SYNTHESIS: A solution of 2.3 g
2,5-dimethoxy-4-(methylthio)benzaldehyde (see under 2C-T for its
synthesis) in 7.5 mL nitroethane was treated with 0.45 g anhydrous
ammonium acetate and heated on the steam bath for 6 h. The excess
solvent/reagent was removed under vacuum leaving a mass of orange
crystals as residue. These were ground up under 10 mL MeOH,
col-lected by filtration, washed with a little MeOH, and air dried to
provide 2.6 g crude
1-(2,5-dimethoxy-4-methylthiophenyl)-2-nitropropene. After
recrystallization from 140 mL boiling MeOH, filtering and drying there
was in hand 1.8 g of bright orange crystals with a mp of 137-138 °C.
Anal. (C12H15NO4S) C,H,N,S.
A suspension of 1.4 g LAH in 10 mL anhydrous Et2O and 40 mL anhydrous
THF was put under an inert atmosphere and, with good stirring, brought
up to a gentle reflux. A solution of 1.8 g
1-(2,5-dimethoxy-4-methylthiophenyl)-2-nitropropene in 30 mL anhydrous
THF was added dropwise at a rate that maintained the reflux. Heating
and stirring were maintained for an additional 7 h, then the reaction
mixture was allowed to return to room temperature. There was added
1.6 mL H2O (dissolved in a little THF), followed by 1.6 mL 15% NaOH,
and finally another 4.8 mL H2O. Stirring was continued until all the
curdy solids had turned white. The reaction mixture was filtered, and
the filter cake washed with THF. The filtrate and the washings were
combined, and the solvent removed under vacuum. The residue was 1.3 g
of a colorless oil that solidified. Its mp of 90-93 °C was improved
slightly to 91-93 °C with recrystallization from hexane. The product
was dissolved in 25 mL warm IPA, neutralized with concentrated HCl
(0.57 mL required) and then diluted with 100 mL anhydrous Et2O. After
a moment's delay, the white crystalline product appeared. It was
removed by filtration, washed with Et2O, and air dried to provide 1.2
g 2,5-dimethoxy-4-methylthioamphetamine hydrochloride (ALEPH) with a
mp of 200-201 °C. Recrystallization from IPA gave an analytical
sample with a mp of 204-205 °C. Anal. (C12H20ClNO2S) C,H; N: calcd,
5.04; found, 5.52.
DOSAGE: 5 - 10 mg.
DURATION: 6 - 8 h.
QUALITATIVE COMMENTS: (with 5 mg) The initial hints of action were
physical--warming of first the legs, and then a comfortable warmth
spread over the entire body. Intense intellectual stimulation, one
that inspired the scribbling of some 14 pages of handwritten notes.
Which is a pretty good record for an experience that is almost
entirely non-verbal. The afterglow was benign and rich in empathy for
everything. And by the sixth hour I was quite hungry.
(with 10 mg) There was a rapid shift of frame of reference that made
simple tasks such as reading and tuning the radio quite alien. I
happened to catch the eyes of Pretty Baby, the cat, at the same moment
she looked at me, and she turned and fled. I am able to interact with
people on the telephone quite well but mechanical things, such as
arranging flowers or alphabetizing names, are beyond me. Driving
would be impossible.
EXTENSIONS AND COMMENTARY: This specific compound is probably the
first sulfur-containing phenethylamine to have been evaluated as a
potentially active CNS stimulant or psychedelic. It was a complete,
total, absolute unknown. The first trials were made at the
sub-microgram level, specifically at 0.25 micrograms, at 11:30 AM on
September 3, 1975. Part of this extreme precaution was due to the
uniqueness of a new heteroatom in a phenethylamine system. But part
was due to the strange manic excitement that occurred at the time of
the isolation and characterizing of the final product in the
laboratory. Although it was certainly all placebo response, I was
jumpy and unable to stay in the lab for more than a few minutes at a
time. Maybe dust in the air? Maybe some skin contact with the free
base? Now, I know there was nothing, but the possibility of
extraordinary potency was real, and I did indeed wash everything down
anyway. In fact, it took a total of 18 trials to work the
experimental dosage up to as much as a single milligram. In
retrospect, overly cautious. But retrospection, as they say, is
cheap.
The 5 milligram experiment, briefly quoted from above, is the stuff of
Chapter 14 of this book, important in that it gives an interesting
example of some thought processes associated with psychedelic
intoxication, ego-inflation, and what might be thought of as bits of
mania. As is always the case with peak experiences that happen to be
catalyzed by drugs, this extraordinary event could not be duplicated.
At 7 milligrams there was an uneventful +1, and some 10 milligrams was
needed to generate a full +3 experience. The first clue of the
erratic nature of the Aleph family came from an independent assay by a
colleague of mine, one who was very familiar with such states of
consciousness, but for whom this was not a time for peak experiences.
At 10 milligrams he told me that he had had only mild effects which he
found relatively uninteresting.
As it stands, ALEPH remains relatively unexplored. Its two positional
isomers are entered here as ORTHO-DOT and META-DOT. Three higher
homologues have been more thoroughly looked at, and the generic name
ALEPH (the first letter of the Hebrew alphabet) was given this group
on the basis that they might have extraordinary properties in common.
But the real treasure came in the exploring of the 2-carbon
homologues, the compounds that make up the 2C-T family. Here, there
proved to be much less uncertainty as to reasonable dosages, and much
more richness in the subjective nature of the experience.
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