SYNTHESIS: To a solution of 19.7 g 2,5-dimethoxy-4-ethylbenzaldehyde
(see the recipe for 2C-E for its preparation) in 72 g glacial acetic
acid there was added 6.5 g anhydrous ammonium acetate and 10.2 g
nitroethane. After heating for 1.75 h on the steam bath, the reaction
mixture was cooled in a wet ice bath, diluted with 10 mL H2O, and
seeded with a small crystal of product. The yellow crystals were
removed by filtration (7.6 g wet with acetic acid) and another 2.25 g
was obtained from the mother liquors with additional H2O. The
combined fractions were recrystallized from 25 mL boiling MeOH, to
give 6.5 g fine yellow crystals of
1-(2,5-dimethoxy-4-ethyl)-2-nitropropene, with a mp of 67.5-68.5 °C.
Anal. (C13H17NO4) C,H,N.
A suspension of 6.5 g LAH in 500 mL well stirred anhydrous Et2O was
held at reflux under an inert atmosphere, with the return of the
condensed solvent passing through a Soxhlet thimble containing 6.5 g
1-(2,5-dimethoxy-4-ethylphenyl)-2-nitropropene. After the addition of
the nitrostyrene was complete, the stirred suspension was maintained
at reflux for an additional 18 h, then cooled to room temperature.
The excess hydride was destroyed with 500 mL 8% H2SO4, added
cautiously until the hydrogen evolution ceased, then at a speed that
allowed the formed solids to disperse. The phases were separated, the
aqueous phase washed once with Et2O, treated with 150 g potassium
sodium tartrate, and finally made basic (pH >9) with 5% NaOH. This
was extracted with 3x100 mL CH2Cl2, the extracts pooled, and the
solvent removed under vacuum. The residue, 7.9 g of a clear oil, was
dissolved in 100 mL anhydrous Et2O and saturated with anhydrous HCl
gas. After standing at room temperature for 2 h, the crystalline
2,5-dimethoxy-4-ethylamphetamine hydrochloride (DOET) was removed by
filtration, washed with Et2O, and air dried to constant weight. There
was obtained 5.9 g of lustrous white crystal with a mp of 190-191 °C.
Recrystallization from CH3CN or EtOAc increased the mp to 194-195 °C.
Anal. (C13H22ClNO2) C,H,N.
DOSAGE: 2 - 6 mg.
DURATION: 14 - 20 h.
QUALITATIVE COMMENTS: (with 1.0 mg) This was a very gentle, relaxing
level, but there were no psychedelic effects that were apparent.
Easy, and relaxed, and I am in no way intoxicated or turned on. But I
was in the throes of my menstrual period, and the cramps (and the
accompanying irritability) were completely knocked out. Perhaps this
is why I felt so relaxed and at peace.
(with 2.5 mg) There is much, too much, movement with my eyes closed.
And an awful lot there with my eyes open. The movement on the
concrete floor in the basement when I went downstairs for wood for the
fireplace, was too much. I felt almost sea-sick. And I am having
reality problems--I cannot seem to find my centering point of
reference. There has to be a place to pin myself down to, and it is
not findable anywhere I look. And my legs are twitching, and feeling
as if they are falling asleep, and I had a crawling sensation on my
body, so the body is not at peace either. In the morning I was still
++, but there is a clear indication that I am repairing. Anyway, I
survived the experience. This is definitely not my thing.
(with 4 mg) Just after an hour into the experiment, I was surprised
by the awareness of some effects--I had forgotten that I had taken
something. At the second hour, it was real, but subtle. As a
psychotomimetic or STP-like thing, there is very little there. But as
a mood energizer, it is really a ++ or more. The clinical literature
is right--none of the hallucinogenic effects, but one brings into
play whatever one wants to. Worked at cleaning up the office until 11
PM. I slept well. This has none of the LSD or STP seriousness.
(with 6 mg) The onset was slow, and subtle. But the effects are
fully there in about three or so hours. Everything I smelled was
vivid, as are all the colors and shapes; they are clean, beautiful,
serenely self-contained. No visual movement. The eyes-closed fantasy
images tend to take off on their own, however, and they are extremely
rich. I don't see any dark corners. I believe it might well be
possible to be creative with this, and there is no suggestion of body
depletion, of body load.
(with 7 mg) A hot day. Unbelievably lovely erotic-to-divine, deep
loving, open, not much visual, eyes-closed form-image-symbol. Sleep
attempts very shallow, slight `thinness', with an anticipation of
darts. Intellect and feeling-emotion area intact and functioning at
all times. Next morning still at a plus one. Incredible material.
Perhaps best at 6 to 7 milligrams, no higher due to body load.
EXTENSIONS AND COMMENTARY: The original code for this compound was
DOE, which was completely logical based on DOM being the methyl member
of this series (DO for the removal of the oxygen, desoxy, and M for
putting a methyl in its place). And the putting of the ethyl thence
should be DOE. This was fine until it was pointed out to me by a
close colleague that DOE was a classic abbreviation for
desoxyephedrine, a synonym for methamphetamine. The pressure to add
the RTS of the RETS of the ethyl was heightened by looking ahead to
other members of the series. DOA became DOAM, DOE became DOET, but
DOM was already too firmly set in popular usage. And, anyway, DOME
really looked strange.
The original publications of the action of DOM clearly documented the
compound as being a psychedelic and one with a sizeable measure of
potential abuse. And, it is not a surprise that it was quickly
shuffled into a legal classification that effectively precluded any
further study of it. So, when this immediate homologue of DOM was
studied and discussed in the literature, all reported dosages were
those that were at the lowest levels, and no disturbing hints of
abusability were mentioned. And this particular homologue has so far
escaped the attention and restrictive action of the drug enforcement
agencies, although the specific wording of the Controlled Substance
Analogue Enforcement Act of 1986 might make this point moot, at least
as far as human trials are concerned. At modest levels, DOET has the
reputation of being a cognitive enhancer and is largely free of those
sensory distortions that would catch the attention of the authorities
who cannot tolerate drugs that distort the senses. The higher levels
mentioned here have never been put into the published literature. It
must be noted that there is a considerable variation of individual
responses to this material. The effective dose range stated is quite
broad. Some people are quite sensitive. This is, after all, one of
the Classic Ladies, namely HECATE.
The young experimental subject who had the dramatic relief from
menstrual cramps at the one milligram dose tried the compound again
the following month, and again had complete relief. But another
volunteer, also plagued with severe cramping at that particular time
of month, found no relief at all. A 50% success rate. No one else
has, to my knowledge, explored this particular property.
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