Ian & Stuart's Australian Mac: Not for Sale/Another.not.for.sale (Australia).iso/hold me in your arms/ravers/mdmafaq

Text File | 1994-06-29 | 50KB | 975 lines

MDMA Frequently-Asked-Questions Document
First Author/Editor: Jon M. Taylor ([e-mail])
Last Major Update: 15-Feb-94 rjesse ([e-mail])
Last Minor Update: 27-May-94 rjesse ([e-mail])
FAQ Maintainer:  Brian Behlendorf ([e-mail])

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 Granquists's new survey
 - Added more references


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.

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 ([e-mail]), assembler of the first proto-FAQ
     for MDMA.

     Chris Klausmeier ([e-mail]), 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 ([e-mail]), author of the new Chemistry
     survey inserted into the FAQ 27 May 1994, and provider of general wisdom.

     Robert Jesse ([e-mail]), 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 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.

  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:
------------

ftp://ursa-major.spdcc.com/pub/pihkal
  the text of book 2 of PiHKAL with all the syntheses
http://stein1.u.washington.edu:2012/pharm/pihkal-ht/pihkal.index.html
  html version of PiHKAL
ftp://hemp.uwec.edu/pub/drugs/psychedelics/mdma/mdma.mda.syntheses
ftp.hmc.edu:/pub/drugs/mdma/mdma.mda.syntheses.Z

  the synthesis of MDP-2-P from PiHKAL, plus the Leukart reaction from
  Psychedelic Chemistry.
ftp.hmc.edu:/pub/drugs/mdma/mdma.synth.Z
  this is the 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.


==============================================================================


V. 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 the alt.drugs FTP archive (FTP.HMC.EDU in
/pub/drugs).


Organizations:
--------------

MAPS (Multidisciplinary Association for Psychedelic Studies), 1801 Tippah
Ave., Charlotte, NC 28205.  704 358-9830.  [e-mail].

End of FAQ.==================================================================