#38. 5-MEO-DMT
TRYPTAMINE, 5-METHOXY-N,N-DIMETHYL; INDOLE, 5-METHOXY-3-[2-(DIMETHYLAMINO)ETHYL]; 5-METHOXY-N,N-DIMETHYLTRYPTAMINE; 5-METHOXY-3-[2-(DIMETHYLAMINO)ETHYL]INDOLE; N,N,O-TRIMETHYLSEROTONIN; N,N,O-TMS; BUFOTENINE METHYL ETHER; O-METHYLBUFOTENINE; OMB
source :
http://www.erowid.org/library/books_online/tihkal/tihkal38.shtml
SYNTHESIS : To a cooled and well-stirred solution of 16 g 5-methoxyindole in 200 mL anhydrous Et2O there was added, dropwise, 25 g oxalyl chloride. Stirring was continued for an additional 10 min, then the red solids were removed by filtration, washed lightly with Et2O, and returned to the reaction beaker as a suspension in 200 mL fresh anhydrous Et2O. To this there was added a solution of 8.5 g dimethylamine in 25 mL anhydrous Et2O which discharged the red color. Stirring was continued for an additional 0.5 h, and the solids were removed by filtration and washed with Et2O. These were suspended in H2O, filtered, and washed alternately with H2O and Et2O. Recrystallization from THF / Et2O provided 20 g (75%) 5-methoxy-N,N-dimethylindol-3-ylglyoxylamide, mp 223-223.5 °C, as fine white crystals.
To a well-stirred suspension of 11.7 g LAH in 350 mL anhydrous Et2O there was added, in small portions, a suspension of 18.5 g 5-methoxy-N,N-dimethylindol-3-ylglyoxylamide in 200 mL hot benzene. The last of the solids were rinsed in with anhydrous Et2O and the mixture held at reflux for 1.5 h. After cooling with an external ice bath, the reaction complex and excess hydride were decomposed by the cautious addition of H2O. The inorganic solids were removed by filtration, the filter cake washed with additional Et2O, the filtrate and washing were combined and dried over anhydrous MgSO4, and the solvents removed under vacuum. The residue was distilled at the KugelRohr to provide a colorless fraction distilling at 160-170 °C at 0.6 mm/Hg, that crystallized on cooling. There was thus obtained 12.8 g (78%) 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) which on recrystallization from hexane had a mp 69-70 °C. The hydrochloride salt can be made by passing a stream of hydrogen chloride gas through an Et2O solution of the base. It, upon recrystallization from EtOH / Et2O, had a mp of 145-146 °C.
DOSAGE : 6 - 20 mg, smoked; 2 - 3 mg, i.v.
DURATION : 1 - 2 hrs
QUALITATIVE COMMENTS : (with 6 mg, smoked) "I felt it in a minute -- not really light head, but the head feels close to the lower parts of the body -- close to the ground -- knees weak -- distinct shakes. I peaked at 2 or three minutes. It was quite intense, but not the max of DMT at 30 milligrams and no sensory close-out. Slight nausea on the drop-off -- I am glad I had not eaten anything. Overall comparison to DMT, more potent, slightly faster, but like DMT is largely a simple, stoning drug with no sensory contribution, no intellectual contribution. It's greatest contribution might be to provide a subject the vocabulary of an altered state of consciousness so that, with interesting and constructive drugs, these effects will be familiar, and thus not distractions."
(with 8 mg, smoked) "I was blown away, far away I might add, but only for 10 minutes and effects were gone by half an hour. During this episode mental activity was almost absent. I can't say I wasn't 'impressed' in some way, though it wasn't exactly what I expected. I had read reports with statements varying from 'dwarfs + elves' to 'conk on the head,' the latter of which relates more closely to my experience."
(with perhaps 10 mg, smoked) "Onset was gentle, perhaps over 15 minutes. I felt like all of my blood had turned to concrete. There were no noticeable visual effects, but my hearing was slightly diminished. The whole experience was over after 1 hour."
(with perhaps 15 mg, smoked) "I took a hit from the pipe with five-methoxy in it, and after the 8 to 10 seconds it took to carry the chemical to my brain I remember starting to fall over from my sitting position. My normal physical perceptions dissolved away from my awareness. My ears started to ring and I started to float off. I was acutely aware of a certain resonation of my aural perception, an electrical buzzing that fluctuated in synch with my visual perception. What I saw can only be described as a fantastically subtle multicolored phosphene, completely filling every area visually available. I say it in this way because I was simultaneously losing contact with my body, I could not tell if my eyes were open or shut, although I initially had the feeling that they were darting back and forth, from side to side. These feelings and sensations built up in intensity very quickly, a matter of seconds: I can remember this feeling of building intensity up to a point, and then I was not there in my body or in time. In the 10 to 15 minutes that my body was under the influence of the drug my mind was completely referenceless, there was no way for my consciousness to limit or gauge the stimuli my being was barraged with. I remember switching to a perception where the endless and intricate phosphene was love and the energy of light. I called upon those forces within my being to realign and submit, to let go of all the cogent fears and just exist ... and that innate decision saved me a lot of psychic damage. What is most outstanding about the way it feels is an inability to judge in any way, by any method of the mind ... it is unconquerable, as deep and profound as a totally unconditional love that is life. What a trip, huh?"
(with 15 mg, smoked) "At about 60 seconds after I smoked this free base, I beheld every thought that was going on everywhere in the universe and all possible realities while I was wracked out with this horrible ruthless love. It scared the hell out of me. When I could see again (15 minutes later) it was almost as if there was an echo of a thought in my head saying that I was given an extremely rare look at the true consciousness of it all. I've never been hit this hard since then. A definite ++++."
(with perhaps 20 mg, smoked) "This is a very strong hallucinogen. A twenty minute experience. For me it was like adding the MDMA experience to DMT. DMT for me is terrifying (I still go back though) and I must really think about it before proceeding. The 5-MeO-DMT was much more relaxed, a kind of cosmic consciousness type of experience. I broke into a space similar to DMT but it was more like receiving grace. I felt a little shaky (tremor-like) coming down."
(with 25 mg, smoked) "I placed 25 mg of 5-methoxy-DMT in a stainless steel one-quarter teaspoon and vaporized it over a cigarette lighter collecting the smoke in an upside-down funnel. All smoke was inhaled; the taste was mild -- none of the plastic taste of DMT. About 10 seconds or so after inhaling the last of the smoke, it began with a fast-rising sense of excitement and wonder, with an undertone of "Now you've done it," but dominated by a sense of, "WOW, This Is IT!" There was a tremendous sense of speed and acceleration In perhaps 10 more seconds these feelings built to an intensity I had never experienced before. The entire universe imploded through my consciousness. It's as if the mind is capable of experiencing a very large number of objects, situations and feelings, but normally perceives them only one at a time. I felt that my mind was perceiving them all at once. There was no distance, no possibility of examining the experience. This was simply the most intense experience possible; a singularity, a white-out (as opposed to a black out), I have little memory of the state itself. I have no memory, for example, of whether my eyes were opened or closed. After some seconds or minutes , it started to fade and came to resemble a merely intense psychedelic state. Here I had the feeling, a visualization of being part of the universe of beings, all active in our daily, interwoven tasks, still moving at an incredible rate, and with a longing for a single group / organism awareness and transcendence. In a few more minutes it faded to an alert (+ one) state with an additional sense of awe and wonder, relief, and a strong feeling of gratitude toward the universe in general, for the experience."
(with 30 mg, smoking) "I placed approx. 30 mg of 5-MeO into a pipe, and smoked it, in one toke, without a second thought. An instant later, I was crawled up on my bed (in the fetal position) with my eyes closed, squirming around, screaming (in my head) 'Fuck! You killed yourself!' I repeated this several times, very fearful of death. I didn't see anything, while my eyes were shut, except for a bright white light, that which you see after staring at a bright light. The only other "vision" was one in my mind - I came to the realization that my life would be wasted if I died there. This showed me all of my scripts being discarded and nothing good happening ever again. It was a glimpse into my future, if I died. I concentrated on breathing and that helped me survive (mentally). I walked into the living room and placed a CD into the stereo, and as the first song started, my attention span disappeared, and I walked back into my bedroom. To my surprise, forty minutes had passed, in what I remembered as mere seconds. This scared me, thinking that maybe I had blacked out. I felt the effect for about an hour, it slowly faded away."
(with an unknown but large amount, smoked) I observed the subject pass very quickly into an almost coma-like state. Within seconds his face became purple and his breathing stopped. I pounded his chest, and breathed for him, and he seemed to emerge in consciousness, with the comment, "This is absolute ecstasy." He stopped breathing a second time, and both heart massage and mouth-to-mouth resuscitation was provided. Again, he recovered and managed to maintain a continuing consciousness and achieve a partial recovery. In the awake condition he was increasingly lucid, but on closing his eyes he became possessed with, what he called, "The energy of terror." He could not sleep, as upon closing his eyes he felt threatened in a way he could not tolerate. Three days later, medical intervention with antipsychotic medication was provided, which allowed the recovery of an acceptable behavior pattern in a few more days.
(with 35 mg, orally): "No activity."
(i.v = intra veineuse pour ceux qui ne savent pas)
(with 0.25 mg, i.v.): "A real effect."
(with 0.5 mg, i.v.) "I felt the effects distinctly within a minute, along with some pain at the injection site. In a few minutes I felt a very distinct calming and stilling of my mind. While I could have carried on a conversation about anything and didn't feel the least bit stoned, I found the feeling very recognizable."
(with 0.7 mg, i.v.): "This was basically a +1 experience. After a few instances I felt its motion, very gentle waves. I was thinking about thinking about the experience, about writing about it, and so I was experiencing myself as both observer and editor. This was not overwhelming, but gentle."
(with 1.3 mg, i.v.) "In a few seconds I was participating in exquisite, full body, teeth-chattering shivers that lasted in all about 10 minutes, nearly the duration of the effects. The sensations seemed to come more from my head region, whereas my 'full blown' experiences of smoked 5-MeO-DMT seemed to emanate from my center and heart."
(with 2.3 mg, i.v.) "I remember having a perspective of knowing I was aware and, if not from the start of the experience then very soon into it, knowing I knew I was aware. I thought I was an ocean. I don't remember where I first lost continuity of consciousness (this is a little like a black-out from hard liquor) but I remember being aware of the sounds I was making apparently some time after I began vocalizing. Around the time I thought to change these sounds as I pleased, I also noted with brief wonder that the sound was continuous, not changed by my breathing. I sang my way back."
(with 3.1 mg, i.v.) "I vocalized effortlessly. I was getting in touch with my body. I said, 'Turn off the lights,' and 'I love you,' and then I lost it. I was amazed later to find a roomful of people who had been frightened by the noises they had been amazed to hear, and I was amazed to be told I had made."
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