This is a recipe from
PiHKAL. If you're interested in how the hardlinks
were chosen, read
noding PiHKAL for Everything2.
#84 G-5
3,6-DIMETHOXY-4-(2-AMINOPROPYL)BENZONORBORNANE
SYNTHESIS: A
solution of 3.70 g
3,6-dimethoxy-4-formylbenzonorbornane
(see under
2C-G-5 for its preparation) in 20 g
nitroethane was treated
with 0.88 g
anhydrous ammonium acetate and held at steam bath
tem
perature overnight. The excess
solvent and reagent was removed
under vacuum to yield a
residual yellow oil. This was allowed to
stand at ambient tem
perature for a period of time (about 3 years) by
which time there was a spontaneous
crystallization. The dull yellow
crystals were removed by filtration and, after air drying, weighed
4.28 g. A small sample was re
crystallized repeatedly from MeOH to
provide a pale yellow
analytical sample of
3,6-dimethoxy-4-(2-nitropropenyl)benzonorbornane with a mp of 90-91
°C. Anal. (
C16H19NO4) C,H.
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 4.1 g
3,6-dimethoxy-4-(2-nitropropenyl)benzonorbornane in 20 mL
anhydrous
THF over the course of 10 min. The reaction mixture was stirred and
brought to room tem
perature over the course of 1 h. This was then
brought 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 10 mL IPA followed by 5 mL 5%
NaOH and sufficient
H2O to give a white granular character to the
oxides. The reaction
mixture was filtered, and the filter cake washed with THF. The
filtrate was stripped of
solvent under vacuum providing a pale amber
oil that was
distilled at 125-140 °C at 0.2 mm/
Hg to give 2.5 g of an
almost white oil. This was
dissolved in 10 mL IPA, neutralized with
25 drops of concentrated HCl, and then diluted with 140 mL
anhydrous
Et2O. There appeared, after about two minutes, white
crystals of
3,6-dimethoxy-4-(2-aminopropyl)benzonorbornane hydrochloride (G-5)
which, after filtration and air drying, weighed 2.47 g.
DOSAGE: 14 - 20 mg.
DURATION: 16 - 30 h.
QUALITATIVE COMMENTS: (with 15 mg) As part of the audience at the San
Francisco conference, Angels, Aliens and Archtypes, I could simply
listen and observe without having to participate. Each speaker stood
in a cone of light that was beautifully bright and colorful, casting
everything else on the stage into obscurity. Maybe angels really are
illuminated from above, and the aliens lurk out of sight until it is
their turn. Where does one look for the archetypes? A half of a
cream cheese sandwich was all I could eat, and even at dinner that
evening I was not hungry. Sleep that evening was difficult.
(with 20 mg) Very slow to come on, but then it was up there all of a
sudden. There is an unexpected absence of visual activity despite
being at a full +++. The mental activity is excellent, with easy
writing and a positive flow of ideas. But an absence of the bells and
whistles that are expected with a
psychedelic in full bloom. There is
a real drop by the 16th hour and the next day was free of effect
except for occasional cat-naps.
(with 20 mg) The transition period, which usually lasts for most
compounds for the first hour or two, with this seems to be much
longer. This presages a long-acting material, as usually the slow-in
slow-out rule applies. But there are exceptions. There is an
indifference towards the erotic, but no separation at all from
personal interactions and emotions. I believe in integration, not
separation of all parts of ourselves, distrusting any drug states
(particularly those that have the reputation of being strongly
`cosmic') which divorce the consciousness from the body. And with
this material there is no separation from feelings, only from my
particular color language.
EXTENSIONS AND COMMENTARY: This is as potent as any of the
three-
carbon Ganesha compounds, but it somehow lacks a little
something that would have made it a completely favorite winner.
Perhaps it is the generally commented upon absence of visual and
related sensory entertainment. There seems to be no bodily threat to
discourage further exploration, but there simply was not the drive to
explore it much. The comments concerning the enlargement of the ring
system (mentioned under
2C-G-5) are equally valid here. The
"shrubbery" that is the hallmark of the Ganesha family is, with G-5,
about as bulky as has ever been put onto a centrally active molecule.
The
norbornane group has a one
carbon bridge and a two carbon bridge
sticking out of it at odd angles. The replacement of the one-
carbon
bridge with a second two-
carbon bridge would make the compound G-6.
It would be makeable, but is there really a driving reason to do so?
There is a simplification intrinsic in this, in that G-5 actually has
two centers of asymmetry (the
alpha-carbon atom on the
amphetamine chain,
and the
norbornyl area itself) and so it is really a mixture of two
racemic dia
stereoisomers. G-6 would still be a racemate, but it would
be only a single compound, as are all the other
substituted
amphetamine derivatives.
Someday I may try making G-6, but it's not a high priority right now.
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