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#44 2C-T-8
2,5-DIMETHOXY-4-CYCLOPROPYLMETHYLTHIOPHENETHYLAMINE
SYNTHESIS: To a
solution of 2.8 g of KOH pellets in 25 mL hot MeOH,
there was added a mixture of 5.9 g
2,5-dimethoxythiophenol (see under
2C-T-2 for its preparation) and 5.0 g of
cyclopropylmethyl bromide.
There was an immediate exothermic reaction with spontaneous boiling
and the formation of white
crystals. This was heated on the steam
bath for 4 h, and then added to 400 mL of H2O. After extraction with
3x75 mL
CH2Cl2, the pooled extracts were washed first with dilute
NaOH, then with saturated brine, then the
solvent was removed under
vacuum. The residue, 8.45 g of crude
2,5-dimethoxyphenyl cyclopropyl
methyl sulfide, was
distilled at 120-140 °C at 0.3 mm/
Hg to give a
white oil weighing 7.5 g.
A mixture of 13.5 g POCl3 and 13.5 g N-
methylformanilide was heated
for 10 min on the steam bath. To this claret-colored
solution was
added 7.28 g of
2,5-dimethoxyphenyl cyclopropylmethyl sulfide, and the
spontaneously exothermic mixture was heated for an additional 10 min
on the steam bath, and then quenched in 400 mL of 55 °C H2O with good
stirring. After a few minutes a reddish solid
phase separated. This
was removed by filtration, and washed with additional H2O. After
sucking as dry as possible, this 8.75 g of ochre-colored solid was
dissolved in 14 mL of boiling MeOH, and after cooling, filtering,
washing sparsely with MeOH, and air drying, gave 7.27 g of white solid
crystals of
2,5-dimethoxy-4-(cyclopropylmethylthio)benzaldehyde. The
proton
NMR spectrum was impeccable; CHO 9.38, ArH 7.27, 6.81 2 s.,
O
CH3 3.93, 3.90 2 s., S
CH2 t. 2.96, CH2, m. 1.72, and CH2, t. 1.11.
To a
solution of 6.6 g
2,5-dimethoxy-4-(cyclopropylthio)benzaldehyde
in 82 g of
nitromethane there was added 0.12 g of
anhydrous ammonium
acetate, and the mixture was heated on the steam bath for 6 h. The
reaction mixture was allowed to stand overnight producing a heavy
crystallization crop. Filtration, washing lightly with MeOH, and air
drying gave 4.72 g of orange
crystals of
2,5-dimethoxy-4-cyclopropylmethylthio-beta-nitrostyrene as yellow
crystals. The
evaporation of the mother liquors and grinding of the
resulting solids with MeOH provided another 2.0 g of the product.
A
solution LAH (40 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
1.05 mL 100% H2SO4 dropwise over 10 min, to minimize charring. This
was followed by the addition of 2.95 g
2,5-dimethoxy-4-cyclopropylmethylthio-beta-nitrostyrene as a solid, over
the course of 10 min. After a few min further stirring, the
tem
perature was brought up to a gentle reflux on the steam bath, then
all was cooled again to 0 °C. The excess
hydride was destroyed by the
cautious addition of 6 mL IPA followed by 3 mL 15%
NaOH which gave the
aluminum oxide as a curdy white solid. The reaction mixture was
filtered, and the filter cake washed with additional THF. The
filtrate and washes were stripped of
solvent under vacuum providing
about 1.8 g of a colorless oil. The addition of dilute H2SO4 produced
a thick mass of white solids. This was washed with
CH2Cl2, and the
remaining aqueous
phase, still containing solids, was made basic with
25%
NaOH. The aqueous
phase was extracted with 3x75 mL
CH2Cl2, and
the combined extracts stripped of
solvent under vacuum. The result
was 1.4 g of colorless oil. This was
distilled at 150-165 °C at 0.2
mm/
Hg to give 1.2 g of a white oil. This was
dissolved in 6 mL IPA,
neutralized with 0.6 mL concentrated HCl producing spontaneous white
crystals. These were diluted with 8 mL additional IPA, and suspended
under 60 mL
anhydrous Et2O to provide, after filtering and air drying,
1.13 g of
2,5-dimethoxy-4-cyclo-propylmethylthiophenethylamine
hydrochloride (2C-T-8) as white
crystals.
DOSAGE: 30 - 50 mg.
DURATION: 10 - 15 h.
QUALITATIVE COMMENTS: (with 30 mg) Bad taste, worse smell. But I
like it. I can paint easily, and wouldn't hesitate to take a little
more next time, but this is enough with no one to talk to. Manual
dexterity good. Body rather warm. Wouldn't mind fooling around. In
retrospect, it has a smooth onset, and is not too stimulating. This
is a good one.
(with 40 mg) This is beginning to develop at one and a half hours
into it. High energy, good feeling. I have had a heavy, dense
feeling between me and my work for several days now, but this is
rapidly dissolving, and with this loss, the day continues into one of
the most remarkable experiences I have ever had. Excellent feelings,
tremendous opening of insight and understanding, a real awakening as
if I had never used these materials effectively before. For the next
several hours it was an internal journey for me; I wished to interact
with myself. I cannot recall all the details, but I did review many
aspects of myself and my personal relations. I know that I am the
better for all of this.
(with 40 mg) I first noted the effects at three quarters of an hour,
and at two hours I have pain in my sinuses. My head is split in two--
this is not being two or three different people--this is one person
with a head living in two different universes at the same time. Not a
crisis experience, but one of extreme and prolonged discomfort.
Hypersensitivity to light, noise, motion, with the belief that it
would not go away when the chemical wore off. My visual and spatial
perceptions were divided in two along a vertical axis, with both
halves moving in uncoordinated ways. A feeling that the eyes were
working independently of each other. Nausea without vomiting, even
when I tried to. Vertigo became intolerable if I closed my eyes or
lay down, so I felt that I would never lie down or close my eyes
again. Problems with 'boundaries.' The outside environment seemed to
be getting inside my head. The parts of myself seemed to either
separate uncontrollably or run tog
ether into someone I didn't know. A
late movie, and
Tranxene, and a little sleep all helped me out of
this. However, a buzzing in the head, an uncertain balance, and an
out-of-it feeling lasted for 3 days, and was still faintly present
after a week.
(with 43 mg) For the first two hours I rocked in place and felt quite
happy not trying to 'do' anything useful or expected, but watched some
excellent programs on TV. Later I sat at the typewriter and felt the
energy and the opening of the particular kind of thinking-connection
that I associate with
2C-T-2. I felt this very strongly; I was fully
into my own energy and capable of being aggressive if I decided to. I
was very good humored and completely anchored to the earth. In the
late evening I went to bed and felt that I would not allow myself to
sleep, since the tendency to go completely out of conscious body was
quite strong. However, before I could get up and continue happily
writing, as I intended, I fell asleep. I slept thoroughly, well, and
woke up the next day with good energy and a willingness to get on with
the day.
(with 50 mg) The whole experience was somewhat negative,
self-doubting, paranoid. Basically, I am not in a good place. No
constructive values ever knit, and although there was a lot of
talking, nothing positive developed. I was glad of sleep at about
twelve hours into it, and this aspect of it was completely friendly.
Next day, no deficit. Strange. Maybe too much.
EXTENSIONS AND COMMENTARY: With 2C-T-8, there are as many negatives as
there are positives, and the particular
substitution pattern is not
one to set the world on fire. The first step was made towards the
synthesis of the 3-
carbon counterpart,
2,5-dimethoxy-4-cyclopropylmethylthioamphetamine, ALEPH-8. The above
benzaldehyde (2.2 g) was cooked overnight on the steam bath in
nitroethane (20 mL) containing
ammonium acetate (0.4 g) and when the
solvent was removed, the residue was converted to orange
crystals by
the addition of a little MeOH. This was not pursued further.
Although the
cyclopropylmethyl group was quite something on the
mescaline oxygen atom, it is less appealing on the 2C-T-X
sulfur atom,
and there is even less enthusiasm to put it into an ALEPH. That's the
way it is, and who could have guessed!
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