SYNTHESIS : (from tryptamine) A solution of 1.6 g tryptaminebase in 10 mL isopropanol was treated with 5.1 g propyl iodide and 5.2g diisopropylethyl amine, and stirred at room temperature for 36h. The volatiles were removed under vacuum, and the residue waspartitioned between CH2Cl2 and H2O made basic with NaOH. The organicphase was separated, the aqueous phase extracted with two additionalportions of CH2Cl2, the extracts pooled and the solvent removed undervacuum. The residue, a fluid brown oil weighing 2.75 g, was treatedwith 5 g acetic anhydride and heated on the steam bath for 20min. After cooling, a small amount of ammonium hydroxide was added,and the mixture added to 200 mL 0.5 N H2SO4. This aqueous solution waswashed three times with CH2Cl2 and then made basic with 25% NaOH. Thiswas extracted with 3x40 mL CH2Cl2, the extracts pooled, and thesolvent removed under vacuum. The oily residue was distilled at145-155 °C at 0.08 mm/Hg to give 1.14 g N,N-dipropyltryptamine baseas a white oil. This was dissolved in 5 mL isopropanol, acidified withconcentrated HCl, and diluted with 20 mL anhydrous Et2O to giveN,N-dipropyltryptamine hydrochloride (DPT) as a fine white powder. Theyield 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 basediisopropylethyl amine with an equivalent amount of NaHCO3 yielded thesame product but with a yield of less than 10%.
(from indole) To a well stirred solution of 10 g indole in 150 mLanhydrous Et2O there was added, dropwise over the course of 30 min, asolution of 11 g oxalyl chloride in 150 mL anhydrous Et2O. Stirringwas continued for an additional 15 min during which time there was theseparation of indol-3-ylglyoxyl chloride. This intermediate wasremoved by filtration and used directly in the following step. Thiswas added, in small increments, to 20 mL anhydrous dipropylamine whichwas being stirred. There was then added an excess of 2N HCl, themixture cooled, and the resulting solids removed by filtration. Thesewere recrystallized from aqueous EtOH to give, after air drying, 13.2g indol-3-yl N,N-dipropylglyoxylamide with a mp 95-96 °C. Asolution of 13 g indol-3-yl N,N-dipropylglyoxylamide in 350 mLanhydrous dioxane was added, slowly, to 19 g LAH in 350 mL dioxanewhich was well stirred and held at reflux temperature under an inertatmosphere. After the addition was complete, refluxing was maintainedfor an additional 16 h, the reaction mixture cooled, and the excesshydride destroyed by the cautious addition of wet dioxane. The formedsolids were removed by filtration, washed with hot dioxane, thefiltrate and washings combined, dried over anhydrous MgSO4, and thesolvent removed under vacuum. The brownish residue was dissolved inanhydrous Et2O and saturated with anhydrous hydrogen chloride. Theresulting crystals were recrystallized from benzene/methanol to give11.9 g of N,N-dipropyltryptamine hydrochloride (DPT) with a mp of178-179 °C and an overall yield of 49%.
DOSAGE : 100 - 250 mg, orally
DURATION : 2 - 4 hrs
QUALITATIVE COMMENTS : (with 200 mg, orally) "This startedsooner and was a lot stronger than I had expected. I had troubletalking and I felt very uncomfortable. I think physically I was in achair but I was on a kind of mountain surrounded by clouds. And theclouds talked to me."
(with 250 mg, orally) "I was seeing the Light real strongly. The Lightsort of looked like bright bursts of Light but also like a kind ofSpiritual Tunnel, and it seemed at one point, along with that, I saw aHuman form, but the Vision seemed like I was sort of inside the Beingand 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 limbsbecause the Being seemed to be the tunnel of Light that I was insidein 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 meand I live in them'."
(with 275 mg, orally) "I have smoked this amount one time some whileago, and this is a lot more interesting. And a lot more intense. Withsmoking, there was a body rush that was uncomfortable, and you neverreally know how much went into you, what with pyrolysis and all."
(with 500 mg, orally) "This was intensely visual, and it lasted anexhausting 12 hours. I prefer the smoking route."
(with 100 mg, smoked) "The entire experience lasted only 20 minutes. Ifound the visual experience to be everything. It was a lot more benignthan mushrooms with pretty much no toxic things, more likemescaline."
(with many mg, smoked) "I saw this vision of two hearts rotating. Theywere shaped like the usual heart shape (like a valentine). They filledmost of my vision and were rotating one inside the other. Around theoutside of the hearts there were sparkling jewels or crystals of lightof different colors, maybe four rows deep surrounding them allaround. This vision was totally clear. When I saw this vision, timewas very full and long and complete."
(with 80 mg, i.m.) "I feel light and nervous. I'm way off in a bigcastle with beautiful colors and scenery. I'm back with the girl whoaccused me of fathering her child. It's peaceful. She had everythingshe wanted. My aunt made sure we went to church on Sunday. I see thedevil in front of my face. Everything is going fast. Too fast. It'snot pleasant. Things are going zig-zag. Feels like I'm tired. I feellike an old man in a rocking chair sitting in front of aphonograph. Everything is so mixed up. I'm trying to get myselftogether. I have a vibrating feeling. It makes me feel as though I'mnot here."
(with 100 mg, i..m.) "I was being led by the hand of a wise old manwho I know was God, and we went of to the front of the synagogue. Iwas 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 ascorbatewhich affected the timing, of course. This was strong at this level. Iwas set to go to a target dosage of 60 milligrams, but decided to stopat 12. It was strong, real strong."
(with 36 mg, i.v.) "This was administered as a sterile solution of thefumarate salt, so the actual weight of the drug used is somewhatless. This was a very intense experience, every bit as powerful asthis amount of DMT."
EXTENSIONS AND COMMENTARY : The earliest reports of humanactivity, at 1 mg/Kg, are mentioned under DMT. The clinical trialsfrom which the 80 mg comment above was entered, were conducted on apopulation of physically sound alcoholics. It was not only a study todefine the nature of action of DPT, but to challenge the idea that themetabolism of the dialkyltryptamine on the 6-hydroxyl position mightgive rise to active metabolites. This challenge was in the form ofassaying 6-fluoro-N,N-diethyltrypamine in the same subjects, to see ifit might be an active placebo. This is discussed under that specificcompound, DET. Incidentally, the actual amount of DPT used wasoriginally published as being 1.0 mg/Kg body weight, and I am guessingthat the subject might have been of average weight, about 175 lbs. Inthese studies, dosages were taken up to as high as 1.3 mg/Kg, whichresulted only in a prolongation, not an intensification, of effect. Inall trials, the onset of effects occurred between 10 and 15 minutesfollowing injection.
Studies using lower dosages of DPT (15-30 mg intramuscularly) havebeen explored as adjuncts to psychotherapy with alcoholicpatients. The enhancement of recall of memories and experiences, thegreater emotional expressivenes and self-exploration, coupled with aconsistently short duration, made the drug very attractive. Higherdoses, up in the 100 milligram range, have been explored inpsychotherapy, in the quest for peak experiences. Yet another study,in exploring the interaction of therapy counseling and DPT-inducedpeak experiences with patients who are dying, the i.m. dosage rangewas between 75 and 125 milligrams.
There is a rather remarkable religious group known as the Temple ofthe True Inner Light, in New York City, which has embraced as itsEucharist DPT which they refer to as a powerful Angel of theHost. Their communion is confirmed by either the smoking or thedrinking of the sacrament, and they have been totally unbothered byany agency of the Federal Government, as far as I know. It is not asif they were unknown. Quite on the contrary, I had on one occasionreceived a request for information on the drug from a reporter who waswriting a story on DPT and its use in the church. I asked him just howhe had gotten my name, and he told me that he was given it by someonewithin the DEA. Someone, sometime, should write an essay oncontemporary religions, as to why DPT has flown, why peyote foreverstruggles, and LSD and marijuana have bombed out, when tied toreligion. Is there something about a faith being an "approved"religion? Who gives his approval? Who decides the applicability of thefirst amendment which explicitly states that, "Congress shall make nolaw respecting an establishment of religion, or prohibiting the freeexercise thereof."
I wish the True Inner Light congregation Godspeed, if you will excusethe expression. My impressions of them from our correspondence haveleft me totally convinced of their integrity and dedication. It is anintriguing fact that this tryptamine was commercially available for awhile from at least one small independent supplier of chemicalnovelties, but I believe that this is now no longer a valid source.
An intriguing (and perhaps theoretical) homologue of DPT is the1-propyl counterpart, 1,N,N-tripropyltryptamine, referred to asPDPT. It is claimed that simply reacting tryptamine with an excess ofpropyl bromide put an alkyl group on the indolic 1-position (as statedalso for the ethyl counterpart, sometimes referred to as EDET). In myown experiments with this reaction, I have yet to see any suggestionof 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.
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