This is a recipe from
PiHKAL. If you're interested in how the hardlinks
were chosen, read
noding PiHKAL for Everything2.
#21 3C-BZ
4-BENZYLOXY-3,5-DIMETHOXYAMPHETAMINE
SYNTHESIS: A
solution of 268 g
2,6-dimethoxyphenol and 212 g allyl
bromide in 700 mL dry
acetone was treated with 315 g
anhydrous K2CO3
and held at reflux for 16 h. The
solvent was removed under vacuum,
and the residue
dissolved in H2O and extracted with 3x100 mL
CH2Cl2.
The pooled extracts were washed with 5%
NaOH, then with H2O, and the
solvent removed under vacuum. The residue, which weighed 245 g, was
stirred and heated in an oil bath to 230 °C at which point an
exothermic reaction set in. The heating was maintained at 230 °C for
0.5 h, and then the reaction mixture
distilled. There was obtained a
total of 127 g of
5-allyl-1,3-dimethoxy-2-hydroxybenzene as a
colorless
distillate, that was identical in all respects to natural
5-
methoxyeugenol obtained from Oil of Nutmeg.
A
solution containing 40.4 g 5-
methoxyeugenol and 26.6 g
benzyl
chloride in 65 mL
EtOH was added, all at once, to a hot and well
stirred
solution of 11.7 g KOH in 500 mL
EtOH. The
potassium salt of
the
phenol crystallized out immediately. By maintaining reflux
conditions, this slowly re
dissolved, and was replaced by the steady
deposition of KCl. After 6 h, the reaction mixture was cooled, and
the solids removed by filtration. The filtrate was stripped of
solvent under vacuum to give 57 g of crude
5-allyl-2-benzyloxy-1,3-dimethoxybenzene. This was
dissolved in a
solution of 60 g KOH in 80 mL
EtOH and heated on the steam bath for 16
h. The reaction mixture was quenched in 500 mL H2O, and extracted
with 2x200 mL
CH2Cl2. Removal of the
solvent under vacuum gave 35.6 g
of crude
2-benzyloxy-1,3-dimethoxy-5-propenylbenzene.
To a stirred, ice-cold
solution of 33.6 g of the above impure
2-benzyloxy-1,3-dimethoxy-5-propenylbenzene and 13.6 g
pyridine in 142
mL
acetone, there was added 24.6 g
tetranitromethane. After stirring
for 3 min, there was added a
solution of 7.9 g KOH in 132 mL H2O,
followed by additional H2O. The oily
phase that remained was H2O
washed, and then diluted with an equal volume of MeOH. This slowly
set up to yellow
crystals, which were removed by filtration and washed
sparingly with MeOH. There was obtained 9.2 g
1-(4-benzyloxy-3,5-dimethoxyphenyl)-2-nitropropene with a mp of 84-85
°C. An
analytical sample, from
EtOH, had a mp of 86-87 °C.
To a refluxing suspension of 5.5 g LAH in 360 mL
anhydrous
Et2O under an inert
atmosphere, there was added 8.6 g
1-(4-benzyloxy-3,5-dimethoxyphenyl)-2-nitropropene by letting the
condensing
Et2O leach out a saturated
solution from a modified Soxhlet
condenser. The addition took 1.5 h and the refluxing was maintained
for an additional 4 h. After cooling, the excess
hydride was
destroyed by the cautious addition of 330 mL of 1.5 N H2SO4. The
aqueous
phase was heated up to 80 °C, filtered through paper to remove
a small amount of in
soluble material, and treated with a
solution of 8
g picric acid in 150 mL boiling
EtOH. Cooling in the ice chest
overnight gave globs of the
amine picrate, but no clear signs of
crystallization. These were washed with cold H2O, then
dissolved in
5%
NaOH to give a bright yellow
solution. This was extracted with
3x150 mL
CH2Cl2, the
solvent removed under vacuum, the residue
dissolved in 300 mL
anhydrous Et2O, freed from a little particulate
material by filtration through paper, and then saturated with hydrogen
chloride gas. There was thus obtained, after filtering,
Et2O washing
and air drying, 2.5 g
4-benzyloxy-3,5-dimethoxyamphetamine
hydrochloride (3C-BZ) as a white solid with a mp of 161-164 °C.
DOSAGE: 25 - 200 mg.
DURATION: 18 - 24 h.
QUANTITATIVE COMMENTS: (with 25 mg) I went into an emotionally
brittle place, and for a while I was uncomfortable with childhood
reminiscences. The seeing of my family's
Christmas tree in my mind
was almost too much. I cried.
(with 50 mg) The action is distinct--wakeful--alerting and wound
up.
Hypnogogic imagery, and I could not sleep at night with my mind
doing many uncontrolled, tangential, busy things. I had fleeting
nausea early in the process.
(with 100 mg) I took this in two portions. Following 50 milligrams I
was aware of a slight light-headedness at a half-hour, but there was
little else. At 1 1/2 hours, I took the second 50 milligrams and the
augmentation of effects was noted in another half hour. The
experience quietly built up to about the fifth hour, with some erotic
fantasy and suggestions of changes in the visual field. I could not
sleep until the twelfth hour, and my dreams were wild and not too
friendly. There was no body threat from this, but I was not
completely baseline until the next day. I am not too keen to do this
again--it lasts too long.
(with 100 mg) No effects.
(with 150 mg) This is in every way identical to 100 micrograms of
LSD.
(with 180 mg) I can compare this directly to TMA which was the
material I took last week. Many similarities, but this is
unquestionably more intense than the TMA was at 200 milligrams. It is
hard to separate the degree of impact that this drug has, from the
simple fact that it lasts forever, and I was getting
physically tired
but I couldn't sleep. There is some
amphetamine-like component, more
than with TMA.
EXTENSIONS AND COMMENTARY: Two points are worthy of commentary; the
potency and the promise of 3C-BZ.
As to potency, there is such uncertainty as to the effective dose,
that it is for all intents and purposes impossible to predict just
what dose should be considered for a person's first time with this.
The choice of quotations was made with the intention of giving a
picture of this scatter. A total of ten subjects have explored this
compound, and the very broad range given above, 25 to 200 milligrams,
reflects the degree of variation that has been encountered.
Which is a shame, because the concept of a new ring such as is found
here on the 4-position would have allowed an extremely wide array of
substituents. Electron-rich things,
electron-poor things, heavy
things, light things, and on and on. This could have been a location
of much variation, but it is a possibility that the uncertainties of
dosage might extrapolate to these novel ring
substitutions as well.
Only a single variation was made, the 4-
fluorobenzyl analogue. This
was prepared following exactly the procedure given here for 3C-BZ,
except for the replacement of
benzyl chloride with 4-
fluorobenzyl
chloride. The allyl intermediate was an oil, but the
propenyl isomer
gave solids with a melting point of 59-60 °C from hexane. The
nitrostyrene was a yellow
crystalline solid from
methanol with a
melting point of 98-99 °C. The end product,
3,5-dimethoxy-4-(4-fluorobenzyloxy)amphetamine hydrochloride (3C-FBZ)
was a white solid with a melting point of 149-150 °C. It has been
assayed only up to 4 milligrams and there was absolutely no activity
of any kind observed at that level.
Back to PiHKAL?