMA is thought by many to be a fairly safe drug, as long as you keep track of what your body is telling you (see Section III below for more discussion of safety).
The euphoria that it induces can make it easy to ignore bodily distress signals, so be watchful for things like dehydration (drink lots of water or fruit juices!), muscle cramping, dizziness, exhaustion or overexertion.
Several reports from England tell of dosed ravers dancing themselves into severe dehydration and heat exhaustion that required hospitalization and in a few cases resulted in death. An MDMA overdose is characterized by high pulse or blood pressure, faintness, muscle cramping, or panic attacks.
If you experience any of these symptoms, sit down, rest, and drink some fruit juice, water, or a gatorade-type sports drink.
In the unlikely event someone has a more severe reaction, e.g. loss of consciousness or seizures, get medical help as soon as possible.
Effects: -------- The physical effects of usual doses of MDMA are subtle and variable: some users report dryness of mouth, jaw clenching, teeth grinding, nystagmus (eye wiggles), sweating, or nausea. Others report feelings of profound physical relaxation.
At higher doses (overdoses), the physical effects of MDMA resemble those of amphetamines: fast or pounding heartbeat, sweating, dizziness, restlessness, etc.
The psychological effects are a bit more difficult to describe, since they are many and of widely varying effects. The major ones are:
- Entactogenesis ("touching within") This is a generalized feeling that all is right and good with the world.
People on MDMA often describe feeling "at peace" or experiencing a generalized "happy" feeling. Also, common everyday things may seem to be abnormally beautiful or interesting.
Alexander Shulgin reported that mountains that he had observed many times before appeared to be so beautiful that he could barely stand looking at them.
- Empathogenesis Empathogenesis is a feeling of emotional closeness to others (and to one's self) coupled with a breakdown of personal communication barriers.
People on MDMA report feeling much more at ease talking to others and that any hangups that one may have with regard to "opening up" to others may be reduced or even eliminated. This effect is partially responsible for MDMA's being known as a "hug drug" - the increased emotional
closeness makes personal contact quite rewarding.
Many people use MDMA primarily for this effect, reporting that it makes potentially awkward or uncomfortable social situations (singles bars, dance clubs, etc.) much more easily dealt with. "[Conversation] just flows like water" said one person. "It seems like you know exactly what to say and when to say it.
It's like a filter between what you want to express and what comes out of your mouth that you didn't even know existed is stripped away." This same person also reported that they used to use alcohol for many of these same reasons, but found MDMA to be more effective.
- An enhancement of the senses MDMA can significantly enhance (sometimes distort) the senses - touch, proprioception, vision, taste, smell. MDMAers can sometimes be seen running their hands over differently textured objects repeatedly, tasting and smelling various foods/drinks.
This effect also contributes to the "hug drug" effect because of the novel feeling of running one's hands over skin and having one's skin rubbed by someone else's hands.
Before it was made illegal, MDMA was gaining a reputation among the psychiatric community as a valuable therapeutic tool. People under its influence often report seeing their lives in a whole new light. "I was completely blown away the first time I did X" said the same person quoted above. "I saw some of my problems that I didn't even know I had! All of a sudden, It seemed like the source, nature and sometimes even the solution of all my personal difficulties were completely obvious." Surfacing of repressed memories has also been reported.
Despite the legal risks surrounding Schedule I drugs, some therapists are still using MDMA in their practices. For a report on the subjective experiences and psychological/behavioral sequelae of 20 psychiatrists who took MDMA, see "Phenomenology and Sequelae of 3,4 Methylenedioxy-methamphetamine Use" (Liester, Grob, Bravo, and Walsh) in J. Nervous and Mental Disease, Vol 180, No. 6, June 1992, Serial No. 1315.
Most people find the MDMA state so valuable by itself that it's not clear there's much to be gained from combining MDMA with most other substances (though the combination of of MDMA with LSD seems to have a strong following). Further, combining drugs ("polydrug use" and "polydrug abuse") complicates the medical and behavioral safety picture.
For this reason, it is not a recommended practice in the absence of expert guidance. Here is a chart of commonly encountered drugs and some of their reactions when combined with MDMA: Drug | Reaction Information ============================================================================== Marijuana | Not known for dangerous reactions. MJ is habit-forming for | some users. --------------|--------------------------------------------------------------- LSD | Not known for dangerous reactions. ------------------------------------------------------------------------------ Amphetamines | Amphetamine overdosage probability is dramatically increased. | Strongly discouraged. Speed is addictive. --------------|--------------------------------------------------------------- Cocaine | Same as Amphetamines. Cocaine is addictive. --------------|--------------------------------------------------------------- Heroin or | No dangerous reaction, but the stimulant effect of MDMA may other opiates | mask the opiate's sedative effect and increase the likelihood | of overdose. The opiates are addictive. --------------|--------------------------------------------------------------- Tobacco | Not known for dangerous reactions. Tobacco is highly | addictive and carcinogenic. --------------|--------------------------------------------------------------- Alcohol | Same danger as opiates, also can dangerously exacerbate the | dehydration that MDMA normally causes. Not recommended. | Alcohol is habit-forming for some users. --------------|---------------------------------------------------------------
Note that this chart does not cover cross-reactions of mental effects. This will be covered in the next section. Notes on having a rewarding time: --------------------------------- MDMA is used by different people for different things. Because the drug has such a wide range of effects, it can add to almost any activity. Here are some of the more common activities than people take MDMA and engage in.
- Raves Raves (dance events featuring "house" music) are common settings for taking MDMA. The atmosphere of a Rave is designed to be conducive to enjoying the MDMA experience, in the company of other people who may also be taking MDMA, or who can be as friendly and open without chemical assistance.
MDMA's enhancement of proprioception (deep body sense) makes movement notably pleasant, so Ravers on MDMA often dance for long periods of time (remember to drink water frequently!). The feeling of unity and shared ecstatic joy at a successful Rave can be overwhelmingly wonderful. Some ravers regard this as spiritual or religious practice.
For more info on raves, subscribe to the newsgroup alt.rave or FTP the RAVE FAQ from TECHNO.STANFORD.EDU in the /pub/raves directory. - Self-psychotherapy Since MDMA can catalyze a broad range of psychotherapeutic effects (surfacing of repressed memories, dealing with emotional issues, etc.), MDMAers sometimes will trip by themselves or with a trusted guide, and spend the experience thinking about their lives.
It has been said that "one hit of X [MDMA] is worth 3 months of conventional psychotherapy". Whether that is an exaggeration or not, MDMA has been praised by many psychotherapists as a notably effective means of dealing with personal issues.
People who have had an MDMA experience of this kind often will want to talk to some people they are close to in order to discuss what MDMA has made them more aware of.
- A substitute for speed MDMA is also sometimes used for some of the same things that amphetamines are used for, typically activities that require concentration, motivation, creativity, or energy. Doing homework, studying, writing, playing video games, and dieting are some of the many activities that MDMA may facilitate.
- The sensorium The sensory enhancement of MDMA can make sensual activities unusually enjoyable. Touching can become such an intensely pleasurable sensation that close personal contact (sexual or otherwise) can be quite fun, especially when coupled with MDMA's empathogenic effects. Hugging someone and running your hands over them are such a common thing to see people on MDMA doing that it is known to some as the 'Hug Drug'. Eating, drinking, smelling flowers and even the sensations of waste elimination can become special experiences on MDMA.
MDMA can also be mixed with other drugs for a different experience. The health hazards of each of these combinations were discussed in the section on contraindications. Here are the mental effects: (note that this is based on subjective information. Personal reactions may differ.)
Drug | Information ============================================================================== Marijuana | Fun, but can cloud the mental effects of the MDMA. Have to | smoke more before you notice it. --------------|-----------------------------------------
---------------------- LSD | Can go very well together. LSD and MDMA is commonly known as | "XL" or "candyflipping". Most prefer quite low doses of LSD. -------------------------------------------------------
----------------------- Amphetamines | You're already speeding. Why bother? Health risks noted in | contraindications section. ---
-----------|--------------------------------------------------------------- Cocaine | Similar to Amphetamines. --------------|----------------------------------------------
----------------- Heroin or | In terminal cancer patients, MDMA has restored the lucidity other opiates | that is often obscured by opiates given for pain. ---------
-----|--------------------------------------------------------------- Tobacco | Tastes good, if you're into it. Easy to smoke too much. --------------|----------------------------------------------------
----------- Alcohol | Can cloud the desired effects of MDMA. Dehydrating. --------------|
--------------------------------------------------------------- Drug Quality ------------ To have a rewarding time on MDMA, you need to have good quality MDMA. The only way to maximize your chance of getting the real thing is to know & trust your supplier.
Note that MDMA is not known for causing strong visual distortions. If you take some "MDMA" and notice that a predominant effect is trippy visuals, what you got was probably not pure MDMA, or MDMA at all.
Note on Using MDMA Many Times: ------------------------------ Most users of MDMA who have taken the drug many times report that after a certain number of sessions, varying by person from a few to a few dozen, the desirable effects of the drug are no longer as pronounced. Said one, "it
loses its magic." Another person who used MDMA perhaps a dozen times (separated by weeks to months) noted the dropoff, waited three years (!),
tried an ordinary dose of high-quality MDMA again, and found that the annoyance of the physical side effects outweighed the greatly diminished positive effects.
He has sadly given up the drug. Others who have had fifty or more MDMA sessions still find them to be worthwhile on balance.
This MDMA effect dropoff might be explained by a psychological mechanism: loss of novelty. (On the other hand, people who have experienced MDMA effect dropoff generally report that there is not a similar dropoff in the effects of other psychedelics with which they are equally or more experienced, e.g. LSD .
and DMT.) Or the dropoff might be caused by lasting neurophysiological or neurological "changes" to the brain from repeated sessions, the prior state of the changed structures being necessary for ecstatic MDMA experiences. It is a complex, as-yet-unanswered question whether such changes, if they happen, are best regarded as harmful, neutral, or beneficial. .
If there is a lesson here, perhaps it is to spend your first three, six, or twelve sessions wisely and cherish them. Later sessions may never seem as great. .
============================================================================== III. Safety and Neurotoxicity Discussion ======================================== .
Behavioral Safety Concerns -------------------------- As noted, a primary psychological effect of MDMA is to make the user feel "safe", at peace with the world, pleasantly reconciled to things as they are, and things however they will be. This can remarkably diminish one's ability to make sound judgements during the session. Examples: .
- It becomes easy to want to prolong the MDMA state by taking more and more of the drug (or of other drugs), beyond what you would judge wise or worthwhile when not under its influence. .
- It becomes easier to have unsafe sex. You may "forget," judge that the risk of infection is very small, or feel that infection wouldn't be such a terrible thing after all. If you think you might have sex while on MDMA, it may help you and your partner to stay safe if you lay out safer sex supplies before dosing in a place you'll be sure to see them later, and agree beforehand that you'll use them if the occasion arises. .
Another danger stems from MDMA's lessening of the awareness of pain (whether through chemical analgesia, or through psychological analgesia). Combined with the extra energy the drug gives, it becomes easy to sustain bruises, blisters, or other bodily damage from extensive dancing, hiking, climbing, etc., without noticing it until after the damage is done. .
Under MDMA, it may seem "right" to make immediate changes in relationships (increasing or decreasing commitment) of all kinds. The fresh points of view appreciated during an MDMA session are one of the drug's most prized benefits, but it is probably unwise to actually make lasting relationship changes until you have a chance to see how you would feel about them after the drug and its afterglow wear off. .
Neurotoxicity? -------------- One claimed effect of MDMA use is lowered brain serotonin levels. One study (Peroutka) found no evidence for this, but at least two others (Ricaurte) have found significantly reduced serotonin metabolite levels, the more recent study showing a 30% average difference between the control group of non-MDMA users and the experimental group consisting of people who had used MDMA about 75 times each, on average. (Note though, that some of these studies used psychiatric patients or "polydrug abusers" - not representative user samples.) .
What does this mean for users? Anecdotal evidence from years of legal and illegal use suggests that this is not of much concern for most people. Some folks, however, report periods of depression after using MDMA, on rare occasion severe depression. Considering that a primary action of many antidepressant drugs (MAOIs, SSRIs) is to increase brain serotonin levels, a connection between MDMA use and subsequent depression is not unbelievable. Psychological factors - sadness at returning to an ordinary state of consciousness after ecstasy - may also account for feeling down for a while. In any event, most users report the opposite: feelings of well-being or gentle euphoria in the days following an MDMA session. To get a better understanding of why the serotonin system may be critical to normalcy for some individuals and less so for others, see Listening to Prozac by Peter D. Kramer (Viking 1993). .
The entire book is worthwhile, but note pages 134-136 especially. There is solid experimental evidence that MDMA, administered in large doses and/or repeatedly, causes partial loss of serotonergic neurons in laboratory animals. Uncertain is whether this loss is permanent, reversible, or important. One study found in the rat nearly 100% recovery within a year. In another study (Ricaurte), non-human primates were dosed with MDMA and their brains were examined for morphological changes. Ricaurte found that there was no effect after 2.5 mg/kg oral doses given every two weeks, for a total of eight doses..
But after a single oral dose of 5 mg/kg, he observed a 20% reduction in serotonin and its metabolite 5-HIAA, only in the thalamus & hypothalamus. There appeared to be some regrowth over time, not necessarily complete, and also some "collateral sprouting" - growth of other types of neurons in the reduced serotonin areas. Note that in all of the animal studies, even when there are quite large serotonin system reductions (up to 90% in high MDMA dose rat studies), no behavioral deficits are observed. .
It is also uncertain how these studies would extrapolate to humans - the human brain may well be more or less sensitive, or sensitive in different areas, compared with other animals. In any case, what is known is that there are no reported cases that link behavior changes in humans with MDMA-induced serotonin system changes or neuronal loss. And, the long-term human behavior changes that are noted (in studies and from anecdotal case reports) are generally regarded as positive - lowered impulsiveness and hostility, improved social/interpersonal functioning, changes in religious/spiritual orientation or practice, etc. .
One of the reasons so little is known about the lasting effects of MDMA on the human brain is that no subjects (to date) have recorded their drug use history, then volunteered their brains for post-mortem study. If you would like to consider doing this, you can get donor information at 1-800-UM-BRAIN. .
Studies with live human subjects are also underway - both volunteers and donations are needed. One good source of current info is the Multidisciplinary Association for Psychedelic Studies (MAPS) - see "Organizations" at the end of the FAQ. .
Immune System ------------- Some users of MDMA report an apparent decrease in resistance to disease, especially with frequent MDMA use. It is unknown how much of this may be due to the pharmacological "body load" of MDMA, to staying up all night and dancing, to increased physical contact with people with colds, to suppressed appetite and poor nutrition, etc. .
Preventive Measures ------------------- A fundamental precaution is to stay well hydrated. Drink water frequently during the MDMA session, and moreso if you're physically active. Under the influence, time can pass surprisingly quickly. It is useful if trip guides or trip buddies remind each other to drink water often. .
For those who are concerned about the possibility of serotonin level or serotonin system changes in humans with therapeutic doses of MDMA, some researchers reckon changes can be lessened or prevented by taking antioxidants. In an article titled "Phenethylamines, Free Radicals, and Antioxidants" (MAPS Newsletter, Volume IV Number 1), author Brian Leibovitz suggests in Table 1 taking as a preventive measure the following: 5 mg B-Carotene; 2 grams Bioflavonoids; 100 mg Coenzyme Q10; 2-4 grams L-Ascorbic acid; 1 gram L-Carnitine; 2 grams N-Acetylcysteine (NAC); 250 ug Selenium, and 1,000 IU Vitamin E. "There is nothing magic about the doses listed; it is my best estimate based on present knowledge in nutrition." If you don't feel like buying out the local vitamin store, taking a subset of these (even just the ascorbic acid - vitamin C) could well be helpful. .
And, if you're really concerned, recent non-human animal research suggests that most or all of the serotonin system reduction may be prevented by taking Prozac (fluoxetine) 0-6 hours after taking the MDMA (see McCann and Ricuarte in J. Clinical Psychopharmacology, 13 (3):pp. 214-217, 1993). One might speculate that other SSRI drugs (Zoloft, Paxil) may work too. Note, however, that some people report that Prozac taken before or in the early part of an MDMA session lessens some of the desirable effects of the MDMA. .
Conclusion? ----------- One take on all this information is that there are a great many questions unanswered by research as yet. Thus a conservative, prudent assumption is that the risk of some kind of subtle neurological "damage" in humans from MDMA use is not zero. Yet there is no behavioral evidence of neurological harm in humans (and there is considerable evidence of psychological benefits) - this in many years of legal use (before 1985 in the US), and quite widespread illegal use since then. .
Given any non-zero risk, it makes sense to examine the benefit side of the equation, and take the drug only when you expect to get some tangible positive outcome from it that you feel makes taking the risk worthwhile. .
=============================================================================== IV. Chemistry ============= Introduction: ------------- All information here is to be used at your own risk. The procedures documented in this file, if carried out by unlicensed individuals would violate laws against controlled substances in most countries and could result in criminal charges being filed. If carried out by individuals unskilled at chemistry they could result in serious bodily harm. .
MDMA ("Ecstasy") is a semi-synthetic compound which can be made relatively easily from available precursors. Synthesis instructions exist which can be followed by an amateur with very little knowledge of chemistry. However, people with less than 2 years of college chemistry experience would probably not be capable of sucessfully synthesizing MDMA, and would either botch it in the best case or kill themselves in the worst case. For those interested in the techniques involved in synthesizing MDMA, a good book for self- learning is the following: .
Zubrick, James W. "The Organic Chem Lab Survival Manual: A Students Guide to Techniques." ISBN #0471575046. Wiley John&Sons Inc. 3rd ed. .
It is recommended that this book should be supplemented with at *least* one more of the 'dry' and technical O-Chem lab manuals available at any college bookstore. It is not recommend that the information from these books or herein this file be used to synthesize MDMA for the previously stated reasons. Knowledge, however, is not (yet) illegal. .
Precursors: ----------- The following chemicals are some of the more important ones in the synthesis of MDMA and related chemicals: O || O //\ /\ O //\ /\ O //\ /\\ O //\ /\\ NO2 / \// \/ H / \// \/ \ / \// \/ \\ / \// \/ \\/ / | || / | || || / | || | / | || | CH2 | || CH2 | || || CH2 | || | CH2 | || | \ | || \ | || CH2 \ | || CH3 \ | || CH3 \ /\\ / \ /\\ / \ /\\ / \ /\\ / O \\/ O \\/ O \\/ O \\/ piperonal safrole isosafrole beta-nitroisosafrole O //\ /\ O O //\ /\ Br / \// \/ \// / \// \/ \/ / | || | / | || | CH2 | || | CH2 | || | \ | || CH3 \ | || CH3 \ /\\ / \ /\\ / O \\/ O \\/ MDP-2-P 3,4-methylenedioxy- phenyl-2-bromopropane safrole: 3,4-methylenedioxyallylbenzene, 1-(3,4-methylenedioxyphenyl)-2-propene .
isosafrole: 3,4-methylenedioxypropenylbenzene, 1-(3,4-methylenedioxyphenyl)-1-propene MDP-2-P: 3,4-methylenedioxyphenyl-2-propanone, 3,4-methylenedioxyphenylacetone, 3,4-methylenedioxybenzyl methyl ketone, .
piperonylacetone piperonal: 3,4-methylenedioxybenzaldehyde, heliotropin .
beta-nitroisosafrole: 3,4-methylenedioxyphenyl-2-nitropropene .
safrole, isosafrole, MDP-2-P, piperonal and beta-nitroisosafrole are the most commonly found precursors to MDMA in clandestine labs. .
Synthetic Routes: ----------------- For an overview of MDMA synthetic routes it is suggested that the readers familiarize themselves very thoroughly with the following reference: .
Dal Cason-TA. "An Evaluation of the Potential for Clandestine Manufacture of 3,4-Methylenedioxyamphetamine (MDA) Analogs and Homologs." Journal of Forensic Sciences. Vol 35(3):675-697. May 1990. .
The most common synthetic routes for production of MDA, MDMA, MDE (MDEA), and MDOH are from the precursor MDP-2-P. To get MDP-2-P first a natural source of safrole is acquired. Safrole can be extracted from sassafras oil, nutmeg oil, or several other sources which have been abundantly documented in _Chemical Abstracts_ over the years. The safrole is then easily isomerized into isosafrole when heated with NaOH or KOH. The isosafrole is then oxidized into MDP-2-P. This latter procedure has been most clearly presented in _Phenethylamines I Have Known and Loved_ by Alexander Shulgin under synthesis #109 (MDMA). The synthesis of MDP-2-P from isosafrole will require the use of a vacuum pump to evaporate the solvent from the final product in vacuo. An aspirator will not, unfortunately, be sufficient. .
http://ecstasy.org/testing/labtest0697.html
