SYNTHESIS: To a vigorously stirred suspension of 18.6 g of
5-bromobourbonal in 100 mL CH2Cl2 there was added 14.2 g methyl
iodide, 1.0 g decyltriethylammonium iodide, and 120 mL 5% NaOH. The
color was a deep amber, and within 1 min the top phase set up to a
solid. This was largely dispersed with the addition of another 50 mL
of water. The reaction was allowed to stir for 2 days. The lower
phase was washed with H2O, and saved. The upper phase was treated
with another 100 mL CH2Cl2, 50 mL of 25% NaOH, another g of
decyltriethylammonium iodide, and an additional 50 mL of methyl
iodide. The formed solids dispersed by themselves in a few h to
produce two relatively clear layers. Stirring was continued for an
additional 3 days. The lower phase was separated, washed with H2O,
and combined with the earlier extract. The solvent was removed under
vacuum to give 20.3 g of an amber oil that was distilled at 120-133 °C
at 0.4 mm/Hg to yield 15.6 g of 3-bromo-4-methoxy-5-ethoxybenzaldehyde
as a white crystalline solid with a mp of 52-53 °C.
A mixture of 15.6 g 3-bromo-4-methoxy-5-ethoxybenzaldehyde and 10 mL
cyclohexylamine was heated with an open flame until it appeared free
of H2O. The residue was put under a vacuum (0.5 mm/Hg) and distilled
at 148-155 °C yielding 19.2 g
3-bromo-N-cyclohexyl-4-methoxy-5-ethoxybenzylidenimine as an off-white
crystalline solid with a melting point 66-68.5 °C. Recrystallization
from 100 mL boiling MeOH gave a mp of 67-68.5 °C. The C=N stretch in
the infra-red was at 1640 cm-1. Anal. (C16H22BrNO2) C,H.
A solution of 17 g
3-bromo-N-cyclohexyl-4-methoxy-5-ethoxybenzyl-idenimine in 200 mL
anhydrous Et2O was placed in an atmosphere of He, stirred
magnetically, and cooled with an external dry-ice acetone bath. Then
38 mL of a 1.55 M solution of butyllithium in hexane was added over 2
min, producing a clear yellow solution. There was then added 25 mL of
butyl borate at one time, and the stirred solution allowed to return
to room temperature. This was followed with 100 mL of saturated
aqueous ammonium sulfate. The Et2O layer was separated, washed with
additional saturated ammonium sulfate solution, and evaporated under
vacuum The residue was dissolved in 200 mL of 50% MeOH and treated
with 12 mL of 30% hydrogen peroxide. This reaction was mildly
exothermic, and was allowed to stir for 15 min, then added to an
aqueous solution of 50 g ammonium sulfate. This was extracted with
2x100 mL CH2Cl2, the pooled extracts washed once with H2O, and the
solvent removed under vacuum. The residue was suspended in dilute
HCl, and heated on the steam bath for 0.5 h. Stirring was continued
until the reaction was again at room temperature and then it was
extracted with 2x100 mL CH2Cl2. These extracts were pooled and in
turn extracted with 2x100 mL dilute NaOH. The aqueous extracts were
reacidified with HCl, and reextracted with 2x100 mL CH2Cl2. After
pooling, the solvent was removed under vacuum to yield an oily
residue. This was distilled at 118-130 °C at 0.2 mm/Hg to yield 7.5 g
of 3-ethoxy-5-hydroxy-4-methoxybenzaldehyde as a distillate that set
to white crystals. Recrystallization from cyclohexane gives a product
with a mp of 77-78 °C. Anal. (C10H12O4) C,H.
A solution of 7.3 g of 3-ethoxy-5-hydroxy-4-methoxybenzaldehyde in 100
mL acetone was treated with 5 mL methyl iodide and 8.0 g finely
powdered anhydrous K2CO3, and held at reflux on a steam bath for 6 h.
The solvent was removed under vacuum, and the residue was suspended in
H2O. After making this strongly basic, it was extracted with 3x50 mL
CH2Cl2, the extracts were pooled, and the solvent removed under
vacuum. The residual amber oil was distilled at 110-120 °C at 0.4
mm/Hg to yield 7.3 g of a white oil. This spontaneously set to white
crystals of 3,4-dimethoxy-5-ethoxybenzaldehyde which had a mp of
49-49.5 °C. Anal. (C11H14O4) C,H. This same aldehyde can be
obtained, but in a less satisfactory yield, by the ethylation of
3,4-dimethoxy-5-hydroxybenzaldehyde described under the preparation of
metaproscaline (MP).
A solution of 7.2 g 3,4-dimethoxy-5-ethoxybenzaldehyde in 100 mL
nitromethane containing 0.1 g anhydrous ammonium acetate was held at
reflux for 50 min. The excess nitromethane was removed under vacuum
producing 6.8 g of a red oil which was decanted from some insoluble
material. Addition of 10 mL hot MeOH to the decantings, gave a
homogeneous solution that spontaneously crystallized on cooling. The
yellow crystals were removed by filtration, washed sparingly with MeOH
and air dried yielding 3.5 g yellow crystals of
3,4-dimethoxy-5-ethoxy-beta-nitrostyrene, with a mp of 89.5-90 °C after
recrystallization from MeOH. Anal. (C12H15NO5) C,H.
A solution of 2.0 g LAH in 100 mL anhydrous THF under He was cooled to
0 °C and vigorously stirred. There was added, dropwise, 1.3 mL of
100% H2SO4, followed by the dropwise addition of a solution of 3.1 g
3,4-dimethoxy-5-ethoxy-beta-nitrostyrene in 50 mL anhydrous THF, over the
course of 10 min. The mixture was stirred at 0 °C for a while, and
then brought to a reflux on the steam bath for 30 min. After cooling
again, the excess hydride was destroyed with IPA in THF, followed by
the addition of 20 mL 10% NaOH which was sufficient to convert the
solids to a white and granular form. These were removed by
filtration, the filter cake washed with IPA, the mother liquor and
filtrates combined, and the solvents removed under vacuum. The
residue was added to 150 mL dilute H2SO4, and the cloudy suspension
washed with 2x75 mL CH2Cl2 which removed much of the color. The
aqueous phase was made basic with 25% NaOH, and extracted with 3x50 mL
CH2Cl2. The solvent was removed from these pooled extracts and the
residue distilled at 103-116 °C at 0.25 mm/Hg to provide 2.3 g of a
colorless viscous liquid. This was dissolved in 10 mL IPA,
neutralized with about 25 drops of concentrated HCl, which produced an
insoluble white solid. This was diluted with 40 mL anhydrous Et2O
added slowly with continuous stirring. The white crystalline
3,4-dimethoxy-5-ethoxyphenethylamine hydrochloride (ME) was isolated
by filtration, washed with Et2O, and air dried, and weighed 2.4 g. It
had a mp of 202-203 °C which increased by one degree upon
recrystallization from boiling IPA. Anal. (C12H20ClNO3) C,H.
DOSAGE: 200 - 350 mg.
DURATION: 8 - 12 h.
QUALITATIVE COMMENTS: (with 200 mg) It tasted pretty strong.
However, the taste was soon gone, and an energetic feeling began to
take over me. It continued to grow. The feeling was one of great
camaraderie, and it was very easy to talk to people. Everyone was
talking to everyone else. I found it most pleasant, energetic and at
the same time relaxing, with my defenses down. This material did not
seem to lead to introspection; however, it might if one took it
without other people around. Heightened visual awareness was mild,
but the audio awareness was quite heightened. The feeling of being
with everyone was intense.
(with 250 mg) Initially I took 200 milligrams of metaescaline, and
the experience developed for me very gradually at first, and very
pleasantly. After about one half hour I became aware of a wall that
seemed to shut me in, not unpleasantly. The wall slowly dissolved,
but I was afraid I might get into a negative experience. I felt
immediate relief (from this isolation) upon taking the additional 50
mg (at 2:23 into the experiment) as though glad of the decision. I
lay down outside on a blanket. There was a marvelous feeling inside,
although no imagery. I felt the wall dissolve completely, and I
desired to join the group. From this point on the experience was most
enjoyable, euphoric. Although not dramatic like some psychedelics, it
was most rewarding for me personally. I felt a marvelous bond with
everyone present, with clear-headed, excellent thinking, and excellent
communication. All in all, a most rewarding and enjoyable experience.
Afterwards I felt much strengthened, with good energy and good
insight. I have a strong feeling that the group tailored the nature
of the experience, and that I and others were most desirous of group
interaction. I feel that one could do a lot of other things with it
if one turned one's attention to it.
(with 275 mg) Onset of both physical and mental change was slow
relative to other psychochemicals. Very gradual internal stirrings
were felt at about the hour-and-a-half point. These were mostly
feelingful rather than cognitive, and were quite pleasurable. At
about the two-and-a-half hour point I grew quite thirsty, and drank a
pint of beer. Almost immediately, and quite unexpectedly, I tomsoed
to a much higher level and remained there for another three hours
until the whole experience waned. [The verb, to tomso, means a sudden
rekindling of the drug-induced altered state with a small amount of
alcohol. It is explained in the recipe for TOMSO.] During the
experience heights, and in fact before it reached its height, talking
was easy and unimpeded. The transference feelings so characteristic
of MDMA were basically not there. But for purposes of psychotherapy,
there were some advantages: fluent associations, undefended positions,
and general bonaise.
(with 400 mg) Ingested 300 milligrams at about 1:30 in the afternoon.
Very quiet climb. Occasional yawns. Matter-of-fact view of the
world. No rosy glow. At the end of the second hour, I seem to be
stuck at a ++. Take another 100 milligrams at 3:45 PM. Still tastes
awful. Feel a small head-rush fifteen minutes after taking the
supplement, and within a half hour I am completely +3. For a while
this was a sterner mescaline. Saw the eternal, continual making of
choices, all opposites continually in motion with each other. Yin and
yang everywhere, giving life to every molecule. The universe itself
keeps alive by the action-reaction, the yes-no, the black-white,
male-female, plus-minus. All life is a continual making of choices on
all levels. Then I closed my eyes, and I found myself floating up to
the very top of a temple, where there was radiant light and a sense of
homecoming. Making love is a clear stream over and through rocks and
canyons--the earth and sky make love, and the rocks make love to
other rocks, and the water is the teasing, fondling, living and moving
actions of loving. To realize that, on some level, all existence
makes love to all other existence. The Japanese Garden: a structured
way of laying out a small glimpse into cosmic love-making, so that it
can be read by other human souls. All loving, when direct and free
and undemanding, is a touching of the Source. The hardest lesson, of
course, is how to love yourself that same way. And it remains both
the first lesson of Kindergarten and the Ph.D. final. I was able to
drift into sleep at about 4:00 AM.
EXTENSIONS AND COMMENTARY: The reorientation of the single ethyl group
of escaline (E) to the meta-position produces metaescaline (ME). In
cats, in studies of over 50 years ago, the two compounds produced
similar effects at similar dosages. In man, ME also appears to be
similar to mescaline in potency. However, a subtle difference is
apparent between ME and Peyote, the natural source of mescaline. With
Peyote itself, the initial taste of the crude cactus is more than just
foul; it might better be described as unbelievably foul. But in the
middle of a Peyote experience, the taste of the cactus is truly
friendly. When ME was retasted in the middle of an experience, the
taste was still foul.
There are other distinctions from mescaline. Unlike mescaline or
Peyote, there is rarely any body discomfort during the early phase of
intoxication, no nausea and only an occasional comment suggesting
hyperreflexia. And, also unlike mescaline, most subjective reports on
ME claim that music produces little imagery, and the exaggeration of
color perception is more reserved. Appetite is normal, the tastes and
textures of food are unusually rewarding. No subject has ever
expressed a reluctance to repeat the experience. Sleep is easy,
refreshing, and the following day seems free from residue.
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