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PiHKAL. If you're interested in how the hardlinks
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noding PiHKAL for Everything2.
a,a-DIMETHYL-3,4-METHYLENEDIOXY-PHENETHYLAMINE; 3,4-METHYLENEDIOXYPHENTERMINE
SYNTHESIS: To 150 mL of THF, under an
atmosphere of
nitrogen, there
was added 11.2 g
diisopropylamine, and the
solution was cooled with
external dry ice/IPA. There was then added 48 mL of a 2.3 M
solution
of
butyllithium in hexane, dropwise, with good stirring. This was
warmed to room tem
perature, stirred for a few min, and then all was
cooled again in the dry ice bath. Following the dropwise addition of
4.4 g of
isobutyric acid there was added 10.5 mL
hexamethylphosphoramide. Again, the stirred reaction mixture was
brought to room tem
perature for about 0.5 h. There was then added,
drop-wise, 8.5 g
3,4-methylenedioxybenzyl chloride and the mixture
allowed to stir overnight at room tem
perature. The reaction mixture
was poured into 100 mL 10% HCl, and the excess THF was removed under
vacuum. The acidic aqueous residue was extracted with 2x150 mL
Et2O.
These extracts were pooled, washed with 10% HCl, and then extracted
with 3x75 mL of 4 N
Na2CO3. These extracts were pooled, made acidic
with HCl, and again extracted with
Et2O. After drying the pooled
extracts with
anhydrous MgSO4, the
solvent was removed under vacuum to
give a residue that spontaneously
crystallized. Recrystallization
from hexane yielded 6.5 g of
2,2-dimethyl-3-(3,4-methylenedioxyphenyl)propionic acid as white
crystals with a mp of 71-73 °C. The
NMR spectrum in CDCl3 showed the
alpha-dimethyl groups as a sharp singlet at 1.18 ppm. Anal.
(
C12H14O4) C,H.
The
triethylamine salt of
2,2-dimethyl-3-(3,4-methylenedioxyphenyl)propionic acid (5.4 g
amine,
11.4 g acid) was
dissolved in 10 mL H2O and diluted with sufficient
acetone to maintain a clear
solution at ice-bath tem
perature. A
solution of 6.4 g
ethyl chloroformate in 40 mL
acetone was added to
the 0 °C
solution over the course of 30 min, followed by the addition
of a
solution of 4.1 g
sodium azide in 30 mL H2O. Stirring was
continued for 45 min while the reaction returned to room tem
perature.
The aqueous
phase was extracted with 100 mL
toluene which was washed
once with H2O and then dried with
anhydrous MgSO4. This organic
solution of the azide was heated on a steam bath until
nitrogen
evolution had ceased, which required about 30 min. The
solvent was
removed under vacuum and the residue was
dissolved in 30 mL
benzyl
alcohol. This
solution was heated on the steam bath overnight.
Removal of the excess
benzyl alcohol under vacuum left a residue 13.5
g of
1-(N-(
benzyloxycarbonyl)amino)-1,1-
dimethyl-2-(
3,4-methylenedioxyphenyl)
ethane
as an amber oil. The
dimethyl group showed, in the
NMR, a sharp
singlet at 1.30 ppm in CD
CH3. Anal. (
C19H21NO4) C,H. This
carbamate
was reduced to the primary
amine (below) or to the
methylamine (see
under
MDMP).
A
solution of 3.27 g of
1-
N-(benzyloxycarbonyl)amino-1,1-
dimethyl-2-(
3,4-methylenedioxyphenyl)
ethane
in 250 mL absolute
ethanol was treated with 0.5 g 10% palladium on
carbon. This mixture was shaken under hydrogen at 35 pounds pressure
for 24 h. The
carbon was removed by filtration through Celite, and
the filtrate titrated with HCl. The
solvent was removed under vacuum,
and the residue allowed to
crystallize. This produce was
re
crystallized from an
EtOH/EtOAc mixture to provide
a,a-dimethyl-3,4-methylenedioxyphenethylamine hydrochloride (
MDPH).
The white
crystals weighed 1.63 g and had a mp of 180-181 °C. Anal.
(
C11H16ClNO2) C,H,N.
DOSAGE: 160 - 240 mg.
DURATION: 3 - 5 h.
QUALITATIVE COMMENTS: (with 120 mg) The alert was felt in forty
minutes and I was pretty much there at an hour and twenty. Quite like
MDA, simple, with no lines, no colors, no motion, no fantasy. I am
pleasantly stoned. The
anorexia is real, as is the impotency. The
drop from the 4th to the 6th hour was softened by a modest amount of
wine, and this proved to be extremely intoxicating. My speech was
slurred, and there was later amnesia for the rather aggressive and
uninhibited behavior that occurred. I felt that there was more drug
than
alcohol contributing to this episode. My dream patterns were
disturbingly unreal.
(with 160 mg) A very quiet development. There was no body load
whatsoever. And no visual, and I saw it fading away all too soon.
This might be a good promoter, like MDPR. I felt refreshed and
relaxed on the following morning.
(with 200 mg) This has an inordinately foul taste. I felt slightly
queasy. There were short daydreams which were quickly forgotten. I
see no values that are worth the hints of physical problems, a little
eye mismanagement and some clenching of teeth, and a tendency to
sweat. I was able to sleep at only five hours into it, but there were
a couple of darts. This is not as rewarding (stoning) as
MDA, and has
none of the magic of
MDMA. It was a short-lived plus two.
EXTENSIONS AND COMMENTARY: What is the train of thought that leads
from the structure of a known compound (which is active) to the
structure of an unknown one (which may or may not be active)?
Certainly the extrapolations involve many what-if's and maybe's. The
path can be humorous, it certainly can be tortuous, and it often calls
for special things such as faith, insight, and intuition. But can one
say that it is logical?
Logic is a tricky thing to evaluate. One of the earliest
approaches was laid down by
Aristotle, in the form of the
syllogism.
In it there are three lines consisting of two premises and a
conclusion, a form that is called a "mood." All are statements of
relationships and, if the premises are true, there are only certain
conclusions that may logically follow. For example:
Every man is a lover.
Every chemist is a man.
Therefore, every chemist is a lover.
Letting lover be the major term "a" and letting chemist be the minor
term "b" and letting man be the middle term "m", this reduces to:
Every m is a,
Every b is m.
Therefore, every b is a
and it is a valid mood called Barbara.
Of the 256 possible combinations of all's and some's and none's and
are's and are-not's, only 24 moods are valid. The reasoning here with
MDPH goes:
Some stimulants when given a methylenedioxy ring are MDMA-like.
Some ring-unsubstituted 1,1-dimethylphenylethylamines are stimulants.
Therefore, some ring-unsubstituted 1,1-dimethylphenylethyl
amines when given a methylenedioxy ring are MDMA-like.
In symbolic form this is:
Some m is a, and
Some b is m, then
Some b is a
and this is not one of the 24 valid moods. Given the first premise as
some m is a, there is only one valid
syllogism form that can follow,
and this is known as Disamis, or:
Some m is a, and
Every m is b, then
Some b is a
which translates as:
Some stimulants when given a methylenedioxy group are MDMA-like.
Every stimulant is a ring-unsubstituted 1,1-dimethylphenyl ethylamine.
Therefore, some ring-unsubstituted 1,1-dimethylphenylethyl
amines when given a methylenedioxy group are MDMA-like.
The conclusion is the same. But the second premise is false so the
entire reasoning is illogical. What is the false second premise? It
is not a fact that every stimulant is a
phentermine. There are lots
of stimulants that are not
phentermines.
So much for applying syllogistics to
pharmacology.
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