SYNTHESIS: A solution of 5.8 g of homosyringonitrile (see under E for
its synthesis), 100 mg decyltriethylammonium iodide, and 10 g n-propyl
bromide in 50 mL anhydrous acetone was treated with 6.9 g finely
powdered anhydrous K2CO3 and held at reflux for 10 h. An additional 5
g of n-propyl bromide was added to the mixture, and the refluxing
continued for another 48 h. The mixture was filtered, the solids
washed with acetone, and the combined filtrate and washes stripped of
solvent under vacuum. The residue was suspended in acidified H2O, and
extracted 3x175 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 9.0 g of a
deep yellow oil. This was distilled at 132-142 °C at 0.3 mm/Hg to
yield 4.8 g of 3,5-dimethoxy-4-(n)-propoxyphenylacetonitrile as a
clear yellow oil. Anal. (C13H17NO3) C H N.
A solution of 4.7 g 3,5-dimethoxy-4-(n)-propoxyphenylacetonitrile in
20 mL THF was treated with 2.4 g powdered sodium borohydride. To this
well-stirred suspension there was added, dropwise, 1.5 mL
trifluoroacetic acid. There was a vigorous gas evolution from the
exothermic reaction. Stirring was continued for 1 h, then all was
poured into 300 mL H2O. This was acidified cautiously with dilute
H2SO4, and washed with 2x75 mL CH2Cl2. The aqueous phase was made
basic with dilute NaOH, extracted with 2x75 mL CH2Cl2, the extracts
pooled, and the solvent removed under vacuum. The residue was
distilled at 115-125 °C at 0.3 mm/Hg to give 1.5 mL of a colorless oil
which upon dissolving in 5 mL IPA, neutralizing with 27 drops
concentrated HCl, and dilution with 25 mL anhydrous Et2O yielded 1.5 g
3,5-dimethoxy-4-(n)-propoxyphenethylamine hydrochloride (P) as
spectacular white crystals. The catalytic hydrogenation process for
reducing the nitrile (see under E) also succeeded with this material.
The mp was 170-172 °C. Anal. (C13H22ClNO3) C,H,N.
DOSAGE: 30 - 60 mg.
DURATION: 8 - 12 h.
QUALITATIVE COMMENTS: (with 30 mg) Proscaline dulled my sense of pain
and made the other senses really sharp. Everything felt really soft,
and clean and clear. I could feel every hair my hand was touching. I
felt so relaxed and at ease. I know that under the appropriate
circumstances, this material would lead to uninhibited eroticism.
(with 35 mg) The whole experiment was very quiet. There was no
nystagmus, no anorexia, and insignificant visuals with the eyes
closed. I was restless with a bit of tremor for the first couple of
hours, and then became drowsy. Would I do this again? Probably not.
It doesn't seem to offer anything except speculation about the nature
of the high. The high was pleasant, but quite uneventful.
(with 40 mg) For me there was a deep feeling of peace and
contentment. The euphoria grows in intensity for several hours and
remains for the rest of the day making this one of the most enjoyable
experiences I have ever had. It was marvel-ous talking and joking
with the others. However, I was a little disappointed that there was
no enhanced clarity and no deep realizations. There was not a problem
to be found. There were no motivations to discuss anything serious.
If I had any objection, it would be with the name, not the
pharmacology.
(with 60 mg) The development of the intoxication was complete in a
couple of hours. I feel that there is more physical effect than
mental, in that there is considerable irritability. This should
probably be the maximum dose. Despite feeling quite drunk, my
thinking seems straight. The effects were already waning by the fifth
hour, but sleep was not possible until after the twelth hour. There
was no hangover the next day.
EXTENSIONS AND COMMENTARY: There is a very early report describing the
human use of proscaline tucked away in the Czechoslovakian literature
that describes experiments at up to 80 milligrams. At these dosages,
there were reported some difficulty with dreams, and the residual
effects were still apparent even after 12 hours.
The amphetamine homologue of proscaline,
3,5-dimethoxy-4-(n)-propoxy-amphetamine is an unexplored compound.
Its synthesis could not be achieved in parallel to the description
given for P. Rather, the propylation of syringaldehyde to give
3,5-dimethoxy-4-(n)-propoxybenzaldehyde, followed by coupling with
nitroethane and the reduction of the formed nitrostyrene with lithium
aluminum hydride would be the logical process. Following the
reasoning given under E, the initials for this base would be 3C-P, and
I would guess it would be active, and a psychedelic, in the 20 to 40
milligram range.
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