SYNTHESIS : To a well-stirred solution of 1.25 g
5-methoxyindole in 15 mL TBME there was added dropwise a solution of
1.1 g oxalyl chloride in 15 mL TBME, over the course of 20
min. Stirring was continued for an additional 10 min during which time
there was the separation of 5-methoxyindol-3-ylglyoxyl chloride as a
tomato-red crystal, which was removed by filtration and washed with a
small amount of TBME. The loose crystals were added, a bit at a time,
to 2.0 mL well-stirred pyrrolidine, and the stirring continued until
the red color had dissipated and the solids had returned to room
temperature as a cream-colored paste. There was then added 80 mL of 1
N HCl which produced a product with a loose crystalline texture. This
was removed by filtration yielding, after air drying at 100 °C to
constant weight, 1.13 g of a cream colored material with a mp in the
180-195 °C area. Recrystallized from 15 mL of boiling MeOH gave,
after cooling and filtering,
5-methoxyindol-3-yl-N,N-tetramethyleneglyoxylamide as a white
crystalline solid weighing, after air-drying to constant weight, 0.65
g (28%) with a mp of 211-212 °C. IR (in cm-1): 700, 741, 792, 1013,
1150, 1188, with a broad carbonyl centered at about 1620 and the
indolic NH stretch seen as a broad peak at 3160.

A solution of 0.52 g
5-methoxyindol-3-yl-N,N-tetramethyleneglyoxylamide in 15 mL anhydrous
dioxane was added, slowly, to 0.80 g LAH in 15 mL dioxane which was
well-stirred and held at reflux temperature under an inert
atmosphere. After the addition was complete, reflux was maintained for
an additional 16 h, the reaction mixture cooled, and the excess
hydride destroyed by the cautious addition of wet dioxane. The formed
solids were removed by filtration, washed with hot dioxane, the
filtrate and washings combined, dried over anhydrous MgSO4, and the
solvent removed under vacuum. The pale amber residue was distilled at
the KugelRohr at 160-170 °C at 0.05 mm/Hg to give 0.11 g (23%) of
5-methoxy-N,N-tetramethylenetryptamine as an off-white oil that did
not crystallize. MS (in m/z): C5H10N+ 84 (100%);
methoxyindolemethylene+ 160 (4%); parent ion 244 (6%). The
hydrochloride salt was prepared by treating an Et2O solution of the
free base with anhydrous hydrogen chloride gas, and recrystallizing
the formed solids from MeOH/benzene. The mp was 164-167 °C.

DOSAGE : 0.5 – 2 mg, orally

DURATION : several hours

QUALITATIVE COMMENTS : (with 0.5 mg, orally) “This stuff is an
absolute poison. Within minutes I noticed what can only be called
ear-ringing without any ear-ringing. Intense tinnitus with no sound,
most uncomfortable. There were two waves of nausea and vomiting of
yellow bilious stuff, with thick mucus for saliva. I can’t think
straight — muddled. I can’t get answers to questions because I simply
cannot form the questions. Eyes closed to music gave no images, but
the music sounded OK. Recovery was quite rapid, and I was together
again in a few hours. Never again.”

(about 1 mg, smoking) “I managed to vaporize about a milligram of the
material, and there was nothing profound. There was a slight feeling
of calmness. As I felt sure that this material would be a quieting
agent, I managed to vaporize and inhale what might have been up to
another milligram. There were no psychedelic effects manifested, and I
fell asleep easily 10 minutes later.”

(with 3 mgs, smoking) “Initially the compound exhibited a
5-MeO-DMT-like effect. There was a total loss of self-identity in a
nearly instantaneous rush. I felt as if the top of my head was blown
off at the inset of the drug experience. My observers told me that I
had been unconscious for four hours. I remember reentering with the
feeling ‘God is Love.’ After completely coming to, I felt very
nauseous, and threw up in the bathroom several times. I felt drained
and sick for the rest of the evening as well as mentally slow. By the
next morning I was more alert and responsive, I have absolutely no
memory of anything that transpired while I was on the compound.”

(with 3 mgs, smoking) “I inhaled the vaporized sample at 10 past
noon. There was quite a rush. There were none of the shifting shapes,
colors and forms of DMT. Nor was it acute with clarity or energy as
with my many experiences with 5-MeO-DMT. The effect was intense but
not terrifying, with a full body buzz and with humming resonance as I
fell backwards into something where all memory was lost. I was told
that at 18 past noon, I was unconscious. Something over an hour later,
I started flailing, rolling about, quivering and shaking, and had very
constricted pupils. In another hour I was able to talk lucidly, but
quietly. In yet another hour, I was nauseous and tried for the
bathroom, but didn’t make it. The people who were watching me were
alarmed. My actions were scary. And my skin looked funny for several
days afterwards. There are long-lasting properties of this. My first
exposure was with perhaps a milligrams (smoked, also) and the effects
were substantial, with rough edges and minor dysphoria.”

(with 4 mgs, smoking) “This was the free base. I remember the pipe,
and the inhalation and, with the pouring of a small glass of scotch, I
settled down in front of the TV to watch a re-run of Star Trek. That
was it. I came to some time later in the front room of a professional
ally of mine, who had by chance discovered me walking down the street
near his house. I do not recall, nor have I been able to regain any
memories of the time I was ‘out there.’ I apparently experienced no
physical discomfort from the drug. In fact I distinctly remember
feeling very comfortable when I awoke. Clearly this compound is some
weird-ass shit.”

EXTENSIONS AND COMMENTARY : Again, as with other compounds in
these writings, there is an irresistible urge to present
generalizations. But with this particular material, there are obvious
unresolved problems with both dosage or duration, as such I am limited
to the few comments provided above. Dosage? A very few milligrams
parenterally, but with smoking such small amounts it is hard to
accurately estimate the actual dosages received. Duration? One subject
could be fine the next morning, and another could be still aware of
wrongness a week later. I am uncomfortable with any compound that
seems to be widely variable in its impact on different people.

The qualitative aspects of these (and other) reports imply some
individual variability. It is always easy to look at tryptamines such
as this one, or the others in these recipes, and say, “We know that
they are psychedelics. And maybe good ones or maybe bad ones. So we
should look at them with that preconceived notion in mind.” But
looking objectively at this particular compound, 5-MeO-pyr-T, we are
far away from any vocabulary of psychedelics. How is it different
from, say, what one might expect from a Fentanyl analogue? Here is a
collection of trials that describe parenteral administration, and the
quick development of an anesthesia. This compound may not be the new
Fentanyl because of the nausea during what would be the recovery
period. But what are the chances that, perhaps not with this compound,
but with any of the obvious analogues that are screaming to be
assayed, there just might be a useful clinical tool?

There is another message of warning. Here one must accept the eloquent
argument that, for the structuring of an experiment with an unknown
and thus undefined new drug, there must be observers present who are
both sober and sympathetic. The heroic and macho, “I’ll do it my way,”
can lead to both psychological problems and physical risks. As with
scuba diving, always work with a partner.

With both pyr-T and 4-HO-pyr-T, there are two additional ring
analogies that are natural companions to 5-MeO-pyr-T. These are the
piperidine and the morpholine counterparts, 5-MeO-mor-T and
5-MeO-pip-T. Both compounds are in the literature, and an entry
reference to them can be gotten from the “known tryptamines”
appendix. Along with the pyrrolidine material I had made a reasonable
supply of the amides for these other two, both by way of the
5-methoxyindole and oxalyl chloride procedure given above. With
piperidine, there is
5-methoxyindol-3-yl-N,N-pentamethyleneglyoxylamide, mp 167-169 °C
and IR, (in cm-1), 730, 780, 811, 928, 1033, 1161, a broad carbonyl at
1600 and a broad indolic NH stretch at 3190. With morpholine, the
corresponding glyoxylamide melted at 193-194 °C, with an IR
spectrum (in cm-1), of 747, 791, 856, 925, 976, 1043 and 1122, the
carbonyl at 1620 and the broad NH at 3150.

With the rather unexpected, and unencouraging descriptions of the
pyrrolidine tryptamines in general, and this one in particular, I was
not too blinding a hurry to explore the two heterocyclic
analogues. The amides are still on the shelf in the lab. If some good
reason comes forth to assay the final amines, they can be made with a
dash of lithium aluminum hydride, but until then I have other things
to do.


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