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'''Dipropyltryptamine (DPT)'''  
{{SummarySheet}}
{{SubstanceBox/DPT}}
'''N,N-Dipropyltryptamine''' (also known as '''Dipropyltryptamine''', '''DPT''',  and '''"The Light"''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::tryptamine]] class. It is closely related to [[DMT]] and is reported to be uniquely similar in its hallucinogenic intensity, albeit with a moderately longer duration and greater unpredictability relative to DMT and other psychedelic tryptamines.


== Hallucinogenic Properties ==
DPT was first synthesized in 1950.<ref>{{cite journal|last1=Li|first1=J. X.|last2=Rice|first2=K.|last3=France|first3=C. P.|year=2007|title=Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity|journal=Behavioural Pharmacology|issn=0955-8810|eissn=1473-5849|oclc=22170289|volume=18|issue=4|pages=283-288|doi=10.1097/FBP.0b013e3281f19ca0|pmid=17551320}}</ref> Human use was first reported in 1973, where it was researched in low doses as an adjunct to therapy for alcoholism.<ref>{{cite journal|last1=Grof|first1=S.|last2=Soskin|first2=R. A.|last3=Richards|first3=W. A.|last4=Kurland|first4=A. A.|title=DPT as an Adjunct in Psychotherapy of Alcoholics|year=1973|journal=International Pharmacopsychiatry|issn=0020-8272|oclc=1753673|doi=10.1159/000467979|pmid=4150711|volume=8|issue=1|pages=104-115}}</ref> It has also been researched in high doses to induce peak experiences for terminal cancer patients.<ref>{{cite journal|last1=Richards|first1=W. A.|last2=Rhead|first2=J. C.|last3=Dileo|first3=F. B.|last4=Yensen|first4=R.|last5=Kurland|first5=A. A.|title=The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients|year=1977|volume=9|issue=1|journal=Journal of Psychedelic Drugs|pages=1-10|issn=0022-393X|oclc=7565359|doi=10.1080/02791072.1977.10472020}}</ref> It has gained some notoriety for its adoption as the primary sacrament for the "Temple of the True Inner Light" in the United States, a Christian off-shoot organization who believe in the ritual use of [[psychedelics]] and refer to them as "the true flesh of God."<ref>{{cite web|title=Temple of the True Inner Light|access-date=January 9, 2020|url=http://psychede.tripod.com/}}</ref>


DPT is commonly consumed via [[insufflation]] or [[orally]]. Many report the experience of insufflation to be very congestive and painful which, with the rapidness of onset, does not give the user much time to acclimate themselves to its powerful effects. It can also be administered [[intramuscular|intramuscularly]] or via [[vaporization]] after conversion to the freebase form. Smoking the freebase is reported to be the preferred route used by the "Temple of True Inner Light". More experienced members ingest a DPT tea. {{citation needed}}


While dipropyltryptamine is chemically similar to dimethyltryptamine, the effects are markedly different.
Very little data exists about the pharmacological properties, metabolism, and toxicity of DPT, and it has relatively little history of human usage. It has long been available on the [[research chemicals]] market as a legal, grey-market alternative to [[DMT]], and commercially distributed through online vendors. Many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with [[hallucinogens]]. It is highly advised to approach this powerful [[psychedelic]] substance with the proper amount of precaution and [[Responsible drug use#Hallucinogens|harm reduction practices]] when using it.


The most prominent features of the DPT experience are increased significance or intensity of music, colors take on a new intensity or appearance, the body may have a buzz or vibratory feeling, a pleasant sensation of warmth, complete ego loss, apparitions of faces, and visions of bizarre creatures and alien lands.
==Chemistry==
{{drugbox |
DPT, or N,N-dipropyltryptamine, is a synthetic indole molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. DPT contains two propyl groups carbon chains bound to the terminal amine R<sub>N</sub> of its tryptamine backbone.  
| IUPAC_name = 3-[2-(dipropylamino)ethyl]indole
| image = DPT.svg.png
| image2= DPT-3d-sticks.png
| width = 150px
| width2= 150px
| CAS_number = 61-52-9
| ATC_prefix =  
| ATC_suffix =
| PubChem = 6091
| C=16 | H=24 | N=2
| molecular_weight = 244.38 g/mol
| smiles = CCCN(CCC)CCC1=CNC2=C1C=CC=C2
| melting_point = 174.5
| melting_high = 178
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU = 
| pregnancy_US =
| pregnancy_category = 
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Ingestion]], [[inhalation]], [[intravenous therapy|intravenous]] or [[intramuscular injection|intramuscular]] [[Injection (medicine)|injection]]
}}
While seeing other beings under the influence of DPT is not uncommon, the perspective is more as an observer or watcher, as contrasted to the more personal real-feeling entity contact reported with '''[[DMT]]'''.


Also reported is a loss of ego boundary; for example, the boundary between the self and a table may not be easy to distinguish. Difficulty distinguishing other boundaries is common as well. For example, different colors may be difficult to distinguish. Other sensory input may also become blended. This is distinct from synaesthesia.
DPT has a number of substituted analogs such as [[4-HO-DPT]] or [[4-AcO-DPT]].


A user may also encounter the feeling of experiencing the life of someone else, or having had all possible experiences simultaneously. One may have the experience of seeing the universe from different locations in space and time.
==Pharmacology==
{{pharmacology}}
{{Further|Serotonergic psychedelic}}
Studies on rodents have found that the effectiveness with which a selective 5-HT<sub>2A</sub> receptor antagonist blocks the behavioral actions of this compound strongly suggest that the 5-HT<sub>2A</sub> receptor is an important site of action for DPT, but the modulatory actions of a 5-HT<sub>1A</sub> receptor antagonist also imply a 5-HT<sub>1A</sub>-mediated component to the actions of DPT.<ref>{{cite journal | vauthors=((Fantegrossi, W.)), ((Reissig, C.)), ((Katz, E.)), ((Yarosh, H.)), ((Rice, K.)), ((Winter, J.)) | journal=Pharmacology Biochemistry and Behavior | title=Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): Possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents | volume=88 | issue=3 | pages=358–365 | date= January 2008 | url=https://linkinghub.elsevier.com/retrieve/pii/S0091305707002894 | issn=00913057 | doi=10.1016/j.pbb.2007.09.007}}</ref> The role of these interactions and how they result in the [[psychedelic]] experience remains the subject of ongoing scientific investigation.


Visuals are often geometric, wavy, and/or spiraled. Other visual distortions and hallucinations tend to be experienced in the peripheral vision. The self or the environment may take on a stylized cartoon-like look or feel. Pleasant flashes of light and sparkles are also common.
==Subjective effects==
Relative to psychedelic tryptamines like DMT, DPT is often reported to be similar in its [[hallucinogenic]] intensity, albeit with a moderately longer duration and more challenging effects. DPT experiences are often described as a "bizarre", "unsettling", and "darker" version of DMT experiences. DPT is reported to be more sensual and physical than DMT and other psychedelics with a corresponding amount of adverse physical effects.  


At light to moderate doses, users often report a slight sense of anaesthetization and relaxation. As the dose increases, hyper-awareness of one's heart rate and breathing increases and body tremors and loss of muscle control are often reported. The effects of DPT can range from strong euphoria and sensuality to nausea, panic, and intense states dysphoria even within the same experience.


== Dose ==
{{Preamble/SubjectiveEffects}}
{{effects/base


Smoked: When smoked, the effects of '''DPT''' have an onset in minutes and a duration of less than one hour. Dosage ranges from 30-100 mg.
|{{effects/physical|
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of DPT is generally more prominent to that of the better known [[DMT]]. There is often the sensation of limbs feeling disconnected from the body, a force pinning the body to the surface on which it lay and body tremors which can often make the user feel aware of but not in control of their body.
**'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Physical autonomy]]'''
*'''[[Effect::Changes in felt bodily form]]'''
*'''[[Effect::Changes in felt gravity]]''' - At higher doses, physical feelings of moving through spaces at quick speeds or being completely pinned down are common.
*'''[[Effect::Abnormal heartbeat]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Headaches]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Excessive yawning]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Increased libido]]''' - This effect appears to occur with more regularity and intensity than other psychedelic tryptamines.  


Insufflation: Average onset for insufflation of DPT is five to fifteen minutes, and typical dosage ranges from 45-225 mg, but the most popular dose is around 100 mg.
}}
{{effects/visual|
====Enhancements====
*'''[[Effect::Visual acuity enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
*'''[[Effect::Magnification]]'''


Intramuscular: When injected into the muscle, onset ranges from one minute to fifteen minutes. Typical dosage ranges from 20-110 mg.
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])''
*'''[[Effect::After images]]'''
*'''[[Effect::Colour replacement]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Environmental patterning]]'''
*'''[[Effect::Recursion]]'''
*'''[[Effect::Scenery slicing]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Visual haze]]'''


Intravenous: When injected intravenously, onset ranges from five to fifteen seconds. Typical dosage ranges from 10-75 mg.
====[[Effect::Geometry]]====
DPT visual geometry can be described through its variations as intricate in complexity, both abstract and concrete in form, more digital than organic in feel, choppy and only loosely structured in organization, brightly lit, multicolored in scheme, sharp in its edges, fast in speed, simultaneously smooth and glitching in motion, immersive in depth, and consistent in intensity. At higher doses, it is more likely to result in states of  [[Effect::8A Geometry|level 8A geometry]] over level 8B.  


Oral Ingestion: DPT is metabolized by the enzyme monoamine oxidase. While DPT is orally active on its own, the combination with a monoamine oxidase inhibitor (MAOI) can increase the length and intensity of the experience. Oral dosages of 150 - 250 mg are commonly reported, with an onset of 20-60 minutes (depending on stomach content).
====Hallucinatory states====
DPT produces a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of any other commonly used psychedelic barring [[DMT]] and [[ibogaine]]. These effects include:


*'''[[Effect::Transformations]]'''
*'''[[Effect::Machinescapes]]''' - These are reported to be more common with [[DPT]] than with [[DMT]], which lends to its common description as feeling more "industrial" and futuristic, while [[DMT]] visuals can often be described as "ancient" or "earthy" in feel.
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - As with [[DMT]], DPT produces high level internal hallucinations at appropriate doses more consistently than most other [[psychedelics]]. They are more common within dark environments and can be comprehensively described through their [[Internal_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, non-autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental narrative in their overall theme, with a tendency towards chaotic disorganization and incoherence.
*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - These are more common within dark environments and can be comprehensively described through their [[External_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, non-autonomous in controllability, geometry-based in style and typically of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental narrative in their overall theme, with a tendency towards chaotic disorganization and incoherence.


}}
|{{effects/cognitive|


== From [[TiHKAL]] by Ann and Alexander [[Shulgin]] ==
*'''[[Effect::Anxiety]]''' & '''[[Effect::Paranoia]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Cognitive euphoria]]''' & '''[[Effect::Cognitive dysphoria]]'''
*'''[[Effect::Déjà vu]]'''
*'''[[Effect::Emotionality enhancement]]'''
*'''[[Effect::Feelings of impending doom]]'''
**'''[[Effect::Catharsis]]'''
**'''[[Effect::Rejuvenation]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Personal meaning enhancement]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Confusion]]'''
*'''[[Effect::Language suppression]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Simultaneous emotions]]'''
*'''[[Effect::Spatial disorientation]]'''
*'''[[Effect::Autonomous voice communication]]'''
*'''[[Effect::Multiple thought streams]]'''
*'''[[Effect::Thought disorganization]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''


TRYPTAMINE, N,N-DIPROPYL; INDOLE, 3-[2-(DIPROPYLAMINO)ETHYL]; N,N-DIPROPYLTRYPTAMINE; 3-[2-(DIPROPYLAMINO)ETHYL]INDOLE
}}
{{effects/multisensory|
*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.


=== 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%.
{{effects/transpersonal|
Many reports indicate that while [[DPT]] possesses the raw [[hallucinogenic]] power to induce transpersonal states traditionally associated with "classical psychedelics", it does so in a significantly less consistent fashion due to the utter bizarreness and oft-noted "sinister", chaotic, or "forceful" undertones that can be present throughout the experience. What insights it can lead the user to typically occur during the aftermath and integration phase that follows, which shares some qualities of a typical near-death experience.


(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%.
*'''[[Effect::Spirituality enhancement]]'''
*'''[[Effect::Existential self-realization]]'''
*'''[[Effect::Perception of predeterminism]]'''
*'''[[Effect::Perception of eternalism]]'''
*'''[[Effect::Perceived exposure to inner mechanics of consciousness]]'''
*'''[[Effect::Unity and interconnectedness]]'''


}}
}}
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:DPT]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:


=== DOSAGE ===
*[https://www.erowid.org/experiences/subs/exp_DPT.shtml Erowid Experience Vaults: DPT]
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."
==Toxicity and harm potential==
{{toxicity}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
The toxicity and long-term health effects of recreational DPT do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because DPT is a [[research chemical]] with very little history of human usage. There has been one death associated with the use DPT and seizures, but the dose is unknown.<ref>{{Citation | vauthors=((Tribune, B. D. S.)) | title=Carver County teen’s death puts spotlight on ease of purchasing synthetic drugs online | url=https://www.startribune.com/carver-county-teen-s-death-puts-spotlight-on-ease-of-purchasing-synthetic-drugs-online/330344661/}}</ref>


(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."
Anecdotal reports from those who have taken DPT suggests that negative health effects are not likely to occur from simply trying it by itself at low to moderate doses and using it sparingly (although nothing can be guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.


(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."
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


(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."
===Tolerance and addiction potential===
DPT is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. As with most psychedelics, it is reported to be self-limiting.


(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."
Tolerance to the effects of DPT has been shown to not be built in animal models.<ref>{{cite journal|last1=Smith|first1=D. A.|last2=Bailey|first2=J. M.|last3=Williams|first3=D.|last4=Fantegrossi|first4=W. E.|title=Tolerance and Cross-Tolerance to Head Twitch Behavior Elicited by Phenethylamine- and Tryptamine-Derived Hallucinogens in Mice|year=2014|journal=Journal of Pharmacology and Experimental Therapeutics|volume=351|issue=2|pages=485-491|doi=10.1124/jpet.114.219337|pmid=    25271256|pmc=4309922|issn=0022-3565|eissn=1521-0103|oclc=1606914}}</ref> However, it has been reported to be able to build slightly relative to [[DMT]], although still to an insignificant degree compared to most psychedelics.


(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."
===Dangerous interactions===
{{DangerousInteractions/Intro}}


(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."
*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>{{cite journal|last1=Talaie|first1=H.|last2=Panahandeh|first2=R.|last3=Fayaznouri|first3=M. R.|last4=Asadi|first4=Z.|last5=Abdollahi|first5=M.|title=Dose-independent occurrence of seizure with tramadol|year=2009|journal=Journal of Medical Toxicology|volume=5|issue=2|pages=63-67|doi=10.1007/BF03161089|issn=1556-9039|eissn=1937-6995|oclc=163567183|pmid=19415589|pmc=3550327}}</ref> and LSD also has the potential to induce seizures in susceptible individuals. and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
*'''[[Stimulants]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis.{{citation needed}}
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{citation needed}}


==Legal status==


=== EXTENSIONS AND COMMENTARY ===
*'''Germany''': DPT is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> as of July 18, 2019.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf|title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27|pages=1083-1094|publication-date=July 17, 2019|access-date=January 1, 2020|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref>
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.
*'''Latvia''': DPT is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref>
*'''New Zealand''': DPT is an analogue of DMT, therefore it is a Class C controlled substance in New Zealand.<ref>{{cite web|title=Schedule 1 Class A controlled drugs|url=http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html#DLM436576|work="Reprint as at 13 August 2019: Misuse of Drugs Act 1975"|access-date=January 7, 2020|publisher=Parliamentary Counsel Office}}</ref>
*'''Sweden''': Following its sale as a [[designer drug]], DPT was made illegal in Sweden on January 26, 2016.<ref>{{cite web|url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2016/januari/31-nya-substanser-klassas-som-narkotika-eller-halsofarlig-vara|title=31 nya substanser klassas som narkotika eller hälsofarlig vara|publisher=Folkhälsomyndigheten [Public Health Agency of Sweden]|access-date=January 1, 2020|publication-date=January 26, 2016|language=sv}}</ref>
*'''Switzerland''': DPT is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''': DPT is a Class A controlled substance in the United Kingdom as a result of the tryptamine catch-all clause.<ref>{{cite web|title=Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=January 7, 2020|publisher=UK Government}}</ref>
*'''United States''': DPT is unscheduled in most of the United States. However, some states prohibited DPT, making it illegal to buy, sell, or possess:
**'''Florida''': DPT is a Schedule I controlled substance.<ref>{{cite web|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|title=Title XLVI: Chapter 893: Drug Abuse Prevention And Control|work=The 2019 Florida Statutes|access-date=January 10, 2020|publisher=The Florida Legislature}}</ref>
**'''Maine''': DPT is a Schedule X controlled substance.<ref>http://legislature.maine.gov/statutes/17-a/title17-Asec1102.html</ref>
**'''Oklahoma''': DPT is a Schedule I controlled substance.<ref>{{cite web|archive-url=https://web.archive.org/web/20190709113340/http://www.oscn.net/applications/oscn/DeliverDocument.asp?CiteID=98866|archive-date=July 9, 2019|url=http://www.oscn.net/applications/oscn/DeliverDocument.asp?CiteID=98866|title=Section 2-204 - Schedule I|work=Oklahoma Statutes Citationized|date=January 11, 2019|access-date=January 10, 2020|publisher=Oklahoma Judicial Center}}</ref>


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.
==See also==


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."
*[[Responsible use]]
*[[Research chemical]]
*[[Psychedelics]]
*[[Tryptamines]]
*[[DMT]]
*[[DET]]


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.
==External links==


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.
*[https://en.wikipedia.org/wiki/Dipropyltryptamine DPT (Wikipedia)]
*[https://www.erowid.org/chemicals/dpt/dpt.shtml DPT (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=9 DPT (TiHKAL / Isomer Design)]


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.
==Literature==
[[Category:Tryptamines]]
[[Category:Drugs]]
[[Category:TiHKAL]]
[[Category:Shulgin]]


{{TiHKAL}}
*Soskin, R.A., Grof, S., & Richards, W.A. (1973). Low doses of Dipropyltryptamine in psychotherapy. Archives of General Psychiatry, 28 6, 817-21.
*Richards, W. A., Rhead, J. C., DiLeo, F. B., Yensen, R., & Kurland, A. A. (1977). The peak experience variable in DPT-assisted psychotherapy with cancer patients. Journal of Psychedelic Drugs, 9(1), 1-10. http://dx.doi.org/10.1080/02791072.1977.10472020
*Grof, S., Soskin, R. A., Richards, W. A., & Kurland, A. A. (1972). DPT as an adjunct in psychotherapy of alcoholics. International Pharmacopsychiatry, 8(1), 104-115. PMID: 4150711
*Li, J., Rice, K.C., & France, C.P. (2007). Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity. Behavioural Pharmacology, 18 4, 283-8.


==References==
<references />


[[sv:DPT]]
[[Category:Substance]]
[[es:DPT]]
[[Category:Psychoactive substance]]
[[Category:Hallucinogen]]
[[Category:Entheogen]]
[[Category:Psychedelic]]
[[Category:Tryptamine]]
[[Category:Research chemical]]

Revision as of 15:39, 28 January 2023

Summary sheet: DPT

Template:SubstanceBox/DPT N,N-Dipropyltryptamine (also known as Dipropyltryptamine, DPT, and "The Light") is a lesser-known psychoactive class::psychedelic substance of the chemical class::tryptamine class. It is closely related to DMT and is reported to be uniquely similar in its hallucinogenic intensity, albeit with a moderately longer duration and greater unpredictability relative to DMT and other psychedelic tryptamines.

DPT was first synthesized in 1950.[1] Human use was first reported in 1973, where it was researched in low doses as an adjunct to therapy for alcoholism.[2] It has also been researched in high doses to induce peak experiences for terminal cancer patients.[3] It has gained some notoriety for its adoption as the primary sacrament for the "Temple of the True Inner Light" in the United States, a Christian off-shoot organization who believe in the ritual use of psychedelics and refer to them as "the true flesh of God."[4]

DPT is commonly consumed via insufflation or orally. Many report the experience of insufflation to be very congestive and painful which, with the rapidness of onset, does not give the user much time to acclimate themselves to its powerful effects. It can also be administered intramuscularly or via vaporization after conversion to the freebase form. Smoking the freebase is reported to be the preferred route used by the "Temple of True Inner Light". More experienced members ingest a DPT tea. [citation needed]

Very little data exists about the pharmacological properties, metabolism, and toxicity of DPT, and it has relatively little history of human usage. It has long been available on the research chemicals market as a legal, grey-market alternative to DMT, and commercially distributed through online vendors. Many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with hallucinogens. It is highly advised to approach this powerful psychedelic substance with the proper amount of precaution and harm reduction practices when using it.

Chemistry

DPT, or N,N-dipropyltryptamine, is a synthetic indole molecule of the tryptamine class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R3 to an amino group via an ethyl side chain. DPT contains two propyl groups carbon chains bound to the terminal amine RN of its tryptamine backbone.

DPT has a number of substituted analogs such as 4-HO-DPT or 4-AcO-DPT.

Pharmacology

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This pharmacology section is incomplete.

You can help by adding to it.

Further information: Serotonergic psychedelic

Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of this compound strongly suggest that the 5-HT2A receptor is an important site of action for DPT, but the modulatory actions of a 5-HT1A receptor antagonist also imply a 5-HT1A-mediated component to the actions of DPT.[5] The role of these interactions and how they result in the psychedelic experience remains the subject of ongoing scientific investigation.

Subjective effects

Relative to psychedelic tryptamines like DMT, DPT is often reported to be similar in its hallucinogenic intensity, albeit with a moderately longer duration and more challenging effects. DPT experiences are often described as a "bizarre", "unsettling", and "darker" version of DMT experiences. DPT is reported to be more sensual and physical than DMT and other psychedelics with a corresponding amount of adverse physical effects.

At light to moderate doses, users often report a slight sense of anaesthetization and relaxation. As the dose increases, hyper-awareness of one's heart rate and breathing increases and body tremors and loss of muscle control are often reported. The effects of DPT can range from strong euphoria and sensuality to nausea, panic, and intense states dysphoria even within the same experience.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

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Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include: {{#ask: |format=ul|Columns=1}} Additional experience reports can be found here:

Toxicity and harm potential

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This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

The toxicity and long-term health effects of recreational DPT do not seem to have been studied in any scientific context and the exact Toxicity::toxic dose is unknown. This is because DPT is a research chemical with very little history of human usage. There has been one death associated with the use DPT and seizures, but the dose is unknown.[6]

Anecdotal reports from those who have taken DPT suggests that negative health effects are not likely to occur from simply trying it by itself at low to moderate doses and using it sparingly (although nothing can be guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this substance.

Tolerance and addiction potential

DPT is Addiction potential::not habit-forming and the desire to use it can actually decrease with use. As with most psychedelics, it is reported to be self-limiting.

Tolerance to the effects of DPT has been shown to not be built in animal models.[7] However, it has been reported to be able to build slightly relative to DMT, although still to an insignificant degree compared to most psychedelics.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

Legal status

  • Germany: DPT is controlled under the NpSG (New Psychoactive Substances Act)[9] as of July 18, 2019.[10] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[11]
  • Latvia: DPT is a Schedule I controlled substance.[12]
  • New Zealand: DPT is an analogue of DMT, therefore it is a Class C controlled substance in New Zealand.[13]
  • Sweden: Following its sale as a designer drug, DPT was made illegal in Sweden on January 26, 2016.[14]
  • Switzerland: DPT is a controlled substance specifically named under Verzeichnis E.[15]
  • United Kingdom: DPT is a Class A controlled substance in the United Kingdom as a result of the tryptamine catch-all clause.[16]
  • United States: DPT is unscheduled in most of the United States. However, some states prohibited DPT, making it illegal to buy, sell, or possess:
    • Florida: DPT is a Schedule I controlled substance.[17]
    • Maine: DPT is a Schedule X controlled substance.[18]
    • Oklahoma: DPT is a Schedule I controlled substance.[19]

See also

External links

Literature

  • Soskin, R.A., Grof, S., & Richards, W.A. (1973). Low doses of Dipropyltryptamine in psychotherapy. Archives of General Psychiatry, 28 6, 817-21.
  • Richards, W. A., Rhead, J. C., DiLeo, F. B., Yensen, R., & Kurland, A. A. (1977). The peak experience variable in DPT-assisted psychotherapy with cancer patients. Journal of Psychedelic Drugs, 9(1), 1-10. http://dx.doi.org/10.1080/02791072.1977.10472020
  • Grof, S., Soskin, R. A., Richards, W. A., & Kurland, A. A. (1972). DPT as an adjunct in psychotherapy of alcoholics. International Pharmacopsychiatry, 8(1), 104-115. PMID: 4150711
  • Li, J., Rice, K.C., & France, C.P. (2007). Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity. Behavioural Pharmacology, 18 4, 283-8.

References

  1. ↑ Li, J. X.; Rice, K.; France, C. P. (2007). "Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity". Behavioural Pharmacology. 18 (4): 283–288. doi:10.1097/FBP.0b013e3281f19ca0. eISSN 1473-5849. ISSN 0955-8810. OCLC 22170289. PMID 17551320. 
  2. ↑ Grof, S.; Soskin, R. A.; Richards, W. A.; Kurland, A. A. (1973). "DPT as an Adjunct in Psychotherapy of Alcoholics". International Pharmacopsychiatry. 8 (1): 104–115. doi:10.1159/000467979. ISSN 0020-8272. OCLC 1753673. PMID 4150711. 
  3. ↑ Richards, W. A.; Rhead, J. C.; Dileo, F. B.; Yensen, R.; Kurland, A. A. (1977). "The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients". Journal of Psychedelic Drugs. 9 (1): 1–10. doi:10.1080/02791072.1977.10472020. ISSN 0022-393X. OCLC 7565359. 
  4. ↑ "Temple of the True Inner Light". Retrieved January 9, 2020. 
  5. ↑ Fantegrossi, W., Reissig, C., Katz, E., Yarosh, H., Rice, K., Winter, J. (January 2008). "Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): Possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents". Pharmacology Biochemistry and Behavior. 88 (3): 358–365. doi:10.1016/j.pbb.2007.09.007. ISSN 0091-3057. 
  6. ↑ Tribune, B. D. S., Carver County teen’s death puts spotlight on ease of purchasing synthetic drugs online 
  7. ↑ Smith, D. A.; Bailey, J. M.; Williams, D.; Fantegrossi, W. E. (2014). "Tolerance and Cross-Tolerance to Head Twitch Behavior Elicited by Phenethylamine- and Tryptamine-Derived Hallucinogens in Mice". Journal of Pharmacology and Experimental Therapeutics. 351 (2): 485–491. doi:10.1124/jpet.114.219337. eISSN 1521-0103. ISSN 0022-3565. OCLC 1606914. PMC 4309922 Freely accessible. PMID 25271256. 
  8. ↑ Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. eISSN 1937-6995. ISSN 1556-9039. OCLC 163567183. PMC 3550327 Freely accessible. PMID 19415589. 
  9. ↑ "Anlage NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019. 
  10. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in Deutsch). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020. 
  11. ↑ "§ 4 NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019. 
  12. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in latviešu). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020. 
  13. ↑ "Schedule 1 Class A controlled drugs". "Reprint as at 13 August 2019: Misuse of Drugs Act 1975". Parliamentary Counsel Office. Retrieved January 7, 2020. 
  14. ↑ "31 nya substanser klassas som narkotika eller hälsofarlig vara" (in svenska). Folkhälsomyndigheten [Public Health Agency of Sweden]. January 26, 2016. Retrieved January 1, 2020. 
  15. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in Deutsch). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  16. ↑ "Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved January 7, 2020. 
  17. ↑ "Title XLVI: Chapter 893: Drug Abuse Prevention And Control". The 2019 Florida Statutes. The Florida Legislature. Retrieved January 10, 2020. 
  18. ↑ http://legislature.maine.gov/statutes/17-a/title17-Asec1102.html
  19. ↑ "Section 2-204 - Schedule I". Oklahoma Statutes Citationized. Oklahoma Judicial Center. January 11, 2019. Archived from the original on July 9, 2019. Retrieved January 10, 2020. 
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