QUALITATIVE COMMENTS: (with 160 mg followed at 2 h by 60 5gs LSD) RThe visual phenomena were extraordinary. We were at the beach just south of Mendocino. In anything that had ever been living, there was an endlessly deep microcosm of detail. Endless, and forever more microscopic in intricacy. A sea urchin shell, a bit of driftwood, a scrap of dried seaweed, each was a treasure of jewels. I have never had such wealth of visual eroticism and bliss before. Later, we visited the pygmy forest, but these living fossils were not as magical.
(with 160 mg followed at 2 h by 60 5gs LSD) RWe both felt the first effects at about 30 minutes, and an hour later we found ourselves in a startling folie-a-deux, involved in reliving the origins of manUs arrival on earth. We were deep in a tropic environment, defending ourselves against the nasties of nature (insects, threatening things, blistering heat) and determining that man could indeed live here and perhaps survive. A shared eyes-closed fantasy that seemed to be the same script for both of us.
(with 160 mg followed at 2 h by100 5gs LSD) RThis proved to be almost too intoxicating, and a problem arose that had to have a solution.
The entire research group was here, and all were following this same regimen. Two hours into the second half of the experiment a telephone call came that reminded me of a promise I had made to perform in a social afternoon with the viola in a string quartet. Why did I answer the phone? My entire experience was, over the course of about 20
minutes, pushed down to a fragile threshold, and I drove about 10
minutes to attend a swank afternoon event and played an early Beethoven and a middle Mozart with an untouched glass of expensive Merlot in front of me. I could always blame the booze. I declined the magnificent food spread, split, and returned to my own party.
Safely home, and given 20 more minutes, I was back into a rolling +++
and I now know that the mind has a remarkable ability to control the particular place the psyche is in.
(with 200 mg followed at 2 h by 60 5gs LSD) RThere was a steady climb from the half-hour point to about 2 hours. There was not the slightest trace of anything sinister. There was simply a super tactile person-to-person window. I had an overpowering urge to go out and interact with other people. To see, to talk, to be with others.
There are unending fantasies of things erotic. Perhaps being with others should be circumspect. By evening the effects had largely worn off, but this was an incredible day, beautiful and unexpectedly relaxing.
EXTENSIONS AND COMMENTARY: There is need for more commentary. It must be noted that all of the above comments used rather modest dosages of LSD. The notes of this period, some two years of exploring interactions of the MD series of compounds as preludes to true psychedelics, are difficult to distill into a simple pattern. Most of these studies used LSD in the 60-100 microgram range which is fundamentally a modest level. Many trials were made where the challenge of acid plopped right on top of an active residue of another drug was more in keeping with the RpiggybackS argument. An illustration of this is a trial in which the primer was MDMA followed at 5 hours (this is at a time of almost no effect) with a larger dose of LSD (250 micrograms). The LSD overwhelmed the residual numbing of the MDMA, and the generated state was overwhelmingly erotic and out of body. There can be no way of analytically organizing such a gemisch of drug-drug interactions with any logic that would allow a definitive interpretation. And LSD is not the only agent that can be used to challenge the Rbody windowS such as that produced by MDPR. 2C-B, 2C-T-2 and 2C-T-7 have all been used with fine success as well.
In general, the use of an MD compound (looking at it as a stimulant and primer) followed by a psychedelic, brings about an exaggeration and enhancement of the latter compound. Much work must be done in this area to make sense of it all.
119 ME; METAESCALINE; 3,4-DIMETHOXY-5-ETHOXYPHENETHYLAMINE
SYNTHESIS: To a vigorously stirred suspension of 18.6 g of 5-bromobourbonal in 100 mL CH2Cl2 there was added 14.2 g methyl iodide, 1.0 g decyltriethylammonium iodide, and 120 mL 5% NaOH. The color was a deep amber, and within 1 min the top phase set up to a solid. This was largely dispersed with the addition of another 50 mL
of water. The reaction was allowed to stir for 2 days. The lower phase was washed with H2O, and saved. The upper phase was treated with another 100 mL CH2Cl2, 50 mL of 25% NaOH, another g of decyltriethylammonium iodide, and an additional 50 mL of methyl iodide. The formed solids dispersed by themselves in a few h to produce two relatively clear layers. Stirring was continued for an additional 3 days. The lower phase was separated, washed with H2O, and combined with the earlier extract. The solvent was removed under vacuum to give 20.3 g of an amber oil that was distilled at 120-133 !C
at 0.4 mm/Hg to yield 15.6 g of 3-bromo-4-methoxy-5-ethoxybenzaldehyde as a white crystalline solid with a mp of 52-53 !C.
A mixture of 15.6 g 3-bromo-4-methoxy-5-ethoxybenzaldehyde and 10 mL
cyclohexylamine was heated with an open flame until it appeared free of H2O. The residue was put under a vacuum (0.5 mm/Hg) and distilled at 148-155 !C yielding 19.2 g
3-bromo-N-cyclohexyl-4-methoxy-5-ethoxybenzylidenimine as an off-white crystalline solid with a melting point 66-68.5 !C. Recrystallization from 100 mL boiling MeOH gave a mp of 67-68.5 !C. The C=N stretch in the infra-red was at 1640 cm-1. Anal. (C16H22BrNO2) C,H.
A solution of 17 g
3-bromo-N-cyclohexyl-4-methoxy-5-ethoxybenzyl-idenimine in 200 mL
anhydrous Et2O was placed in an atmosphere of He, stirred magnetically, and cooled with an external dry-ice acetone bath. Then 38 mL of a 1.55 M solution of butyllithium in hexane was added over 2
min, producing a clear yellow solution. There was then added 25 mL of butyl borate at one time, and the stirred solution allowed to return to room temperature. This was followed with 100 mL of saturated aqueous ammonium sulfate. The Et2O layer was separated, washed with additional saturated ammonium sulfate solution, and evaporated under vacuum The residue was dissolved in 200 mL of 50% MeOH and treated with 12 mL of 30% hydrogen peroxide. This reaction was mildly exothermic, and was allowed to stir for 15 min, then added to an aqueous solution of 50 g ammonium sulfate. This was extracted with 2x100 mL CH2Cl2, the pooled extracts washed once with H2O, and the solvent removed under vacuum. The residue was suspended in dilute HCl, and heated on the steam bath for 0.5 h. Stirring was continued until the reaction was again at room temperature and then it was extracted with 2x100 mL CH2Cl2. These extracts were pooled and in turn extracted with 2x100 mL dilute NaOH. The aqueous extracts were reacidified with HCl, and reextracted with 2x100 mL CH2Cl2. After pooling, the solvent was removed under vacuum to yield an oily residue. This was distilled at 118-130 !C at 0.2 mm/Hg to yield 7.5 g of 3-ethoxy-5-hydroxy-4-methoxybenzaldehyde as a distillate that set to white crystals. Recrystallization from cyclohexane gives a product with a mp of 77-78 !C. Anal. (C10H12O4) C,H.
A solution of 7.3 g of 3-ethoxy-5-hydroxy-4-methoxybenzaldehyde in 100
mL acetone was treated with 5 mL methyl iodide and 8.0 g finely powdered anhydrous K2CO3, and held at reflux on a steam bath for 6 h.
The solvent was removed under vacuum, and the residue was suspended in H2O. After making this strongly basic, it was extracted with 3x50 mL
CH2Cl2, the extracts were pooled, and the solvent removed under vacuum. The residual amber oil was distilled at 110-120 !C at 0.4
mm/Hg to yield 7.3 g of a white oil. This spontaneously set to white crystals of 3,4-dimethoxy-5-ethoxybenzaldehyde which had a mp of 49-49.5 !C. Anal. (C11H14O4) C,H. This same aldehyde can be obtained, but in a less satisfactory yield, by the ethylation of 3,4-dimethoxy-5-hydroxybenzaldehyde described under the preparation of metaproscaline (MP).
A solution of 7.2 g 3,4-dimethoxy-5-ethoxybenzaldehyde in 100 mL
nitromethane containing 0.1 g anhydrous ammonium acetate was held at reflux for 50 min. The excess nitromethane was removed under vacuum producing 6.8 g of a red oil which was decanted from some insoluble material. Addition of 10 mL hot MeOH to the decantings, ga
ve a homogeneous solution that spontaneously crystallized on cooling. The yellow crystals were removed by filtration, washed sparingly with MeOH
and air dried yielding 3.5 g yellow crystals of 3,4-dimethoxy-5-ethoxy-'-nitrostyrene, with a mp of 89.5-90 !C after recrystallization from MeOH. Anal. (C12H15NO5) C,H.
A solution of 2.0 g LAH in 100 mL anhydrous THF under He was cooled to 0 !C and vigorously stirred. There was added, dropwise, 1.3 mL of 100% H2SO4, followed by the dropwise addition of a solution of 3.1 g 3,4-dimethoxy-5-ethoxy-'-nitrostyrene in 50 mL anhydrous THF, over the course of 10 min. The mixture was stirred at 0 !C for a while, and then brought to a reflux on the steam bath for 30 min. After cooling again, the excess hydride was destroyed with IPA in THF, followed by the addition of 20 mL 10% NaOH which was sufficient to convert the solids to a white and granular form. These were removed by filtration, the filter cake washed with IPA, the mother liquor and filtrates combined, and the solvents removed under vacuum. The residue was added to 150 mL dilute H2SO4, and the cloudy suspension washed with 2x75 mL CH2Cl2 which removed much of the color. The aqueous phase was made basic with 25% NaOH, and extracted with 3x50 mL
CH2Cl2. The solvent was removed from these pooled extracts and the residue distilled at 103-116 !C at 0.25 mm/Hg to provide 2.3 g of a colorless viscous liquid. This was dissolved in 10 mL IPA, neutralized with about 25 drops of concentrated HCl, which produced an insoluble white solid. This was diluted with 40 mL anhydrous Et2O
added slowly with continuous stirring. The white crystalline 3,4-dimethoxy-5-ethoxyphenethylamine hydrochloride (ME) was isolated by filtration, washed with Et2O, and air dried, and weighed 2.4 g. It had a mp of 202-203 !C which increased by one degree upon recrystallization from boiling IPA. Anal. (C12H20ClNO3) C,H.
DOSAGE: 200 - 350 mg.
DURATION: 8 - 12 h.
QUALITATIVE COMMENTS: (with 200 mg) It tasted pretty strong.
However, the taste was soon gone, and an energetic feeling began to take over me. It continued to grow. The feeling was one of great camaraderie, and it was very easy to talk to people. Everyone was talking to everyone else. I found it most pleasant, energetic and at the same time relaxing, with my defenses down. This material did not seem to lead to introspection; however, it might if one took it without other people around. Heightened visual awareness was mild, but the audio awareness was quite heightened. The feeling of being with everyone was intense.
(with 250 mg) Initially I took 200 milligrams of metaescaline, and the experience developed for me very gradually at first, and very pleasantly. After about one half hour I became aware of a wall that seemed to shut me in, not unpleasantly. The wall slowly dissolved, but I was afraid I might get into a negative experience. I felt immediate relief (from this isolation) upon taking the additional 50
mg (at 2:23 into the experiment) as though glad of the decision. I lay down outside on a blanket. There was a marvelous feeling inside, although no imagery. I felt the wall dissolve completely, and I desired to join the group. From this point on the experience was most enjoyable, euphoric. Although not dramatic like some psychedelics, it was most rewarding for me personally. I felt a marvelous bond with everyone present, with clear-headed, excellent thinking, and excellent communication. All in all, a most rewarding and enjoyable experience.
Afterwards I felt much strengthened, with good energy and good insight. I have a strong feeling that the group tailored the nature of the experience, and that I and others were most desirous of group interaction. I feel that one could do a lot of other things with it if one turned one's attention to it.
(with 275 mg) Onset of both physical and mental change was slow relative to other psychochemicals. Very gradual internal stirrings were felt at about the hour-and-a-half point. These were mostly feelingful rather than cognitive, and were quite pleasurable. At about the two-and-a-half hour point I grew quite thirsty, and drank a pint of beer. Almost immediately, and quite unexpectedly, I tomsoed to a much higher level and remained there for another three hours until the whole experience waned. [The verb, to tomso, means a sudden rekindling of the drug-induced altered state with a small amount of alcohol. It is explained in the recipe for TOMSO.] During the experience heights, and in fact before it reached its height, talking was easy and unimpeded. The transference feelings so characteristic of MDMA were basically not there. But for purposes of psychotherapy, there were some advantages: fluent associations, undefended positions, and general bonaise.
(with 400 mg) Ingested 300 milligrams at about 1:30 in the afternoon.
Very quiet climb. Occasional yawns. Matter-of-fact view of the world. No rosy glow. At the end of the second hour, I seem to be stuck at a ++. Take another 100 milligrams at 3:45 PM. Still tastes awful. Feel a small head-rush fifteen minutes after taking the supplement, and within a half hour I am completely +3. For a while this was a sterner mescaline. Saw the eternal, continual making of choices, all opposites continually in motion with each other. Yin and yang everywhere, giving life to every molecule. The universe itself keeps alive by the action-reaction, the yes-no, the black-white, male-female, plus-minus. All life is a continual making of choices on all levels. Then I closed my eyes, and I found myself floating up to the very top of a temple, where there was radiant light and a sense of homecoming. Making love is a clear stream over and through rocks and canyons Q the earth and sky make love, and the rocks make love to other rocks, and the water is the teasing, fondling, living and moving actions of loving. To realize that, on some level, all existence makes love to all other existence. The Japanese Garden: a structured way of laying out a small glimpse into cosmic love-making, so that it can be read by other human souls. All loving, when direct and free and undemanding, is a touching of the Source. The hardest lesson, of course, is how to love yourself that same way. And it remains both the first lesson of Kindergarten and the Ph.D. final. I was able to drift into sleep at about 4:00 AM.
EXTENSIONS AND COMMENTARY: The reorientation of the single ethyl group of escaline (E) to the meta-position produces metaescaline (ME). In cats, in studies of over 50 years ago, the two compounds produced similar effects at similar dosages. In man, ME also appears to be similar to mescaline in potency. However, a subtle difference is apparent between ME and Peyote, the natural source of mescaline. With Peyote itself, the initial taste of the crude cactus is more than just foul; it might better be described as unbelievably foul. But in the middle of a Peyote experience, the taste of the cactus is truly friendly. When ME was retasted in the middle of an experience, the taste was still foul.
There are other distinctions from mescaline. Unlike mescaline or Peyote, there is rarely any body discomfort during the early phase of intoxication, no nausea and only an occasional comment suggesting hyperreflexia. And, also unlike mescaline, most subjective reports on ME claim that music produces little imagery, and the exaggeration of color perception is more reserved. Appetite is normal, the tastes and textures of food are unusually rewarding. No subject has ever expressed a reluctance to repeat the experience. Sleep is easy, refreshing, and the following day seems free from residue.
From: [email protected]
Newsgroups: sci.med,sci.chem,alt.drugs Subject: PiHKAL: The Chemical Story. File 5 of 6
(I'm posting this for a friend.)
This is part 5 of 6 of the second half of PiHKAL: A Chemical Love Story, by Alexander Shulgin and Ann Shulgin. Please forgive any typos or misprints in this file; further, because of ASCII limitations, many of the typographical symbols in the original book could not be properly represented in these files.
If you are seriously interested in the chemistry contained in these files, you should order a copy of the book PiHKAL. The book may be purchased for $22.95 ($18.95 + $4.00 postage and handling) from Transform Press, Box 13675, Berkeley, CA 94701. California residents please add $1.38 State sales tax.
At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern effor
ts to obtain legal approval to do work with these compounds in human beings.... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herin, without being familiar with that drug's action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law.
120 MEDA; 3-METHOXY-4,5-ETHYLENEDIOXYAMPHETAMINE
Pihkal Page 110