3-Thiometaescaline · 4,5-Dimethoxy-3-ethylthiophenethylamine
#163 3-TME SYNTHESIS: A solution of 13.0 g of 3-bromo-N-cyclohexyl-4,5-dimethoxybenzylidenimine (see under for its preparation) in 125 mL anhydrous Et2O in a He atmosphere was cooled with an external dry ice acetone bath to -80 °C with good stirring. To this clear pale yellow solution there was added 32 mL 1.55 M butyllithium in hexane (about a 25% excess) which was stirred for 10 min producing a fine white precipitate. There was then added 7.0 g diethyl disulfide. The dry ice bath was removed and the reaction stirred as it came to room temperature. This was then added to 300 mL dilute HCl and the aqueous phase separated and heated on the steam bath for 45 min. A yellow oil was formed with a nearly colorless aqueous overhead. This was removed by decantation, and the remaining oil was diluted with a little MeOH and additional concentrated HCl. After further heating on the steam bath, this was added to the separated phase, all was cooled and extracted with 2×50 mL CH2Cl2. Removal of the solvent from these pooled extracts gave 11.8 g of a residue that was distilled. The product, 3-ethylthio-4,5-dimethoxybenzaldehyde boiling at 106–125 °C at 0.4 mm/Hg and was an almost colorless oil weighing 8.3 g. Anal. (C11H14O3S) C,H.
To a solution of 8.2 g 3-ethylthio-4,5-dimethoxybenzaldehyde in 125 mL nitromethane, there was added 1.0 g of anhydrous ammonium acetate and the mixture was heated on the steam bath for 1.5 h. The reaction mixture was stripped of nitromethane under vacuum, and the residual red oil was dissolved in 20 mL of boiling MeOH. This was decanted from a small amount of insolubles, and allowed to cool to room temperature. After considerable manipulation of a small sample with dry ice cooling, a seed of crystal was obtained, which successfully promoted crystallization of the entire MeOH solution. After standing for 1 h, the product 3-ethylthio-4,5-dimethoxy-β-nitrostyrene was removed by filtration and, after air drying, weighed 3.2 g with a mp of 96–98 °C. Upon recrystallization from MeOH, the mp was tightened to 98–99 °C. Anal. (C12H15NO4S) C,H.
AH was prepared in the usual manner from a suspension of 2.0 g LAH in 75 mL anhydrous THF, cooled to 0 °C and well stirred in an inert atmosphere of He, and treated with 1.33 mL of 100% H2SO4 added dropwise. There was added, dropwise and over the course of 10 min, a solution of 3.1 g 3-ethylthio-4,5-dimethoxy-β-nitrostyrene in 15 mL anhydrous THF. At the end of the addition, the reaction mixture was returned to room temperature, and finally heated on the steam bath for 10 min. After cooling again, there was added enough IPA to decompose the excess hydride and sufficient 10% NaOH to convert the aluminum oxide to a white, easily filterable mass. This was removed by filtration, the filter cake washed with additional IPA, and the filtrate and washes combined and the solvent removed under vacuum. This was dissolved in 100 mL of dilute H2SO4, which was washed with 2×50 mL CH2Cl2. The aqueous phase was made basic with NaOH, extracted with 2×50 mL CH2Cl2, and the extracts pooled and the solvent removed under vacuum to yield a residue of a colorless oil. This was distilled at 160–170 °C at 1.0 mm/Hg yielding 2.6 g of a colorless liquid. This was dissolved in 12 mL IPA, neutralized with 24 drops of concentrated HCl and diluted with 25 mL anhydrous Et2O. The clear solution was decanted from a little solid material, and the decantings diluted with a further 50 mL anhydrous ether. The still clear solution became cloudy after a few min, and then there was the slow formation of 3-ethylthio-4,5-dimethoxyphenethylamine hydrochloride (3-TME) as a fine white crystalline product. Removal by filtration, washing with Et2O, and air drying yielded 2.8 g of white gran-ular solids that melted at 171–172 °C. Anal. (C12H20ClNO2S) C,H.
DOSAGE: 60–100 mg.
DURATION: 10–15 h.
QUALITATIVE COMMENTS: (with 60 mg) “As important as the experience was, itself, I feel that it was in the two or three days that followed that it had the most profound impact on me. It was at the time of the death of my wife’s mother, and I found that I could look directly towards death and its ramifications. Including my own death. I felt very close to the Higher Powers that seemed to make their presence felt all around. And there was still the deep internal strength that was the direct product of the 3-TME experience. I feel it very strongly, still, but I have no desire to repeat the experience right away. It is almost as if the effects are still in evidence, and one should take one’s time in letting it manifest all its ramifications. But it is certainly an experience one should have once a year, if not oftener.”
(with 100 mg) “I was aware of the development quite early, and by the end of an hour and a half, I was in quite a remarkable state. I was extremely disinhibited, with easy verbal play and easily self-revealing, but not at too deep a level. There was great fun with a set of water colors but, when a used Kleenex became my canvas, the others failed to share my humor. I drove home at midnight with considerable care and was unable to sleep for another two hours. I would be very willing to repeat this experiment, at this level, to see if the good humor of it all was a consistent property.”
(with 100 mg) “I had a sudden revelation—what I called the wet-paint theory of Christ. How does one find and identify the Messiah? It is most simple. All of life is nothing more than a freshly painted fence separating us from the rest of the world. And the fence has many, many signs on it that say: Beware. Don’t Touch. Wet Paint. And if you touch too soon, indeed you get a dirty finger because the paint really is still wet. But the very first man to touch it and find it dry? There is your natural leader, your Son of God, and all those who touch later than He are the followers of the leader who first touched and found the paint dry.”
EXTENSIONS AND COMMENTARY: A short unraveling of the codes used here for the various materials is very much needed. There are 3’s and 4’s and M’s and I’s and incipient confusion. is . That much is simple. All homologs are the first letter of the homolog. is E, is P, etc. If the group is at the three-position, then the term “meta” is used and an M preceeds the name of the homolog, i.e., is . The number (3- or 4- or 5-) gives the position of the sulfur, which is represented by the prefix “Thio” so this compound, 3-TME, has the sulfur at the 3-position, and by chance, the ethyl group there as well.
Here is a brief presentation of the needed Rosetta Stone:
Number of
ethyl groups
all three are
oxygen atoms
One oxygen is re-
placed with sulfur
none
one
3-TME
two
three
13 May 2016 · Creative Commons BY-NC-SA ·

About PiHKAL · info

This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also 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 PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering information

PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. 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 PiHKAL 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.
PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.
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