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To a solution
of 12.4 g 2,3,4-trimethoxybenzaldehyde
mL glacial acetic acid, there was added 7 mL nitroethane
and 4.1 g
anhydrous ammonium acetate
, and all was held at reflux temperature
1.5 h. To the cooled and well stirred reaction mixture, H2O was added
slowly, dropping out an oily crystalline
solid mass. This was
separated by filtration, and ground under a quantity of 50% aqueous
acetic acid, and re-filtered. The 6.5 g of crude product was
d from boiling MeOH to give, after air drying to constant
weight, 5.0 g of 2-nitro-1-(2,3,4-trimethoxyphenyl)propene
, with a mp
of 56-57 °C. Anal. (C12H15NO5
To a gently refluxing suspension of 3.0 g LAH in 300 mL anhydrous Et2O
under a He atmosphere
, there was added 3.65 g
by allowing the condensing
drip into a shunted Soxhlet thimble containing the nitrostyrene
and effectively adding a warm saturated solu-tion of it dropwise.
ing was maintained for 5 h following the completion of the
addition of the nitrostyrene
. The milky reaction mixture was cooled
and the excess hydride
destroyed by the addition of 200 mL 10% H2SO4.
When the aqueous and Et2O
layers were finally clear, they were
separated, and 75 g of potassium sodium tartrate
d in the
aqueous fraction. NaOH
(25%) was then added until the pH
was >9, and
this was then extracted with 3x75 mL CH2
Cl2. Evaporation of the
under vacuum produced 2.5 g of a nearly colorless clear oil
that was dissolve
d in 300 mL anhydrous Et2O
which was saturated with
HCl gas. The product, 2,3,4-trimethoxyamphetamine
(TMA-3) separated as a fine white solid. This was
removed by filtration, Et2O
washed, and air dried to constant weight.
The yield was 1.65 g of a product which, after recrystal
IPA, had a mp of 148-149 °C. Anal. (C12H20ClNO3
greater than 100 mg.
(with 100 mg) There were no effects at all. No
eye dilation, no believable diversion from complete normalcy.
Appetite was normal, as well.
EXTENSIONS AND COMMENTARY:
There is a small lesson to be learned from
this completely inactive compound. There is no way of saying that it
is or is not in-active. All that can be said is that trials were made
(in this case using three separate individuals) at an oral level of
100 milligrams. And, at this level, nothing happened. And since a
bottom threshold for mescaline would be perhaps 200 milligrams, it can
be honestly said that the activity of this compound, if expressed
relative to mescaline (using mescaline units) is less than 2 M.U. Had
200 milligrams been inactive, it would have been less than 1.0 M.U.
If 2 grams had been inactive, it would have been less than 0.1 M.U.
But the actual printed form, activity < 2.0 M.U. was accepted by many
readers as indicating that TMA-3 was active, but at dosages greater
than 100 milligrams. All that can be said is, if there is activity,
then it will be at oral levels greater than 100 milligrams At the
moment, as far as I know, this compound is not active in man, but then
I know of no trials in excess of 100 milligrams.
This admonition applies to all the published M.U. values that are
preceded by the "less than" sign, the "<."
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