SYNTHESIS: A solution of 100 g of 2,5-dimethoxybenzaldehyde in 220 g
nitromethane was treated with 10 g anhydrous ammonium acetate, and
heated on a steam bath for 2.5 h with occasional swirling. The
deep-red reaction mixture was stripped of the excess nitromethane
under vacuum, and the residue crystallized spontaneously. This crude
nitrostyrene was purified by grinding under IPA, filtering, and
air-drying, to yield 85 g of 2,5-dimethoxy-beta-nitrostyrene as a
yellow-orange product of adequate purity for the next step. Further
purification can be achieved by recrystallization from boiling IPA.
In a round-bottomed 2 L flask equipped with a magnetic stirrer and
placed under an inert atmosphere, there was added 750 mL anhydrous
THF, containing 30 g LAH. There was then added, in THF solution, 60 g
2,5-dimethoxy-beta-nitrostyrene. The final solution was a dirty
yellow-brown color, and it was kept at reflux temperature for 24 h.
After cooling, the excess hydride was destroyed by the dropwise
addition of IPA. Then 30 mL 15% NaOH was added to convert the
inorganic solids to a filterable mass. The reaction mixture was
filtered and the filter cake washed first with THF and then with MeOH.
The combined mother liquors and washings were freed of solvent under
vacuum and the residue suspended in 1.5 L H2O. This was acidified
with HCl, washed with with 3x100 mL CH2Cl2, made strongly basic with
25% NaOH, and reextracted with 4x100 mL CH2Cl2. The pooled extracts
were stripped of solvent under vacuum, yielding 26 g of oily residue,
which was distilled at 120-130 °C at 0.5 mm/Hg to give 21 g of a white
oil, 2,5-dimethoxy-phenethylamine (2C-H) which picks up carbon dioxide
from the air very quickly.
To a well-stirred solution of 24.8 g 2,5-dimethoxyphenethylamine in 40
mL glacial acetic acid, there was added 22 g elemental bromine
dissolved in 40 mL acetic acid. After a couple of min, there was the
formation of solids and the simultaneous evolution of considerable
heat. The reaction mixture was allowed to return to room temperature,
filtered, and the solids washed sparingly with cold acetic acid. This
was the hydrobromide salt. There are many complicated salt forms,
both polymorphs and hydrates, that can make the isolation and
characterization of 2C-B treacherous. The happiest route is to form
the insoluble hydrochloride salt by way of the free base. The entire
mass of acetic acid-wet salt was dissolved in warm H2O, made basic to
at least pH 11 with 25% NaOH, and extracted with 3x100 mL CH2Cl2.
Removal of the solvent gave 33.7 g of residue which was distilled at
115-130 °C at 0.4 mm/Hg. The white oil, 27.6 g, was dissolved in 50
mL H2O containing 7.0 g acetic acid. This clear solution was vigorous
stirred, and treated with 20 mL concentrated HCl. There was an
immediate formation of the anhydrous salt of
2,5-dimethoxy-4-bromophenethylamine hydrochloride (2C-B). This mass
of crystals was removed by filtration (it can be loosened considerably
by the addition of another 60 mL H2O), washed with a little H2O, and
then with several 50 mL portions of Et2O. When completely air-dry,
there was obtained 31.05 g of fine white needles, with a mp of 237-239
°C with decomposition. When there is too much H2O present at the time
of adding the final concentrated HCl, a hydrated form of 2C-B is
obtained. The hydrobromide salt melts at 214.5-215 °C. The acetate
salt was reported to have a mp of 208-209 °C.
DOSAGE: 12 - 24 mg.
DURATION: 4 - 8 h.
QUALITATIVE COMMENTS: (with 16 mg) A day at the Stanford museum.
Things were visually rich, yet I felt that I was reasonably
inconspicuous. The Rodin sculptures were very personal and not
terribly subtle. I saw Escher things in the ceiling design, when I
decided to sit in a foyer somewhere and simply pretend to rest.
Walking back, the displays seen in the bark of the eucalyptus trees,
and the torment and fear (of others? of themselves?) in the faces of
those who were walking towards us, were as dramatic as anything I had
seen in the art galleries. Our appetites were enormous, and we went
to a smorgasbord that evening. A rich experience in every possible
way.
(with 20 mg) The drug effect first became known to me as a shift of
colors toward golden and rose tones. Pigments in the room became
intensified. Shapes became rounder, more organic. A sensation of
lightness and rivulets of warmth began seeping through my body.
Bright lights began pulsing and flashing behind my closed lids. I
began to perceive waves of energy flowing through all of us in unison.
I saw all of us as a gridwork of electrical energy beings, nodes on a
bright, pulsating network of light. Then the interior landscape
shifted into broader scenes. Daliesque vistas were patterned with
eyes of Horus, brocades of geometric design began shifting and
changing through radiant patterns of light. It was an artist's
paradise--representing virtually the full pantheon of the history of
art.
(with 20 mg) The room was cool, and for the first hour I felt cold
and chilled. That was the only mildly unpleasant part. We had been
hanging crystals earlier that day, and the visions I had were
dominated by prismatic light patterns. It was almost as if I became
the light. I saw kaleidoscopic forms--similar to, but less intense
than, when on acid--and organic forms like Georgia O'Keefe flowers,
blossoming and undulating. My body was flooded with orgasms--
practically from just breathing. The lovemaking was phenomenal,
passionate, ecstatic, lyric, animal, loving, tender, sublime. The
music was voluptuous, almost three-dimensional. Sometimes the sound
seemed distorted to me, underwater like. This was especially so for
the less good recordings--but I could choose to concentrate on the
beauty of the music or the inadequacy of the sound's quality, and
mostly chose to concentrate on the beauty.
(with 24 mg) I am totally into my body. I am aware of every muscle
and nerve in my body. The night is extraordinary--moon full.
Unbelievably erotic, quiet and exquisite, almost unbearable. I cannot
begin to unravel the imagery that imposes itself during the finding of
an orgasm. Trying to understand physical/spiritual merging in nature
--.
EXTENSIONS AND COMMENTARY: Four quotations were chosen arbitrarily
from literally hundreds that have worked their ways into the files.
The vast majority are positive, ranging from the colorful to the
ecstatic. But not all are. There are people who choose not to go
into the corporeal but, rather, prefer the out-of-body experience.
They express discomfort with 2C-B, and seem to lean more to the
Ketamine form of altered state, one which dissociates body from mind.
There have been reports of several overdoses that prove the intrinsic
safety of this compound. Prove is used here in the classic British
sense; i.e., to challenge. "The proof of the pudding is in the
eating," is not a verification of quality, but an inquiry into the
quality itself. (The French simplify all this by using two separate
verbs for prove.) One overdose was intentional, the other accidental.
(with 64 mg) I found only mild visual and emotional effects at the 20
milligram dose, so I took the remaining 44 milligrams. I was
propelled into something not of my choosing. Everything that was
alive was completely fearsome. I could look at a picture of a bush,
and it was just that, a picture, and it posed no threat to me. Then
my gaze moved to the right, and caught a bush growing outside the
window, and I was petrified. A life-form I could not understand, and
thus could not control. And I felt that my own life-form was not a
bit more controllable. This was from the comments of a physician who
assured me that he saw no neurological concerns during this dramatic
and frightening experience.
(with 100 mg) I had weighed correctly. I had simply picked up the
wrong vial. And my death was to be a consequence of a totally stupid
mistake. I wanted to walk outside, but there was a swimming pool
there and I didn't dare fall into it. A person may believe that he
has prepared himself for his own death, but when the moment comes, he
is completely alone, and totally unprepared. Why now? Why me? Two
hours later, I knew that I would live after all, and the experience
became really marvelous. But the moment of facing death is a unique
experience. In my case, I will some day meet it again, and I fear
that I will be no more comfortable with it then than I was just now.
This was from the comments of a psychologist who will, without doubt,
use psychedelics again in the future, as a probe into the unknown.
Many of the reports that have come in over the years have mentioned
the combination of MDMA and 2C-B. The most successful reports have
followed a program in which the two drugs are not used at the same
time, nor even too closely spaced. It appears that the optimum time
for the 2C-B is at, or just before, the final baseline recovery of the
MDMA. It is as if the mental and emotional discoveries can be
mobilized, and something done about them. This combination has
several enthusiastic advocates in the psychotherapy world, and should
be the basis of careful research when these materials become legal,
and accepted by the medical community.
A generalized spectrum of 2C-B action can be gleaned from the many
reports that have been written describing its effects. (1) There is a
steep dose response curve. Over the 12 to 24 milligram range, every 2
milligrams can make a profound increase or change of response.
Initially, one should go lightly, and increase the dosage in
subsequent trials by small increments. A commonly used term for a
level that produces a just perceptible effect is "museum level." This
is a slightly-over-threshold level which allows public activities
(such as viewing paintings in a museum or scenery watching as a
passenger in a car) to be entered into without attracting attention.
There can be considerable discomfort associated with being in the
public eye, with higher doses. (2) The 2C-B experience is one of the
shortest of any major psychedelic drug. Wherever you might be, hang
on. In an hour or so you will be approaching familiar territory
again. (3) If there is anything ever found to be an effective
aphrodisiac, it will probably be patterned after 2C-B in structure.
There are two "Tweetios" known that are related to 2C-B. (See recipe
#23 for the origin of this phrase.) The 2-EtO- homologue of 2C-B is
4-bromo-2-ethoxy-5-methoxyphenethylamine, or 2CB-2ETO. The
unbrominated benzaldehyde (2-ethoxy-5-methoxybenzaldehyde) had a
melting point of 47.5-48.5 °C, the unbrominated nitrostyrene
intermediate a melting point of 76-77 °C, and the final hydrochloride
a melting point of 185-186 °C. The hydrobromide salt had a melting
point of 168.5-169.5 °C. It seems that one gets about as much effect
as can be had, with a dosage of about 15 milligrams, and increases
above this, to 30 and to 50 milligrams merely prolong the activity
(from about 3 hours to perhaps 6 hours). At no dose was there an
intensity that in any way resembled that of 2C-B.
The 2,5-DiEtO- homologue of 2C-B is
4-bromo-2,5-diethoxyphenethylamine, or 2CB-2,5-DIETO. The
unbrominated impure benzaldehyde (2,5-diethoxybenzaldehyde) had a
melting point of about 57 °C, the unbrominated impure nitrostyrene
intermediate a melting point of about 60 °C, and the final
hydrochloride a melting point of 230-231 °C. The hydrobromide salt
had a melting point of 192-193 °C. At levels of 55 milligrams, there
was only a restless sleep, and strange dreams. The active level is
not yet known.
I have been told of some studies that have involved a positional
rearrangement analogue of 2C-B. This is
2-bromo-4,5-dimethoxyphenethylamine (or 6-BR-DMPEA). This would be
the product of the elemental bromination of DMPEA, and it has been
assayed as the hydrobromide salt. Apparently, the intravenous
injection of 60 milligrams gave a rapid rush, with intense visual
effects reported, largely yellow and black. Orally, there may be some
activity at the 400 to 500 milligram area, but the reports described
mainly sleep disturbance. This would suggest a stimulant component.
The N-methyl homologue of this rearranged compound was even less
active.
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