SYNTHESIS: To a solution of 165 g 1,4-dimethoxybenzene in 1 L of
CH2Cl2, in a well ventilated place and well stirred, there was
cautiously added 300 mL chlorosulfonic acid. With about half the acid
chloride added, there was a vigorous evolution of HCl gas and the
generation of a lot of solids. As the addition was continued, these
redissolved to form a clear, dark green solution. Towards the end of
the addition, some solids were again formed. When everything was
stable, there was added 2 L H2O, a few mL at a time, commensurate with
the vigor of the reaction. The two phases were separated, and the
aqueous phase extracted with 2x75 mL CH2Cl2. The original organic
phase and the extracts were combined and the solvent removed under
vacuum. The residue weighed 162 g and was quite pure
2,5-dimethoxybenzenesulfonyl chloride, a yellow crystalline solid with
a mp of 115-117 °C. It need not be further purified for the next
step, and it appears to be stable on storage. The sulfonamide, from
this acid chloride and ammonium hydroxide, gave white crystals from
EtOH, with a mp of 147.5-148.5 °C.
The following reaction is also a very vigorous one and must be
performed in a well ventilated place. To a solution of 400 mL 25%
H2SO4 (V/V) in a beaker at least 2 L in size, there was added 54 g of
2,5-dimethoxybenzenesulfonyl chloride, and the mixture was heated on a
steam bath. The yellow crystals of the acid chloride floated on the
surface of the aqueous layer. There should be 80 g of zinc dust at
hand. A small amount of Zn dust was placed at one spot on the surface
of this chapeau. With occasional stirring with a glass rod, the
temperature was allowed to rise. At about 60 or 70 °C an exothermic
reaction took place at the spot where the zinc was placed. Additional
dollups of zinc were added, and each small exothermic reaction site
was spread about with the glass stirring rod. Finally, the reaction
spread to the entire solid surface layer, with a melting of the acid
chloride and an apparent boiling at the H2O surface. The remainder of
the 80 g of zinc dust was added as fast as the size of the reaction
container would allow. After things subsided again, the heating was
continued for 1 h on the steam bath. After the reaction mixture had
cooled to room temperature, it was filtered through paper in a Buchner
funnel, and the residual metal washed with 100 mL CH2Cl2. The
two-phase filtrate was separated, and the lower, aqueous phase was
extracted with 2x75 mL CH2Cl2. The addition of 2 L H2O to the aqueous
phase now made it the upper phase in extraction, and this was again
extracted with 2x75 mL CH2Cl2. The organic extracts were pooled (H2O
washing is more trouble than it is worth) and the solvent removed
under vacuum. The light amber residue (30.0 g) was distilled at 70-80
°C at 0.3 mm/Hg to yield 25.3 g 2,5-dimethoxythiophenol as a white
oil. This chemical is certainly not centrally active, but it is a
most valuable precursor to all members of the 2C-T family.
To a solution of 3.4 g of KOH pellets in 75 mL boiling EtOH, there was
added a solution of 10.0 g 2,5-dimethoxythiophenol in 60 mL EtOH
followed by 10.9 g ethyl bromide. The reaction was exothermic with
the immediate deposition of white solids. This was heated on the
steam bath for 1.5 h, added to 1 L H2O, acidified with HCl, and
extracted with 3x100 mL CH2Cl2. The pooled extracts were washed with
100 mL of 5% NaOH, and the solvent removed under vacuum. The residue
was 2,5-dimethoxyphenyl ethyl sulfide which was a pale amber oil,
weighed about 10 g and which was sufficiently pure for use in the next
reaction without a distillation step.
A mixture of 19.2 POCl3 and 18.0 g N-methylformanilide was heated
briefly on the steam bath. To this claret-colored solution there was
added the above 2,5-dimethoxyphenyl ethyl sulfide, and the mixture
heated an additional 20 min on the steam bath. This was then added to
500 mL of well-stirred warm H2O (pre-heated to 55 °C) and the stirring
continued for 1.5 h by which time the oily phase had completely
solidified to a brown sugar-like consistency. The solids were removed
by filtration, and washed with additional H2O. After being sucked as
dry as possible, these solids were dissolved in 50 mL boiling MeOH
which, after cooling in an ice-bath, deposited almost-white crystals
of 2,5-dimethoxy-4-(ethylthio)-benzaldehyde. After filtration, modest
washing with cold MeOH, and air drying to constant weight, there was
obtained 11.0 g of product with a mp of 86-88 °C. Recrystallization
of a small sample again from MeOH provided an analytical sample with
mp 87-88 °C. Anal. (C11H14O3S) C,H.
To a solution of 11.0 g 2,5-dimethoxy-4-(ethylthio)benzaldehyde in 100
g of nitromethane there was added 0.5 g of anhydrous ammonium acetate,
and the mixture was heated on the steam bath for 80 min (this reaction
progress must be monitored by TLC, to determine the point at which the
starting aldehyde has been consumed). The excess nitromethane was
removed under vacuum leaving a residue that spontaneously set to
orange-red crystals. These were scraped out to provide 12.9 g crude
2,5-dimethoxy-4-ethylthio-beta-nitrostyrene with a mp of 152-154 °C. A
sample recrystallized from toluene was pumpkin colored and had a mp of
148-149 °C. Another sample from acetone melted at 149 °C sharp, and
was light orange. From IPA came spectacular fluorescent orange
crystals, with a mp 151-152 °C. Anal. (C12H15NO4S) C,H.
A suspension of 12.4 g LAH in 500 mL anhydrous THF was stirred under
He. To this there was added 12.4 g
2,5-dimethoxy-4-ethylthio-beta-nitrostyrene in a little THF, and the
mixture was held at reflux for 24 h. After the reaction mixture had
returned to room temperature, the excess hydride was destroyed by the
cautious addition of 60 mL IPA, followed by 20 mL of 5% NaOH followed,
in turn, by sufficient H2O to give a white granular character to the
oxides. The reaction mixture was filtered, and the filter cake washed
first with THF and then with MeOH. Removing the solvents from the
combined filtrate and washings under vacuum provided 9.5 g of a yellow
oil. This was added to 1 L dilute HCl and washed with 2x100 mL CH2Cl2
which removed all color. After making the aqueous phase basic with
25% NaOH, it was extracted with 3x100 mL CH2Cl2, the extracts pooled,
and the solvent removed under vacuum to provide 7.3 g of a pale amber
oil. Distillation at 120-130 °C at 0.3 mm/Hg gave 6.17 g of a clear
white oil. This was dissolved in 80 mL IPA and neutralized with
concentrated HCl, forming immediate crystals of
2,5-dimethoxy-4-ethylthiophenethylamine hydrochloride (2C-T-2). An
equal volume of anhydrous Et2O was added and, after complete grinding
and mixing, the salt was removed by filtration, washed with Et2O, and
air dried to constant weight. The resulting white crystals weighed
6.2 g.
DOSAGE: 12 - 25 mg.
DURATION: 6 - 8 h.
QUALITATIVE COMMENTS: (with 12 mg) I don't feel this for fully an
hour, but when I do it is quite a weight. It feels good to work it
through. It is OK to be with pain. You can't eliminate it. And it
is OK to contact your deep pools of anger. And all of it stems from
the lack of acknowledgment. All the macho carrying on, the fights,
the wars, are ways of demanding attention, and getting even for not
having had it in one's life. I am experiencing more deeply than ever
before the importance of acknowledging and deeply honoring each human
being. And I was able to go through and resolve some judgments with
particular persons.
(with 20 mg) I chose 2C-T-2 at this dose level because the lateness
of getting started, and I wanted a shorter experience with my daughter
and her family around. I feel, however, that I have somewhat less of
a body load with 2C-T-7. Today I was badly in need of the help that
might possibly come from this material, and today it was my ally. I
sorely needed the type of help that it afforded. The result was to
work off the heavy feeling of tiredness and lack of motivation that
had been hounding me. The next day I felt that I had dropped my
burden.
(with 20 mg) There is a neutralness to this. I am at the maximum,
and I am asking myself, 'Am I enjoying this?' And the answer is, 'No,
I am experiencing it.' Enjoyment seems beside the point. It is a
rather intensely matter-of-fact +3. Is it interesting? Yes, but
mostly in expectation of further developments. Is it inspiring? No.
Is it negative? No. Am I glad I took it? Yes. Not glad. Satisfied
and contented. This is a controlled +3. No threat. The body is all
right. Not superbly healthy--but OK. Of no interest, either way.
If I were to define the body's state, I would have to define it in
image. The image is of a not comfortable state of being clenched.
Clenched? Well, carefully bound in control.
(with 22 mg) A slow onset. It took an hour for a plus one, and
almost another two hours to get to a +++. Very vivid fantasy images,
eyes closed, but no blurring of lines between "reality" and fantasy.
Some yellow-grey patterns a la psilocybin. Acute diarrhea at about
the fourth hour but no other obvious physical problems. Erotic
lovely. Good material for unknown number of possible uses. Can
explore for a long time. Better try 20 milligrams next time.
(with 25 mg) I was at a +++ in an hour! It is most difficult to do
even ordinary things. I took notes but now I can't find them. This
is much too high for anything creative, such as looking at pictures or
trying to read. Talking is OK. And to my surprise I was able to get
to sleep, and a good sleep, at the seven hour point.
EXTENSIONS AND COMMENTARY: There is a considerable parallel between
2C-T-2 and 2C-T-7, and both have proven to be excellent tools for
introspection. The differences are largely physical. With 2C-T-2,
there is more of a tendency to have physical disturbances such as
nausea and diarrhea. And the experience is distinctly shorter. With
2C-T-7, physical disturbances are less common, but you are into the
effects for almost twice as long. Both have been frequently used in
therapy as follow-ups to MDMA.
A point of potential misidentification should be mentioned here.
2C-T-2 has occasionally been called, simply, T-2. This abbreviated
nickname has also been used for T-2 Toxin, a mycotoxin of the
Tricothecene group, formed mainly by the Fusarium spp. This is the
infamous "warfare agent" in Southeast Asia, which was finally
identified as bee feces rather than a Soviet military adventure. T-2
and 2C-T-2 are radically different compounds.
All three Tweetios of 2C-T-2 have been made and looked at through
human eyes. The 2-EtO-homologue of 2C-T-2 is
2-ethoxy-4-ethylthio-5-methoxyphenethylamine, or 2CT2-2ETO. The
benzaldehyde (2-ethoxy-4-ethylthio-5-methoxybenzaldehyde) had a
melting point of 73-75 °C, the nitrostyrene intermediate a melting
point of 122-123 °C, and the final hydrochloride a melting point of
202-204 °C. Fifty milligrams was a completely effective level. The
effects were felt very quickly. Vision was blurred, and there were
intense eyes-closed visuals and the generation of a pleasant,
contemplative mood. Baseline was re-established in five or six hours,
but sleep was restless, with weird dreams. Nasal administration
showed considerable variation between individuals, but a typical dose
was 10 milligrams.
The 5-EtO-homologue of 2C-T-2 is
5-ethoxy-4-ethylthio-2-methoxyphenethylamine, or 2CT2-5ETO. The
benzaldehyde (5-ethoxy-4-ethylthio-2-methoxybenzaldehyde) had a
melting point of 49 °C, but it was impure. The nitrostyrene
intermediate melted at 107-108 °C, and the final hydrochloride had a
melting point of 180 °C. At levels of 20 milligrams, there was a
slow, gentle climb to a full effect at the third or fourth hour. The
flooding of thoughts and easy conversation lasted for many hours, and
on some occasion a sedative was needed at the 16 hour point. There
was a feeling of being drained for the following day or two. Some
intoxication was still noted in the second day. Again it is true
here, as had been stated as a generality, that the 5-Tweetio analogues
have potencies similar to that of the parent compound, but show a much
longer duration. The nickname of "forever yours" had been applied.
There may indeed be insight, but 24 hours' worth is an awful lot of
insight.
The 2,5-DiEtO-homologue of 2C-T-2 is
2,5-diethoxy-4-ethylthiophen-ethylamine, or 2CT2-2,5DIETO. The
benzaldehyde, 2,5-diethoxy-4-(ethylthio)benzaldehyde, had a melting
point of 84-85 °C, the nitrostyrene intermediate a melting point of
123-124 °C, and the final hydrochloride a melting point of 220-221 °C.
Levels that were evaluated from 10 to 50 milligrams were not
particularly different in intensity, but were progressively longer in
duration. At 50 milligrams there was a nervousness and edginess
during the early part of the experience, but for the next several
hours there was evident both energy and high attentiveness. There
were few if any sensory alterations. There were no negatives on the
following day. The duration was perhaps nine hours.
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