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#82 G-3
2,5-DIMETHOXY-3,4-(TRIMETHYLENE)AMPHETAMINE; 5-(2-AMINOPROPYL)-4,7-DIMETHOXYINDANE
SYNTHESIS: A
solution of 3.7 g of
2,5-dimethoxy-3,4-(trimethylene)benzaldehyde (see preparation under
2C-G-3) in 15 mL
nitroethane was treated with 0.7 g
anhydrous ammonium
acetate and heated on the steam bath for 2.5 h. The excess
solvent
was removed under vacuum leaving some 5 mL of a deep orange-red oil
which on cooling, spontaneously
crystallized. This was finely ground
under 10 mL MeOH, filtered, washed sparingly with MeOH, and air dried
to give 3.6 g of orange
crystals with a strong smell of old
acetamide.
The mp was 92-93 °C. All was re
crystallized from 30 mL boiling MeOH
to give, after filtering and drying, 2.9 g of
1-(2,5-dimethoxy-3,4-(trimethylene)phenyl)-2-nitropropene as yellow
crystals with a mp of 93-94 °C. Anal. (
C14H17NO4) C,H,N.
Fifty milliliters of 1 M LAH in THF was placed in an inert
atmosphere,
well stirred, and cooled to 0 °C with an external ice-bath. There was
added, dropwise, 1.35 mL of 100% H2SO4 at a rate slow enough to
minimize charring. There was then added, dropwise, 2.8 g
1-(2,5-dimethoxy-3,4-(trimethylene)phenyl)-2-nitropropene in 15 mL
THF. At the end of the addition, the stirring was continued for an
additional 0.5 h, and then the reaction mixture was held at reflux on
the steam bath for another 0.5 h. After cooling again to ice-bath
tem
perature, the excess
hydride was destroyed with the addition of 11
mL IPA, followed by 5.5 mL 5%
NaOH which converted the inorganic mass
through a cottage cheese stage into a loose, filterable texture. The
solids were removed by filtration, washed with additional THF, and the
combined filtrates and washes stripped of
solvent under vacuum. There
was obtained 2.51 g of a white oil that was
distilled at 115-135 °C at
0.2 mm/
Hg to give 1.83 g of a clear colorless oil. This was
dissolved
in 8 mL IPA, neutralized with 28 drops of concentrated HCl, and
diluted with 140 mL
anhydrous Et2O. In about 0.5 h there started a
slow snowfall of fine fluffy white
crystals which was allowed to
continue until no additional
crystals appeared. After filtering,
Et2O
washing and air drying, there was obtained 1.81 g of
2,5-dimethoxy-3,4-(trimethylene)amphetamine hydrochloride (G-3) with a
mp of 157-159 °C. Anal. (
C14H22ClNO2) C,H.
DOSAGE: 12 - 18 mg.
DURATION: 8 - 12 h.
QUALITATIVE COMMENTS: (with 12 mg) There was a warmth, a mellowness,
as things developed. No body disturbance at all, but then there were
no visuals either which, for me on this particular occasion, was
disappointing. The day was consumed in reading, and I identified
completely with the character of my fictional hero. It was a
different form of fantasy. I think I prefer music as a structural
basis for fantasy.
(with 18 mg) I am at a plus three, but I am not at all sure of why it
is a plus three. With my eyes closed, there are puffy clouds, but no
drama at all. Music was not exciting. There could well have been
easy
eroticism, but there was no push in that direction. No great
amount of appetite. Not much of anything, and still a plus three.
Simply lying still and surveying the body rather than the visual scene
gave some suggestions of
neurological sensitivity, but with getting up
and moving about and doing things, all was fine. The next morning I
was perhaps moving a bit more slowly than usual. I am not sure that
there would be reward in going higher.
EXTENSIONS AND COMMENTARY: In a comparison between the 2-
carbon
compound (
2C-G-3) and the 3-
carbon compound (G-3) the vote goes
towards the
phenethylamine (the 2-
carbon compound). With the first
member of this series (
2C-G versus GANESHA) this was a stand-off, both
as to quantitative effects (potency) and qualitative effects (nature
of activity). Here, with the somewhat bulkier group located at the
definitive
3,4-positions, the nod is to the shorter chain, for the
first time ever. The potency differences are small, and maybe the
amphetamine is still a bit more potent. But there are hints of
discomfort with this latter compound that seem to be absent with the
phenethylamine. The more highly
substituted compounds (q.v.) more
clearly define these differences.
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