Tryptamine, 5-methoxy-2,N,N-trimethyl · Indole, 3-[2-(dimethylamino)ethyl]-5-methoxy-2-methyl · 5-Methoxy-2,N,N-trimethyltryptamine · 5-Methoxy-2-methyl-DMT · 3-[2-(Dimethylamino)ethyl]-5-methoxy-2-methylindole · Indapex
#45 5-MeO-TMT SYNTHESIS: To a stirred solution of 7.16 g of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (indomethacin) in 150 mL CHCl3 there was added, dropwise, 4.4 mL oxalyl chloride and the reaction mixture held under reflux conditions for 2.5 h. Removal of the solvent under vacuum produced a thick yellow oil which was dissolved in 150 mL of CH2Cl2. There was then added, in small portions, 40% aqueous dimethylamine until the aqueous phase remained basic to pH paper. The phases were separated, and the organic phase was washed sequentially with H2O, dilute HCl, and finally saturated saline, then stripped of solvent under vacuum. The residue was dissolved in 20 mL ethyl acetate EtOAc and in a few minutes the product crystallized out. This was recrystallized from a hot aceton/water acetone/H2O mixture yielding, after filtration and air drying to constant weight, 5.08 g 1-(p-chlorobenzoyl)-5-methoxy-2,N,N-trimethylindole-3-acetamide as pale yellow, fine needles.
To a suspension of 5.0 g of 1-(p-chlorobenzoyl)-5-methoxy-2,N,N-trimethylindole-3-acetamide in a mixture of 80 mL isopropanol IPA and 20 mL H2O there was added 1.0 g KOH and the mixture was stirred at room temperature for 1.5 h. The starting material gradually dissolved over this period. The excess isopropanol IPA was removed under vacuum, and the residue partitioned between ethyl acetate EtOAc and H2O. The organic phase was separated, then washed sequentially with H2O, dilute HCl, H2O and finally saturated brine. After drying with anhydrous Na2SO4, the evaporation of the solvent yielded a white product that was recrystallized from a small quantity of boiling ethyl acetate EtOAc that was allowed to cool slowly. There was obtained, after filtration and air drying, 1.44 g of 5-methoxy-2,N,N-trimethylindole-3-acetamide as white crystals.
To 40 mL of stirred anhydrous THF in a round-bottomed flask equipped with a reflux condenser and in an atmosphere of argon, there was added 2.70 g 5-methoxy-2,N,N-trimethylindole-3-acetamide. There was then added 20 mL of 1.0 molar LiAlH4 in THF (there was a rapid evolution of bubbles) and the reaction mixture was held at reflux conditions for 2.5 h. The mixture was cooled to room temperature and treated with 8 mL of a 50% solution of isopropanol in H2O 1:1 solution of IPA and H2O. There was then added 2.0 mL 15% aqueous NaOH followed by an additional 2.0 mL H2O. The suspension was filtered, the solids washed with 2×20 mL THF, the filtrate and washings combined, and the solvent removed under vacuum. The solid residue was dissolved in 25 mL 0.5 molar HCl, washed with CH2Cl2, made basic with 25% aqueous NaOH, and extracted with 3×40 mL CH2Cl2. Removal of the solvent under vacuum yielded a light yellow oil. This was distilled at 0.25 mm/Hg to yield a fraction boiling at 155–160 °C, weighing 1.52 g that was a pale yellow oil. This slowly set up as a milky crystalline solid, 5-methoxy-2,N,N-trimethyltryptamine (Indapex) which had a mp of 90–92 °C.
DOSAGE: 75–150 mg, orally
DURATION: 5–10 hrs h
QUALITATIVE COMMENTS:with 65 mg, orally) “I felt the first intoxication at an hour. I was relaxed along with subtle day-dreaming to “Hearts of Space” music. I was sexually stimulated, with some heightening of intensity of orgasm. At the three hour point I seemed pretty much baseline. The rest of the day went without difficulty.”
(with 90 mg, orally) “This was ingested in a capsule. Effects were first noted at 55 minutes with a feeling of relaxation and a mild impairment of fine motor skills. Sexual activity was initiated at the 90 minute point. Spinal tingles were felt and, although erection may have been slightly more difficult than normal to maintain, orgasm was phenomenal. This potentiation was confirmed three more times over the next three hours! Mild stomach fullness was felt but no other GI problems were noted. Significant appetite suppression was noted for the first five hours, after which food tasted fine. Music evoked closed-eye drifting of thoughts but no true visuals occurred with eyes open or closed. A faint tremor of the jaw and fingers could be noted with careful examination. The effects were barely noticeable at the five hour point, and were completely gone at seven hours. Sleep was broken by awakening every few hours with moderate thirst and dream activity seemed enhanced. There were no side-effects the following morning.”
(with 120 mg, orally) “Unlike what I was told might happen, no sexual feelings were even remotely felt at any time during this experience. Thoughts seemed poorly connected and there was a feeling of being drugged with a sedative. Moderate chills and cold sensations occurred for several hours, requiring first a jacket and later a heating blanket. Time seemed moderately slowed and both respiration and pulse were reduced. Mild stomach fullness was noted, with indigestion. I was not hungry. No other GI problems occurred. Everything faded at about the five hour point, when I got very hungry and thirsty. My sleep was not comfortable, and the next morning I was still a little bit jittery.”
(with 150 mg, orally) "No effects were felt until the 55 minute point, when a mild degree of intoxication began. At seventy minutes mild nausea and gastric fullness was apparent. There was a loss of fine motor skills and I found it hard to walk. My peripheral visual field has a waviness to it. Both television and a radio talk show became completely uninteresting and difficult to follow, and a feeling of sadness and despair became overwhelming. No music could change these feelings, although there definitely were pronounced closed-eye visuals by the 100 minute point. Emotions were extremely labile, going from profound crying to calm and back in a period of twenty minutes. I saw every defect and failure in my life and, although very sad, I recognized some things that I will correct in the future. Apparent body temperature fluctuations were continuous, going from being hot to chilled over and over again (actual body temperature was not measured). It was impossible to get comfortable for several hours. The stomach distress continued throughout the entire experience, with a moderately severe stomach aching during the third and fourth hours.
“By the sixth hour I could again watch television, and I did so while waiting for the experience to end. Some residual effects were still present at nine hours, but sleep thereafter was uneventful. No eating, or even drinking of water, was possible until the eighth hour, at which time small sips of water were tolerated. I awoke several times during the night and took in additional small amounts of water, but still arose the next morning very dehydrated. There were no other apparent hang-over effects.”
EXTENSIONS AND COMMENTARY: This is certainly a hallucinogenic at a dosage of 150 mg orally, and can be compared with 300 mg of hydrochloride. This exact same chemical, if you were to remove that tiny, little, bitty methyl group at the indolic 2-position, would become the remarkably potent material . But this latter stuff must be smoked or injected to show any activity at all. It is known that a methyl group on the alpha-carbon of a tryptamine blocks assess of a deaminating enzyme allowing oral activity. I wonder if the methyl group on the 2-position is doing the same job of getting in the way.
At modest dosages in the 70–80 mg area orally, Indapex is both relaxing and sexually stimulating. The highest dosages studied seem to reveal a toxic component and few subjects chose to repeat these levels.
30 July 2016 · Creative Commons BY-NC-SA ·

About TiHKAL · info

This version of Book II of TiHKAL is based on the Erowid online version created by Bo Lawler with the help of Erowid, from content generously provided in electronic format by the Authors.
The Erowid online version does not always align precisely with the printed version. Text appears to have been inserted, deleted, or changed at various points. Where the two are seen to diverge both the Erowid and print versions are given. Sharp-eyed readers are encouraged to report novel discrepancies.
As with PiHKAL, I’ve again attempted to reproduce the typographic style of the printed edition. I’ve again made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The history page has further details.

Cautionary note

“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 efforts 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 herein, 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.”
Alexander T. Shulgin

Copyright notice

The copyright for Book I of TiHKAL has been reserved in all forms and it may not be distributed. Book II of TiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering information

TiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of tryptamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.
Though Sasha and Ann have put Book II of TiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them — and there’s still nothing quite like holding a real book in your hands.
TiHKAL (ISBN 0-9630096-9-9) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.
Transform Press,
Box 13675
Berkeley, CA 94701

510 · 934 · 4930 (voice)
510 · 934 · 5999 (fax)