SYNTHESIS: A solution of 6.96 g 2,5-dimethoxyamphetamine hydrochloride
(2,5-DMA) in 250 mL H2O was made basic with aqueous NaOH and extracted
with 3x75 mL CH2Cl2. After removal of the solvent from the pooled
extracts under vacuum, the residual free base was dissolved in 36 g
glacial acetic acid and, with good stirring, cooled to 0 °C with an
external ice bath. There was then added, with a Pasteur pipette, 3 mL
of liquid chlorine. The generation of HCl was evident, and the
reaction was allowed to stir for an additional 3 h. The mixture was
then poured into 300 mL H2O and washed with 3x100 mL Et2O. The
aqueous phase was made basic with NaOH and extracted with 3x150 mL
CH2Cl2. After removal of the solvent from the pooled extracts, the
residue was dissolved in Et2O and saturated with anhydrous HCl gas.
There was the formation of a heavy oily precipitate. The ether
supernatent was decanted, and the residue was intimately mixed with
200 mL of fresh anhydrous Et2O. Everything set up as an off-white
crystalline mass weighing 2.3 g. This was dissolved in 12 mL of
boiling MeOH and diluted with 230 mL boiling Et2O. The clear solution
was quickly filtered to give a clear, pale amber mother liquor, which
soon started depositing lustrous white crystals. After filtering,
Et2O washing, and air drying to constant weight, there was obtained
1.4 g of 2,5-dimethoxy-4-chloroamphetamine hydrochloride (DOC) From
the mother liquors (from the original HCl saturation) an equal amount
of product could be obtained by exploiting the acetone insolubility of
the hydrochloride salt of the product. The published mp of this salt,
from acetone/EtOH, is 187-188 °C. A sample of this hydrochloride
salt, prepared from the amino analogue via diazotization and eventual
hydrolysis of an acetylated precursor, was recrystallized from
EtOH/ether and had a mp of 193-194.5 °C.
DOSAGE: 1.5 - 3.0 mg.
DURATION: 12 - 24 h.
QUALITATIVE COMMENTS: (with 1.6 mg) I was hit with a slightly light
head; the effects were quite real. I was disconnected, and somehow
spacey, but this was a favorable spacey which was kind of fun.
Somewhere at about the sixth hour I realized that I was beginning to
drop off a bit, but six hours later yet, there was still a lot of
memory. This is a long thing.
(with 2.4 mg) This is what I might call an archetypical psychedelic.
Everything is there in spades, with few if any of the subtle graces,
the `gentle images' and `gentle fantasies' of the 2-carbon
phenethylamines. This is the works. There are visuals, and there are
interpretive problems with knowing just where you really are. The
place where nothing makes sense, and yet everything makes sense. I
have just slept for a few hours, and now I am awake and it has been
eighteen hours, and there is a lot still going on, although I have a
relaxed, good feeling. Anyone who uses this had better have 24 hours
at their disposal.
(with 2.4 mg) Here I am at the sixth hour, and I am still roaring
along at a full plus three. I have established that this material is
neither anti-erotic nor anorexic. The body is very comfortable, and
so is the mind. There is an interesting aspect, perhaps peculiar only
to this experiment and under these conditions. With my eyes closed
the fantasy is a completely dark screen, lovely and seductive, subtle,
and yet light must be deliberately brought in. This is not in any way
negative for being in the dark, but is just unusual. I will have to
try this in the daylight next time, to see what the eyes-closed brings
to the mind-screen. At 24 hours, I have found that my sleep was not
too great. My dreams were tight, and I kept defending against
trouble; the nervous system was too alert. I was in a good humor,
though, and I still am. This is excellent stuff, but start early in
the day.
EXTENSIONS AND COMMENTARY: It is clear that the three halo-amphetamine
derivatives, DOI, DOB and DOC, are all pretty much of the same
potency. And all of them very long lived. The difference between the
various halogen atoms was brought up under the 2C-C discussion. DOC
is clearly a long-lasting, dyed-in-the-wool psychedelic.
In the making of this, by the procedures that have been followed in
Canada, there are two chemical intermediates which might, some day, be
looked at as potential psychedelics under their own colors. Reduction
of the compound that is called DON in this Book II
(2,5-dimethoxy-4-nitroamphetamine hydrochloride) with Pd/charcoal and
hydrogen, gives the 4-amino derivative. This is
2,5-dimethoxy-4-aminoamphetamine dihydrochloride, DOA, which melts at
248-250 °C. And the reduction of an oxime intermediate gives rise to
the acetamido analogue, 2,5-dimethoxy-4-acetamidoamphetamine
hydrochloride, DOAA, with a mp of 249-250 °C. Neither compound has
been tasted, but someday this omission will be corrected. DOA and
DOAA have a sinister ring to them, however, and some changes of
terminology might be needed. DOA, in the coroner's vocabulary, means
Dead-On-Arrival. But then, AMA (the American Medical Association)
just happens to also mean (in the jargon of emergency medicine)
Against-Medical-Advice. Everything averages out, somehow. Remember
that the amyl homolog (amyl at the 4-position) follows the 4-letter
convention of all of the DOM homo-logues, and has the code name of
DOAM. Thus, DOA, amino; DOAA, acetamido, and DOAM, amyl.
One must learn to keep one's sense of humor. The immortal humorist
Wavy Gravy once said, "If you can't laugh at life, it just isn't funny
anymore." The code name of this compound,
2,5-dimethoxy-4-chloroamphetamine is, after, all, DOC. This should
certainly appeal to some physicians.
Back]
]