SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under E for
its preparation), 100 mg decyltriethylammonium iodide, and 13.6 g
allyl iodide in 50 mL anhydrous acetone was treated with 6.9 g finely
powdered anhydrous K2CO3 and held at reflux for 16 h. The color
changed from a near-black to a light yellow. The mixture was
filtered, the solids washed with acetone, and the solvent from the
combined filtrate and washes removed under vacuum. The residue was
suspended in acidified H2O, and extracted with 3x100 mL CH2Cl2. The
pooled extracts were washed with 2x50 mL 5% NaOH, once with dilute HCl
(which lightened the color of the extract) and then stripped of
solvent under vacuum giving 12.4 g of an amber-colored oil. This was
distilled at 125-137 °C at 0.1 mm/Hg to yield 5.7 g of
3,5-dimethoxy-4-allyloxyphenylacetonitrile as a yellow oil. Anal.
(C13H15NO3S) C,H.
A suspension of 4.0 g LAH in 150 mL anhydrous THF under N2 was cooled
to 0 °C and vigorously stirred. There was added, dropwise, 2.8 mL
100% H2SO4, followed by 5.5 g
3,5-dimethoxy-4-allyloxyphenylacetonitrile in 10 mL anhydrous THF.
The reaction mixture was stirred at 0 °C for a few min, then brought
to a reflux on the steam bath for 30 min. After cooling back to room
temperature, there was added sufficient IPA to destroy the excess
hydride, followed by sufficient 10% NaOH to form granular solids.
These were removed by filtration, and washed with 20 mL IPA. The
filtrate and washes were stripped of solvent under vacuum andthe
residue added to 100 mL dilute H2SO4. This was washed with 2x50 mL
CH2Cl2, made basic with aqueous NaOH, and extracted with 2x75 mL
CH2Cl2. These extracts were pooled, the solvent removed under vacuum,
and the residue distilled at 110-120 °C at 0.4 mm/Hg to give 4.9 g of
a colorless oil. This was dissolved in 15 mL IPA, neutralized with
concentrated HCl (55 drops required), and diluted with 50 mL Et2O.
The product was removed by filtration, washed with Et2O, and air dried
to give 4.9 g of 3,5-dimethoxy-4-allyloxyphenethylamine hydrochloride
(AL) as white crystals.
DOSAGE: 20 - 35 mg.
DURATION: 8 - 12 h.
QUALITATIVE COMMENTS: (with 24 mg) I first became aware of something
in about 10 minutes, a pleasant increase in energy. By 20 minutes it
was getting pronounced and was a nice, smooth development. During the
next hour positive and negative feelings developed simultaneously.
Following a suggestion, I ate a bit of food even though I had not been
hungry, and to my surprise all the negative feelings dropped away. I
felt free to join the others wherever they were at. I moved into the
creative, free-flowing kind of repertoire which I dearly love, and
found everything enormously funny. Much of the laughter was so deep
that I felt it working through buried depressions inside me and
freeing me. From this point on, the experience was most enjoyable.
The experience was characterized by clear-headedness and an abundance
of energy which kept on throughout the day and evening. At one point
I went out back and strolled along to find a place to worship. I had
a profound sense of the Presence and great love and gratitude for the
place, the people, and the activities taking place. The come-down
from the experience was very gradual and smooth. Food tasted
wonderful. I went to bed late, and quite ready for bed, although the
energy was still running. However, sleep was not long in coming.
(with 24 mg) The onset was extremely gradual and graceful, with the
first alert that one could really sense at about 50 minutes. This was
succeeded by a slow gentle climb to the peak at one hour and fifteen
minutes. The experience itself left all of the sensory modalities
functional; speech was cogent and rather fluid. In fact, there was an
unusual ease of free association. All throughout the session, the
talk was high in spirits and somehow indicative of an inner
excitement. Affect was entirely pleasant, but not exalting nor
conducive to insight or to problem solving. There were no
requirements for withdrawal into the self. The material seemed wholly
social in nature. No visual, auditory or olfactory sharpening was in
evidence. The plateau for this material seemed unusually long. I was
unable to sleep for several hours, and took 25 mg Librium before sleep
arrived. The next day was a lethargic and slow one, with the inner
feeling that the effects had not worn off until the middle of the day
following ingestion.
(with 35 mg) I was a distinct +1 in 35 minutes and a +2 by the end of
the hour. My head congestion in no way cleared up, absolving the
material from having that particular virtue. The entire experience
was somewhat dissociated--I could not connect with my feelings.
Although my mind remained clear, there was a hangover feeling at the
end of the experiment.
EXTENSIONS AND COMMENTARY: This compound was first explored in Prague
by Leminger. He provided only the synthetic details and the statement
that it was the most active compound that he had studied, with
activity at 20 milligrams, with perceptual changes, color enhancement,
and difficult dreams during sleep that night. Some effects persisted
for more than 12 hours. Dosages above 35 milligrams remain
unexplored.
As AL is one of the most potent 3,4,5-trisubstituted phenethylamines
yet described, and since the corresponding amphetamines are of yet
greater potency, it would be a good guess that
4-allyloxy-3,5-dimethoxyamphetamine (3C-AL) would be an interesting
compound to explore. It could be made from syringaldehyde in reaction
with allyl iodide, followed by the formation of a nitrostyrene with
nitroethane, followed by reduction with aluminum hydride. It is, as
of the present time, both unsynthesized and unexplored.
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