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#163 3-TME
3-THIOMETAESCALINE; 4,5-DIMETHOXY-3-ETHYLTHIOPHENETHYLAMINE)
SYNTHESIS: A
solution of 13.0 g of
3-bromo-N-
cyclohexyl-4,5-
dimethoxybenzylidenimine (see under MP 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 tem
perature. 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 2x50
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 in
solubles, and allowed to cool to room
tem
perature. 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-beta-nitrostyrene was
removed by filtration and, after air drying, weighed 3.2 g with a mp
of 96-98 °C. Upon re
crystallization 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-beta-nitrostyrene in 15 mL
anhydrous THF. At the end of the addition, the reaction mixture was
returned to room tem
perature, 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
2x50 mL
CH2Cl2. The aqueous
phase was made basic with
NaOH, extracted
with 2x50 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.
Mescaline is mescaline.
That much is simple. All
homologs are the first letter of the
homolog. Escaline is E, Proscaline 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., ME is Metaescaline. 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 all three are One oxygen is re-
ethyl groups oxygen atoms placed with sulfur
none M 3-TM
4-TM
one E 3-TE
4-TE
ME 3-TME
4-TME
5-ME
two SB 3-TSB
4-TSB
ASB 3-TASB
4-TASB
5-TASB
three TRIS 3-T-TRIS
4-T-TRIS
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