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#88 HOT-7
2,5-DIMETHOXY-N-HYDROXY-4-(n)-PROPYLTHIOPHENETHYLAMINE
SYNTHESIS: A well-stirred
solution of 1.77 g
2,5-dimethoxy-beta-nitro-4-(n-propylthio)styrene (see under
2C-T-7 for
its preparation) in 20 mL
anhydrous THF was placed in an He
atmosphere
and treated with 1.5 mL of 10 M
borane-dimethyl sulfide complex. This
was followed by the addition of 0.2 g
sodium borohydride, and the
stirring was continued at room tem
perature for a week. The
volatiles
were removed under vacuum, and the residue was treated with 20 mL
dilute HCl and heated on the steam bath for 30 min. The cooled yellow
solution set up as solids. The addition of H2O was followed by
sufficient
K2CO3 to make the aqueous
phase basic. All efforts to work
with an acidified aqueous
phase resulted in terrible emulsions. The
basic
phase was extracted with 3x75 mL
CH2Cl2, and the pooled extracts
washed with H2O, then stripped of
solvent under vacuum. The
residual
yellow oil was
dissolved in 20 mL IPA, neutralized with 15 drops of
concentrated HCl, and then diluted with 50 mL
anhydrous Et2O. After a
few minutes stirring, a white
crystalline solid separated. This was
removed by filtration, washed with
Et2O, and air dried to constant
weight to provide 0.83 g of
2,5-dimethoxy-N-hydroxy-4-(n)-
propylthiophenethylamine hydrochloride
(HOT-7).
DOSAGE: 15 - 25 mg.
DURATION: 6 - 8 h.
QUALITATIVE COMMENTS: (with 15 mg) I am lightheaded, and maybe a
little tipsy. I am well centered, but I don't want to go outside and
meet people. Shades of
alcohol woozy. The effects were going already
by the fifth hour and were gone by the seventh hour. I would call it
smoothly stoning.
(with 22 mg) The transition into the effects was a bit difficult,
with a faint awareness in the tummy. But by the second hour it was
quite
psychedelic, and the body was not thought of again, except in
terms of sexual fooling around. Very rich in eyes-closed imagery, and
very good for interpretive and conceptual thinking. But the eyes-open
visuals were not as much as they might have been. At the seventh
hour, drifted into an easy sleep.
(with 22 mg) The experience was very positive, but at each turn there
seemed to be a bit of sadness. Was it a complete plus three
experience? Not quite. But it didn't miss by much. The erotic
explorations somehow just failed to knit by the thinnest of margins.
It was a truly almost-magnificent experience.
EXTENSIONS AND COMMENTARY: There is a working hypothesis that has been
growing in substance over the last few years in this strange and
marvelous area of
psychedelic drugs. It all was an outgrowth of the
rather remarkable coincidence that I had mentioned in the discussion
that followed
MDOH. There, an assay of what was thought to be MDOH
gave a measure of activity that was substantially identical to
MDA,
and it was later found out that the material had decomposed to form
MDA. So, MDA was in essence rediscovered. But when the true, valid,
and undecomposed sample of
MDOH was actually in hand, and assayed in
its own rights, it was found to have a potency that really was the
same as
MDA. So, the working hypothesis goes something like this:
AN N-HYDROXY AMINE HAS APPROXIMATELY THE SAME POTENCY AND THE SAME
ACTION AS ITS N-
HYDROGEN COUNTERPART.
Maybe the N-hydroxy compound reduces to the N-H material in the body,
and the latter is the intrinsically active agent. Maybe the N-H
material oxidizes to the N-hydroxy material in the body, and the
latter is the intrinsically active agent. Either direction is
reasonable, and there is precedent for each. The
equivalence of
MDA
and
MDOH was the first suggestion of this. And I have made a number
of NH vs. NOH challenges of this hypothesis. The interesting 2C-T-X
series has provided a number of
amines that are amenable to
N-
hydroxylation, and this is the first of them. And, after all, if
you put a hydroxy (HO) group on a thio material (T), you have a HOT
compound.
So, as far as
nomenclature is concerned, the family of N-hydroxy
analogues of N-H
amines is known as the HOT family.
How does HOT-7 compare with 2C-T-7? They are almost identical. The
same range of dose (centering on 20 milligrams) and if anything,
perhaps slightly less long lived. Lets try some other N-hydroxys!
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