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Into 1 L H2O that was being stirred magnetic
ally, there was
added, in sequence, 62 g toluhydroquinone
, 160 mL 25% NaOH
, and 126 g
. After about 2 h, the reaction mixture was no longer
basic, and another 40 mL of the 25% NaOH
was added. Even with
stirring for a few additional days, the reaction mixture remained
basic. It was quenched in 2.5 L H2O, extracted with 3x100 mL CH2
and the pooled extracts stripped of solvent
under vacuum. The
remaining 56.4 g of amber oil was distill
ed at about 70 °C at 0.5
to yield 49.0 g of 2,5-dimethoxytoluene
as a white liquid. The
aqueous residues, on acidification, provided a phenolic
ed at 75-100 °C at 0.4 mm/Hg
to give 5.8 g of a pale yellow
that partially crystallize
d. These solids (with mp of
54-62 °C) were removed by filtration, and yielded 3.1 g of a solid
which was recrystallize
d from 50 mL hexane containing 5 mL toluene
This gave 2.53 g of a white crystalline
product with a mp of 66-68 °C.
A second recrystal
lization (from hexane) raised this mp to 71-72 °C.
The literature value given for the mp of 2-methyl-4-methoxyphenol
70-71 °C. The literature value given for the mp of the isomeric
is 44-46 °C. This phenol, on ethylation
, which leads directly to the 2-carbon
(one of the Tweetios) and the 3-carbon
Classic Lady IRIS.
A mixture of 34.5 g POCl3 and 31.1 g N-methylformanilide
for 10 min on the steam bath, and then there was added 30.4 g of
. Heating was continued for 2.5 h, and the
viscous, black, ugly mess was poured into 600 mL of warm H2O and
stirred overnight. The resulting rubbery miniature-rabbit-droppings
product was removed by filtration and sucked as free of H2O as
possible. The 37.2 g of wet product was extracted on the steam-bath
with 4x100 mL portions of boiling hexane which, after decantation
cooling, yielded a total of 15.3 g of yellow crystalline
This, upon recrystal
lization from 150 mL boiling hexane, gave pale
s which, when air dried to constant weight, represented
8.7 g of 2,5-dimethoxy-4-methylbenzaldehyde
, and had a mp of 83-84 °C.
) C,H,N. The Gattermann aldehyde
synthesis gave a
better yield (60% of theory) but required the use of hydrogen cyanide
gas. The malononitrile
derivative, from 5.7 g of the aldehyde
in absolute EtOH
, treated with a drop of
, was an orange crystalline
product. A sample
d from EtOH
gave a mp of 138.5-139 °C.
of 8.65 g 2,5-dimethoxy-4-methylbenzaldehyde
in 30 g
was treated with 1.1 g anhydrous ammonium acetate
heated for 50 min on the steam bath. Stripping off the excess
under vacuum yielded orange crystal
s which weighed 12.2
g. These were recrystallize
d from 100 mL IPA providing yellow
s of 2,5-dimethoxy-4-methyl-beta-nitrostyrene
which weighed, when
dry, 7.70 g. The mp was 117-118 °C, and this was increased to 118-119
°C upon recrystal
lization from benzene
To a well stirred suspension of 7.0 g LAH in 300 mL of warm THF under
an inert atmosphere
, there was added 7.7 g
in 35 mL THF over the course of
0.5 h. This reaction mixture was held at reflux for 24 h, cooled to
, and the excess hydride
destroyed with 25 mL IPA.
There was then added 7 mL 15% NaOH
, followed by 21 mL H2O. The
granular gray mass was filtered, and the filter cake washed with 2x50
mL THF. The combined filtrate and washes were stripped of their
s under vacuum to give a residue weighing 7.7 g which was
ed at 90-115 °C at 0.3 mm/Hg
to provide 4.90 g of a clear,
white oil, which crystallize
d in the receiver. This was dissolve
25 mL IPA, and neutralized with concentrated HCl which produced
s of the salt. These were dispersed with 80 mL
, filtered, and washed with Et2O to give, after air
drying to constant weight, 4.9 g of fluffy white crystal
(2C-D). The mp was
213-214 °C which was not improved by recrystal
lization from CH3CN
mixture, or from EtOH
. The hydrobromide
salt had a mp of 183-184 °C.
, from the free base in pyridine
treated with acetic
, was a white crystalline
solid which, when recrystallize
from aqueous MeOH, had a mp of 116-117 °C.
20 - 60 mg.
4 - 6 h.
(with 10 mg) There is something going on, but
it is subtle. I find that I can just slightly redirect my attention
so that it applies more exactly to what I am doing. I feel that I can
learn faster. This is a `smart' pill!
(with 20 mg) Butterflies in stomach whole time. OK. This is about
the right level. In retrospect, not too interesting. Primarily a
stimulant, not entirely physically
pleasant. The visual is not too
exciting. I am easily distracted. One line of thought to another. I
feel that more would be too stimulating.
(with 30 mg) I was into it quite quickly (not much over
three-quarters of an hour) and got up to a ++ by the end of an hour.
There is something unsatisfactory about trying to classify this level.
I had said that I was willing to increase the dose to a higher level,
to break out of this not-quite-defined level into something
delic. But I may not want to go higher. Under different
circumstances I would not mind trying it at a considerably lower
dosage, perhaps at the 10 or 15 milligrams. I do not have a
comfortable label on this material, yet.
(with 45 mg) There was a rocket from the half-hour to the one and a
half hour, from nothing up to a +++. Somehow the intimacy and the
erotic never quite knit, and I feel that I am always waiting for the
experience to come home. Talking is extremely easy, but something is
missing. Appetite is good. I am down by the fifth hour, and sleep is
comfortable. This compound will take some learning.
(with 75 mg) This is a +++, but the emphasis is on talking, not on
personal interacting. I am putting out, but my boundaries are intact.
I was able to sleep at the sixth hour. Communication was excellent.
This is fast on, but not too long lived. Maybe a therapy tool?
(with 150 mg) A truly remarkable psyche
delic, one which could compare
favorably with 2C-B
. There are intense colors, and I feel that more
would be too much.
EXTENSIONS AND COMMENTARY:
Wow! This particular compound is what I
call a pharmacological
tofu. It doesn't seem to do too much by
itself, always teasing, until you get to heroic
levels. But a goodly
number of experimental therapists have said that it is excellent in
extending the action of some other materials. It seems to boost the
waning action of another drug, without adding its own color to the
experience. Yet, the comment above, on the high level of 150
milligrams, is a direct quote from the use of this compound in Germany
(where it is called LE-25) in therapeutic research.
This is probably the most dramatic example of the loss of potency from
(DOM, active at maybe 3 milligrams) to a phenethylamine
(only one tenth as active). It is so often the case that the first of
a series is not the most interesting nor the most potent member. As
intriguing and as difficult-to-define as the 2C-D story might be, the
next higher homologue
of this set, 2C-E
, is maximally active at the 15
to 20 milligram level, and is, without any question, a complete
and the N,N-dimethyl homologue
s of 2C-D have been
d from 2C-D. The N-monomethyl
compound was obtained by the
of the Schiff's base formed between 2C-D and
with methyl sulfate
, followed by hydrolysis; the
salt had a melting point of 150-151 °C, from EtOH
compound resulted from the action of formaldehyde
acid on 2C-D; the hydrochloride
salt had a melting point of 168-169 °C
. These two compounds were some ten times less
effective in interfering with conditioned responses in experimental
rats. There is no report of their having been explored in man.
I have learned of an extensive study of ethoxy homologue
s of a number
of the phenethylamines
in the 2C-X series; they have been collectively
called the "Tweetios." This Sylvester and Tweety-bird allusion came
directly from the compulsive habit of trying to alleviate the boredom
of driving long distances (not under the influence of anything) by the
attempt to pronounce the license plates of cars as they passed. The
first of this series of compounds had a name that indicated that there
was an ethoxy group at the 2-position, or 2-EtO
, or Tweetio, and the
rest is history. In every compound to be found in the 2C-X family,
there are two methoxy groups, one at the 2-position and one at the
5-position. There are thus three possible tweetio compounds, a
-, a 5-EtO- and a 2,5-di-EtO-. Those that have been evaluated in
man are included after each of the 2C-X's that has served as the
prototype. In general, the 2-EtO
- compounds have a shorter duration
and a lower potency, the 5-EtO
- compounds have a relatively unchanged
potency and a longer time duration; the 2,5-di-EtO
very weak, if active at all.
of 2C-D is
, or 2CD-2ETO
) had a melting point
of 60.5-61 °C, the nitrostyrene
intermediate a melting point of
110.5-111.5 °C, and the final hydrochloride
a melting point of 207-208
°C. The hydrobromide
salt had a melting point of 171-173 °C. At
levels of 60 milli-grams, there was the feeling of closeness between
couples, without an appreciable state of intoxication. The duration
was about 4 hours.
of 2C-D is
, or 2CD-5ETO
) had a melting point of
81-82 °C, and the details of this synthesis are given in the recipe
for IRIS. The nitrostyrene
intermediate had a melting point of
112.5-113.5 °C and the final hydrochloride
salt had a melting point of
197-198 °C. The hydro-bromide
salt had a melting point of 158-159 °C.
At dosage levels of 40 to 50 milli-grams, there was a slow, gradual
climb to the full effects that were noted in about 2 hours. The
experience was largely free from excitement, but with a friendly
openness and outgoingness that allowed easy talk, interaction, humor,
and a healthy appetite. The duration of effects was 12 hours.
of 2C-D is
, or 2CD-2,5-DIETO. The
) had a melting point of
102-103 °C, the nitrostyrene
intermediate a melting point of 108-109
°C, and the final hydrochloride
salt a melting point of 251-252 °C.
At a level of 55 milligrams, a plus one was reached, and what effects
there were, were gone after four hours.
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