SYNTHESIS : (from tryptamine) A solution of 1.6 g tryptamine
base in 10 mL isopropanol was treated with 5.1 g propyl iodide and 5.2
g diisopropylethyl amine, and stirred at room temperature for 36
h. The volatiles were removed under vacuum, and the residue was
partitioned between CH2Cl2 and H2O made basic with NaOH. The organic
phase was separated, the aqueous phase extracted with two additional
portions of CH2Cl2, the extracts pooled and the solvent removed under
vacuum. The residue, a fluid brown oil weighing 2.75 g, was treated
with 5 g acetic anhydride and heated on the steam bath for 20
min. After cooling, a small amount of ammonium hydroxide was added,
and the mixture added to 200 mL 0.5 N H2SO4. This aqueous solution was
washed three times with CH2Cl2 and then made basic with 25% NaOH. This
was extracted with 3x40 mL CH2Cl2, the extracts pooled, and the
solvent removed under vacuum. The oily residue was distilled at
145-155 °C at 0.08 mm/Hg to give 1.14 g N,N-dipropyltryptamine base
as a white oil. This was dissolved in 5 mL isopropanol, acidified with
concentrated HCl, and diluted with 20 mL anhydrous Et2O to give
N,N-dipropyltryptamine hydrochloride (DPT) as a fine white powder. The
yield was 1.10 g (45%) with a mp of 174-176 °C. IR (in cm-1): 759,
774, 831, 987 (br.), 1084, 1101. The replacement of the organic base
diisopropylethyl amine with an equivalent amount of NaHCO3 yielded the
same product but with a yield of less than 10%.
(from indole) To a well stirred solution of 10 g indole in 150 mL
anhydrous Et2O there was added, dropwise over the course of 30 min, a
solution of 11 g oxalyl chloride in 150 mL anhydrous Et2O. Stirring
was continued for an additional 15 min during which time there was the
separation of indol-3-ylglyoxyl chloride. This intermediate was
removed by filtration and used directly in the following step. This
was added, in small increments, to 20 mL anhydrous dipropylamine which
was being stirred. There was then added an excess of 2N HCl, the
mixture cooled, and the resulting solids removed by filtration. These
were recrystallized from aqueous EtOH to give, after air drying, 13.2
g indol-3-yl N,N-dipropylglyoxylamide with a mp 95-96 °C. A
solution of 13 g indol-3-yl N,N-dipropylglyoxylamide in 350 mL
anhydrous dioxane was added, slowly, to 19 g LAH in 350 mL dioxane
which was well stirred and held at reflux temperature under an inert
atmosphere. After the addition was complete, refluxing 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 brownish residue was dissolved in
anhydrous Et2O and saturated with anhydrous hydrogen chloride. The
resulting crystals were recrystallized from benzene/methanol to give
11.9 g of N,N-dipropyltryptamine hydrochloride (DPT) with a mp of
178-179 °C and an overall yield of 49%.
DOSAGE : 100 - 250 mg, orally
DURATION : 2 - 4 hrs
QUALITATIVE COMMENTS : (with 200 mg, orally) "This started
sooner and was a lot stronger than I had expected. I had trouble
talking and I felt very uncomfortable. I think physically I was in a
chair but I was on a kind of mountain surrounded by clouds. And the
clouds talked to me."
(with 250 mg, orally) "I was seeing the Light real strongly. The Light
sort of looked like bright bursts of Light but also like a kind of
Spiritual Tunnel, and it seemed at one point, along with that, I saw a
Human form, but the Vision seemed like I was sort of inside the Being
and outside, and the Human was inside me and appeared to be outside,
but I didn't see the being's face or clearly see the various limbs
because the Being seemed to be the tunnel of Light that I was inside
in the Vision, and seemed much larger than me. As King Jesus said:
(St. John 6,56) 'Whoever eats my Flesh and drinks my Blood lives in me
and I live in them'."
(with 275 mg, orally) "I have smoked this amount one time some while
ago, and this is a lot more interesting. And a lot more intense. With
smoking, there was a body rush that was uncomfortable, and you never
really know how much went into you, what with pyrolysis and all."
(with 500 mg, orally) "This was intensely visual, and it lasted an
exhausting 12 hours. I prefer the smoking route."
(with 100 mg, smoked) "The entire experience lasted only 20 minutes. I
found the visual experience to be everything. It was a lot more benign
than mushrooms with pretty much no toxic things, more like
mescaline."
(with many mg, smoked) "I saw this vision of two hearts rotating. They
were shaped like the usual heart shape (like a valentine). They filled
most of my vision and were rotating one inside the other. Around the
outside of the hearts there were sparkling jewels or crystals of light
of different colors, maybe four rows deep surrounding them all
around. This vision was totally clear. When I saw this vision, time
was very full and long and complete."
(with 80 mg, i.m.) "I feel light and nervous. I'm way off in a big
castle with beautiful colors and scenery. I'm back with the girl who
accused me of fathering her child. It's peaceful. She had everything
she wanted. My aunt made sure we went to church on Sunday. I see the
devil in front of my face. Everything is going fast. Too fast. It's
not pleasant. Things are going zig-zag. Feels like I'm tired. I feel
like an old man in a rocking chair sitting in front of a
phonograph. Everything is so mixed up. I'm trying to get myself
together. I have a vibrating feeling. It makes me feel as though I'm
not here."
(with 100 mg, i..m.) "I was being led by the hand of a wise old man
who I know was God, and we went of to the front of the synagogue. I
was handed a Torah for me to carry as a sign that I had been accepted,
and forgiven, and that I had come home."
(with 12 mg, i.v.) "We were using an i.v. drip with sodium ascorbate
which affected the timing, of course. This was strong at this level. I
was set to go to a target dosage of 60 milligrams, but decided to stop
at 12. It was strong, real strong."
(with 36 mg, i.v.) "This was administered as a sterile solution of the
fumarate salt, so the actual weight of the drug used is somewhat
less. This was a very intense experience, every bit as powerful as
this amount of DMT."
EXTENSIONS AND COMMENTARY : The earliest reports of human
activity, at 1 mg/Kg, are mentioned under DMT. The clinical trials
from which the 80 mg comment above was entered, were conducted on a
population of physically sound alcoholics. It was not only a study to
define the nature of action of DPT, but to challenge the idea that the
metabolism of the dialkyltryptamine on the 6-hydroxyl position might
give rise to active metabolites. This challenge was in the form of
assaying 6-fluoro-N,N-diethyltrypamine in the same subjects, to see if
it might be an active placebo. This is discussed under that specific
compound, DET. Incidentally, the actual amount of DPT used was
originally published as being 1.0 mg/Kg body weight, and I am guessing
that the subject might have been of average weight, about 175 lbs. In
these studies, dosages were taken up to as high as 1.3 mg/Kg, which
resulted only in a prolongation, not an intensification, of effect. In
all trials, the onset of effects occurred between 10 and 15 minutes
following injection.
Studies using lower dosages of DPT (15-30 mg intramuscularly) have
been explored as adjuncts to psychotherapy with alcoholic
patients. The enhancement of recall of memories and experiences, the
greater emotional expressivenes and self-exploration, coupled with a
consistently short duration, made the drug very attractive. Higher
doses, up in the 100 milligram range, have been explored in
psychotherapy, in the quest for peak experiences. Yet another study,
in exploring the interaction of therapy counseling and DPT-induced
peak experiences with patients who are dying, the i.m. dosage range
was between 75 and 125 milligrams.
There is a rather remarkable religious group known as the Temple of
the True Inner Light, in New York City, which has embraced as its
Eucharist DPT which they refer to as a powerful Angel of the
Host. Their communion is confirmed by either the smoking or the
drinking of the sacrament, and they have been totally unbothered by
any agency of the Federal Government, as far as I know. It is not as
if they were unknown. Quite on the contrary, I had on one occasion
received a request for information on the drug from a reporter who was
writing a story on DPT and its use in the church. I asked him just how
he had gotten my name, and he told me that he was given it by someone
within the DEA. Someone, sometime, should write an essay on
contemporary religions, as to why DPT has flown, why peyote forever
struggles, and LSD and marijuana have bombed out, when tied to
religion. Is there something about a faith being an "approved"
religion? Who gives his approval? Who decides the applicability of the
first amendment which explicitly states that, "Congress shall make no
law respecting an establishment of religion, or prohibiting the free
exercise thereof."
I wish the True Inner Light congregation Godspeed, if you will excuse
the expression. My impressions of them from our correspondence have
left me totally convinced of their integrity and dedication. It is an
intriguing fact that this tryptamine was commercially available for a
while from at least one small independent supplier of chemical
novelties, but I believe that this is now no longer a valid source.
An intriguing (and perhaps theoretical) homologue of DPT is the
1-propyl counterpart, 1,N,N-tripropyltryptamine, referred to as
PDPT. It is claimed that simply reacting tryptamine with an excess of
propyl bromide put an alkyl group on the indolic 1-position (as stated
also for the ethyl counterpart, sometimes referred to as EDET). In my
own experiments with this reaction, I have yet to see any suggestion
of 1-alkylation.
The homologue with only one propyl group on the nitrogen,
N-propyltryptamine or NPT, has been made according to the same recipe,
and is discussed under NET.
