TiHKAL #37 5-MEO-DIPT

SYNTHESIS : To a solution of 3.0 g 5-methoxytryptamine (see under melatonin for its preparation) in 20 mL sulfolane (tetramethylenesulfone) there was added 8.2 g diisopropylethyl amine and 10.7 g 2-iodopropane, and the two-phase mixture was heated on the steam bath with frequent shaking. After 3 h, the mixture was brought back to room temperature and stirred vigorously for an additional 16 h. After the removal of all volatiles under vacuum, the residue (30 g) was diluted with 100 mL H2O, which gave a clear solution. The addition of 10 mL 5% aqueous NaOH produced a cloudy suspension that was extracted with 3x40 mL hexane. These pooled extracts were stripped of solvent to yield 1.0 g of an almost colorless oil that was distilled at the KugelRohr. A small cut at 100 °C (at 0.01 mm / Hg) proved to be largely residual sulfolane (about 0.01 g) and the bulk of the product distilled at 140-150 °C to give a viscous white oil, 0.80 g. This was dissolved in 3.5 mL IPA and neutralized with 15 drops of concentrated HCl. The addition of five drops of anhydrous Et2O instigated crystallization, and the product was removed by filtration, washed with 4:1 IPA / Et2O mixture, and air-dried. There was thus obtained 0.85 g of a fine white crystalline product, 5-methoxy-N,N-diisopropyltryptamine hydrochloride (5-MeO-DIPT), with a mp 181-182 °C (17%). IR (in cm-1): 731, 809, 826, 931, 1035, 1064, with an NH at 3165. MS (in m/z): C7H16N+ 114 (100%); C4H10N+ 72 (31%); methoxyindolemethylene+ 160 (12%); parent ion 274 (<1%). There was no detectable 5-MeO-NIPT by GC (<1%).

QUALITATIVE COMMENTS : (with 6 mg, orally) "Effects were present in twenty minutes, and I took my portable radio into the garden at forty minutes just to pull weeds. Each weed had special significance, and my cat Ms. joined me and agreed with me. This is excessively strange. The radio was discussing a President Ford fund-raiser, and continued with word sequences such as fund, fun, profun, profound, profane, refrain, and on and on. A car drove by with sitar music playing on its radio! Why not. And by my hour number three, I am back where I started. That was quite a morning."

(with 6 mg, orally) "Talking wasn't really interesting, music wasn't interesting, nothing was very interesting. One hour in and I felt turned on as if a wave passed over my body, and then the wave went back to the ocean, or wherever waves go. I was getting hungry but I didn't want to go to the kitchen, as I didn't want to interact with anyone I might encounter. What remains with me the longest was the awareness of vibrations, and what felt best was the stillness. Was back to baseline in 4 hours."

(with 7 mg, orally) "In one hour I was in a marvelous, sexy place. Everything was shaded with eroticism. Sex was explosive, and in another three hours I was completely ready for the outside, public world. As a short term aphrodisiac, this leaves 2C-B in the dust."

(with 10 mg, orally) "Colors on the edges of the wiggles of the eye, a sort of Jessie Allen running design with color contrasts and sparkle. Peoples' faces were interesting, quite serious, and not completely friendly. Well after everything had cleared, later in the evening, there was a residual good clean feeling. This is a definite sense-distorter. I am not completely sure I like it."

(with 10 mg, orally) "We found it to be outstanding -- combining the best characteristics of two other like products while contributing a penetrating efficaciousness of its own."

(with 12 mg, orally) "Had prepared for this experience during the day, and was looking forward to the time with my partner. Flowers, candles, fluffy pillows, arranged for food, etc. Large pillar type candles and the glow was nice and warm. Warm was comfort and comfort was good. Warm led into a wonderful sexual turn on, where my entire body was alive and alert. This was one hour into the trip. This wonderful sexual turn on was the feeling of a bud about to unfold into a full-blown beautiful flower, which happened during love making. The flower continued to fill out fuller and fuller for a couple of hours, and then just remained a full-blown beautiful wonderful flower, and I fell asleep with this feeling."

(with 12 mg, orally) "Remembering how hungry I got during my last 6 mg. experience and without any dietary restriction I ate a vegetarian burrito four hours earlier. It took an hour for me to turn on. I have never experienced such an increase of the peristalsis process in moving the burrito through my colon and with each defecation I would become a little more turned on. As I became more turned on the greater I felt the sense of hypertension. A mind / body load became uncomfortable. It was never psychedelic in the way of acid or psilocybe. My muscles, gluteus maximus, the lateral rotators that connect to the trochanter and the large muscles that connect to the hamstrings, all contracted and spasmed. Psychologically it was as though my conservative instinct, my sense of Being, became extremely agitated. I felt completely unnerved, with the only relief offered was by having sex. As the effects of this material were rather extreme, I never felt as though I was having a psychedelic experience. Maybe because it was all about dealing with body load and discomfort."

(with 12 mg, orally) "There was a very strange, almost paranoid session of listening to music, about an hour and a half into it. The program was a program of Irish music called "The Thistle and Shamrock" but I had paid no attention to the announcement. What was being played were three nativity pieces with song and words, from strange places. What I heard were three distant, fraudulent selections with generically meaningless words, mumbled so as to sound authentic. Everything was faked. It was "hearts of space" music in the worst possible taste. My neutral observer was completely taken in by it all, and quite enjoyed it. It turned out that I was wrong, the music was strange but of good quality. It was my interpretation that was screwed up."

(with 12 mg, orally) "My experience with this material was different in its action than anything I had tried in the past -- it came on quicker but with much less intensity. I really enjoyed the mellowness, and it sort of waved in and out. I came down after almost an hour, smoked a little marijuana, and went back up to where I had been previously. I could do this around my children, and they would know I was happy but doubted they would realize just exactly what was up. I liked it and would consider a public event (craft fair, street fair, window shopping) very adventurous. No hangover; sleep excellent."

(with 12 mg, orally) "Awful, awful taste. Quickly aware and in the second half hour I rapidly shot up to a +++ in a very LSD-like manner, without the visuals. Time was quite slowed down during this come-on. Erotic world was fantastic, explosive, almost scary. Rapid drop-off, and by the fourth hour I am clear of any effects."

EXTENSIONS AND COMMENTARY : Here is a rather fast-acting psychedelic-like drug, with suggestions of LSD action but with essential differences. It has a lot of things going for it. It is short-lived, a virtue in many people's minds. It may vie with 2C-B as a potential aphrodisiac. It is reasonably easy to synthesize. It is of a pretty high potency. The physical side-effects are minimal. These are the positive points.

But there are points that are neutral or actually negative, and they must be considered. A fair number of people who have explored 5-MeO-DIPT have said that there are some uncomfortable aspects with the experience. Not only are there few if any visual enhancements, but the altered state they entered was one that they simply couldn't use. They couldn't make intuitive leaps. That they were wasting their time.

On the neutral, but scientifically exciting, edge there is again some musical sound distortions that remind one of the actions of the analogue without the 5-methoxy group, DIPT. With DIPT, there was a physical harmonic distortion of the sounds that were heard. With 5-MeO-DIPT (again, two isopropyl groups on the basic nitrogen) these perversions involved musical character and interpretation. None of the comments suggested harmonic structure. I do believe that these two drugs, having such an intimate structural resemblance but with their different distortions of music interpretation, would be rewarding to explore more fully with the view of objectively defining these changes. 5-MeO-DIPT is a mixed bag. But it is a bag that I predict will demand a great deal of interest sometime in the future, especially if the erotic enhancement at a low dose proves to be a consistent property.

There is an interesting story associated with the first publication of the chemistry and pharmacology of this compound, in 1981. My co-author was a Michael Carter, in England. We had discussed a number of potentially interesting tryptamines and agreed upon making a small handful to make and evaluate. We had, some six years earlier, co-published a paper describing a new and exciting phenethylamine which we called 2C-B, and we expected to work together, in our separate labs, on a number of research projects. And indeed, I heard from Michael, from a new address, and he sent me his samples and reports of the new compounds we had decided to make, including 5-MeO-DIPT. Our synthetic materials were spectroscopically identical and the human trials had shown that they were very similar. Along with the samples and a letter there came the draft of a possible paper. I wrote back to Michael my own version of the paper, to his new address, and the letter was returned as undeliverable -- no forwarding address available! Again I sent it back, with full first class postage and a clear request to forward it if necessary -- and this time it simply never came back at all.

The issue sat there for a year or two, and I hoped that something would occur. Nothing. I finally wrote to the telephone company in London (Michael had said something about eventually moving up to London) and asked if they could possibly send me the addresses of all the Michael F. Carter that had telephone service in the greater London area. Bless their hearts, they sent back a list of twenty names. And a statement that they were appreciative of having the middle initial, as without that the list would have been in the hundreds.

I wrote to each and every one of these Michael F. Carter the same letter phrased in a way that required no answer if it was the wrong person, but which would inspire immediate answer from the right Michael F. Carter. No answer. Was he alive? Could some unthinkable thing have happened to him associated with his drug experimentation, either personally or legally? There was absolutely no way to tell, so Michael, somewhere out there, if you read this please drop me a note if you wish to and are able to.

So I justify the paper pretty much with his ideas in it, crossed my fingers as I used my address for both authors, and sent it off for publication. The paper appeared and I sincerely hope that I did the right thing.

#37. 5-MEO-DIPT