This is a recipe from
PiHKAL. If you're interested in how the hardlinks
were chosen, read
noding PiHKAL for Everything2.
#31 2C-G-N
1,4-DIMETHOXYNAPHTHYL-2-ETHYLAMINE
SYNTHESIS: A
solution of 17.5 g
1,4-naphthaquinone in 200 mL MeOH was
heated to the boiling point, and treated with 28.5 g stannous
chloride
at a rate that maintained a continuous rolling boil. At the
completion of the addition, the reaction mixture was saturated with
anhydrous hydrogen
chloride, and held at reflux on the steam bath for
2 h. The reaction mixture was poured into 700 mL H2O and treated with
aqueous
NaOH. During the addition there was transient development of
a curdy white solid which re
dissolved when the system became strongly
basic. This was extracted with 3x200 mL
CH2Cl2 and the pooled
extracts were washed first with H2O, then with dilute HCl, and finally
again with H2O. Removal of the
solvent under vacuum yielded 15.75 g
of a low melting black flaky
crystalline material which was
distilled
at 160-180 °C at 0.05 mm/
Hg to give 14.5 g of an amber, solid mass
with a mp of 78-86 °C. Re
crystallization from 75 mL boiling MeOH
provided
1,4-dimethoxynaphthalene as white
crystals melting at 87-88
°C.
A mixture of 20.0 g POCl3 and 22.5 g N-
methylformanilide was allowed
to stand at room tem
perature for 0.5 h which produced a deep claret
color. To this there was added 9.4 g
1,4-dimethoxynaphthalene and the
mixture was heated on the steam bath. The reaction mixture quickly
became progressively darker and thicker. After 20 min it was poured
into 250 mL H2O and stirred for several h. The solids were removed by
filtration, and washed well with H2O. The wet crude product (a dull
yellow-orange color) was
dissolved in 125 mL boiling
EtOH to give a
deep red
solution. On cooling, this
deposited a heavy crop of
crystals that was removed by filtration, and washed with cold
EtOH.
There was obtained, after air-drying to constant weight, 7.9 g
1,4-dimethoxy-2-naphthaldehyde as white
crystals with a mp of 119-121
°C. This was not improved by further re
crystallization. The
malononitrile derivative, from the
aldehyde and malononitrile in
EtOH
with a drop of
triethylamine, had a mp of 187-188 °C.
A
solution of 3.9 g
1,4-dimethoxy-2-naphthaldehyde in 13.5 g
nitromethane was treated with 0.7 g
anhydrous ammonium acetate, and
heated on the steam bath for 1 h. The excess reagent/
solvent was
removed under vacuum giving a residue that spontaneously
crystallized.
This crude product was removed with the aid of a few mL MeOH, and
pressed on a sintered funnel with modest MeOH washing. There was
obtained 3.6 g (when dry) of old-gold colored
crystals with a mp of
146-148 °C. Re
crystallization from 140 mL boiling
EtOH gave 3.0 g
1,4-dimethoxy-2-(2-nitro-vinyl)naphthalene as deep gold-colored
crystals with a mp of 146-147 °C. A small sample, upon
re
crystalization from MeOH, melted at 143-144 °C. Anal. (
C14H13NO4)
C,H.
A
solution of LAH (50 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 1.32 mL 100% H2SO4 dropwise, to minimize charring. This was
followed by the addition of 2.80 g
1,4-dimethoxy-2-(2-nitrovinyl)naphthalene in 40 mL
anhydrous THF.
There was an immediate loss of color. After 1 h stirring at 0 °C, the
tem
perature was brought up to a gentle reflux on the steam bath for 20
min, then all was cooled again to 0 °C. The excess
hydride was
destroyed by the cautious addition of 7 mL IPA followed by 5.5 mL 5%
NaOH. The reaction mixture was filtered, and the filter cake washed
with several portions of THF. The combined filtrate and washings were
stripped of
solvent under vacuum providing 3.6 g of a pale amber oil
that was
distilled at 145-160 °C at 0.2 mm/
Hg to give 1.25 g of
product as an absolutely white oil. This was
dissolved in 7 mL IPA,
and neutralized with concentrated HCl forming immediate
crystals of
the
hydrochloride salt in the
alcohol solvent. Thirty mL of
anhydrous
Et2O was added, and after complete grinding and mixing, the
hydrochloride salt was removed by filtration,
Et2O washed, and air
dried to constant weight. The spectacular white
crystals of
1,4-dimethoxynaphthyl-2-ethylamine hydrochloride (2C-G-N) weighed 1.23
g and had melting properties of darkening at 190 °C, and decomposing
in the 235-245 °C area. Anal. (
C14H18ClNO2) C,H.
DOSAGE: 20 - 40 mg.
DURATION: 20 - 30 h.
QUALITATIVE COMMENTS: (with 24 mg) The effects were interestingly
colored by the reading of Alan Watts' Joyous Cosmology during the
coming-on period. The only body negatives were some urinary retention
and a feeling of a shallow but continuing
amphetamine stimulation.
But not enough to be actually jingly, nor to interfere with sleep that
evening. There is not much
psychedelic here, but there is something
really going on anyway. This has some similarities to the
anti
depressant world.
(with 35 mg) Much writing, much talking, and there was considerable
residual awareness the next day. Somehow this material is not as
friendly as the other 2C-G's.
(with 35 mg) Thinking is clear. No fuzziness, no feeling of being
pushed. None of the walking on the fine middle line between light and
dark that is the excitement and the threat of LSD. This is just a
friend, an ally, which invites you to do anything you wish to.
comment added two days later RMy sleep was not deep enough, but it
was pleasant and relatively resting. The whole next day I was feeling
happy, but with an overlay of irritability. Strange mixture. By
bedtime the irritability had become a mild
depression. I feel that
there might have been a threshold continuing for a couple of days.
The character of my dreaming had the stamp of drug on it. This
compound, in retrospect, presents some problems that cause a faint
unease.
EXTENSIONS AND COMMENTARY: There is always a wish in the design of new
compounds to find something that is of interesting activity, with an
aromatic ring at some location pretty much away from the site of
activity. This would then allow some subtle fine-tuning of the nature
of the action by putting any of a wide range of
electron pushing or
electron pulling groups on that ring. But here, with 2C-G-N, by the
time the ring got put into place, the activity was already on the
wane, and the action was too long, and there are indicators of some
not completely friendly effects. Ah well, some other molecule, some
other time.
Back to PiHKAL?