SYNTHESIS: To a solution of 3.9 g 1,4-dimethoxy-2-naphthaldehyde (see
under 2C-G-N for the preparation) in 13.5 mL nitroethane there was
added 0.7 g anhydrous ammonium acetate, and the mixture heated on the
steam bath for 5 h. The deep orange reaction mixture was stripped of
excess solvent under vacuum. The residue was a red oil that, upon
dilution with two volumes MeOH, immediately set to orange crystals.
This crude product (mp 115-118 °C) was recrystallized from 70 mL EtOH
to yield, after filtering and air drying, 3.3 g of
1-(1,4-dimethoxy-2-naphthyl)-2-nitropropene as gold-orange crystals,
with a mp of 121-123 °C. Recrystallization from MeOH gave a
gold-colored product with a mp of 119-120 °C. Anal. (C15H15NO4)
C,H,N.
A solution of LAH (50 mL of 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 3.12 g 1-(1,4-dimethoxy-2-naphthyl)-2-nitropropene
in 40 mL anhydrous THF. After stirring for 1 h, the temperature was
brought up to a gentle reflux on the steam bath for 0.5 h, and then
all was cooled again to 0 °C. The excess hydride was destroyed by the
cautious addition of 16 mL IPA followed by 6 mL 5% NaOH to give a
white, filterable, granular character to the oxides, and to assure
that the reaction mixture was basic. The reaction mixture was
filtered, and the filter cake washed with additional THF. The
combined filtrate and washes were stripped of solvent under vacuum
providing 3.17 g of a deep amber oil. Without any further
purification, this was distilled at 140-160 °C at 0.3 mm/Hg to give
1.25 g of a pale yellow oil. This was dissolved in 8 mL IPA,
neutralized with 20 drops of concentrated HCl, and diluted with 60 mL
anhydrous Et2O which was the point at which the solution became
slightly turbid. After a few min, fine white crystals began to form,
and these were eventually removed, washed with Et2O, and air dried to
provide 1.28 g 1,4-dimethoxynaphthyl-2-isopropylamine hydrochloride
(G-N) as the monohydrate salt. The mp was 205-206 °C. Even after 24
h drying at 100 °C under vacuum, the hydrate salt remained intact.
Anal. (C15H20ClNO2aH2O) C,H.
DOSAGE: unknown.
DURATION: unknown,
EXTENTIONS AND COMMENTARY: The evaluation of this compound is not yet
complete. An initial trial at the 2 milligram level showed neither
central action, nor toxicity. It could be guessed from the activity
of the two-carbon counterpart, that an active level will be found in
the tens of milligrams area. But, as of the moment, this level is not
known to anyone, anywhere, because no one has yet defined it. And
when the potency is finally found out, the nature of the activity will
also have been found out, all the result of a magical interaction of a
virgin compound with a virgin psyche. At the immediate moment, the
nature of G-N is not only unknown, it has not yet even been sculpted.
There can be no more exciting area of research than this, anywhere in
the sentient world.
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