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#41 2C-T-4
2,5-DIMETHOXY-4-(i)-PROPYLTHIOPHENETHYLAMINE
SYNTHESIS: To a
solution of 2.5 g of KOH pellets in 40 mL hot
EtOH,
there was added 5.4 g
2,5-dimethoxythiophenol (see under
2C-T-2 for
its preparation) and 8.7 g
isopropyliodide. White solids appeared in
a few min, and the reaction mixture was heated on the steam bath
overnight. This mixture was added to 200 mL H2O followed by
additional aqueous
NaOH to raise the
pH to a deep purple-blue on
universal
pH paper. This was extracted with 3x75 mL
CH2Cl2. The
pooled extracts were stripped of
solvent under vacuum, and the residue
distilled at 100-110 °C at 0.2 mm/
Hg to yield 6.9 g of
2,5-dimethoxyphenyl isopropyl sulfide as a pale yellow oil. It has a
very light, pleasant smell of apples.
A mixture of 4.8 g POCl3 and 4.5 g N-
methylformanilide was stirred and
allowed to stand at room tem
perature for 1 h To this claret-colored
solution was added 3.0 g of
2,5-dimethoxyphenyl isopropyl sulfide,
producing an exothermic reaction and immediate reddening. This was
heated for 0.5 h on the steam bath, then quenched in 200 mL of warm
H2O producing immediate
crystals. Stirring was continued for a few
min, and then the solids were removed by filtration, washed with H2O
and sucked as dry as possible. When they were ground up under an
equal weight of cold MeOH, refiltered and air dried, they gave 2.35 g
of
2,5-dimethoxy-4-(i-propylthio)benzaldehyde as pale yellow solids
(in some runs this was a pale lime-green color) with a mp of 89-90 °C.
A wasteful re
crystallization from MeOH gave pale yellow crystals with
a mp of 90 °C sharp.
To a
solution of 6.7 g
2,5-dimethoxy-(i-propylthio)benzaldehyde in 40
g of
nitromethane there was added 0.10 g of
anhydrous ammonium
acetate, and the mixture was heated on the steam bath for 2 h. The
excess reagent/
solvent was removed under vacuum yielding 8.9 g of
orange solids. This was re
crystallized from 200 mL boiling MeOH
providing 6.2 g of
2,5-dimethoxy-beta-nitro-4-(i-propyl-thio)styrene as
lustrous golden orange platelets.
A
solution of LAH (80 mL of a 1 M solution in THF) was cooled, under
He, to 0 °C with an external ice bath. With good stirring there was
added 2.1 mL 100% H2SO4 dropwise, to minimize charring. This was
followed by the addition of 5.74 g
2,5-dimethoxy-beta-nitro-4-(i-propylthio)styrene as a solid, a bit at a
time. After 15 min further stirring, the tem
perature was brought up
to a gentle reflux on the steam bath for another 15 min, then allowed
to stand at room tem
perature overnight. After cooling again to 0 °C,
the excess
hydride was destroyed by the addition of 7 mL IPA followed
by 6 mL 15%
NaOH which was sufficent to give a white granular
character. The reaction mixture was filtered and the filter cake
washed with THF. The filtrate and washings were pooled, stripped of
solvent under vacuum providing 3.9 g of a pale amber oil which was
dissolved in 250 mL dilute H2SO4. This was washed with 3x75 mL
CH2Cl2
which removed the
residual yellow color. After making basic with 25%
NaOH, the product was extracted with 3x75 mL
CH2Cl2 and the
solvent
removed under vacuum to give 2.72 g of a residue which was
distilled
at 140-145 °C at 0.2 mm/
Hg to give 2.42 g of a clear white oil. This
was
dissolved in 25 mL IPA, and neutralized with concentrated HCl.
This gave a clear
solution which, with good stirring, was diluted with
100
anhydrous Et2O to provide 2.40 g
2,5-dimethoxy-4-(i)-propyl-thiophenethylamine hydrochloride (2C-T-4)
as white
crystals.
DOSAGE: 8 - 20 mg.
DURATION: 12 - 18 h.
QUALITATIVE COMMENTS: (with 8 mg) Visual effects set in at about two
hours. There was much color enhancement, particularly of green, and
some flowing of colors. The bright impressionistic picture of the
little girl, in the bathroom, was particularly good for the visuals to
take over, especially when I was concentrating on urinating. The
shadows in the large picture above the fireplace would change
constantly. I could not either control or turn off these effects
during the middle period (3-6 hours). From the physical point of
view, something early in the experience simply didn't feel right.
Both my lower legs tended to fall asleep, and this seemed to spread to
my hands and lower arms. It was uncomfortable and although I was
apprehensive at first it didn't get any worse with time so I ignored
it. This is not one my favorite materials, and it takes too long to
wear off. If I were to do it again I would settle for 4 or 5
milligrams. It may well cut out the extremity problem amd still allow
for a pleasant experience.
(with 9 mg) An important characteristic of this experience was the
sense of letting go and flowing with it. Just follow where it leads.
This seemed to lead to a growing
euphoria, a feeling of clearing out
of body residues, and the handling of very impressive insights. My
thinking continued to grow in clarity, visual perception was
crystal
clear, and it was a joy to simply look over the scenery, enjoy the
beauty, enjoy the companionship, and ponder whatever came to mind.
This clarity of body and mind lasted the rest of the evening with a
wonderful feeling of peace and centeredness. I still felt a lot of
push from the chemical at bed time, causing some tiredness, and
allowing very little sleep. I kept working at what had taken place,
all night, just to release the experience.
(with 14 mg) Very rational, benign, and good humored. The insight
and calm common to the 2C-T's are present, with less of the push of
body-energy which makes
2C-T-2 difficult for some people. There are
no particular visuals, but then I tend to screen them out
consistently, except in cases of mescaline and LSD and
psilocybin, so
I can't judge what others would experience in the visual area. The
eyes-closed imagery is very good without being compelling. The
decline is as gradual and gentle as the onset. I am fully capable of
making phone calls and other normal stuff. Music is marvelous, and
the body feels comfortable throughout.
(with 14 mg) Persistent cold feet, and an uncertain stomach when
moving around. Brilliant color trails
reminiscent of
2C-B. But a
change is occurring and I can't talk myself out of it. There are dark
corners. If I were with other people, this would bring out the worst
in me, which can be pretty bad.
(with 19 mg) I was caught by the TV. Leonard Bernstein conducting
West Side Story. I think I know every note. This was a 1985
rehearsal with the goofs and the sweat. And now Peter, Paul and Mary,
grown older along with the songs we all sang. Where Have All the
Flowers Gone--and an audience of grown-older people singing Puff the
Magic
Dragon like earnest children and probably crying along with me.
It is good to have lived through the 60's and not to be in them now.
Now there's a new song about El
Salvador and it's the battle all over
again on a different field, but it will always be so, until and
unless. Now, in the 80's, I don't get really angry anymore. I am
more warrior than angry
protester, and that's a much better way to be.
In fact, I am quite happy to be where I am. I know a lot more about
the game, and what it is, and why it is played, and I have a good idea
about my part in it, and I like the part I've chosen.
(with 22 mg) The transition took place over three hours, an alert in
30 minutes followed by a slow and gentle climb. I found it difficult,
not
physically but mentally since I was for a while locked into the
illogical and disconnected aspects of human experiences and
expressions, particularly laws and pronouncements and unseeing
prejudices, most of which I was picking up from reading the Sunday
paper book reviews. As time went on, things became less pushy and I
came to be at ease with very positive feelings about everything going
on. No self-rejecting aspect at all. Sleep was excellent, but the
next day things went slowly and I had to nap a bit. Next time, maybe
18 milligrams.
EXTENSIONS AND COMMENTARY: There are shades of the variability of the
Alephs. Some observers are overwhelmed with colors and visual
activity; others volunteer their absence. And a very wide range of
dosages represented, from an estimated 4 or so milligrams for full
effects, to something over 20 milligrams without any loss of control.
That is an unusually wide lattitude of activity. And a rich variety
of effects that might be experienced. The same wide range of
effective dosages was also observed with the corresponding Tweetio.
The 2-
EtO-
homologue of 2C-T-4 is
2-ethoxy-5-methoxy-4-(i)-propylthiophenethylamine, or
2CT4-
2ETO. The
benzaldehyde (
2-ethoxy-5-methoxy-4-(i-propylthio)benzaldehyde had a
melting point of 43-44 °C, the
nitrostyrene intermediate a melting
point of 77-79 °C, and the final
hydrochloride a melting point of
153.5-154 °C. There were practically no differences between trials at
5 milligram increments within the 10 and 25 milligram range. Each
produced a gentle plus two level of effect which lasted for some 10
hours. A code name of "tenderness" was felt to be appropriate, as
there was a peaceful meditative inner receptiveness and clarity noted,
with an honest connection felt with those who were present during the
experience. Sleep was not comfortable.
I have heard 2C-T-4 referred to as T-4. There is a potent explosive
used by terrorists called
cyclotrimethylenetrinitramine, known by the
code name RDX, or T-4. There is also a T-4 term that refers to
thyroxine, an amino acid in the body. The drug 2C-T-4 is neither an
explosive nor an amino acid, I am happy to say.
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