Pihkal

by Alexander Shulgin

  (with 200 mg and a 75 mg supplement) RA very strong climb, and a very good, interior feeling. It has some of the MDMA properties, but it is difficult to concentrate on any one point. There is a tendency to slide off. Excellent emotional affect; music is fine but not gripping. Someone had used the phrase, mental nystagmus, and there is something valid there. The supplement was taken at the 2 hour point when I was already aware of some dropping, and its action was noticed in about a half hour.

  (with 230 mg) Physically, there was a bit of dry mouth but no teeth clenching, some nystagmus, maybe the slightest bit of dizziness, very anorexic, and it is not a decongestant. Mentally, it is extremely benign and pleasant, funny and good-humored. No visuals. Peaceful.

  Easy silences, easy talking. More stoning than MDMA.

  EXTENSIONS AND COMMENTARY: In general, all subjects who have explored J have accepted it and commented favorably. Perhaps those who have used supplements (in an imitation of the common MDMA procedure) achieved an additional period of effect, but also tended to drop to baseline afterwards more rapidly. The physical side effects, such as teeth clench and nystagmus, were infrequent. The consensus is that J

  is a bit more RstoningS than MDMA, more like MDA, but with a chronology that is very much the same.

  Two nomenclature problems have to be faced in the naming of these compounds. One deals with the Chemical Abstracts terminology as contrasted with the logical and intuitive terminology. The other invokes the concept of the Muni-Metro, delightfully simple, but neither Chemical Abstracts-approved nor intuitive in form. The first problem is addressed here; the second is discussed where it better belongs, under the N-methyl homologue of J (see under METHYL-J).

  In short, the two-ring system of J, or of any of the MDA-MDMA family of drugs, can be named as one ring being attached to the other, or by a single term that encompasses both. The first procedure, an old friend with chemists and the one that had been used for years in the abstracting services, calls the combination methylenedioxybenzene and, as a prefix, it becomes methylenedioxyphenyl-something. The benzene or the phenyl-something is the foundation of the name, and there happens to be a methylenedioxy-ring attached to it. On this basis, this compound J should be named as if it had no methylenedioxy ring anywhere, and then simply attach the new ring as an afterthought. So, the one-ring parent of J is 1-phenyl-2-aminobutane, and J is 1-(3,4-methylenedioxyphenyl)-2-aminobutane (or, to be a purist, the amino should alphabetically come first, to give 2-amino-1-(3,4-methylene-dioxyphenyl)butane). The synthesis of the chemical intermediates given above uses this old-fashioned nomenclature.

  But the name currently in vogue for this two-ring system is 1,3-benzodioxole. As a prefix it becomes 1,3-benzodioxol-5-yl-something, and so J would be called 1-(1,3-benzodioxol-5-yl)-2-aminobutane. This is the source of the code name BDB. And the N-methyl homologue, the alpha-ethyl analogue of MDMA, is named MBDB, or METHYL-J, and is with its own separate entry in this footnote.

  There is a psychological nuance to this new nomenclature. The virtues and potential medical value of MDMA lie in its most remarkable property of facilitating communication and introspective states without an overlay of psychedelic action. This property has prompted the coining of a new pharmacological class name, Entactogen, which comes from the Greek roots for Rtouching within.S But MDMA has been badly smeared in both the public and the scientific view, by its wide popular misuse, its precipitous placement into a Schedule I category of the Federal Drug Law, and a flood of negative neurotoxicological findings in animal studies. There are some properties of both this compound and its methyl-homologue that suggest this RentactogenS

  world, so why not avoid the RMDS prefix that, in many eyes, is pejorative? Stick with the totally obscure chemical names, and call them BDB and MBDB. Or, even more simply, J and METHYL-J.

  95 LOPHOPHINE; 3-METHOXY-4,5-METHYLENEDIOXYPHENETHYLAMINE

  SYNTHESIS: A solution of 50 g myristicinaldehyde (3-methoxy-4,5-methylenedioxybenzaldehyde, see under MMDA for its preparation) in 200 mL acetic acid was treated with 33 mL nitromethane and 17.4 g anhydrous ammonium acetate and held on the steam bath for 5

  h. The reaction mixture was diluted with a little H2O and cooled in an external ice-acetone bath. A heavy crop of yellow crystals formed, which were removed by filtration, washed with cold acetic acid, and dried to constant weight. There was thus obtained 19.3 g 3-methoxy-4,5-methylenedioxy-'-nitrostyrene with a mp of 210-212 !C.

  The mother liquors were diluted with H2O, and extracted with 3x100 mL

  CH2Cl2. The pooled extracts were washed with 5% NaOH, and the solvent removed under vacuum yielding 34 g of a dark residue that was largely unreacted aldehyde. This residue was reprocessed in acetic acid with nitromethane and ammonium acetate, as described above, and provided an additional 8.1 g of the nitrostyrene with the same mp.

  A suspension of 25 g LAH in 1.5 L anhydrous Et2O in an inert atmosphere was stirred magnetically, and brought up to a gentle reflux. Through a Soxhlet condenser modified to allow Et2O to return continuously to the reaction mixture, there was added 27.0 g of 3-methoxy-4,5-methylenedioxy-'-nitrostyrene. The addition require many h, and when it was completed, the reaction was held at reflux for an additional 9 days. After cooling the reaction mixture in an external ice bath, the excess hydride was destroyed by the cautious addition of dilute H2SO4. The final amount used was 1800 mL H2O

  containing 133 g H2SO4. The phases were separated, and the aqueous phase was washed with 2x100 mL Et2O. To it was then added 625 g potassium sodium tartrate, and sufficient base to bring the pH to >9.

  This was extracted with 3x250 mL CH2Cl2, and the pooled extracts stripped of solvent under vacuum. The residue was dissolved in anhydrous Et2O and saturated with anhydrous HCl gas, giving a heavy crystallization of salts. These were removed by filtration, Et2O

  washed, and air dried, to give 17.7 g 3-methoxy-4,5-methylenedioxyphenethylamine (LOPHOPHINE) as an off-white solid with a mp of 160-161 !C. This was dissolved in CH3CN

  containing 5% EtOH, decolorized with activated charcoal, filtered, and the removed charcoal washed with boiling CH3CN. Slow cooling of the solution provided 11.7 g of a white product which melted at 164-164.5

  !C.

  DOSAGE: greater than 200 mg.

  DURATION: unknown.

  QUALITATIVE COMMENTS: (with 150 mg) Between two and five hours, very peaceful and euphoric mood elevation, similar to mescaline, but without any visual distortion. Mild enhancement of color perception, possibly a function of mood elevation. There was no nausea, no eyes-closed vision. Slept easily that evening.

  (with 250 mg) Possibly something of a threshold effect from 2:30 to 4:30 of the experiment. Intangible, and certainly there is nothing an hour later.

  EXTENSIONS AND COMMENTARY: It looks as if this compound is not active.

  There is an excellent argument as to why it really should be, and the fact that it is not active is completely unexpected. Let me try to explain.

  Quite simply, mescaline is a major component and a centrally active alkaloid of the Peyote plant. It is a phenethylamine, which can undergo a cyclization within the plant to produce a pile of derivatives (tetrahydroisoquinolines) such as anhalonine and O-methylanhalonidine that are marvelously complex alkaloids, all natural components of this magical cactus. But there is another pile of derivatives (tetrahydroisoquinolines) such as anhalonine, and lophophorine, and peyophorine which are the logical cyclization products of another phenethylamine which does not exist in the cactus.

  It should be there, but it is not. If it were there it would be the natural precursor to a host of bicyclic alkaloids, but it is absent.

  This is 3-methoxy-4,5-methylenedioxyphenethylamine. I feel that some day it will be discovered as a plant component, and when it is it can be given a name that reflects the generic binomial of the plant. And since the plant has been known as Lophophora williamsii, why not give a name to this compound (which should be in the plant), one derived from the Latin name, but one that has never befor
e been used? What about LOPHOPHINE? And so, I have named it, but I have not found it, nor has anyone else. Yet.

  It is inevitable that this simple and most appealing precursor will be found to be present in the cactus, at some future time when we will have tools of sufficient sensitivity to detect it. And certainly, it would be reasonable to expect it to be an active psychedelic, and to be as interesting in man as its close cousin, mescaline. But, at the present time, LOPHOPHINE is not known to be present in the plant, and it is not known to be active in man. I am confident that both statuses will change in the future.

  96 M; MESCALINE; 3,4,5-TRIMETHOXYPHENETHYLAMINE

  SYNTHESIS: A solution of 20 g 3,4,5-trimethoxybenzaldehyde, 40 mL

  nitromethane, and 20 mL cyclohexylamine in 200 mL of acetic acid was heated on the steam bath for 1 h. The reaction mixture was then diluted slowly and with good stirring, with 400 mL H2O, which allowed the formation of a heavy yellow crystalline mass. This was removed by filtration, washed with H2O, and sucked as dry as possible.

  Recrystallization from boiling MeOH (15 mL/g) yielded, after filtration and air drying, '-nitro-3,4,5-trimethoxystyrene as bright yellow crystals weighing 18.5 g. An alternate synthesis was effective, using an excess of nitromethane as solvent as well as reagent, if the amount of ammonium acetate catalysis was kept small.

  A solution of 20 g 3,4,5-trimethoxybenzaldehyde in 40 mL nitromethane containing 1 g anhydrous ammonium acetate was heated on the steam bath for 4 h. The solvent was stripped under vacuum and the residual yellow oil was dissolved in two volumes of hot MeOH, decanted from some insolubles, and allowed to cool. The crystals formed are removed by filtration, washed with MeOH and air dried yielding 14.2 g. of bright yellow crystals of '-nitro-3,4,5-trimethoxystyrene. The use of these proportions but with 3.5 g ammonium acetate gave extensive side-reaction products even when worked up after only 1.5 h heating.

  The yield of nitrostyrene was, in this latter case, unsatisfactory.

  To a gently refluxing suspension of 2 g LAH in 200 mL Et2O, there was added 2.4 g '-nitro-3,4,5-trimethoxystyrene as a saturated Et2O

  solution by use of a Soxhlet extraction condenser modified to allow the continuous return of condensed solvent through the thimble. After the addition was complete, the refluxing conditions were maintained for another 48 h. After cooling the reaction mixture, a total of 150

  mL of 1.5 N H2SO4 was cautiously added, destroying the excess hydride and untimately providing two clear phases. These were separated, and the aqueous phase was washed once with 50 mL Et2O. There was then added 50 g potassium sodium tartrate, followed by sufficient NaOH to bring the pH >9. This was then extracted with 3x75 mL CH2Cl2, and the solvent from the pooled extracts was removed under vacuum. The residue was distilled at 120-130 !C at 0.3 mm/Hg giving a white oil that was dissolved in 10 mL IPA and neutralized with concentrated HCl.

  The white crystals that formed were diluted with 25 mL Et2O, removed by filtration, and air dried to provide 2.1 g 3,4,5-trimethoxyphenethylamine hydrochloride (M) as glistening white crystals. The sulfate salt formed spectacular crystals from water, but had a broad and uncharacteristic mp. An alternate synthesis can employ 3,4,5-trimethoxyphenylacetonitrile, as described under '-D.

  DOSAGE: 200-400 mg (as the sulfate salt), 178-256 mg (as the hydrochloride salt).

  DURATION: 10-12 h

  QUALITATIVE COMMENTS: (with 300 mg) I would have liked to, and was expecting to, have an exciting visual day, but I seemed to be unable to escape self-analysis. At the peak of the experience I was quite intoxicated and hyper with energy, so that it was not hard to move around. I was quite restless. But I spent most of the day in considerable agony, attempting to break through without success. I learned a great deal about myself and my inner workings. Everything almost was, but in the final analysis, wasnUt. I began to become aware of a point, a brilliant white light, that seemed to be where God was entering, and it was inconceivably wonderful to perceive it and to be close to it. One wished for it to approach with all one's heart.

  I could see that people would sit and meditate for hours on end just in the hope that this little bit of light would contact them. I begged for it to continue and come closer but it did not. It faded away not to return in that particular guise the rest of the day.

  Listening to Mozart's Requiem, there were magnificent heights of beauty and glory. The world was so far away from God, and nothing was more important than getting back in touch with Him. But I saw how we created the nuclear fiasco to threaten the existence of the planet, as if it would be only through the threat of complete annihilation that people might wake up and begin to become concerned about each other.

  And so also with the famines in Africa. Many similar scenes of joy and despair kept me in balance. I ended up the experience in a very peaceful space, feeling that though I had been through a lot, I had accomplished a great deal. I felt wonderful, free, and clear.

  (with 350 mg) Once I got through the nausea stage, I ventured out-of-doors and I was aware of an intensification of color and a considerable change in the texture of the cloth of my skirt and in the concrete of the sidewalk, and in the flowers and leaves that were handed me by an observer. I experienced the desire to laugh hysterically at what I could only describe as the completely ridiculous state of the entire world. Although I was afraid of motion, I was persuaded to take a ride in a car. The driver turned on the radio and suddenly the music 'The March of the Siamese Children'

  from 'The King and I' became the most perfect background music for the parody of real life which was indeed the normal activity of Telegraph Avenue on any Saturday morning. The perfectly ordinary people on their perfectly ordinary errands were clearly the most cleverly contrived set of characters all performing all manners of eccentric activities for our particular hilarity and enjoyment. I felt that I was at the same time both observing and performing in an outrageous moving picture. I experienced one moment of transcendant happiness when, while passing Epworth Hall, I looked out of the window of the car and up at the building and I was suddenly in Italy looking up at a gay apartment building with its shutters flung open in sunshine, and with its window boxes with flowers. We stopped at a spot overlooking the bay, but I found the view uninteresting and the sun uncomfortable.

  I sat there on the seat of the car looking down at the ground, and the earth became a mosaic of beautiful stones which had been placed in an intricate design which soon all began to move in a serpentine manner.

  Then I became aware that I was looking at the skin of a beautiful snake Q all the ground around me was this same huge creature and we were all standing on the back of this gigantic and beautiful reptile.

  The experience was very pleasing and I felt no revulsion. Just then, another automobile stopped to look at the view and I experienced my first real feeling of persecution and I wanted very much to leave.

  (with 400 mg) During the initial phase of the intoxication (between 2

  and 3 hours) everything seemed to have a humorous interpretation.

  People's faces are in caricature, small cars seem to be chasing big cars, and all cars coming towards me seem to have faces. This one is a duchess moving in regal pomp, that one is a wizened old man running away from someone. A remarkable effect of this drug is the extreme empathy felt for all small things; a stone, a flower, an insect. I believe that it would be impossible to harm anything Q to commit an overt harmful or painful act on anyone or anything is beyond oneUs capabilities. One cannot pluck a flower Q and even to walk upon a gravel path requires one to pick his footing carefully, to avoid hurting or disturbing the stones. I found the color perception to be the most striking aspect of the experience. The slightest difference of shade could be amplified to extreme contrast. Many subtle hues became phosphorescent in intensity. Saturated colors were often unchanged, but they were surrounded by cascades of new colors tumbling over the edges.

  (with 400 mg) It took a long time to come on and I was afraid that I had done it wrong but my concerns were so
on ended. The world soon became transformed where objects glowed as if from an inner illumination and my body sprang to life. The sense of my body, being alive in my muscles and sinews, filled me with enormous joy. I watched Ermina fill to brimming with animal spirit, her features tranformed, her body cat-like in her graceful natural movement. I was stopped in my tracks. The world seemed to hold its breath as the cat changed again into the Goddess. As she shed her clothes, she shed her ego and when the dance began, Ermina was no more. There was only the dance without the slightest self-consconciousness. How can anything so beautiful be chained and changed by other's expectations? I became aware of myself in her and as we looked deeply into one another my boundaries disappeared and I became her looking at me.

  EXTENSIONS AND COMMENTARY: Mescaline is one of the oldest psychedelics known to man. It is the major active component of the small dumpling cactus known as Peyote. It grows wild in the Southwestern United States and in Northern Mexico, and has been used as an intimate component of a number of religious traditions amongst the native Indians of these areas. The cactus has the botanical name of Lophophora williamsii or Anhalonium lewinii and is immediately recognizable by its small round shape and the appearance of tufts of soft fuzz in place of the more conventional spines. The dried plant material has been classically used with anywhere from a few to a couple of dozen of the hard tops, called buttons, being consumed in the course of a ceremony.

  Throughout the more recently published record of clinical human studies with mescaline, it has been used in the form of the synthetic material, and has usually been administered as the sulfate salt.

  Although this form has a miserable melting point (it contains water of crystallization, and the exact melting point depends on the rate of heating of the sample) it nonetheless forms magnificent crystals from water. Long, glistening needles that are, in a sense, its signature and its mark of purity. The dosages associated with the above Rqualitative commentsS are given as if measured as the sulfate, although the actual form used was usually the hydrochloride salt. The conversion factor is given under RdosageS above.