From the Ecstasy FAQ, available (with a whole bunch of really good drug info) at www.lycaeum.org:

Dosing
Usual doses of MDMA range from around 80 to 160 milligrams (orally)...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....

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.

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....

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.
- Empathogenesis: A feeling of emotional closeness to others (and to one's self) coupled with a breakdown of personal communication barriers.
- An enhancement of the senses: MDMA can significantly enhance (sometimes distort) the senses - touch, proprioception, vision, taste, smell.

Ecstasy was first introduced as an appetite- suppressant in 1912 by the German Drug Company Merck. It faded away shortly after its introduction only reappearing once to be tested as a substance for psychological warfare in 1953 by the U.S. Army. It was finally reintroduced to the world in the sixties as a tool for psychotherapy by Alexander Shulgen, a biochemist at UC Berkeley who researched psychoactive drugs. For about ten or fifteen years, it was happily used for therapy and experimental purposes and now dominates not only the rave and club scenes but is becoming a mainstream drug used by many subcultures. If you know what is good for you and are emotionally stable try Ectasy, its tasty and fucking on E, forget about it, its perfect.

like snorting horseradish!

MDMA is also a series of CDs made by MTV's DJ Skribble and another famous DJ, Anthony Acid. It has some really good mixing and a bunch of great tribal beats. The second CD is great and I am listening to it now. It has a very interesting mix of "let there be house" which is a club classic that is often poorly mixed. If you've never tried house music and want to this is a good place to start.

Some crude ASCII structural diagrams for MDMA and related chemicals. See also the Lycaeum and PiHKAL.

MDMA (3,4-methylenedioxy-N-methylamphetamine):

                  NH
   O   /\   /\   / \
  / \ /--\ /  \ /   CH3
 /   ||  ||    |
CH2  ||  ||    CH3
 \   ||  ||    
  \ / \--/
   O   \/
MDA (3,4-methylenedioxyamphetamine)
                  NH2
   O   /\   /\   /
  / \ /--\ /  \ / 
 /   ||  ||    |
CH2  ||  ||    CH3
 \   ||  ||    
  \ / \--/
   O   \/
MMDA (3-methoxy-4,5-methylenedioxyamphetamine)
                  NH2
   O   /\   /\   /
  / \ /--\ /  \ / 
 /   ||  ||    |
CH2  ||  ||    CH3
 \   ||  ||    
  \ / \--/
   O   \/
        |
        OCH3
methamphetamine (N-methylamphetamine)
             NH
  /\   /\   / \
 /--\ /  \ /   CH3
||  ||    |
||  ||    CH3
||  ||    
 \--/
  \/
Bupropion (1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone; the active ingredient of Wellbutrin and Zyban)
         O    H 
        ||    N
   /\   /\   / \  /
  /--\ /  \ /   \/
 ||  ||    |    /\
 ||  ||    |   /  \  
 ||  ||    
  \--/  
   \/    
    |     
    Cl    
PEA (phenethylamine)
            NH2
  /\   /\  /
 /--\ /  \/
||  ||
||  ||
||  ||    
 \--/
  \/
dopamine (3,4-dioxyphenethylamine):
               NH2
HO   /\   /\  /
  \ /--\ /  \/
   ||  ||
   ||  ||
   ||  ||    
  / \--/
HO   \/

The Essential Psychedelic Guide by D. M. Turner

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Ecstasy

The Heart Opening Psychedelic

INTENSITY: 2 to 4

MATERIAL:

Ecstasy is a synthetic compound developed in 1914 as a potential dietary aid. However, its psychoactive effects were not discovered until the mid-Seventies. It was used widely in therapy from this time until 1985 when it was made illegal. Its chemical name is 3,4-methylenedioxymethamphetamine (MDMA), commonly known as "X", "E", or "Adam." It usually comes as a white crystalline powder or made into tablets.

DOSAGE:

125 mg. (1/8th of a gram) is generally considered a single dose of ecstasy. This amount will produce an experience lasting about four hours total, with the intensity dropping off a couple hours into the high. Many recreational X users do what's called "double dosing," taking an additional 125 mg. as soon as the first dose starts wearing off. My personal preference is to take one large dose of 150 to 170 mg. which produces an intense but short lasting experience. I prefer this method because it reduces the side effects a double dose of X can produce. Ecstasy should be taken on an empty stomach. If one ingests it on a full stomach they might not get high at all, or may have a delayed trip.

THE HIGH:

When ecstasy is coming on it feels fantastically exhilarating. Users report feeling blissed out, energetic, and emotionally opened and loving. The ride up usually lasts 30 minutes to an hour. One then reaches a plateau where they'll be for the next one to two hours, followed by a slow drift back to baseline. Taking multiple doses will change the timing of these periods.

Most X users report that their first couple of experiences are like being in heaven, and leave a strong impression. Experiences after this are still enjoyable but can't match the initial ride. After numerous X trips, I've concluded that lasting and beneficial experiences are derived primarily from deep bonding with other people while one is high. Nearly all of my better X experiences happened when I was with either one other person or a small group of close friends. This framework for using ecstasy closely parallels how it was used in therapeutic settings. Ecstasy's ability to allow emotions to flow more easily and naturally, and to create an atmosphere of nonjudgment and acceptance, is conducive to deep bonding and healing. I find that the more general feeling of "connectedness," which users report feeling with larger groups of people at events such as raves, tends to dissipate, leaving one feeling hollow by the time the drug wears off.

Ecstasy is not really "psychedelic" in the same way as other substances in this journal. It does not have the potential to produce the fine level of detail in hallucinations that is possible with substances like LSD or mushrooms. Indeed many users experience no visual phenomena at all with ecstasy. Ecstasy also does not heighten one's senses to the level of infinite sharpness that is common with the traditional psychedelics. Ecstasy is sometimes called an empathogen because of its ability to facilitate emotional empathy and communication. I've also heard it referred to as a "selective psychedelic." I think this describes it the best. Ecstasy opens one's mind in a psychedelic way, but much of the personality and perceptual structure are left intact that would be diminished on other, non-selective psychedelics. This makes ecstasy usable by many people who could not handle the effects of something like LSD. With ecstasy one does not go through the dissolution of identity, and can not get into the multitude of "weird" head spaces that can be experienced during an LSD trip. More than any other psychedelic, ecstasy seems to produce very similar experiences in different people, generally described as loving and emotionally opened. While advantageous to the novice psychedelic user, ecstasy's limited experience-producing range provides a low ceiling to the more adventurous psychonaut.

Ecstasy rarely produces a bad experience, but there are some negative aspects to ecstasy's signature. I find ecstasy can be one of the hardest psychedelics to come down from, particularly if I've double dosed. I tend to feel depressed as the blissful ecstasy feelings slip away. My previous personality feels "sticky" at this point, and I feel I have less options choosing my return personality than I would returning from the traditional psychedelics. Ecstasy also produces some side effects: a speedy feeling throughout the experience, often accompanied by jaw clenching (it is in the amphetamine family), a loss of appetite, and sometimes a hangover the next day.

SAFETY FACTORS:

Ecstasy is the only psychedelic I've used which leaves me feeling any less than perfect the next day, and this experience seems to be common among most users of ecstasy. Based on this, I suspect that ecstasy is not the most benign substance to take into one's body, and I've reduced my consumption to an infrequent basis.

There have been a few cases of people who died from heat stroke following the use of ecstasy in dance clubs. They became dehydrated after dancing for hours without drinking any fluids. Although this is rare, it's a reminder for one to pay attention to their body's basic needs while using ecstasy or any other substance.

I've read numerous clinical articles on ecstasy. There does not appear to be conclusive evidence one way or the other as to whether it causes any type of damage to humans, or whether any potential damage caused is permanent or reversible. However, many who are concerned with safe use have gleaned suggestions from these articles.

Although large doses of ecstasy produced some neurotoxicity 1 in lab animals, damage was significantly less to non-existent with a smaller dose (equivalent to 100-150 mg. for most humans.) Other experiments showed that a single dose of Prozac (a prescription anti-depressant drug) will completely block the neurotoxic effects ecstasy can produce in lab animals.

The Prozac can be taken up to six hours after the ecstasy. I've taken Prozac toward the end of about 20 X trips, and in most cases I've felt better the next day than I normally do after taking ecstasy alone. Prozac is considered a controversial drug. Some of the people to whom it was prescribed on a regular basis claim it gave them suicidal tendencies. Apparently a small percentage of the people who try Prozac have some type of negative mental reaction. Several people I know have first tried Prozac by itself, to see what their reaction to it is, before taking it at the end of an ecstasy trip.

As mentioned above, taking ecstasy without Prozac, especially multiple doses, has a tendency to give one a hangover the next day. This can leave one feeling physically drained and mentally frizzled. One's chances of feeling bad the next day can be greatly reduced by taking just a single dose of X. Another method of reducing or eliminating this hangover is to take amino acids such as DL-Phenylalanine (DLPA) or other neurotransmitter precursors prior to and after ingesting the ecstasy. These nutrients are available from health food and vitamin stores and are frequently included in "smart drinks." I've also read that all of the phenethylamine drugs produce free radicals, and that taking antioxidant formulas, also available at most health food stores, can help prevent damage from their use.

COMBINATIONS:

LSD - Ecstasy is frequently taken with LSD, a combination commonly known as "candyflip." I find the feelings produced by this combination can be much deeper and more visual than on ecstasy alone. But since the ecstasy has a much heavier signature than the acid, I tend to experience more of an intensified ecstasy high, and lose the depth I would experience on acid alone. If taken around the same time, the ecstasy will wear off first, while the residual high from the acid provides for a smoother recovery.

NITROUS OXIDE - Using nitrous with X is growing in popularity, particularly in the rave scene. See the LSD chapter for information on nitrous oxide.

Ecstasy may be significantly intensified and possibly dangerous if combined with MAO inhibitors. See the 2C-B chapter.

1 Neurotoxicity was measured in these cases as a reduction in the levels of serotonin, a neurotransmitter present in the brain tissue.

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This is a recipe from PiHKAL. If you're interested in how the hardlinks were chosen, read noding PiHKAL for Everything2.


#109 MDMA

MDM; ADAM; ECSTASY; 3,4-METHYLENEDIOXY-N-METHYLAMPHETAMINE


SYNTHESIS: (from MDA) A solution of 6.55 g of 3,4-methylenedioxyamphetamine (MDA) as the free base and 2.8 mL formic acid in 150 mL benzene was held at reflux under a Dean Stark trap until no further H2O was generated (about 20 h was sufficient, and 1.4 mL H2O was collected). Removal of the solvent gave an 8.8 g of an amber oil which was dissolved in 100 mL CH2Cl2, washed first with dilute HCl, then with dilute NaOH, and finally once again with dilute acid. The solvent was removed under vacuum giving 7.7 g of an amber oil that, on standing, formed crystals of N-formyl-3,4-methylenedioxyamphetamine. An alternate process for the synthesis of this amide involved holding at reflux for 16 h a solution of 10 g of MDA as the free base in 20 mL fresh ethyl formate. Removal of the volatiles yielded an oil that set up to white crystals, weighing 7.8 g.

A solution of 7.7 g N-formyl-3,4-methylenedioxyamphetamine in 25 mL anhydrous THF was added dropwise to a well stirred and refluxing solution of 7.4 g LAH in 600 mL anhydrous THF under an inert atmosphere. The reaction mixture was held at reflux for 4 days. After being brought to room temperature, the excess hydride was destroyed with 7.4 mL H2O in an equal volume of THF, followed by 7.4 mL of 15% NaOH and then another 22 mL H2O. The solids were removed by filtration, and the filter cake washed with additional THF. The combined filtrate and washes were stripped of solvent under vacuum, and the residue dissolved in 200 mL CH2Cl2. This solution was extracted with 3x100 mL dilute HCl, and these extracts pooled and made basic with 25% NaOH. Extraction with 3x75 mL CH2Cl2 removed the product, and the pooled extracts were stripped of solvent under vacuum. There was obtained 6.5 g of a nearly white residue which was distilled at 100-110 ° C at 0.4 mm/Hg to give 5.0 g of a colorless oil. This was dissolved in 25 mL IPA, neutralized with concentrated HCl, followed by the addition of sufficient anhydrous Et2O to produce a lasting turbidity. On continued stirring, there was the deposition of fine white crystals of 3,4-methylenedioxy-N-methylamphetamine hydrochloride (MDMA) which were removed by filtration, washed with Et2O, and air dried, giving a final weight of 4.8 g.

(from 3,4-methylenedioxyphenylacetone) This key intermediate to all of the MD-series can be made from either isosafrole, or from piperonal via 1-(3,4-methylenedioxyphenyl)-2-nitropropene. To a well stirred solution of 34 g of 30% hydrogen peroxide in 150 g 80% formic acid there was added, dropwise, a solution of 32.4 g isosafrole in 120 mL acetone at a rate that kept the reaction mixture from exceeding 40 ° C. This required a bit over 1 h, and external cooling was used as necessary. Stirring was continued for 16 h, and care was taken that the slow exothermic reaction did not cause excess heating. An external bath with running water worked well. During this time the solution progressed from an orange color to a deep red. All volatile components were removed under vacuum which yielded some 60 g of a very deep red residue. This was dissolved in 60 mL of MeOH, treated with 360 mL of 15% H2SO4, and heated for 3 h on the steam bath. After cooling, the reaction mixture was extracted with 3x75 mL Et2O, the pooled extracts washed first with H2O and then with dilute NaOH, and the solvent removed under vacuum The residue was distilled (at 2.0 mm/108-112 ° C, or at about 160 ° C at the water pump) to provide 20.6 g of 3,4-methylenedioxyphenylacetone as a pale yellow oil. The oxime (from hydroxylamine) had a mp of 85-88 ° C. The semicarbazone had a mp of 162-163 ° C.

An alternate synthesis of 3,4-methylenedioxyphenylacetone starts originally from piperonal. A suspension of 32 g electrolytic iron in 140 mL glacial acetic acid was gradually warmed on the steam bath. When quite hot but not yet with any white salts apparent, there was added, a bit at a time, a solution of 10.0 g of 1-(3,4-methylenedioxyphenyl)-2-nitropropene in 75 mL acetic acid (see the synthesis of MDA for the preparation of this nitrostyrene intermediate from piperonal and nitroethane). This addition was conducted at a rate that permitted a vigorous reaction free from excessive frothing. The orange color of the reaction mixture became very reddish with the formation of white salts and a dark crust. After the addition was complete, the heating was continued for an additional 1.5 h during which time the body of the reaction mixture became quite white with the product appeared as a black oil climbing the sides of the beaker. This mixture was added to 2 L H2O, extracted with 3x100 mL CH2Cl2, and the pooled extracts washed with several portions of dilute NaOH. After the removal of the solvent under vacuum, the residue was distilled at reduced pressure (see above) to provide 8.0 g of 3,4-methylenedioxyphenylacetone as a pale yellow oil.

To 40 g of thin aluminum foil cut in 1 inch squares (in a 2 L wide mouth Erlenmeyer flask) there was added 1400 mL H2O containing 1 g mercuric chloride. Amalgamation was allowed to proceed until there was the evolution of fine bubbles, the formation of a light grey precipitate, and the appearance of occasional silvery spots on the surface of the aluminum. This takes between 15 and 30 min depending on the freshness of the surfaces, the temperature of the H2O, and the thickness of the aluminum foil. (Aluminum foil thickness varies from country to country.) The H2O was removed by decantation, and the aluminum was washed with 2x1400 mL of fresh H2O. The residual H2O from the final washing was removed as thoroughly as possible by shaking, and there was added, in succession and with swirling, 60 g methylamine hydrochloride dissolved in 60 mL warm H2O, 180 mL IPA, 145 mL 25% NaOH, 53 g 3,4-methylenedioxyphenylacetone, and finally 350 mL IPA. If the available form of methylamine is the aqueous solution of the free base, the following sequence can be substituted: add, in succession, 76 mL 40% aqueous methylamine, 180 mL IPA, a suspension of 50 g NaCl in 140 mL H2O that contains 25 mL 25% NaOH, 53 g 3,4-methylenedioxyphenylacetone, and finally 350 mL IPA. The exothermic reaction was kept below 60 ° C with occasional immersion into cold water and, when it was thermally stable, it was allowed to stand until it had returned to room temperature with all the insolubles settled to the bottom as a grey sludge. The clear yellow overhead was decanted and the sludge removed by filtration and washed with MeOH. The combined decantation, mother liquors and washes, were stripped of solvent under vacuum, the residue suspended in 2400 ml of H2O, and sufficient HCl added to make the phase distinctly acidic. This was then washed with 3x75 mL CH2Cl2, made basic with 25% NaOH, and extracted with 3x100 mL of CH2Cl2. After removal of the solvent from the combined extracts, there remained 55 g of an amber oil which was distilled at 100-110 ° C at 0.4 mm/Hg producing 41 g of an off-white liquid. This was dissolved in 200 mL IPA, neutralized with about 17 mL of concentrated HCl, and then treated with 400 mL anhydrous Et2O. After filtering off the white crystals, washing with an IPA/Et2O mixture, (2:1), with Et2O, and final air drying, there was obtained 42.0 g of 3,4-methylenedioxy-N-methylamphetamine (MDMA) as a fine white crystal. The actual form that the final salt takes depends upon the temperature and concentration at the moment of the initial crystallization. It can be anhydrous, or it can be any of several hydrated forms. Only the anhydrous form has a sharp mp; the published reports describe all possible one degree melting point values over the range from 148-153 ° C. The variously hydrated polymorphs have distinct infrared spectra, but have broad mps that depend on the rate of heating.

DOSAGE: 80 - 150 mg.

DURATION: 4 - 6 h.

QUALITATIVE COMMENTS: (with 100 mg) MDMA intrigued me because everyone I asked, who had used it, answered the question, 'What's it like?' in the same way: 'I don't know.' 'What happened?' 'Nothing.' And now I understand those answers. I too think nothing happened. But something seemed changed. Before the 'window' opened completely, I had some somatic effects, a tingling sensation in the fingers and temples--a pleasant sensation, not distracting. However, just after that there was a slight nausea and dizziness similar to a little too much alcohol. All these details disappeared as I walked outside. My mood was light, happy, but with an underlying conviction that something significant was about to happen. There was a change in perspective both in the near visual field and in the distance. My usually poor vision was sharpened. I saw details in the distance that I could not normally see. After the peak experience had passed, my major state was one of deep relaxation. I felt that I could talk about deep or personal subjects with special clarity, and I experienced some of the feeling one has after the second martini, that one is discoursing brilliantly and with particularly acute analytical powers.

(with 100 mg) Beforehand, I was aware of a dull, uncaring tiredness that might have reflected too little sleep, and I took a modest level of MDMA to see if it might serve me as a stimulant. I napped for a half hour or so, and woke up definitely not improved. The feeling of insufficient energy and lack of spark that I'd felt before had become something quite strong, and might be characterized as a firm feeling of negativity about everything that had to be done and everything I had been looking forward to. So I set about my several tasks with no pleasure or enjoyment and I hummed a little tune to myself during these activities which had words that went: 'I shouldn't have done that, oh yes, I shouldn't have done that, oh no, I shouldn't have done that; it was a mistake.' Then I would start over again from the beginning. I was stuck in a gray space for quite a while, and there was nothing to do but keep doing what I had to do. After about 6 hours, I could see the whole mental state disintegrating and my pleasant feelings were coming back. But so was my plain, ornery tiredness. MDMA does not work like Dexedrine.

(with 120 mg) I feel absolutely clean inside, and there is nothing but pure euphoria. I have never felt so great, or believed this to be possible. The cleanliness, clarity, and marvelous feeling of solid inner strength continued throughout the rest of the day, and evening, and through the next day. I am overcome by the profundity of the experience, and how much more powerful it was than previous experiences, for no apparent reason, other than a continually improving state of being. All the next day I felt like 'a citizen of the universe' rather than a citizen of the planet, completely disconnecting time and flowing easily from one activity to the next.

(with 120 mg) As the material came on I felt that I was being enveloped, and my attention had to be directed to it. I became quite fearful, and my face felt cold and ashen. I felt that I wanted to go back, but I knew there was no turning back. Then the fear started to leave me, and I could try taking little baby steps, like taking first steps after being reborn. The woodpile is so beautiful, about all the joy and beauty that I can stand. I am afraid to turn around and face the mountains, for fear they will overpower me. But I did look, and I am astounded. Everyone must get to experience a profound state like this. I feel totally peaceful. I have lived all my life to get here, and I feel I have come home. I am complete.

(with 100 mg of the "R" isomer) There were the slightest of effects noted at about an hour (a couple of paresthetic twinges) and then nothing at all.

(with 160 mg of the "R" isomer) A disturbance of baseline at about forty minutes and this lasts for about another hour. Everything is clear by the third hour.

(with 200 mg of the "R" isomer) A progression from an alert at thirty minutes to a soft and light intoxication that did not persist. This was a modest +, and I was at baseline in another hour.

(with 60 mg of the "S" isomer) The effects began developing in a smooth, friendly way at about a half-hour. My handwriting is OK but I am writing faster than usual. At the one hour point, I am quite certain that I could not drive, time is slowing down a bit, but I am mentally very active. My pupils are considerably dilated. The dropping is evident at two hours, and complete by the third hour. All afternoon I am peaceful and relaxed, but clear and alert, with no trace of physical residue at all. A very successful ++.

(with 100 mg of the "S" isomer) I feel the onset is slower than with the racemate. Physically, I am excited, and my pulse and blood pressure are quite elevated. This does not have the 'fire' of the racemate, nor the rush of the development in getting to the plateau.

(with 120 mg of the "S" isomer) A rapid development, and both writing and typing are impossible before the end of the first hour. Lying down with eyes closed eliminates all effects; the visual process is needed for any awareness of the drug's effects. Some teeth clenching, but no nystagmus. Excellent sleep in the evening.

EXTENSIONS AND COMMENTARY: In clinical use, largely in psychotherapeutic sessions of which there were many in the early years of MDMA study, it became a common procedure to provide a supplemental dosage of the drug at about the one and a half hour point of the session. This supplement, characteristically 40 milligrams following an initial 120 milligrams, would extend the expected effects for about an additional hour, with only a modest exacerbation of the usual physical side-effects, namely, teeth clenching and eye twitching. A second supplement (as, for instance, a second 40 milligrams at the two and a half hour point) was rarely felt to be warranted. There are, more often than not, reports of tiredness and lethargy on the day following the use of MDMA, and this factor should be considered in the planning of clinical sessions.

With MDMA, the usual assignments of activity to optical isomers is reversed from all of the known psychedelic drugs. The more potent isomer is the "S" isomer, which is the more potent form of amphetamine and methamphetamine. This was one of the first clear distinctions that was apparent between MDMA and the structurally related psychedelics (where the "R" isomers are the more active). Tolerance studies also support differences in mechanisms of action. In one study, MDMA was consumed at 9:00 AM each day for almost a week (120 milligrams the first day and 160 milligrams each subsequent day) and by the fifth day there were no effects from the drug except for some mydriasis. And even this appeared to be lost on the sixth day. At this point of total tolerance, there was consumed (on day #7, at 9:00 AM) 120 milligrams of MDA and the response to it was substantially normal with proper chronology, teeth clench, and at most only a slight decrease in mental change. A complete holiday from any drug for another 6 days led to the reversal of this tolerance, in that 120 milligrams of MDMA had substantially the full expected effects. The fact that MDMA and MDA are not cross-tolerant strengthens the argument that they act in different ways, and at different sites in the brain.

A wide popularization of the social use of MDMA occurred in 1984-1985 and, with the reported observation of serotonin nerve changes in animal models resulting from the administration of the structurally similar drug MDA, an administrative move was launched to place it under legal control. The placement of MDMA into the most restrictive category of the Federal Controlled Substances Act has effectively removed it from the area of clinical experimentation and human research. The medical potential of this material will probably have to be developed through studies overseas.

A word of caution is in order concerning the intermediate 3,4-methylene-dioxyphenylacetone, which has also been called piperonylacetone. A devilish ambiguity appeared in the commercial market for this compound, centered about its name. The controversy focused on the meaning of the prefix, piperonyl, which has two separate chemical definitions. Let me try to explain this fascinating chaos in non-chemical terms. Piperonyl is a term that has been used for a two-ring system (the methylenedioxyphenyl group) either without, or with, an extra carbon atom sticking off of the side of it. Thus, piperonylacetone can be piperonyl (the two-ring thing without the extra carbon atom attached) plus acetone (a three carbon chain thing); the total number of carbons sticking out, three. Or, piperonylacetone can be piperonyl (the two-ring thing but with the extra carbon atom attached) plus acetone (a three carbon chain thing); the total number of carbons sticking out, four.

Does this make sense?

The three carbon sticking out job gives rise to MDA and to MDMA and to many homologues that are interesting materials discussed at length in these Book II comments. This is the usual item of commerce, available from both domestic and foreign suppliers. But the four-carbon sticking out job will produce totally weird stuff without any apparent relationship to psychedelics, psychoactives or psychotropics whatsoever. I know of one chemical supply house which supplied the weird compound, and they never did acknowledge their unusual use of the term piperonyl. There is a simple difference of properties which might be of value. The three carbon (correct) ketone is an oil with a sassafras smell that is always yellow colored. The four carbon (incorrect) ketone has a weak terpene smell and is white and crystalline. There should be no difficulties in distinguishing these two compounds. But unprincipled charlatans can always add mineral oil and butter yellow to otherwise white solids to make them into yellow oils. Caveat emptor.


Back to PiHKAL?

Ecstasy.

Oh, just the word. For anyone who has taken the drug, MDMA or Ecstasy (XTC, X, Fuel (for all you Chicago people), E), you know why I say "Just the word can make my spine tingle".
And so, having spent the last two years of my life fully enjoying this drug, I will relate to you the first time that I took that pivotal drug and exactly what happened to my psyche and soul since.
I remember the first time that feeling came upon me. I was walking back and forth, pacing... my eyes were wide

...as if i had just discovered the true purpose to life...

And I knew immediatly that I had found something very special. This "joy", this "happiness", this "love" that I have found took every single drop of fear and paranoia out of my body for those beautiful four hours and I loved everyone, everything was perfect and nothing could ever destroy that.
Well, I was wrong. Ever come down off Ecstasy?
It's like experiencing the most perfect elation you can possibly imagine and then someone taking it away from you, only to leave it a few inches beyond your reach, getting further and further away. And you know... if you take another pill to get that joy back... you're only making it worse .

This is the irony of Ecstasy.

It will bring you the greatest, most powerful buzz in the entire world and you will have thought you have figured out the secrets of the UNIVERSE and everyone LOVES you for it... but you know what?
You haven't. Its just a drug. A feeling. And even though I love Ecstasy more than any other feeling in the entire world, I must say farewell to this love of my life. Why?
Well, I found something else . After doing tremendously ridiculous amounts of this drug, I found that I had become a synthetic human being walking around in a daze, searching for more of the drug that made my life tolerable.
Life can be tolerable, you just have to take in the good with the bad. Don't get me wrong, I am still very happy that I took Ecstasy and was able to experience that pure joy but now I know I have a long road of recovery ahead of me, full of struggles that I must face alone.
That was how I fell in love with Ecstasy...

...and how you will too...

Taking E one night is like a month of Jenny Craig

Surprising though it may sound, Ecstasy (MDMA) is incredibly effective as a weight loss drug. It burns fat at an incredible rate, and it is not uncommon for someone taking the drug to lose 5 pounds or more in one night. The weight loss is not water loss for E tends to inhibit sweat, but rather raises the heartbeat so that the blood transports oxygen to the cells faster, resulting in extra energy and facilitating the burning of body fat. Not bad for a nonaddictive drug.

Now, before you start calling me mad, I am certainly not advocating the use of E as a weight loss drug. Although it may be effective as one, its use is too dangerous to be warranted for something as commonplace as weight problems. Long-term brain damage can result after just a few uses. The problem is that because the damage doesn't manifest itself until long after the drug usage, people presume E is safe and continue using it, further hurting their brain.

I would never even consider trading my brain for physical appearance, and would hope that you feel the same way.

There's a lot of talk about the positive effects of Ecstasy, but none of the writeups so far has mentioned the short-term after effects.

With all that serotonin and other neurotransmitters being 'dumped' into your synapse, many people experience a period of depression as the brain slowly restores its chemical balance. I would imagine that this is similar to the effect that cocaine has once the high has worn off. The time it takes to recover varies from person to person, as well as the frequency of their usage.

For myself, it usually lasts a day or so. Everything around me just seems 'blah'. I find that I am moved to tears by the stupidest things. I tell myself that it's not really me, it's just a chemical thing, and everything will be ok shortly. It's hard to remember that when you're watching a gazelle get taken down by some predator on a nature documentary, and feeling an incredible swell of sadness that you just can't shake.

With any drug, a first-time user may discover that they either do or do not enjoy the drug's effects. Some drugs, such as DXM or DMT, are not appealing to the majority of users. MDMA, however, has one of the highest "approval" rates of all recreational drugs. Assuming one obtains a pure pill, it is pretty difficult for someone to have a bad time while under its influence.

That being said, there is plenty of hard evidence out there that frequent MDMA use IS harmful. While studies based on infrequent users are currently inconclusive (although so far signs suggest it's probably fine), those who take MDMA at recreational doses more than once every two weeks have been definitively shown to take on some amount of brain damage, affecting the overall cognitive ability of those individuals. Although it is not yet clear whether this damage is permanent or temporary, it has been shown to last at least a year or two.

A more immediate risk of MDMA is dehydration. Many users become energetic while rolling, and will more likely than not want to run around or dance (yup, this means all you ravers out there.) It is not uncommon to push your body's endurance a ways beyond what you would otherwise take on. Dehydration is probably the most severe risk for users of pure MDMA, so remember to take some breaks and cool off once in a while, as well as drinking water frequently.

Note that consumption of alcohol while on MDMA is a VERY bad idea; it complicates your bodily processes in all sorts of nasty ways, the most obvious of which is that alcohol is in itself a dehydrant. It should also be mentioned that anyone regularly taking anti-depressants/MAOIs should steer clear of MDMA; not only will they not feel the effects, they will be taking a very serious health risk. (There was even an episode of Dawson's Creek that dealt with this.)

Finally, any prospective user should be familiar with all of the drug's effects, and be prepared to accept any consequences of their actions while under the influence. In other words, unless you're confident in your ability to control yourself in this altered state of mind, don't be surprised to wake up next to your idiotic ex-boyfriend and totally regret telling him the night before that you loved him all along, which for some inexplicable reason seemed like a good idea at the time.

How Ecstasy (MDMA) Works

Methylenedioxymethamphetamine or MDMA for short is the key ingredient in the drug labelled "ecstasy." MDMA is still relatively new, being first used in a similar manner to speed for an appetite supressant, and also was experimented with as an anti depressant, in around 1910-20. MDMA is now used mainly in the rave scene, because it is often mixed with speed. The result of this is that the user will stay awake all night, and also happy all night.

MDMA works as a neurotransmitter, which means that (basically) it is a brain chemical. The MDMA causes serotonin to be released into the brain, and this chemical is a mood regulator. When the brain's receptors are flooded by serotonin it causes the users mood to elate, which is the euphoria many users describe.

However, when the receptors are flooded, another process takes place, it is called re-uptake, where the brain realises its serotonin supplies have depleted it tries to take serotonin back up. By now, however, the serotonin has mixed with another brain chemical called dopamine The result is that these two turn into hydrogen peroxide, yes the stuff you use to dye your hair white. The brain re-uptakes the hydrogen peroxide and this damages the receptors, so excessive use of MDMA can cause these receptors to melt and either not grow back or grow back differently, and this can lead to long term depression, as your brain cannot control its mood regulator.

There is one way to stop the re-uptake but it will also stop your roll. This SHOULD NOT be done if you have been using dietary supplements such as 5-HPT or a number of other things, and I am saying it simply because of the theory behind it, it is not intended to be used as a guide. Basically, don't try this. it is not worth it.

After around 5 hours your brain starts to try to re-uptake, and if an SSRI is taken then, this blocks the re-uptake valves, and prevents damage. Serotonin syndrome can occur by doing this though, when too much serotonin is trapped and this can cause the individual to go into a coma.

After taking ecstasy for the first time last weekend, I wrote up a lengthy timeline of the whole experience. It should be noted that this was my ecstasy experience, and for anyone else it could be very different. The timings are given relative to when I swallowed the pill (0215 on a Sunday morning) Moreover, I don't know for sure what the composition of the pill I took was (though it was probably MDMA or 2-CB). Finally, remember that MDMA, and most related psychedelics, are illegal almost everywhere in the world.

Tom's first experience pilling.

T -3:00 I get ready. I put on my Cyberdog logo t-shirt, blue jeans and a few bead braclets and necklases. Put dummy on necklace. Hide pills (1 o.k, 2 sudafed) in Maglite, having removed battery.

T -2:00 Meet up with mates. Have a few tokes on a joint as I'm walking down to South Ken station. Grab more cash than i'll probably need. Get tube to Brixton

T -1:45 Start queueing for Convergence at The Fridge. Give up and go to Club 414 after 90 minutes.

T 0:00 I get into Club 414 after precursory search. Go to bar and grab Red Bull. Down o.k and sudafed with Red Bull. Head for dance floor (packed and playing Hard Techno).

T +0:15 I start to notice the presence of other people on the dancefloor more. Knocking into people and things feels more noticeable than it should. At this point i'm not entirely sure if pills are working properly.

T +0:30 As before, but more pronounced. At this point, i'm sure the e is doing something, but I'm not sure if I like it.

T +0:45 From my pill reports, this is when i should come up, but whilst dancing I still only feel more awake, and more aware of the other ravers. When I go and sit down, I really feel the effects of what i've taken. Despite sitting somewhat awkwardly against the wall, I feel very warm and happy, and all stimuli feel pleasurable. Drinking cold water feels very enjoyable. The feel of the leg of the guy next to me feels warm and sexual. I realise that I have come up, big time.

T +1:00 I go upstairs to meet my friends, who i find in an e-puddle in the corner. Although I don't feel self conscious when they talk about how it's my first time on e, I don't feel confident enough to join in their rubbing and stroking. After chatting, inanely, for a few minutes, I head back downstairs. I knock into a guy on the way down, who is carrying a cup of coffee. It splashes on me, and i appologise to him. The feeling of the hot coffee on my skin, which i'd expect to hurt, is pleasurable. It seems that any stimulation is enjoyable.

T +1:30 After a bit more dancing, I go to the toilets to splash myself with water (a very enjoyable experience) and refill my water bottles. There isn't a mirror in the toilets, so i can't see what a state i'm in. The classic side effectof grinding teeth starts to manifest itself, and I put my dummy in my mouth. It feels so good! For the next 75 minutes, I alternate between dancing, and cuddling my friends. Dancing seems more natural and easier than when sober. My legs don't start to hurt, and i'm not as awkward as usual. When cuddling and back rubbing my mates, I enjoy every stimulation in a very pleasurable way; my entire body is an erogenous zone.

Overall, the high is closer to dope than alcohol, though saying e is like dope is completely inaccurate. Though the feeling is similar, it is stronger with e, more loved up, and, obviously, as e is an amphetamine-related stimulant, it makes you want to dance rather than lounge about. The biggest difference from dope or alcohol is however the way it makes you react to stimulation, the feeling that every touch is sexual, and that all music is banging.

T +2:45 The feeling of total happiness starts to fade slightly, though I still feel much happier than usual. The effects of touch and music are still enhanced a lot. I continue to alternate between dancing and sitting down, and drink a lot. The feeling of the sweat running down my face is very enjoyable, but it is only on feeling this that I realise i'm losing a lot of fluid and not replacing it, as i don't feel thirsty. I drink more than I think i need in order to make up for this.

T: +3:45 As i continue to come down, I feel progressively less euphoric, and more peaceful, as we leave the club. I bid farewell to my friends, who are staying for the afterparty. I hug some of them again, and thank Adam for safely guiding me through a highly enjoyable night. When i ask someone how much of a state i look, he comments that my "pupils are like planets", which I realise could be an issue when I get security to let me in at my halls of residence.

T: +4:30 Finally get onto tube after a 45 minute wait. There are dozens of other clubbers on the train. I come a (distant) second, in terms of attracting attention, to a bunch of cybers who've clearly just left Torture Garden. A few middle aged clubbers look at me, in what i think is a "I was there once" way, on seeing my massively dilated pupils, and that i'm chewing energeticly on a dummy.

T: +5:15 I get back to Southside, and go to the security lodge, as i'm missing my swipe card. The security guard stares at the dummy round my neck, and my eyes, and obviously knows that i'm in a right state. He lets me in without question. I go and watch mindless children's TV over an hour, as i am wide awake. I text my brother, and best friend, in order to comment on the quality of the pills. I rehydrate with Sprite. I see two people I know, both of whom fail to notice the state that i'm in. When i point out my dummy and pupils to Dick, a friend of about 10 years, he seems unimpressed. I can't gauge Simon's reaction. I am still feeling peaceful, and the stimulation of the Sprite can, the sofa, dawn, birds, all seem very different to normal, and are still very enjoyable.

T: +6:30 I go to bed, despite feeling rather awake. The covers feel silky and cool, despite being neither. I'm asleep in less than 5 minutes.

T: +12:00 I wake up. I feel less tired than i should, after the exercise and lack of sleep. Everything I touch and see still feels different, and my mood is still elevated above baseline. I watch Arsenal v. Liverpool on TV. The other guys there also don't notice my pilledness until i mention it

T: +14:00 I'm still not feeling normal. I sit around in my room for an hour writing this. Afterwards i put on some Ash and Foo Fighters and chill for a bit. I cuddle pillows, stroke things, and suck my dummy. I spend the rest of the afternoon doing nothing much, except phoning friends,

T: +17:00 I put a pizza in the oven for supper. Whilst it's cooking, I have a shower and change. The shower, like everything else, feels different, as though it's at an ideal temperature. The pizza tastes delicious, despite being from Sainsbury's. I go to Southside bar for the pub quiz. I'm still not baseline! I have a few drinks, and perform rather as expected in the quiz. I remember what a sea breeze cocktail is, for no apparent reason.

T:+21:00 After the quiz I sit around watching TV a bit, and chat to some in the kitchen. We talk inanely, mainly about me, for a while. Sonia quizzes me somewhat over my e usage. Her and her friend seem convinced that i'm still high. Sort of true.

T: +24:00 I go to bed, at 2am, exactly a day after dropping. I am still noticing some effects, specifically that everything feels so comfortable and warm. I get to sleep, eventually.


Overall, it was a highly enjoyable experience, and no, I didn't get abjectly depressed over the next couple of days. Like everything, best done in moderation.

This is a post I wrote on the Ecstasy group on Yahoo Groups, just thought I would share.

Hey, before I post this I just want to say I know where you guys are coming from and I've been there and I don't claim to know everything, or really anything at all. I just want to tell you how I feel, just like the guy who posted this initially - so don't take offense to anything I say here, just my opinion. Oh, and this isn't religious B.S., I don't deal in myths.

I understand your position completely, I was in your shoes once. People didn't understand me, or at least I didn't think they did. Everyone seemed so goddamned selfish and shit - no one cared about anyone else unless they gained something from it. For the most part, that's true. People are money-grubbing assholes and they always will be. Mankind, all throughout history, has been in constant pursuit of power and has stepped on anyone or anything that's come in his path to that power - why can't he just chill out and be happy with his surroundings?

Well, he's not going to. Mankind is the way it is and nothing is going to change that until popular culture changes. Cultural and societal influences over time have caused us to have to evolve in order to succeed. And by succeed I don't mean driving the most expensive car on the block - by succeed I mean SURVIVE. Live comfortably and have everything you NEED - not everything you WANT. That's success.

Now, taking into account our new definition of success... What kinds of things do we need to survive? Well, I guess the most obvious would be food, shelter, etc. But what do these really equate to? I would say most of these things combined (food, shelter, etc.) would fit under the term "health." I would venture to say that health is probably the most important aspect of survival in any species, and mankind is no different. Health includes physical and mental health - and in order to be mentally healthy we must have happiness.

I guess we should really be examining the "happiness" aspect of survival. Of course, unless you're happy with your environment it's really difficult to rationalize survival. "Why should I try to stay alive if shit sucks this bad???" Definitely a good point... And I agree. Why try if nothing makes you happy?

But what makes us TRULY happy? Not the happiness that lasts 6-10 hours, but happiness that lasts for 6-10 years, even a lifetime.

In order to figure that out, we first have to figure out what happiness is. Happiness is truly created by a mixture of chemical and electrical reactions in the brain which in turn tell the brain to create certain emotional and physical responses in the body and mind.

Certainly E makes us happy and makes us more loving towards others - but how does it do so? It causes the brain to flood with one of the chemicals that causes such a response - serotonin. So, in essence it is just as real as any happiness you'll ever feel - but, this kind of happiness causes damage to the receptors in the brain that allow us to feel happy. So - you feel intensely happy for a short period of time, and then hinder your ability to stay happy later. (and by later I mean later in life, not after you come down) That doesn't seem like an acceptable tradeoff.

True happiness, I argue, comes from acheivement. When you got an A in a class in HS or college, did you feel accomplished? When you got a job that you wanted because you worked hard for it, how did that make you feel? Did you wake up the next day thinking, "Fuck, my head hurts and I feel like dogshit?" Nah, I'll bet that feeling lasted a while longer. And I'll bet that whether or not you think about that A or that job you got, it's following you and backing you up. Intelligence and perseverence pay off - I'll guarantee it.

If you wake up one day when you're 30 on the floor of some fucking rave at 7am you're going to think about all the shit you could have done with your life, and I'll feel for you because I know a lot of people who've done that. Lots of really intelligent people - artists, programmers, etc.

Anyway, I'm a long winded bastard. I prefer my serotonin in time-release form, the natural way. I used to eat pills in college - up to 6 at a time, and I know people who did way more. I took acid so much I know I fucked myself up - but - it can be repaired to a certain extent. I'll tell you to your face right now that I am ten times happier than I ever was. You don't have to be a selfish money- grubbing pig of an asshole to succeed - you just need to be smarter than they are.

And let me tell you - That's not hard at all.

Peace, J

Earlier in this node, raverDave said:
"Of course, nothing except for crystal meth fucks your brain up like E does. Because so much serotonin is released into you synapses, your serotonin reuptake transporters go into overdrive. Their job is to move excess serotonin from the synapse to a place inside the neuron where a chemical degrades the serotonin into Monoamine Oxidase."
Two clarifications:

Serotonin does NOT degrade into Monoamine Oxidase. Monoamine oxidase is a chemical produced by the brain that deactivates certain compounds, such as serotonin, MDMA, and methamphetamine, by stripping the NH3 molecule from the compound, hence rendering it inactive. This is the reason why it is dangerous to take MAO Inhibitors together with MDMA, methamphetamine, or similiar compounds. MAO-Inhibitors temporarily suppress monoamine oxidase, meaning that the brain cannot "defuse" these chemicals.

Secondly, and a slightly more subtle point, is the fact that the way methamphetamine fucks up your brain is completely different from the way ecstasy fucks up your brain. Ecstasy causes damage to the serotonin receptors leading to problems with mood, sleep, and appetite, while methamphetamine accelerates the natural decay of the dopamine system, causing premature Parkinson's Disease.

+'s and -'s of MDMA consumation in a simple COMPARATION :


It was a small club .
Such a big beautiful place.

Half of the lights didn't even work.
The lights were in neon colors and they were running upon my face.

There were few nice guys but nothing special.
People were so beautiful that night.

At about 3 a.m. i started to feel tired.
I don't know what time it was,but I felt like i am in love with the world all night long.

It was a bit cold too.
I was surrounded by a huge cloud of warm,pure love.

Some asshole came into my face.
A good-looking guy came and started a conversation with me.

I told him to get off my back.....
I hugged him......

Because he was talking about some camels or something?
Because I couldn't recognize what he's saying.

What a druggie retard.
Anyway I felt a connection with him.

I accidentally pushed some clumpsy girl on the dancefloor.
I bumped into a pretty girl,but i apologized to her.

She looked me like I am some freak or something.
Then she called me to dance with her and her friends.

I spent the night looking for my friends......
I spent the night dancing like I'm mad with people i don't know....

Because they took MDMA.
Because I took MDMA .

What a bunch of morons.
I loved it!

I couldn't wait to get in my warm,cozy bed and I fell asleep like a baby.
Some guy dropped me off to the wrong street.

*snore*
I walked until i recognized my house.Don't have a clue how I got here.

*snore* "umpf...." *snore*
I can't get no sleep .


2 D A Y S A F T E R

A brand new fresh day.Not attending any "parties" tonight.Haha.Got a promotion today.
*snore*

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