SYNTHESIS: To a solution of 3.4 g of KOH pellets in 50 mL hot MeOH,
there was added a mixture of 6.8 g 2,5-dimethoxythiophenol (see under
the recipe for 2C-T-2 for its preparation) and 7.4 g (n)-propylbromide
dissolved in 20 mL MeOH. The reaction was exothermic, with the
deposition of white solids. This was heated on the steam bath for 0.5
h, added to 800 mL H2O, additional aqueous NaOH added until the pH was
basic, and extracted with 3x75 mL CH2Cl2. The pooled extracts were
washed with dilute NaOH, and the solvent removed under vacuum. The
residue was 2,5-dimethoxyphenyl (n)-propyl sulfide which was obtained
as a pale yellow oil, and which weighed 8.9 g. It had a light
pleasant fruity smell, and was sufficiently pure for use in the next
reaction without distillation.
A mixture of 14.4 g POCl3 and 13.4 g N-methylformanilide was heated
for 10 min on the steam bath. To this claret-colored solution was
added 8.9 g of 2,5-dimethoxyphenyl (n)-propyl sulfide, and the mixture
heated an additional 25 min on the steam bath. This was then added to
800 mL of well-stirred warm H2O (pre-heated to 55 °C) and the stirring
continued until the oily phase had completely solidified (about 15
minutes). The resulting brown sugar-like solids were removed by
filtration, and washed with additional H2O. After sucking as dry as
possible, they were dissolved in an equal weight of boiling MeOH
which, after cooling in an ice-bath, deposited pale ivory colored
crystals. After filtration, modest washing with cold MeOH, and air
drying to constant weight, there was obtained 8.3 g of
2,5-dimethoxy-4-(n-propyl-thio)benzaldehyde with a mp of 73-76 °C.
Recrystallization from 2.5 volumes of MeOH provided a white analytical
sample with mp 76-77 °C. The NMR spectrum in CDCl3 was textbook
perfect, with the two aromatic protons showing singlet signals at 6.81
and 7.27 ppm, giving assurance that the assigned location of the
introduced aldehyde group was correct.
To a solution of 4.0 g 2,5-dimethoxy-(n-propylthio)benzaldehyde in 20
g of nitromethane there was added 0.23 g of anhydrous ammonium
acetate, and the mixture was heated on the steam bath for 1 h. The
clear orange solution was decanted from some insoluble material and
the excess nitromethane removed under vacuum. The orange-yellow
crystalline material that remained was crystallized from 70 mL boiling
IPA which, on slow cooling, deposited
2,5-dimethoxy-beta-nitro-4-(n)-propylthiostyrene as orange crystals.
After their removal by filtration and air-drying to constant weight,
they weighed 3.6 g, and had a mp of 120-121 °C. Anal. (C13H17NO4S)
C,H.
A solution of LAH (132 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 3.5 mL 100% H2SO4 dropwise, to minimize charring. This was
followed by the addition of 8.4 g
2,5-dimethoxy-beta-nitro-4-(n)-propylthiostyrene in 50 mL anhydrous THF.
There was an immediate loss of color. 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 IPA (21 mL required) followed by
sufficent 5% NaOH to give a white granular character to the oxides,
and to assure that the reaction mixture was basic (15 mL was used).
The reaction mixture was filtered and the filter cake washed first
with THF and then with IPA. The filtrate and washes were combined and
stripped of solvent under vacuum providing about 6 g of a pale amber
oil. Without any further purification, this was distilled at 140-150
°C at 0.25 mm/Hg to give 4.8 g of product as a clear white oil. This
was dissolved in 25 mL IPA, and neutralized with concentrated HCl
forming immediate crystals of the hydrochloride salt in the alcohol
solvent. An equal volume of anhydrous Et2O was added, and after
complete grinding and mixing,
2,5-dimethoxy-4-(n)-propylthiophenethylamine hydrochloride (2C-T-7)
was removed by filtration, Et2O washed, and air dried to constant
weight. The resulting spectacular white crystals weighed 5.2 g.
DOSAGE: 10 - 30 mg.
DURATION: 8 - 15 h.
QUALITATIVE COMMENTS (with 20 mg) A wonderful day of integration and
work. Took about 2 hours for the onset. Some nausea on and off--
that seemed to cycle periodically throughout the day. Visuals were
great, much like mescaline but less sparkly. Lots of movement and
aliveness--velvety appearance and increased depth perception. Neck
and shoulder tension throughout the day along with legs. I would
periodically notice extreme tightness of muscles, and then relax.
Working was very integrative. Back and forth constantly between
wonderful God-space--similar to MDMA but more grounded--then always
back to sadness. I felt that it really showed me where I was
unfinished, but with self-loving and tolerance. Tremendous processing
and letting go. Seeing things very clearly and also able to laugh at
my trips. Lots of singing. In spite of shoulder tension, vocal
freedom and facility were very high. I felt my voice integrated and
dropped in a way it never had before, and that remained for several
days. Able to merge body, voice, psyche and emotions with music and
then let go of it as a role. I also realized and gave myself
permission to do whatever it takes to get free. I let go of Dad with
tragic arias. The next day I let go of Mom by singing Kaddish for
her, and merging with it.
(with 20 mg) I lay down with music, and become engrossed with being
as still as possible. I feel that if I can be totally, completely
still, I will hear the inner voice of the universe. As I do this, the
music becomes incredibly beautiful. I see the extraordinary
importance of simply listening, listening to everything, to people and
to nature, with wide open receptivity. Something very, very special
happens at the still point, so I keep working on it. When I become
totally still, a huge burst of energy is released. And it explodes so
that it takes enormous effort to quiet it all down in order to be
still again. Great fun.
(with 25 mg) This was a marvelous and strange evening. This 2C-T-7
is good and friendly and wonderful as I remember it. I think it is
going to take the place of 2C-T-2 in my heart. It is a truly good
material. I got involved with a documentary on television. It was
about certain people of Bolivia, people living in the high mountains
and about a small village which--perhaps alone among all the places
in the country--maintains the old Inca ways, the old traditions, the
old language. Which is, I gather, against the law in Bolivia. It
showed a yearly meeting of shamans and it was quite clear that
hallucinogens played a major part in this meeting. The shaman faces,
male and female, were startling in their intensity and earthy depth.
The Virgin Mary is worshipped as another version of the ancient Pacha
Mama, the Earth Mother. Wonderful dark, vivid look at places and
people who are not usually to be seen or even known about.
(with 30 mg) The visuals have an adaptable character to them. I can
use them to recreate any hallucinogenic substance I have known and
loved. With open eyes, I can go easily into LSD flowing visuals, or
into the warm earth world of Peyote, or I can stop them altogether.
With closed eyes, there are Escher-like graphics with a lot of
chiaroscuro, geometric patterns with oppositional play of sculptured
light and dark values. Green light.
EXTENSIONS AND COMMENTARY: If all the phenethylamines were to be
ranked as to their acceptability and their intrinsic richness, 2C-T-7
would be right up there near the top, along with 2C-T-2, 2C-B,
mescaline and 2C-E. The range is intentionally extended on the lower
side to include 10 milligrams, as there have been numerous people who
have found 10 or so milligrams to be quite adequate for their tastes.
One Tweetio related to 2C-T-7 has been made and evaluated. This is
the 2-EtO-homologue of 2C-T-7,
2-ethoxy-5-methoxy-4-(n)-propylthiophenethyl-amine, or 2CT7-2ETO. The
benzaldehyde (2-ethoxy-5-methoxy-4-(n-propyl-thio)benzaldehyde had a
melting point of 69-71 °C, the nitrostyrene intermediate a melting
point of 106-106.5 °C, and the final hydrochloride a melting point of
187-189 C!. At the 20 milligram level, the effects were felt quickly,
and the eyes-closed visuals were modest but real. It was very
short-lived, with baseline recovery at about the fifth hour. The next
day there was an uncomfortable headache which seemed on an intuitive
level to be an after-effect of the compound.
The unusual properties of a number of N-methyl-N-(i)-propyltryptamines
suggested the possibility of something like a similar set of
N-methyl-N-(i)-propylphenethylamines. Why not try one from 2C-T-7?
The thought was, maybe N-methylate this compound, then put on an
isopropyl group with reductive alkylation, using acetone as the carbon
source and sodium cyanoborohydride. Towards this end, the free base
of 2C-T-7 (from one gram of the hydrochloride) was refluxed for 2 h in
1.3 g butyl formate, and on removing the solvent/reactant the residue
spontaneously crystallized. This formamide (0.7 g) was reduced with
lithium hydride in cold THF to provide
2,5-dimethoxy-4-(n)-propyl-N-methyl-phenethylamine, METHYL-2C-T-7,
which distilled at 150-170 °C at 0.4 mm/Hg. A very small amount of
the hydrochloride salt was obtained (65 milligrams) and it had a brown
color. Too small an amount of an impure product; the entire project
was dropped.
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