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N-HYDROXY-MDA; 3,4-METHYLENEDIOXY-N-HYDROXYAMPHETAMINE
SYNTHESIS: To a well stirred
solution of 14.8 g
hydroxylamine
hydrochloride in 120 mL MeOH there was added 3.6 g of
3,4-methylenedioxyphenylacetone (see under
MDMA for its preparation)
followed by 1.0 g
sodium cyanoborohydride. The oxime, prepared from
the
ketone and
hydroxylamine in MeOH with
pyridine, may be
substituted
for these two components. Concentrated HCl was added over the course
of a couple of days, to keep the
pH near neutrality. When the
reaction was complete, it was added to H2O, made strongly acidic with
HCl, and washed with 3x100 mL
CH2Cl2. The aqueous
phase was made
basic with 25%
NaOH, and reextracted with 3x100 mL of
CH2Cl2. The
extracts were pooled, and the
solvent removed under vacuum to give 1.7
g of an oily residue which, with pumping under a hard vacuum for a few
minutes, changed to a white solid. This can be Kugelrohred if the
vacuum is sufficiently good to keep the tem
perature during the
distillation below 100 °C. The extremely viscous
distillate formed
crystals immediately upon wetting with IPA. It was
dissolved in 20 mL
of warm IPA and neutralized with concentrated HCl, with the
titration
end-point being red rather than orange on universal
pH paper. Modest
addition of
Et2O allowed the formation of
3,4-methylenedioxy-N-
hydroxyamphetamine hydrochloride (
MDOH) as white
crystals, which weighed 1.4 g when air dried. If the tem
perature of
distillation exceeded 100 °C, there was extensive decomposition during
distillation, with the formation of
3,4-methylenedioxyamphetamine
(
MDA) and the oxime of the
ketone. Under these circumstances, the
only base isolated was
MDA. The surest isolation procedure was to
obtain
MDOH as the free base, as a
crystalline solid which could be
re
crystallized from 5 volumes of boiling IPA. The free base had a mp
of 94-95 °C (and should not be confused with the oxime of
3,4-methylenedioxyphenylacetone which has a mp of 86-88 °C since the
mixed mp is depressed, mp 56-62 °C, or with the free base of
MDA which
is an oil). Anal. (
C10H13NO3) N. The
hydrochloride salt had a mp of
149-150 °C (and should not be confused with the
hydrochloride of
MDA
which has a mp of 185-186 °C since the mixed mp is depressed, mp
128-138 °C). Anal. (
C10H14ClNO3) N.
Acetic anhydride can serve as a
useful tool for distinguishing these materials.
MDA gives an N-
acetyl
derivative with an mp of 92-93 °C.
MDOH gives an N,O-
diacetyl
derivative with a mp of 72-74 °C. M
ethylenedioxyphenylacetone oxime
gives an O-
acetyl derivative that is an oil.
DOSAGE: 100 - 160 mg.
DURATION: 3 - 6 h.
QUALITATIVE COMMENTS: (with 100 mg) I felt hampered the first hour by
some internal barrier, which prevented total enjoyment. However, this
began to break through in a wonderful way just before the supplement
was offered. Since I felt I was beginning to move through the
barrier, I declined the supplement, particularly since I was anxious
to compare the after-effects with my first experience. I had found
the first time very remarkable, but felt unusually tired for several
days following. I feel it is important to know wh
ether this is a
specific drug-induced effect, or the result of
psychological
phenomena. The experience continued in a rich, meaningful way. There
was a marvelous inner glow, the warmth from all the other participants
was wonderful to feel, nature was most beautiful. There were no
dramatic breakthroughs, or rushes of insight or energy, but just a
wonderful contemplative space where things gently unfolded as you put
your attention on them.
(with 100 mg) The material came on fairly rapidly. In about 30
minutes, I was intensely intoxicated, and more deeply than with
MDMA.
It was a glorious feeling, and beauty was everywhere enhanced. With
eyes closed it felt marvelous, and it was appealing to pursue the
inner experience. I did notice an internal dryness which was
characteristic of
MDMA, and I had similar difficulty in urinating, but
not as intense as with
MDMA.
(with 120 mg) The colors of the market-place, of all the fresh foods,
constituted a beautiful mosaic. Nothing practical, simply a real
treasure to be used with individual intention and enjoyment.
Everything was seen with new eyes, new meanings, faces, figures, the
colors of the
rainbow subconsciously individually applied. A
'soul-scape'. The following day very exhausted, tired, back-pain.
EXTENSIONS AND COMMENTARY: The first time that
MDOH was
synthesized,
it had inadvertently and unknowingly been converted to
MDA. And the
search for proper dosage and characterization of effects of this
product was, of course, the rediscovery of the dosage and the effects
of
MDA. It is one of the world's most remarkable coincidences that
after the second synthesis of
MDOH, when MDOH had really and truly
been actually prepared, the brand new search for proper dosage and
characterization of effects revealed that they were almost identical
to the earlier observations for (the inadvertently produced)
MDA.
This reminds me of my speculations in the discussion of both FLEA and
the HOT compound where they also showed paired
molecular structures
with their prototypes that differ only by a single oxygen atom.
Again, might there be some
metabolic interconversion within the body?
The immediate thought would be that the oxygen atom (the hydroxy
group) might be
metabolically removed, and the effects of either drug
are due to the action of
MDA. But the opposite direction is in many
ways more appealing, the in vivo conversion of
MDA to
MDOH. Why more
appealing? For one thing,
oxidative changes are much more common in
the body than reductive changes. For another, the conversion of
amphetamine to N-
hydroxyamphetamine is an intermediate in the
conversion of
amphetamine to
phenylacetone, a known
metabolic process
in several animal species. And that intermediate,
N-
hydroxyamphetamine, is a material that gives the famous
cytochrome
P-450 complex that has fascinated biochemists studying the so-called
NADPH-dependent
metabolism.
I would put my money on the likelihood of
MDA going to
MDOH if it
should turn out that the two drugs interconvert in the body. And in
that case, it would be
MDOH, or another
metabolite on down the line
that is common to both
MDA and
MDOH, that is the factor intrinsic to
the intoxication that is produced. Human
metabolic studies are
needed, and they have not yet been done.
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