MDMA Frequently-Asked-Questions
First Author/Editor: Jon M. Taylor (jmt0165@u.cc.utah.edu)
Last Major Update: 15-Feb-94 R. Jesse (bob@hyperreal.com)
Last Minor Update: 27-May-94 R. Jesse (bob@hyperreal.com)
FAQ Maintainer: Brian Behlendorf (brian@wired.com)
Changes in 15-Feb and 27-May revisions:
- Modified dosing information; added supplemental dosing note
- Added III. Safety and Neurotoxicity Discussion
- Added Note on Using MDMA Many Times
- Replaced Chemistry section with Lamont Granquist's new survey
- Added more references
Table of Contents:
- Introduction
- General
- Safety & Neurotoxicity Discussion
- Chemistry
- Miscellany
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.
Many people on the net have provided, knowingly or not, much of
the information that went into making this FAQ document. In
particular, the largest contributors were:
- David Honig (honig@ics.uci.edu), assembler of the first proto-FAQ
for MDMA.
- Chris Klausmeier (cklausem@jarthur.cs.hmc.edu), manager of the
current alt.drugs ftp site, where Jon got most of the info that went
into the first editions of the FAQ.
- Lamont Granquist (lamontg@cs.washington.edu), author of the new
Chemistry survey inserted into the FAQ 27 May 1994, and provider of
general wisdom.
- Robert Jesse (bob@hyperreal.com), author/editor of the first
Neurotox, Behavioral Safety Concerns, and Using MDMA Many Times
sections.
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.
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.
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.
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.
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 obtain the alt.rave
FAQ from TECHNO.STANFORD.EDU.
- 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.
--------------|---------------------------------------------------------------
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Once the MDP-2-P is synthesized there are several synthetic routes which
can be taken:
- Sodium Cyanoborohydride
- Aluminum Amalgam
- Sodium Borohydride
- Raney Nickel Catalysis
- Leukart Reaction via N-formyl-MDA
- Leukart Reaction via N-methyl-N-formyl-MDA
The sodium cyanoborohydride method is probably the one most attractive to
clandestine chemists. From the Dal Cason reference:
"It requires no knowledge of chemistry, has a wide
applicability, offers little chance of failure, produces
good yields, does not require expensive chemical apparatus
or glassware, and uses currently available (and easily
synthesized) precursors"
The aluminum amalgam synthesis is often used but has a slightly higher
risk of failure and is not as versatile. The Raney Ni synthesis is
more dangerous and requires special equipment to be done right
(although this scheme is used in a significant number of clandestine
labs). The sodium borohydride requires harsher conditions for the
chemicals (ie. reflux) than sodium cyanoborohydride or aluminum
amalgam and produces lower yields. The Leukart reaction is 2-step
with lower yields and requires chemical apparatus.
There are also two synthetic methods which proceed directly from
safrole rather than through isosafrole. The first is the Ritter
reaction which goes through the intermediate N-acetyl-MDA. The Ritter
reaction is time-consuming, requires a degree of laboratory skill and
produces poor yields. The other method uses HBr to produce
3,4-methylenedioxyphenyl-2-bromopropane which is then converted into
MDA or MDMA. This scheme produces poor yields, and Dal Cason
referenced the australian journal _ANALOG_ where a hazard had been
documented. It is, however, attractive for its sheer simplicity. It
requires no specialized chem equipment or reagents at all.
Beta-nitroisosafrole is a less used precursor, but there is a large
literature on the synthesis and reduction of nitro alkenes. This
synthetic route isn't as popular due to the easier availability of
precursors for MDP-2-P, and it also results in MDA which must then be
further processed to give MDMA or any other N-alkyl homolog of MDA.
There are numerous ways to convert beta-nitroisosafrole to MDA:
LiAlH4, AlH3, electrolytic, Na(Hg), BH3 - THF / NaBH4, Raney Ni
catalyst, Pd / BaSO4 catalyst, Zn (Hg). Beta-nitroisosafrole, when
used, is commonly synthesized from piperonal. Beta-nitroisosafrole
can also be used as a precursor for MDP-2-P, but this is not commonly
done.
There are other synthetic routes, such as the use of substituted
3,4-methylenedioxycinnamic acid or the construction of alkyenedioxy
bridges from dihydroxy compounds. These, however, are typically not
used for a variety of reasons (difficulty, multiple-step, special
equipment, etc). It is also possible to synthesize N-alkyl
derivatives of MDA from MDA (e.g. synthesizing MDMA from MDA) but
this is not commonly done in clandestine labs.
Methylamine is a chemical which is technically not a "precursor" to
MDMA, but it is necessary in most of the syntheses. It is also a
watched chemical. A private citizen ordering methylamine from a
chemical supply company would get the undivided attention of the local
DEA. Methylamine can be diverted in small quantities by individuals
working in legitimate chemical labs. In some cases this "diversion"
is simply theft. It is not recommended that any persons engage in
this activity, but it remains a common source of methylamine (along
with many other chemicals).
Methylamine can be synthesized through hydrolyzing N-methylacetamide via
refluxing it with concentrated HCl. Dump a gallon of concentrated HCl in a
large RB flask, dump in a mole or two of N-methylacamide and reflux the hell
out of it for about 2 days. This leaves water, methylamine and acetic
acid. Boil off the water, and strip the acetic acid off with a vacuum pump
and what's left is the methylamine. Some acetic acid may be left over, but
it shouldn't affect the cyanoborohydride reaction.
It can also be synthesized by doing a large hypohalite Hofmann
degradation on acetamide with bleach and lye. Heat it up and distill
off the water/methylamine from the basic mush and catch it in HCl.
Boil off the water/acid distillate and the result is methylamine HCl.
N-methylacetamide is unlikely to be watched, and acetamide is almost
certainly not watched.
Some syntheses use N-methylformamide as an alternative to methylamine,
but it is unlikely that there would be any advantage to using it. The
3 syntheses focused on in this file (HBr, cyanoborohydride and
aluminum amalgam) all use methylamine.
Secrets of Methamphetamine Manufacturing has both a synthesis
of methylamine and a synthesis of N-methylformamide, but i haven't had
a chance to peruse the book to comment on them.
Summary:
--------
oil of sassafras -------> safrole ----------> isosafrole --------> MDP-2-P
(extraction) | (isomerization) (synthesis) |
| |
V V
*1. safrole + HBr *1. sodium cyanoborohydride
2. Ritter reaction *2. aluminum amalgam
3. sodium borohydride
piperonal ------> beta-nitroisosafrole 4. Raney Ni catalyst
(synthesis) | 5. Leukart reaction
|
V
[numerous routes to MDA]
* of interest to aspiring kitchen chemists
- the sodium cyanoborohydride method is the preferred method
- the safrole + HBr route is attractive due to its sheer simplicity
- the aluminum amalgam route is as useful as cyanoborohydride, but may
have a slightly higher risk of failure.
- Psychedelic Chemistry:
- Contains instructions for isomerizing safrole,
a synthesis of MDP-2-P from isosafrole, and a synthesis which uses the
Leukart reaction. The synthesis of MDP-2-P is better presented in
PiHKAL and the Leukart reaction is is not a recommended synthesis. Also,
please see "ROAD HAZARDS" below, on the dangerous typos in this
synthesis.
- Secrets of Methamphetamine Manufacturing:
- Contains instructions for
synthesizing MDMA via the safrole + HBr method. This is the simple and
dirty way to synthesize MDMA. Pay attention to the part where it tells you
to make sure that you've got all the ether evaporated before placing it
in the reaction bomb... for your own good. References to the original
journal articles and Chem Abstracts are included. It also has synthesis
instructions for methylamine and N-methylformamide, but i haven't had a
chance to read them.
- PiHKAL #100 (MDA):
- Synthesis of beta-nitroisosafrole from piperonal,
synthesis of MDA from beta-nitroisosafrole using lithium aluminum
hydride, synthesis of MDA from MDP-2-P using sodium cyanoborohydride.
The latter is probably the most useful. Although piperonal is commonly
used to synthesize beta-nitroisosafrole. LAH is somewhat dangerous.
- PiHKAL #105 (MDDM):
- Synthesis of MDDM (N,N-dimethyl-MDA) from MDP-2-P
using sodium cyanoborohydride. This stuff isn't terribly active, its
just another example of a sodium cyanoborohydride synthesis.
- PiHKAL #106 (MDE):
- Synthesis of MDE from MDA via N-acetyl-MDA. Synthesis
of MDE from MDP-2-P using aluminum amalgam. Synthesis of MDE from
MDP-2-P using sodium cyanoborohydride. The latter two are the most
useful. Synthesizing MDE from MDA is not particularly useful to
clandestine chemists.
- PiHKAL #109 (MDMA):
- Synthesis of MDMA from MDA via N-formyl-MDA. Synthesis
of MDP-2-P from isosafrole. Synthesis of MDP-2-P from beta-nitro-
isosafrole. Synthesis of MDMA from MDP-2-P using aluminum amalgam.
The synthesis of MDP-2-P from isosafrole and the aluminum amalgam
synthesis are probably the most useful. The synthesis of MDP-2-P from
beta-nitroisosafrole might be useful, but most often beta-nitroisosafrole
is used to produce MDA directly. Synthesizing MDMA from MDA is not
particularly useful to clandestine chemists.
- PiHKAL #114 (MDOH):
- Synthesis of MDOH from MDP-2-P using sodium
cyanoborohydride. This stuff is active, and the synthesis is useful.
I don't know of any explicit synthesis for MDMA using sodium
cyanoborohydride, but it can be done simply by substituting the
correct number of moles of methylamine for ethylamine in the MDE synthesis.
Also, substituting methylamine for ethylamine in the cyanoborohydride
synthesis produces slightly better yields.
- Chemical Abstracts 52, 11965c (1958):
- In the synthesis of MDA from MDP-2-P
this reference has a misprint that should read "add 100ml H2O" instead
of "add 100ml H2O2" which would cause an explosion. Chemistry is
dangerous, and a little ignorance can cause spectacular pyrotechnics...
- Psychedelic Chemistry:
- The synthesis for MDA/MDMA is the same as the
above Chemical Abstracts reference including the explosive typo. There
is also another typo which should read "75 ml 15% HCl" instead of "57ml
15% HCl." This might simply mess your yields up.
- Et20/THF:
- AKA diethyl ether and tetrahydrofuran. These two chemicals form
explosive peroxides when they are exposed to air for extended periods of
time, and which are easily set off by refluxing (for example). These are
likely the cause of most explosions and fires in amphetamine labs. Do not
play around with these chemicals, and if you use them, know what you are
doing.
- MDP-2-P:
- "piperonylacetone" is an ambiguous term which might refer to the
4-carbon analogue of MDP-2-P. Shulgin has noted that at least one chemical
supply house has sold this 4-carbon analogue as "piperonylacetone." The
correct piperonylacetone (MDP-2-P) is sassafras-smelling oil that is
yellow colored. The incorrect piperonylacetone has a weak terpene smell
and is white and crystalline. Substitution will merely result in some
interesting 4-carbon analogues of MDMA which are probably totally
inactive. See PiHKAL #109 (MDMA).
- LAH:
- Lithium Aluminum Hydride (LiAlH4), is a chemical which explodes on
contact with water, and can be set off by moisture in the air. It should
only be used under an inert atmosphere, which requires special equipment.
There is a lot of misinformation out there about MDMA. Here are
some commonly heard rumors and facts about them.
- Rumor #1: MDMA drains your spinal fluid, ruins your back, etc.
- Untrue. This urban legend apparently started because some
pharmacological studies are done by giving subjects MDMA, then withdrawing
cerebrospinal fluid samples for analysis via spinal tap. It is "MDMA
research", not "MDMA" that may drain your spinal fluid!
- Rumor #2: MDMA causes brain damage similar to Parkinson's disease
- MDMA does not cause Parkinson's disease. This rumor apparently
got started because of confusion between MDMA and MPTP
(1-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine). MPTP can appear as a
contaminant from bad manufacture of a synthetic opiate, and has caused
tragic neural damage to unfortunate recipients of the contaminated
black market opiate. MPTP bears no chemical relation to MDMA, and has
not been associated with MDMA manufacture.
MDMA has several chemical "cousins" which have different effects.
PIHKAL is an excellent reference to find out about them. Briefly,
here are descriptions of some of the more common ones:
- MDA (3,4-methylenedioxyamphetamine):
- MDA was popular for a while during the 70s, when it was known as
the 'Love Drug' (a nickname sometimes associated with MDMA as well).
It is similar to MDMA in its effects, but is slightly more
stimulating. It has been shown in laboratory studies to be
approximately twice as neurotoxic as MDMA, though in some 30 years of
human use, case reports do not suggest that it has caused behavioral
or psychological problems.
- MDE or MDEA (N-ethyl-methylendioxyamphetamine):
- Commonly called "Eve" (if MDMA is "Adam", MDE is "Eve", get it?),
MDE is similar to MDMA, though it seems to turn the subject inwards
and invite less communication than does MDMA, though in some
- MMDA (3-methoxy-4,5-methylenedioxyamphetamine):
- Often confused with the similarly-named but chemically different
MDMA. MMDA is reported to generate interesting, closed-eye
hallucinations - "brain movies", or conscious dreams.
- MBDB (N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine):
- Differs structurally from MDMA only by the addition of an extra
carbon to the MDMA chain. Effects are similar to MDA.
- Adamson-S. Through the Gateway of the Heart.
Four Trees Publications, San Francisco, 1985. 197 pages.
- A collection of stories about drug experiences, primarily with MDMA,
and also with 2C-B and other psychedelics, typically taken with MDMA.
- Beck-J and Marsha Rosenbaum. In Pursuit of Ecstasy.
SUNY Press, 1994.
- Del Cason,-TA. "An Evaluation of the Potential for Clandestine
Manufacture of 3,4-Methylenedioxyamphetamine (MDA) and Analogs and
Homologs." Journal of Forensic Sciences. Vol 35(3):675-697, May
1990.
- Synthesis of MDMA and related chemicals.
- Eisner-B. Ecstacy: the MDMA Story. Ronin Publishing, inc.
Box 1035 Berkeley, CA 94701, 1989 (revised 1993). 228 pages.
- Naranjo-C. The Healing Journey: New Approaches to
Consciousness. Published by Random House (paperback: Ballentine),
1973. 197 pages.
- Accounts of groundbreaking therapeutic uses of MDA, MMDA,
Harmaline, and Ibogaine.
- Peroutka-SJ, ed. Ecstasy: The Clinical, Pharmacological and
Nerotoxicological Effects of the Drug MDMA. Kluwer Academic
Publishers, 1990.
- A collection of authorititative papers on nearly every aspect of MDMA.
- Saunders-N. E for Ecstacy. Published by N. Saunders, 14
Neal's Yard, London WC2H 9DP England, 1993. 318 pages.
- Full overview of MDMA, also includes the latest version of Alexander
Shulgin's MDMA bibliography. Extensive references with summaries.
- Shulgin-AT. "The Background and Chemistry of MDMA."
Journal of Psychoactive Drugs. Vol 18(4)"291-304, Oct-Dec 1986.
- "Suggested entrypoint in the literature to the history, chemistry and
controversy surrounding MDMA - a FAQish document," says lamontg.
- Shulgin-AT, Sargent, and C.Naranjo. 1967. "The chemistry and
psychopharmacology of nutmeg and of several related
phenylisopropylamines." In D.H. Efron [ed.]: Ethnopharmacologic
search for psychoactive drugs. U. S. Dept. of H. E. W., Public Health
Service Publication No. 1645. Pp. 202-214. Discussion: ibid. pp.
223-229. 49
- Shulgin-A and Ann Shulgin. PIHKAL: A Chemical Love Story.
Transform Press, Box 13675, Berkeley, CA 94701, 1991. 1008 pages.
-
The first part of this book contains autobiographical accounts of the
Shulgins' life history and experiments with psychoactive drugs. The
second part describes the synthesis, dosage and effects of 179 different
compounds in the phenethylamine family, including MDMA and several
of its analogues.
Most of these books can be ordered from various places listed in
the addresses FAQ, available from the
alt.drugs FTP archive.
MAPS (Multidisciplinary Association for Psychedelic Studies), 1801
Tippah Ave., Charlotte, NC 28205. 704 358-9830. sylviamaps@aol.com.
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