This is a recipe from
PiHKAL. If you're interested in how the hardlinks
were chosen, read
noding PiHKAL for Everything2.
#39 2C-T
2,5-DIMETHOXY-4-METHYLTHIOPHENETHYLAMINE
SYNTHESIS: A
solution of 149 g
sodium thiosulfate in 300 mL H2O was
vigorously stirred. To this there was added, over the course of 10
min, a
solution of 43.2 g
benzoquinone in 200 mL acetic acid. After
an additional 1 h stirring at room tem
perature, all
volatiles were
removed under vacuum. The
residual syrup slowly set up as
crystals
which, after grinding under brine, were removed by filtration and
washed with additional brine. These were
dissolved in MeOH, clarified
by filtration through a Celite bed, and the clear filtrate stripped of
solvent under vacuum. The yellow, powdery
sodium
2,5-hydroxyphenylthiosulfate weighed 67 g when dry. This intermediate
was
dissolved in aqueous HCl (50 g in 200 mL H2O containing 400 mL
concentrated HCl), cooled with an external ice bath, and treated with
250 g
zinc dust added at a rate that kept the tem
perature below 60 °C.
About 1.5 h were required, and caution must be taken concerning the
poisonous hydrogen
sulfide that evolves. An additional 50 mL
concentrated HCl was added, and the aqueous
phase decanted from the
unreacted
zinc metal. This was extracted with 6x100 mL
Et2O, and
these extracts were pooled, washed with brine, and the
solvent removed
under vacuum to yield 33.1 g of
2,5-dihydroxythiophenol as pale yellow
needles with a mp of 118-119 °C.
A
solution of 118.6 g KOH pellets in 200 mL H2O was placed under N2,
and to it was added 24.0 g
2,5-dihydroxythiophenol. With vigorous
stirring, there was then added 160 g
methyl sulfate at a rate that
maintained the tem
perature at about 60 °C. This took about 2 h.
After the addition was complete, the mixture was held at reflux for 3
h, and allowed to stir at ambient tem
perature overnight. It was then
filtered, and the filtrate extracted with 6x100 mL
Et2O, the extracts
pooled, washed with 2x50 mL brine, dried over
anhydrous Na2SO4, and
the
solvent removed under vacuum. The residue was
distilled at 86-88
°C at 0.04 mm/
Hg to provide 25.9 g of
2,5-dimethoxythioanisole as a
white oil that
crystallized on standing. Its mp was 33-34 °C. An
alternate preparation of this compound follows the direct
methylation
of
2,5-dimethoxythiophenol (see under
2C-T-2 for the preparation of
this common intermediate) with
methyl iodide.
To 40 mL dry
CH2Cl2 there was added 6.07 g
2,5-dimethoxythioanisole,
and this was cooled to 0 °C under N2. To this well stirred
solution
there was added 13.02 g stannic
chloride over the course of 2 min.
This was followed by the drop-wise addition of
dichloromethyl methyl
ether over 5 min, and the reaction mixture allowed to stir for an
additional 15 min. After returning to room tem
perature, it was
stirred for an additional 1 h. The reaction mixture was poured over
15 g ice, and the organic
phase separated, washed with 3x25 mL 3 N
HCl, with 3x50 mL brine and, after drying over
anhydrous Na2SO4, the
solvent was removed under vacuum. The residue was a solid and, after
re
crystallization from MeOH/H2O, gave 5.86 g
2,5-dimethoxy-4-(methylthio)benzaldehyde with a mp of 95-97 °C.
Purification via the
bisulfite complex provided an
analytical sample
with mp of 99-100 C. Anal. (
C10H12O3S) C,H,S. The
malononitrile
derivative (from equal weights of the
aldehyde and
malononitrile in
EtOH with a drop of
triethylamine as
catalyst) was re
crystallized from
an equal volume of
EtOH to give orange
crystals with a mp of 185-186
°C. Anal. (
C13H12N2O2S) C,H,N,S.
A
solution of 2.1 g
2,5-dimethoxy-4-(methylthio)benzaldehyde in 7.5 mL
nitromethane was treated with 0.45 g
anhydrous ammonium acetate and
held at steam bath tem
perature for 6 h. The deep red
solution was
stripped of
solvent to give a residue that spontaneously
crystallized.
This was ground up under 12 mL MeOH, filtered, and washed with MeOH to
yield, after air-drying, 1.7 g of
2,5-dimethoxy-4-methylthio-beta-nitrostyrene as orange solids.
Re
crystallization from
EtOH provided rust-orange colored crystals with
a mp of 165.5-166 °C. Anal. (
C11H13NO4S) C,H,N; S: calcd, 12.56;
found, 11.96.
To a gently refluxing mixture of 1.4 g LAH in 40 mL
anhydrous THF
under an inert
atmosphere there was added, dropwise, 1.7 g
2,5-dimethoxy-4-methylthio-beta-nitrostyrene in 25 mL THF. The refluxing
was continued for 18 h, and the stirring continued for another day at
room tem
perature. There was then added 1.5 mL H2O (diluted with a
little THF), 1.5 mL 15%
NaOH, and finally 4.5 mL H2O. The white
aluminum oxide salts were removed by filtration, and the filter cake
washed with THF. The filtrate and washings were combined and stripped
of
solvent under vacuum yielding a straw-colored residue that
crystallized (mp 81-92 °C without purification). This residue was
dissolved in 25 mL IPA and neutralized with concentrated HCl. The
slightly pink
solution spontaneously
crystallized. There was added
100 mL
anhydrous Et2O, and the white
crystalline mass of
2,5-dimethoxy-4-methylthiophenethylamine hydrochloride (2C-T) was
removed by filtration, washed with
Et2O, and air dried. The final
weight was 1.0 g, and had a mp of 232-237 °C. Re
crystallization from
EtOH provided an
analytical sample with mp 240-241 °C. IPA was not a
good re
crystallization
solvent. Anal. (C11H18ClNO2S) C,H,N,S.
DOSAGE: 60 - 100 mg.
DURATION: 3 - 5 h.
QUALITATIVE COMMENTS: (with 60 mg) Poetry was an easy and natural
thing. Both the reading of it and the writing of it. This is a
potential
MDMA substitute since it opens things up but it doesn't do
anything to get in the way.
(with 75 mg) I am already aware at a quarter of an hour into it! It
develops very quickly but very quietly. There are no visuals at all
but, rather, a
tactile sensitivity, with warm close feelings. This
could be very erotic. There is some fantasy to music, but nothing
very demanding. The viewing of pictures doesn't do much either. The
drop-off was extremely relaxed, with a good body feeling. At the
fifth hour I was able to drift into an excellent, deep sleep with busy
dreams. In the morning I felt refreshed and active, without apparent
deficit.
(with 75 mg) I got up to a thin and fragile plus two, but there was a
continuing feeling of a hooded cloak brought down over my head.
Nothing obvious--it is
transparent--but it somehow separated me from
everything around me. I do not think the overall experiment was worth
it.
(with 100 mg) Material all right, but a little bit along the lines of
a 'generic'
psychedelic effect. Sharper edges than
2C-B. The one
true negative, which has been pretty consistent with this drug, is
that there is a certain emotional removal. One teeny step removed.
One is connected with feelings, certainly, but there is a tendency for
the intellect to be more evident, in me, than the heart. All this is
moderately so. Nothing extreme. Pretty good material, but there are
more inter-esting ones. However, if you are looking for a really
short one, this is one of the answers. For most people. For me, it's
still around 5 to 6 hours long. I wish we had more shorties, indeed.
(with 125 mg) There was some physical tummy uncertainty, but once
that was past, talking was extremely easy. This is probably really
psychedelic, but I am not really sure why, as there is not much in the
way of visuals. Dropping was noted just after hour number three, and
I was at baseline three hours later.
EXTENSIONS AND COMMENTARY: The earliest work with the
sulfur atom was
with the three-
carbon chain materials, the ALEPHs. It was only after
a considerable time of working with them, and trying to come to peace
with their property of being so different from person to person as to
potency, that the two-
carbon homologues were looked at. Although the
first of these (this compound, called 2C-T) was prepared at the same
time as ALEPH-1, there was a lapse of about four years between their
trials. The relatively low potency of 2C-T was a bit discouraging.
But the
methodical pursuit of the higher 2C-T's (to parallel the
higher ALEPHs) proved to be a treasure house, and they have been
explored much further than any of the ALEPHs.
A note on the RTS in 2C-T. Many, in fact most, of the 2C's have their
name based on the last letter of the
amphetamine prototype.
2C-B from
DOB,
2C-C from DOC,
2C-I from DOI,
2C-N from DON, etc. And since the
original name for ALEPH-1 was DOT (the desoxy- and a
thiomethyl group
at the 4-position), the 2C-T naming followed this general pattern.
And as a note on the subsequent numbering, they (both the ALEPHs and
the 2C-T's) are assigned numbers as they are thought up. There is no
structural significance in the number but they have been, like the
houses on the streets in residential Tokyo, assigned numbers in strict
historical order, documenting the sequence of construction rather than
the relative position down the side of the street.
Both of the
homologous mono-ethoxy Tweetios of 2C-T have been
synthesized and evaluated. The 2-
EtO-
homologue of 2C-T is
2-ethoxy-5-methoxy-4-methylthiophenethylamine, or
2CT-
2ETO. The
benzaldehyde (
2-ethoxy-5-methoxy-4-(methylthio)benzaldehyde) was an
oil, the
nitrostyrene intermediate had a melting point of 137-138 °C,
and the final
hydrochloride a melting point of 215-216 °C. The
effects were felt very quickly, and there was a blurring of vision.
However, the highest dose tried, 50 milligrams, was not able to
produce a greater-than-plus one state, and what did occur, lasted for
only 4 hours.
The 5-
EtO-
homologue of 2C-T is
5-ethoxy-2-methoxy-4-methylthio-phenethylamine, or
2CT-
5ETO. The
benzaldehyde (
5-ethoxy-2-methoxy-4-(methyl-thio)benzaldehyde) was
impure, and had a melting point of about 66 °C, the
nitrostyrene
intermediate a melting point of 133-134 °C, and the final
hydrochloride a melting point of 184-185 °C. There was a body
awareness and modest eyes-closed visuals following the use of 30
milligrams of
2CT-
5ETO. The experience was quiet, peaceful,
contemplative, and insightful. The duration was perhaps 15 hours and
Halcion was needed to allow sleep. There were a lot of dreams, and
the next day was restful.
Back to PiHKAL?