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: 20-Jan-96
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
Changes in 1-Jan revision:
* Updated links
* Added some new links
---------------------------------------------------------------------------
Table of Contents:
1. Introduction
o Disclaimer
o Credits
2. General
o Dosing
o Contraindications and
overdose information
o Effects
o Notes on having a rewarding
time
o Drug Quality
o Note on using MDMA many
times
3. Safety & Neurotoxicity Discussion
o Behavioral Safety Concerns
o Neurotoxicity?
o Immune System
o Preventive Measures
o Conclusion
4. Chemistry
o Introduction
o Precursors
o Synthetic Routes
o Methylamine
o Literature
o Net Sources
o Manufacturing Road Hazards
5. Miscellany
o Rumor Control
o Analogues and related
compounds
o Related Reading
o 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.
Credits:
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.
* Lamont Granquist (lamont@hyperreal.com), 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.
---------------------------------------------------------------------------
II. General
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
obtain the alt.rave FAQ from hyperreal.com.
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
some 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 exposure
to
MDMA, the prior state of the changed structures being necessary for
ecstatic MDMA experiences. It is an as-yet-unanswered question whether
such
changes, if they happen, are best regarded as harmful, neutral, or
beneficial.
If you choose to use MDMA, the lesson here may be to spend your first
few
sessions wisely and cherish them. Later sessions may never seem as
ecstatic.
---------------------------------------------------------------------------
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 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.
Once the MDP-2-P is synthesized there are several synthetic routes which
can be taken:
1. Sodium Cyanoborohydride
2. Aluminum Amalgam
3. Sodium Borohydride
4. Raney Nickel Catalysis
5. Leukart Reaction via N-formyl-MDA
6. 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
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.
"Popular" Literature:
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.
Net Sources:
* HTML version of PiHKAL Book II
* The synthesis of MDP-2-P from PiHKAL, plus the Leukart reaction
from
Psychedelic Chemistry.
* Safrole + HBr method out of Secrets of Methamphetamine Manufacturing
Road Hazards:
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.
---------------------------------------------------------------------------
Various and Miscellany
Rumor Control
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.
Analogues and related compounds:
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.
References and Related Reading:
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 hyperreal.com drugs archive.
Organizations:
MAPS (Multidisciplinary Association for Psychedelic Studies), 1801 Tippah
Ave., Charlotte, NC 28205. 704 358-9830. sylviamaps@aol.com.
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