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#62 DOB
2,5-DIMETHOXY-4-BROMOAMPHETAMINE
SYNTHESIS: To a well-stirred
solution of 1.95 g of the free base of
2,5-dimethoxyamphetamine (
2,5-DMA) in 12 mL glacial acetic acid, there
was added 1.8 g elemental
bromine dissolved in 4 mL acetic acid over
the course of 5 min. The slightly exothermic reaction was allowed to
stir for 3 h, and then added to about 200 mL H2O. The cloudy
solution
was washed with 2x100
Et2O, made basic with aqueous
NaOH, and
extracted with 3x100 mL
CH2Cl2. Evaporation of the
solvent from the
pooled extracts gave about 3 mL of a pale amber oil which was
dissolved in 250 mL
anhydrous Et2O and saturated with anhydrous HCl
gas. The fine white
crystals of
2,5-dimethoxy-4-bromoamphetamine
hydrochloride, DOB, were removed by filtration,
Et2O washed, and air
dried. These weighed 1.7 g and had a mp of 195-196 °C.
Re
crystallization from IPA brought this up to 207-208 °C.
Proton NMR
spectroscopy of the
hydrochloride salt in D2O gave confidence that the
bromine atom had uniquely entered the 4-position, in that there were
only two unsplit aromatic hydrogen atoms present, at 6.97 and at 7.20
ppm downfield from external TMS.
DOSAGE: 1.0 - 3.0 mg.
DURATION: 18 - 30 h.
QUALITATIVE COMMENTS: (with 0.4 mg) There was a distinct enhancement
of visual perception, and some strengthening of colors. A clean, cold
feeling of wind on the skin. I felt an enriched emotional affect, a
comfortable and good feeling, and easy sleeping with colorful and
important dreams.
(with 2.0 mg) There was a continuous tremor at the physical level,
and an incredible Moebius strip representation of reality at the
intellectual level. I was able to enter into personal problems
easily, and get out again when I chose to. During the next day, there
were brief lapses of attention, or little fugue states, and it was not
until the following evening that I was completely myself again.
(with 2.8 mg) About three hours into this I had a severe cramp, and
had a near fainting response to the pain, and yet there was no pain!
I felt that I was very near a loss of consciousness, and this was most
disturbing. There were flashes of
depersonalization. I saw rings
around the moon with
prismatic colors, and there were long-lasting
"after-images" following any viewings of points of light. I was still
a good plus 1 at 14 hours, but did manage to sleep. It was the next
day before I was again at baseline.
(with 3.0 mg) This was a complex, but a very good day. It involved
making a large pot of chicken-vegetable soup, and listening to H.L.,
my favorite Saturday morning fundamentalist
Christian radio preacher,
bless Tim. The Democrats are not exactly all anti-
American dupes of
Moscow (or the Devil), but to H.L., they are practically, almost,
next-door to it. The Rapture is supposed to happen tomorrow according
to a certain book, newly published (just in time, looks like) and he
is busy softening the possible disappointment of those who may find
themselves unchanged Monday morning. Wunnerful. It's been one heck
of a good experiment, and I can't understand why we waited nine years
to try this gorgeous stuff. Without going into the cosmic and
delicious details, let's just say it's a great material and a good
level.
(with 0.5 mg of the "R"
isomer) I am underway, and this is a smooth
intoxication. I am completely functional, but still really a plus
two. I would not choose to drive a car. Not very far. I felt a
rather quick dropping to a plus-one at the fifth hour, but there is a
residual stimulation still the following morning.
(with 1.0 mg of the "R"
isomer) By the fourth hour I am absolutely a
+++ and am searching the kitchen for food. But what I eat is only
so-so. There is not the introspection or intensity of 2.0 milligrams
of the racemate material, but this is a rewarding place nonethless.
At the 18th hour, there was some fitful sleep, with bizarre dreams.
The next day I was still hungry for altered spaces, and successfully
challenged the
residual plus one with LSD and, as is usually the case,
acid cut right through the detritus and allowed a direct shot up to a
+++ again.
(with 1.5 mg of the "R"
isomer) This is a +++ but it is vaguely
irrational. I feel a heavy body load, but then the tem
perature
outside is over a hundred degrees and I may not be in the best of all
physical environments. I would not wish any higher dosage. There
were cat-naps at the twelth hour, but most symptoms were still there
at the 18th hour. A good experience. It would be interesting to
compare this, some day, with 3.0 milligrams of the racemate.
(with 0.5 mg of the "S"
isomer) There are no effects at all.
(with 1.0 mg of the "S"
isomer) There is something warm and nice at a
couple of hours into this, but I am no more than threshold, and the
effects are very slight. By the fifth hour there are no longer any
effects.
EXTENSIONS AND COMMENTARY: The stars had clearly lined up in favor of
making DOB and exploring its
biological activity. This preparation
had been completed in 1967 and the report of this compound and its
unprecedently high potency published in 1971. And very shortly, two
additional papers appeared completely independently. One described
DOB made via a different route, and describing high activity in rats.
The other described DOB and a couple of closely related brominated
amphetamines and their action in man.
This is one of the last of the experimental compounds within the
phenethylamine family on which any animal toxicity studies were
performed by me prior to human studies. A mouse injected with 50
mg/Kg (ip) showed considerable twitching and was irritable. Another,
at 100 mg/Kg (ip), had overt shaking at 20 minutes, which evolved into
persistent hyperactivity that lasted several hours. Yet another, at
125 mg/Kg (ip), lost much of her righting reflex within 15 minutes,
entered into convulsions at 50 minutes, and was dead a half hour
later. A fourth mouse, at 150 mg/Kg (ip), entered into spontaneous
convulsions within 10 minutes, and expired in what looked like an
uncomfortable death at 22 minutes following injection. What was
learned? That the LD/50 was somewhere between 100 and 125 mg/Kg for
the mouse. And an effective dose in man of maybe 2 mg (for an 80 Kg
man) is
equivalent to 25 ug/Kg. Therefore the index of safety (the
therapeutic index, the lethal dose divided by the effective dose) is
well over a thousand. I feel that two mice were killed without
anything of value having been received in return.
Actually, it is very likely that the damaging, if not lethal, level of
DOB in man is a lot lower than this ratio would imply. There was a
report of a death of a young lady following the snorting of an amount
of DOB so massive, there was the actual recovery of over nine
milligrams of the drug from her body
tissues in the post-mortem
ex
amination. It was said that she and her companion had thought that
the drug they were using was
MDA and, taking a dosage appropriate for
this, effectively overdosed themselves. He survived, following
convulsions and an extended period (several weeks) of being in a
comatose state. Tragic examples have been reported that involve
arterial
vascular spasm. But in most overdose cases ascribed to DOB,
the identity of the drug has remained unestablished.
As with DOI, the presence of a heavy atom, the
bromine atom, in DOB
makes the
radioactive isotope labelled material a powerful research
tool. Studies with DOB labelled with either 82Br or 77Br have been
used in human subjects to follow the distri
bution of the drug. The
use of a whole body scanner permits the imaging of the intact body,
with the travelings of the radioactivity easily followed from outside.
A fascinating finding is that DOB goes first and foremost to the human
lung where it accumulates for a couple of hours. It is only
afterwards that the brain level builds up. There is a strong
implication that some
metabolic conversion occurs in the lung, and it
is only after this that the truly active
metabolite is available for
central action. This is consistent with the relatively slow onset of
effect, and the very long duration of action.
As with all the other
psychedelics which can and have been studied as
their optical
isomers, it is the "R" isomer of DOB that is the more
active than the racemic mixture, and the "S" is certainly much less
active, but it has never been run up to fully active levels. The
alpha-ethyl homologue of DOB is mentioned under ARIADNE. The
positionally rearranged
isomers of DOB are discussed under
META-DOB.
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