#116 MDPH
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 temperature, 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 temperature 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 temperature. 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 temperature. 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 temperature.
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 CDCH3. 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
recrystallized 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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