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This nOde last updated August 12th, 2003 and is permanently morphing...
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Don't take offense, but if you think that MDMA is Amphetamine then I would avoid table salt if I was you (Sodium Chloride).

MDMA is related to speed, but they are definitely not the same COMPOUND, though they are chemically related.

Apparently some people are mis-informed about what MDMA is and is not.

I invite any of you to read E for internal linkEcstasy by Nicholas Saunders
external linkhttp://ecstasy.org/e4x/  it is a very good reference and is well annotated.

Ecstasy  (E, Adam, X, MDMA) is '3,4 Methylene-dioxy-N-methylamphetamine'


"Many people believe that the name implies a mixture of ingredients but this is wrong - just as internal linkwater is not a mixture of oxygen and hydrogen although its molecule consists of oxygen and hydrogen atoms. Like water, MDMA is a compound, not a mixture. So, although the name contains the word 'amphetamine' and the law refers to MDMA as a 'psychedelic amphetamine', MDMA contains no amphetamine. The amphetamine-like effects may be related to dopamine release."

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This history begins in 1912, when the German company Merck asked for a patent on it. The patent was allowed to expire without being used. They cropped up again when the US army showed an interest in internal linkhallucinogens and commissioned research in 1953/54 on MDA, MDMA and other substances as a truth serum. They proved to be unsuitable for this purpose. The results of this research were not published until 1973. MDA became popular in the Sixties, while MDMA was first identified as a street drug in 1972.

In 1978 internal linkShulgin and Nichols  published a scientific article on the structure and effects of MDA, MDMA and other substances. This knowledge had already been available for some time, however. Among those who knew about it were a number of psychotherapists who increasingly applied MDMA as a psychotherapeutic aid.  In 1981 it acquired its present name, Ecstasy (XTC). This was when its recreational use (as a stimulant) started in the United States. Soon afterwards its use rapidly spread outside the United States as well. In Dallas, where alcohol was prohibited at the Southern Methodist University, students bought legal MDMA as a substitute, paying by credit card. The US consumption rose from 10,000 doses in the whole year of 1976 to 30,000 doses a month in 1985. At the same time the Drug Enforcement Administration (DEA) reported that 30,000 doses a month were being used in the state of Texas alone. A 1987 survey revealed that 40% of students on the campus of Stanford University had used MDMA. In 1985 MDMA was prohibited by the Drug Enforcement Administration, when it was given the same status as heroin and internal linkLSD.

It was first used on Ibiza, where the combination of XTC with dancing to deafening electronic music in an exotic nightlife atmosphere was invented. It spread from there to England and the Netherlands in particular, where a new youth culture emerged which is now spread all over Europe: the 'raves'.

Alexander "Shasha" Shulgin:

'The first effect is very fast, within half an hour of consumption. Most test persons report that the plateau of the effect begins within another half hour to one hour. The symptoms of~intoxication have largely vanished after another two hours, apart from the slight remains of sympathomimetic stimulation, which can last for a number of hours more. There are few physical symptoms of intoxication, and psychological postsymptoms are virtually absent. In qualitative terms, the drug seems to elicit an easily controllable changed state of consciousness with emotional and sensual overtones. In terms of effect, it can be compared with marihuana, internal linkpsilocybin without the hallucinatory component, or low doses of MDA.'

Ten years later, an anonymous informant, a respectable fifty year old, described the effect as follows:

'The drug removes all your neuroses. It takes away the fear of response. There is an overwhelming sense of peace, you are at peace with the world. You feel open, clear, tender. I can't imagine that anyone is angry under its influence, or selfish or mean of internal linkdefensive. You have lots of insight into yourself, real insight, which you hold on to after the experience is gone.'

Operational mechanism of the entactoqens

MDMA increases the secretion of internal linkserotonin in the synapses and inhibits the reuptake of serotonin. MDA andamphetamine also have this effect, but MDMA and MDA inhibit the serotonin reuptake five times as much as amphetamine, and at least 20 times as much as DOM, a genuine hallucinogen. MDA and MDMA are reasonably powerful as inhibitors on the noradrenaline reuptake, which is the main cause of the sympathomimetic effect of MDMA.

MDA inhibits the reuptake of dopamine. MDMA does so to a much lesser degree, and DOM does not do so at all. This too is proof that in this respect MDA and MDMA belong to a completely different category of substances from the
genuine hallucinogens.

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Sadie Plant Digital trance formation

internal linkSadie Plant on Ecstasy

"What really got me started was the mystery of Ecstasy.   MDMA has been around for most of the twentieth century; it had moments of popularity in the '60s,  but it never became a culture until the late '80s."   Why this strange internal linktime-lag, given MDMA's internal linkintense pleasures -- euphoria, hyper-tactile sensuality, overwhelming feelings of internal linktrust, intimacy, and affection?

Internet Wilhelm Reich

Plant's answer was that Ecstasy was "waiting" for the right technology to arrive and "potentiate"  it, to use the pharmacological term for the synergistic interaction of two drugs. "There's something about the clean precision of the MDMA experience that seems to fit internal linkdigital technology, the same technology that enabled the creation of that very precise rhythmic internal linkdance music."

Beyond this, she sees Ecstasy and rave music as training the nervous system and human sensorium in preparation for the internal linkInternet and internal linkvirtual reality. In Writing On Drugs,  she describes how ravers in the raptures of Ecstasy feel "overwhelmed by their own connectivity," merging not just  with music and with the crowd but with machines too: the sound-system, the dazzling lighting effects and lasers, and all the other high-tech elements used to "engineer  atmospheres." Melting what internal linkReich called character armor,  Ecstasy creates a kind of porous, permeable ego that's  supple and open to connection and internal linkcontact. It's a internal linkprocess  that Plant describes as "positive self-destruction, a self-destruction without death-wish."  

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from PiKHAL [ Phenethylamines i Have Known and Loved ] by Alexander Shulgin


(from MDA) A solution of 6.55 g of 3,4-methylenedioxyamphetamine (MDA) as the free base and 2.8 mL formic internal linkacid 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 internal linkfilter 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.
Future Sound of London - Life Forms - bubbles

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 internal linkevolution of fine internal linkbubbles, 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 internal linkwater 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 internal linkfiltering 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 internal linkmoment 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 internal linksomatic 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 internal linktime and internal linkflowing easily from one activity to the next.

(with 120 mg) As the material came on I felt that I was being enveloped, and my internal linkattention 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 internal linkpulse and blood pressure are quite internal linkelevated. This does not have the 'fire' of the racemate, nor the internal linkrush 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 internal linkprocess 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.

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Dr. Charles Grob, a child psychiatrist at UCLA, who in 1994 conducted the first FDA-approved study of the effects of MDMA on human volunteers, asserts that MDMA's capacity to promote empathy could have a powerful impact on geopolitical affairs. "Well, you're not going to get Sharon and Arafat to take MDMA together," he grants, "but let their children get together one day to do it in a medical setting and have a mutually empathetic experience, seeing the humanity of the other side." Grob thinks that MDMA could have a healing effect on Americans rocked to varying degrees by the September 11 attacks, by fostering empathy for the families of victims, and, less directly, for the bereft and disenfranchised anywhere in the world.

MDMA has already proven to be a bonding agent on a vast scale, within the rave movement, which is international in scope, and pacific, empathic, and celebratory in nature. Just as LSD was a bedrock for the Yippie ethos nearly two generations ago, Ecstasy could well become the social glue for a new activism, should an urgent and well-articulated need arise. MDMA internal linkdissolves boundaries for the individual's immersion into a communal group mind, according to author and media theorist internal linkDouglas Rushkoff in an essay entitled "Ecstasy: Prescription for a Cultural Renaissance" (included in _Ecstasy: The Complete Guide by Dr. Julie Holland_, Inner Traditions). "On E, lies are inefficient," he writes, "and the peculiarities and weaknesses they are meant to obscure no longer seem like offenses against nature." Hence the doors of perception are cleansed, but without blowing them off their hinges. MDMA is unique among so-called psychedelics for leaving the ego unthreatened by inducing a pervasive sense of peace and trust that enables fruitful self-inventory, therapeutic healing, and a powerful feeling of appreciation for one's fellows.

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