Dipropyltryptamine: Difference between revisions

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{{Short description|Chemical compound}}
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Use dmy dates|date=March 2024}}
{{Use dmy dates|date=March 2024}}
{{Infobox drug
{{Infobox drug
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| verifiedrevid = 444963386
| verifiedrevid = 444963386
| image = DPT.svg
| image = DPT.svg
| width = 200px
| image_class = skin-invert-image
| width = 225px
| image2 = DPT-3d-sticks.png
| image2 = DPT-3d-sticks.png
| width2 = 200px
| image_class2 = bg-transparent
| width2 = 225px


<!-- Clinical data -->
<!-- Clinical data -->
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| pregnancy_US =  
| pregnancy_US =  
| pregnancy_category =  
| pregnancy_category =  
| routes_of_administration = [[Oral administration|Oral]], [[inhalation]] ([[smoking]]), [[intravenous therapy|intravenous]] or [[intramuscular injection]]<ref name="TiHKAL" />
| routes_of_administration = [[Oral administration|Oral]], [[smoking]], [[intramuscular injection]], [[intravenous injection]]<ref name="TiHKAL" />
| class = [[Serotonin receptor agonist]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| class = [[Serotonin receptor agonist]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix =


<!-- Legal status -->
<!-- Legal status -->
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| legal_UK = Class A
| legal_UK = Class A
| legal_US =  
| legal_US =  
| legal_status =  
| legal_status =


<!-- Pharmacokinetic data -->
<!-- Pharmacokinetic data -->
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| protein_bound =  
| protein_bound =  
| metabolism =  
| metabolism =  
| onset = [[Injection (medicine)|Injection]]: 10–15 minutes<ref name="TiHKAL" />
| onset = [[Oral administration|Oral]]: Fast<ref name="TiHKAL" /><br />[[Injection (medicine)|Injection]]: 10–15 minutes<ref name="TiHKAL" />
| elimination_half-life =  
| elimination_half-life =  
| duration_of_action = 2–4 hours<ref name="TiHKAL" />
| duration_of_action = 2–4 hours (but up to 12 hours at very high doses)<ref name="TiHKAL" /><ref name="TittarelliManocchiPantano2015" />
| excretion =  
| excretion =


<!-- Identifiers -->
<!-- Identifiers -->
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S7272VWU50
| UNII = S7272VWU50
| ATC_prefix = None
| ATC_suffix =
| PubChem = 6091
| PubChem = 6091
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5866
| ChemSpiderID = 5866
| synonyms = DPT; ''N'',''N''-Dipropyltryptamine
| synonyms = DPT; ''N'',''N''-Dipropyltryptamine; "The Light"


<!-- Chemical data -->
<!-- Chemical data -->
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}}
}}


'''''N'',''N''-Dipropyltryptamine''' ('''DPT''') is a [[psychedelic drug]] and [[entheogen]] belonging to the [[substituted tryptamine|tryptamine]] family.<ref name="TiHKAL">{{CiteTiHKAL}}</ref> Use as a [[designer drug]] has been documented by law enforcement officials since as early as 1968.<ref>{{Cite journal|date=April 1968|orig-year=1968|title=Microgram Journal Volume One No. 7|url=https://www.erowid.org/library/periodicals/microgram/microgram_1968_04_v01n07.pdf|journal=Microgram Journal|publisher= [[United States Department of Justice|U.S DOJ]], [[Bureau of Narcotics and Dangerous Drugs]]|volume=One|issue=Seven|pages=23|access-date=5 April 2021}}</ref> However, potential therapeutic use was not investigated until the 1970s.<ref>{{cite journal | vauthors = Grof S, Soskin RA, Richards WA, Kurland AA | title = DPT as an adjunct in psychotherapy of alcoholics. | journal = International Pharmacopsychiatry | date = 1973 | volume = 8 | issue = 1 | pages = 104–15 | doi = 10.1159/000467979 | pmid = 4150711 }}</ref> It is found either as a [[crystalline]] [[hydrochloride]] [[Salt (chemistry)|salt]] or as an oily or crystalline [[base (chemistry)|base]]. It has not been found to occur endogenously. It is a close structural [[Homologous series|homologue]] of [[dimethyltryptamine]] and [[diethyltryptamine]].
'''Dipropyltryptamine''' ('''DPT'''), also known as '''''N'',''N''-dipropyltryptamine''' or as "'''The Light'''", is a [[psychedelic drug]] of the [[substituted tryptamine|tryptamine]] family related to [[dimethyltryptamine]] (DMT).<ref name="TiHKAL">{{CiteTiHKAL }}</ref><ref name="MalacaLoFaroTamborra2020">{{cite journal | vauthors = Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA | title = Toxicology and Analysis of Psychoactive Tryptamines | journal = Int J Mol Sci | volume = 21 | issue = 23 | date = December 2020 | page = 9279 | pmid = 33291798 | pmc = 7730282 | doi = 10.3390/ijms21239279 | doi-access = free | url = }}</ref> It is taken [[oral administration|orally]] or by other [[route of administration|route]]s.<ref name="TiHKAL" />
 
The drug acts as a [[serotonin receptor modulator]], including as a [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]].<ref name="Ray_2010">{{cite journal |vauthors=Ray TS |date=February 2010 |title=Psychedelics and the human receptorome |journal=PLOS ONE |volume=5 |issue=2 |bibcode=2010PLoSO...5.9019R |doi=10.1371/journal.pone.0009019 |pmc=2814854 |pmid=20126400 |doi-access=free |article-number=e9019}}</ref><ref name="Kozell_2023">{{cite journal |vauthors=Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI |date=April 2023 |title=Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)<sub>2A</sub> Receptor (5-HT<sub>2A</sub>R), 5-HT<sub>2C</sub>R, 5-HT<sub>1A</sub>R, and Serotonin Transporter |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=385 |issue=1 |pages=62–75 |doi=10.1124/jpet.122.001454 |pmc=10029822 |pmid=36669875}}</ref><ref name="Blough_2014">{{cite journal |vauthors=Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB |date=October 2014 |title=Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes |journal=Psychopharmacology |volume=231 |issue=21 |pages=4135–4144 |doi=10.1007/s00213-014-3557-7 |pmc=4194234 |pmid=24800892}}</ref><ref name="Nagai_2007">{{cite journal |vauthors=Nagai F, Nonaka R, Satoh Hisashi Kamimura K |date=March 2007 |title=The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain |journal=European Journal of Pharmacology |volume=559 |issue=2–3 |pages=132–137 |doi=10.1016/j.ejphar.2006.11.075 |pmid=17223101}}</ref><ref name="Nelson_1993" /> It is a close structural [[Homologous series|homologue]] of DMT and [[diethyltryptamine]] (DET).<ref name="TiHKAL" /> [[Chemical derivative|Derivative]]s of DPT include [[4-HO-DPT]] and [[5-MeO-DPT]], among others.<ref name="TiHKAL" />
 
DPT was first described in the literature by 1959.<ref name="Barlow_1959" /><ref name="Barlow_1959a" /><ref name="Vane_1959" /> It was encountered as a novel [[designer drug]] by 1968<ref name="Microgram1968" /> and was reported as a possible treatment for [[alcoholism]] in 1973.<ref name="TittarelliManocchiPantano2015" /><ref name="MalacaLoFaroTamborra2020" /><ref name="SoskinGrofRichards1973">{{cite journal |vauthors=Soskin RA, Grof S, Richards WA |date=June 1973 |title=Low doses of Dipropyltryptamine in psychotherapy |url= |journal=Arch Gen Psychiatry |volume=28 |issue=6 |pages=817–821 |doi=10.1001/archpsyc.1973.01750360047006 |pmid=4575167}}</ref> The drug is the [[sacrament]] of the [[Temple of the True Inner Light]], a [[New York City]]-based religious group.<ref name="TiHKAL" /><ref name="DeKorne2011">{{cite book| vauthors = DeKorne J |title=Psychedelic Shamanism, Updated Edition: The Cultivation, Preparation, and Shamanic Use of Psychotropic Plants|url=https://books.google.com/books?id=uNGl_aN-1wAC&pg=PA81|date=26 July 2011|publisher=North Atlantic Books|isbn=978-1-58394-290-1|page=81}}</ref><ref name="Kaplan1987">{{Cite journal | vauthors = Kaplan E|title=Still hippies, after all these years |url=https://books.google.com/books?id=VgDtgAXO7pAC&pg=PA61 |journal=Spy Magazine |date=October 1987 |issue=October 1987 |pages=61}}</ref>


==Use and effects==
==Use and effects==
Doses ranges of DPT of 100 to 250{{nbsp}}mg (but up to 500{{nbsp}}mg) [[oral administration|orally]], 100{{nbsp}}mg [[inhalational administration|smoked]], 15 to 125{{nbsp}}mg [[intramuscular injection|intramuscularly]], and 12 to 36{{nbsp}}mg [[intravenous injection|intravenously]] have been described.<ref name="TiHKAL" /><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref> Its [[duration of action|duration]] is 2 to 4{{nbsp}}hours orally but can last up to 12{{nbsp}}hours with high doses.<ref name="TiHKAL" />
In his book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved''), [[Alexander Shulgin]] lists DPT's dose range as 100 to 250{{nbsp}}mg [[oral administration|orally]] and its [[duration of action|duration]] as 2 to 4{{nbsp}}hours.<ref name="TiHKAL" /><ref name="TittarelliManocchiPantano2015" /> A 500{{nbsp}}mg dose was also reported, which was described as "exhausting" and as lasting 12{{nbsp}}hours.<ref name="TiHKAL" /> The [[onset of action|onset]] and time to peak effects were not given, but it was implied to have a fast onset.<ref name="TiHKAL" /> In addition to oral administration, DPT has been assessed by [[smoking]] at a dose of 100{{nbsp}}mg, by [[intramuscular injection]] at low doses of 15 to 30{{nbsp}}mg, moderate doses of 30 to 70{{nbsp}}mg, and "peak experience" doses of 75 to 125{{nbsp}}mg, and by [[intravenous injection]] at 12 to 36{{nbsp}}mg.<ref name="TiHKAL" /><ref name="Halberstadt_2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] | article-number = 107933 }}</ref>


While DPT is chemically similar to [[dimethyltryptamine]] (DMT), its psychoactive effects have been said to be markedly different.<ref>{{cite book |last = Pinchbeck |first = Daniel | name-list-style = vanc |author-link = Daniel Pinchbeck |title = Breaking Open The Head |publisher = Broadway Books |year = 2003 |isbn = 0-7679-0743-4}}</ref> On the other hand, others have reported similarities to DMT, for instance in terms of intensity.<ref name="TiHKAL" />
The effects of DPT have been reported to include [[psychedelic visual|visual]]s, being intensely visual at high doses, changes in [[time perception]], feeling like one is in a different place like on a mountain in clouds or in a big castle, enhanced [[memory recall|recall of memories]] and experiences, enhanced emotional expressiveness and self-exploration, [[psychedelic entity encounter|entity encounter]]s, and [[religion|religious]] feelings.<ref name="TiHKAL" /><ref name="Pinchbeck2003" /><ref name="SoskinGrofRichards1973" /> Other effects included trouble talking, feeling uncomfortable, [[nervousness]], feeling light, and body rush.<ref name="TiHKAL" /> Given at a high dose intravenously, it was described as every bit as powerful as a psychedelic as DMT.<ref name="TiHKAL" /> According to one account however, DPT and DMT, despite their chemical similarity, "reveal completely different worlds".<ref name="Pinchbeck2003">{{cite book | vauthors = Pinchbeck D | title = Breaking Open The Head: A Psychedelic Journey Into the Heart of Contemporary Shamanism | year = 2003 | author-link = Daniel Pinchbeck | publisher = Broadway Books | isbn = 978-0-7679-0743-9 | pages=262–263,265,272,275–278}}</ref>
 
Other reports have stated effects of DPT including [[visual hallucination|visual]] and [[auditory hallucination]]s, increased color intensity, flashes of light and sparkles, apparitions of faces, increased music appreciation, [[ego dissolution]], [[stimulation]], [[euphoria]], [[mental relaxation|relaxation]], [[paranoia]], [[psychosis]], [[anxiety]], [[nausea]], [[dizziness]], [[muscle tremor]]s, and increased [[heart rate]], among others.<ref name="TittarelliManocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | title = Recreational use, analysis and toxicity of tryptamines | journal = Curr Neuropharmacol | volume = 13 | issue = 1 | pages = 26–46 | date = January 2015 | pmid = 26074742 | pmc = 4462041 | doi = 10.2174/1570159X13666141210222409 | url = | quote = Dipropyl-tryptamine (DPT) was firstly synthesized in the 1950s [34], but it was firstly reported for use in the scientific literature only in 1973 [35], as an adjunct in psychotherapy of alcoholics. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base and, as DET, it has not been found to occur naturally. There are few peer-reviewed experimental studies that try to explain the ways of interaction among DPT and serotonin receptors: Nagai revealed a strong inhibition of 5-HT reuptake in rat synaptosomes [16], and Thiagaraj also observed a moderate affinity partial agonism at the human 5-HT1A receptor [34]. Experiences related to DPT assumption are mostly psychedelic sensations, such as an increase of music and colors intensity, the vision of pleasant flashes of light and sparkles, a complete ego loss, and apparitions of faces. The dosage of DPT, for oral administration, is 100-250 mg and the duration of the psychoactive effects varies from 2 to 4 hours.}}</ref> Its duration is described as much shorter than those of certain other psychedelics like LSD, which can be advantageous in a clinical setting.<ref name="Dutta2012">{{cite journal | vauthors = Dutta V | title = Repression of death consciousness and the psychedelic trip | journal = J Cancer Res Ther | volume = 8 | issue = 3 | pages = 336–342 | date = 2012 | pmid = 23174711 | doi = 10.4103/0973-1482.103509 | doi-access = free | url = | quote = Dipropyltryptamine (DPT), another psychedelic was also examined in two cancer studies in lieu of the LSD, since its properties were similar to LSD but was less time consuming.[38] It took about 1 ½ to 6 hours to act, and its effects too wore off easily unlike the LSD that demanded a considerable amount of time. Post-therapeutically DPT’s benefits would mimic LSD. It was suggested to be a better alternative than LSD, but because of its quick onset, patients often found the sudden psychological upheaval overwhelming.[39]}}</ref><ref name="Richards_1977">{{cite journal | vauthors = Richards WA, Rhead JC, Dileo FB, Yensen R, Kurland AA | title = The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients | journal = Journal of Psychedelic Drugs | volume = 9 | issue = 1 | pages = 1–10 | date = 1977 | doi = 10.1080/02791072.1977.10472020 | issn = 0022-393X | url = https://www.tandfonline.com/doi/full/10.1080/02791072.1977.10472020 | access-date = 8 November 2025 | url-access = subscription }}</ref><ref name="Richards_1980" /> However, it is also said to have a rapid onset that can be psychologically overwhelming.<ref name="Dutta2012" /><ref name="Richards_1980">{{cite journal | vauthors = Richards WA, Rhead JC, Grof S, Goodman LE, Di Leo F, Rush L | title = DPT as an Adjunct in Brief Psychotherapy with Cancer Patients | journal = OMEGA - Journal of Death and Dying | volume = 10 | issue = 1 | pages = 9–26 | date = 1980 | doi = 10.2190/NGUB-V4RM-T7DC-XTH3 | issn = 0030-2228 | url = https://journals.sagepub.com/doi/10.2190/NGUB-V4RM-T7DC-XTH3 | access-date = 8 November 2025 | url-access = subscription }}</ref>


==Side effects==
==Side effects==
[[Side effect]]s of DPT may include [[nausea]], [[paresthesia|numbness]] of the [[tongue]] or [[throat]], [[mydriasis|pupil dilation]], [[tachycardia|increased heart rate]], [[dizziness]], [[anxiety]], [[panic]], [[mental confusion|confusion]], [[paranoia]], [[delusion]]s, and [[seizure]]s (uncommon).{{Citation needed|date=April 2025}}
Although [[substituted tryptamine|tryptamine]]s such as [[psilocybin]] and [[dimethyltryptamine]] (DMT) have relatively well‑characterized [[drug safety|safety]], [[synthetic compound|synthetic]] [[structural analog|analogue]]s like DPT lack thorough [[toxicology|toxicological]] evaluation and are mainly associated with [[anecdotal report]]s of intoxication and a few cases of fatal outcomes when used recreationally.<ref name="Araujo_2015">{{cite journal | vauthors = Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M | title = The hallucinogenic world of tryptamines: an updated review | journal = Archives of Toxicology | volume = 89 | issue = 8 | pages = 1151–1173 | date = August 2015 | pmid = 25877327 | doi = 10.1007/s00204-015-1513-x | bibcode = 2015ArTox..89.1151A }}</ref> The pharmacological similarity of DPT to DMT suggests a generally low intrinsic [[toxicity]] at controlled doses but a pronounced risk of acute adverse reactions, including [[psychomotor agitation|agitation]], [[tachycardia]], [[hyperthermia]], and [[Serotonin syndrome|serotonergic crisis]], particularly in combination with [[monoamine oxidase inhibitor]]s or other [[serotonin|serotonergic]] substances.<ref name="Araujo_2015" />


The use of DPT has been implicated in at least one death due to seizures,<ref>{{cite web | first = Beatrice | last = Dupuy | name-list-style = vanc | work = Star Tribune | date = 1 October 2015  | title = Carver County teen's death puts spotlight on ease of purchasing synthetic drugs online | url = http://www.startribune.com/carver-county-teen-s-death-puts-spotlight-on-ease-of-purchasing-synthetic-drugs-online/330344661/ }}</ref> although details are lacking and the drug has not officially been established as the sole cause of death.
A [[meta-analysis]] of tryptamine psychedelics have further demonstrated cognitive effects through [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] modulation but have not identified persistent [[neurotoxicity]].<ref name="Castelhano_2021">{{cite journal | vauthors = Castelhano J, Lima G, Teixeira M, Soares C, Pais M, Castelo-Branco M | title = The Effects of Tryptamine Psychedelics in the Brain: A meta-Analysis of Functional and Review of Molecular Imaging Studies | journal = Frontiers in Pharmacology | volume = 12 | date = 2021 | pmid = 34658876 | pmc = 8511767 | doi = 10.3389/fphar.2021.739053 | doi-access = free | article-number = 739053 }}</ref> The main safety concerns are acute [[psychophysiological]] and behavioral disturbances rather than long‑term organ toxicity. Overall, DPT is a potent, short‑acting serotonergic hallucinogen with limited safety data and a toxicity profile comparable to related tryptamines such as DMT and [[5-MeO-DMT]].<ref name="Araujo_2015" /><ref name="Castelhano_2021" />


==Interactions==
== Interactions ==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}


==Pharmacology==
==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatleft" style="font-size:small;"
{| class="wikitable floatleft" style="font-size:small;"
|+ DPT activities
|+ DPT activities
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! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM) !! Species
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM) !! Species
|-
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 31.8–1,641 (K<sub>i</sub>)<br />274–>10,000 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />99% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}}) || Human<br />Human
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 31.8–1,641 (K<sub>i</sub>)<br />274–>10,000 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />99% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}}) || Human<br />Human<br />Human
|-
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 854–8,081 (K<sub>i</sub>)<br />1,210 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 854–8,081 (K<sub>i</sub>)<br />1,210 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human
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| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 2,338 || Human
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 2,338 || Human
|-
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 3.0–2,579 (K<sub>i</sub>)<br />26.1–943 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />85–97% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) || Human<br />Human<br />Human
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 3.0–2,579 (K<sub>i</sub>)<br />26.1–943<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />85<sup>a</sup>–97% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) || Human<br />Human<br />Human
|-
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 42 || Human
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 42 || Human
|-
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 281–3,500 (K<sub>i</sub>)<br />444 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />93% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) || Human
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 281–3,500 (K<sub>i</sub>)<br />444<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />93%<sup>a</sup> ({{Abbr|E<sub>max</sub>|maximal efficacy}}) || Human<br />Human<br />Human
|-
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000 || Human
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000 || Human
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| [[Sigma-2 receptor|σ<sub>2</sub>]] || 2,917 || Human
| [[Sigma-2 receptor|σ<sub>2</sub>]] || 2,917 || Human
|-
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 157 (K<sub>i</sub>)<br />157–23,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
| {{Abbrlink|SERT|Serotonin transporter}} || 157–480 (K<sub>i</sub>)<br />157–23,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
|-
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || >10,000 (K<sub>i</sub>)<br />2,900–3,202 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
| {{Abbrlink|NET|Norepinephrine transporter}} || >10,000 (K<sub>i</sub>)<br />2,900–3,202 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
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| {{Abbrlink|DAT|Dopamine transporter}} || 1,500 (K<sub>i</sub>)<br />2,218–9,100 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
| {{Abbrlink|DAT|Dopamine transporter}} || 1,500 (K<sub>i</sub>)<br />2,218–9,100 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) || Human<br />Human<br />Rat
|- class="sortbottom"
|- class="sortbottom"
| colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. '''Refs:''' <ref name="BindingDB">{{cite journal | last=Liu | first=Tiqing | title=BindingDB BDBM84934 N-dipropyltryptamine, 1-Isopropyl-5-hydroxy N::N-dipropyltryptamine, 5-Hydroxy-N | journal=The Journal of Pharmacology and Experimental Therapeutics | date=1993 | volume=265 | issue=3 | pages=1272–1279 | pmid=8510008 | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=84934 | access-date=11 December 2024}}</ref><ref name="KiDatabase">{{cite web | title=PDSP Database | website=UNC | url=https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=dipropyltryptamine&kiAllRadio=all&doQuery=Submit+Query | language=zu | access-date=11 December 2024}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="TyagiSarafCanal2023">{{cite journal | vauthors = Tyagi R, Saraf TS, Canal CE | title = The Psychedelic N,N-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors | journal = ACS Pharmacol Transl Sci | volume = 6 | issue = 10 | pages = 1480–1491 | date = October 2023 | pmid = 37854624 | pmc = 10580393 | doi = 10.1021/acsptsci.3c00137 | url = }}</ref><ref name="KozellEshlemanSwanson2023">{{cite journal | vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI | title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter | journal = J Pharmacol Exp Ther | volume = 385 | issue = 1 | pages = 62–75 | date = April 2023 | pmid = 36669875 | pmc = 10029822 | doi = 10.1124/jpet.122.001454 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC10029822/pdf/jpet.122.001454.pdf}}</ref><ref name="BloughLandavazoDecker2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = }}</ref>
| colspan="3" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. '''Footnotes:''' <sup>a</sup> = Stimulation of {{Abbrlink|IP<sub>1</sub>|inositol phosphate|}} formation. '''Refs:''' <ref name="Ray_2010" /><ref name="Kozell_2023" /><ref name="Blough_2014" /><ref name="Nagai_2007" /><ref name="Nelson_1993">{{cite journal | vauthors = Nelson DL, Lucaites VL, Audia JE, Nissen JS, Wainscott DB | title = Species differences in the pharmacology of the 5-hydroxytryptamine2 receptor: structurally specific differentiation by ergolines and tryptamines | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 265 | issue = 3 | pages = 1272–1279 | date = June 1993 | doi = 10.1016/S0022-3565(25)38269-8 | pmid = 8510008 | url = https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=84934 | access-date = 11 December 2024 }}</ref><ref name="KiDatabase">{{cite web | title = PDSP Database | website = UNC | url = https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=dipropyltryptamine&kiAllRadio=all&doQuery=Submit+Query | language = zu | access-date = 11 December 2024 }}</ref><ref name="Tyagi_2023">{{cite journal | vauthors = Tyagi R, Saraf TS, Canal CE | title = The Psychedelic <i>N</i>,<i>N</i>-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 10 | pages = 1480–1491 | date = October 2023 | pmid = 37854624 | pmc = 10580393 | doi = 10.1021/acsptsci.3c00137 }}</ref>
|}
|}


Studies on rodents have found that the effectiveness with which a selective [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[Receptor antagonist|antagonist]] blocks the behavioral actions of this compound strongly suggests that the 5-HT<sub>2A</sub> receptor is an important site of action for DPT, but the modulatory actions of a [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] antagonist also imply a 5-HT<sub>1A</sub>-mediated component to the actions of DPT.<ref name="pmid17905422">{{cite journal | vauthors = Fantegrossi WE, Reissig CJ, Katz EB, Yarosh HL, Rice KC, Winter JC | title = Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents | journal = Pharmacology, Biochemistry, and Behavior | volume = 88 | issue = 3 | pages = 358–65 | date = January 2008 | pmid = 17905422 | pmc = 2322878 | doi = 10.1016/j.pbb.2007.09.007 }}</ref>
DPT produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]]-like effects, in rodents.<ref name="Halberstadt_2020" /><ref name="Fantegrossi_2008" /> Studies on rodents have found that the effectiveness with which a [[binding selectivity|selective]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[receptor antagonist|antagonist]] blocks the behavioral actions of DPT strongly suggests that the 5-HT<sub>2A</sub> receptor is an important site of action for the drug, but the modulatory actions of a serotonin [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] antagonist also imply a serotonin 5-HT<sub>1A</sub> receptor-mediated component to the actions of DPT.<ref name="Fantegrossi_2008">{{cite journal | vauthors = Fantegrossi WE, Reissig CJ, Katz EB, Yarosh HL, Rice KC, Winter JC | title = Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents | journal = Pharmacology, Biochemistry, and Behavior | volume = 88 | issue = 3 | pages = 358–365 | date = January 2008 | pmid = 17905422 | pmc = 2322878 | doi = 10.1016/j.pbb.2007.09.007 }}</ref> Unusually among most psychedelics, DiPT did not show evidence of behavioral [[drug tolerance|tolerance]] in rodents.<ref name="SmithBaileyWilliams2014">{{cite journal | vauthors = Smith DA, Bailey JM, Williams D, Fantegrossi WE | title = Tolerance and cross-tolerance to head twitch behavior elicited by phenethylamine- and tryptamine-derived hallucinogens in mice | journal = J Pharmacol Exp Ther | volume = 351 | issue = 3 | pages = 485–491 | date = December 2014 | pmid = 25271256 | pmc = 4309922 | doi = 10.1124/jpet.114.219337 | url = }}</ref>


DPT produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]]-like effects, in rodents.<ref name="HalberstadtChathaKlein2020" />
==Chemistry==
[[File:N,N-Dipropyltryptamine.jpg|alt=DPT HCl Powder|thumb|DPT [[hydrochloride]] powder.]]
 
DPT, also known as ''N'',''N''-dipropyltryptamine, is a [[substituted tryptamine]] related to [[dimethyltryptamine]] (DMT).<ref name="TiHKAL" /> It is found either as a [[crystalline]] [[hydrochloride]] [[salt (chemistry)|salt]] or as an oily or crystalline [[base (chemistry)|base]]. The drug is [[synthetic compound|synthetic]] and has not been found to occur [[endogenous]]ly.<ref name="Pinchbeck2003" />
 
===Detection===
DPT changes [[Ehrlich's reagent]] violet and causes the marquis reagent to turn yellow.<ref name="Spratley_2004">{{cite journal | vauthors = Spratley T | title = Analytical Profiles for Five "Designer" Tryptamines | journal = Microgram Journal | volume = 3 | issue = 1–2 | pages = 55 | date = 2004 | url = http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | access-date = 2013-10-09 }}</ref>


==Chemistry==
===Synthesis===
[[File:N,N-Dipropyltryptamine.jpg|alt=DPT HCl Powder|thumb|DPT HCl Powder]]
The [[chemical synthesis]] of DPT has been described.<ref name="TiHKAL" />


DPT changes [[Ehrlich's reagent]] violet and causes the marquis reagent to turn yellow.<ref name='microgram2005'>{{cite journal | title = Analytical Profiles for Five "Designer" Tryptamines
===Analogues===
| journal = Microgram Journal | date = 2004 | first = Trinette | last = Spratley | name-list-style = vanc | volume = 3 | issue = 1–2 | pages = 55| url = http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | access-date = 2013-10-09}}</ref>
[[Structural analog|Analogue]]s of DPT include [[dimethyltryptamine]] (DMT), [[diethyltryptamine]] (DET), [[diisopropyltryptamine]] (DiPT), [[diallyltryptamine]] (DALT), [[methylethyltryptamine]] (MET), [[methylpropyltryptamine]] (MPT), [[ethylpropyltryptamine]] (EPT), [[propylisopropyltryptamine]] (PiPT), [[propylallyltryptamine]] (PALT), [[4-HO-DPT]], [[5-HO-DPT]], and [[5-MeO-DPT]], among others.<ref name="TiHKAL" />


==History==
==History==
DPT was first described in the [[scientific literature]] by 1959.<ref name="BarlowKhan1959a">{{cite journal | vauthors = Barlow RB, Khan I | title = The use of the guinea-pig ileum preparation for testing the activity of substances which imitate or antagonize the actions of 5-hydroxytryptamine and tryptamine | journal = Br J Pharmacol Chemother | volume = 14 | issue = 4 | pages = 553–8 | date = December 1959 | pmid = 13796840 | pmc = 1481908 | doi = 10.1111/j.1476-5381.1959.tb00963.x | url = }}</ref><ref name="BarlowKhan1959b">{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 2 | pages = 265–272 | date = June 1959 | pmid = 13662587 | pmc = 1481803 | doi = 10.1111/j.1476-5381.1959.tb01397.x | url = }}</ref><ref name="Vane1959">{{cite journal | vauthors = Vane JR | title = The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 87–98 | date = March 1959 | pmid = 13651584 | pmc = 1481817 | doi = 10.1111/j.1476-5381.1959.tb00933.x | url = }}</ref>
DPT was first described in the [[scientific literature]] by 1959.<ref name="Barlow_1959">{{cite journal | vauthors = Barlow RB, Khan I | title = The use of the guinea-pig ileum preparation for testing the activity of substances which imitate or antagonize the actions of 5-hydroxytryptamine and tryptamine | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 4 | pages = 553–558 | date = December 1959 | pmid = 13796840 | pmc = 1481908 | doi = 10.1111/j.1476-5381.1959.tb00963.x }}</ref><ref name="Barlow_1959a">{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 2 | pages = 265–272 | date = June 1959 | pmid = 13662587 | pmc = 1481803 | doi = 10.1111/j.1476-5381.1959.tb01397.x }}</ref><ref name="Vane_1959">{{cite journal | vauthors = Vane JR | title = The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 1 | pages = 87–98 | date = March 1959 | pmid = 13651584 | pmc = 1481817 | doi = 10.1111/j.1476-5381.1959.tb00933.x }}</ref> Use of DPT as a [[designer drug]] has been documented by law enforcement officials since as early as 1968.<ref name="Microgram1968">{{Cite journal | title = Microgram Journal Volume One No. 7 | journal = Microgram Journal | volume = One | issue = Seven | pages = 23 | date = April 1968 | orig-year = 1968 | url = https://www.erowid.org/library/periodicals/microgram/microgram_1968_04_v01n07.pdf | publisher = [[United States Department of Justice | U.S DOJ]], [[Bureau of Narcotics and Dangerous Drugs]] | access-date = 5 April 2021 }}</ref> It was described as a treatment for [[alcoholism]] by [[Stanislav Grof]] and colleagues in 1973.<ref name="MalacaLoFaroTamborra2020" /><ref name="TittarelliManocchiPantano2015" /><ref name="SoskinGrofRichards1973" /><ref name="Garcia-RomeuKersgaardAddy2016">{{cite journal | vauthors = Garcia-Romeu A, Kersgaard B, Addy PH | title = Clinical applications of hallucinogens: A review | journal = Exp Clin Psychopharmacol | volume = 24 | issue = 4 | pages = 229–268 | date = August 2016 | pmid = 27454674 | pmc = 5001686 | doi = 10.1037/pha0000084 | url = | quote = Like other classic hallucinogens, research with DMT ceased with the passage of the Controlled Substances Act, and was never investigated as an aid in clinical treatment to the extent LSD was. However, research with dipropyltryptamine (DPT), a closely related synthetic analog of DMT, revealed some promise as an adjunct to psychotherapy both with alcoholics (Grof et al., 1973; Rhead et al., 1977; Soskin et al., 1973), and those with anxiety associated with a terminal cancer diagnosis (Richards et al., 1977; 1980; Richards, 1978).}}</ref> It was also studied for treatment of [[anxiety]] associated with [[terminal cancer]] in the late 1970s.<ref name="Garcia-RomeuKersgaardAddy2016" /> However, it was not further studied for such purposes after 1980.<ref name="Garcia-RomeuRichards2018">{{cite journal | vauthors = Garcia-Romeu A, Richards WA | title = Current perspectives on psychedelic therapy: use of serotonergic hallucinogens in clinical interventions | journal = Int Rev Psychiatry | volume = 30 | issue = 4 | pages = 291–316 | date = August 2018 | pmid = 30422079 | doi = 10.1080/09540261.2018.1486289 | url = | quote = Others, like N, N-dipropyltryptamine (DPT), have been used in preliminary studies showing therapeutic potential (Grof et al., 1973; Richards, 1978; Richards, Rhead, DiLeo, Yensen, & Kurland, 1977; Richards et al., 1980), but have not been examined since.}}</ref>


==Society and culture==
==Society and culture==
===Religious use===
===Religious use===
DPT is used as a [[religious]] [[sacrament]] by the [[Temple of the True Inner Light]], a [[New York City]] offshoot of the [[Native American Church]]. The Temple believes DPT and other [[entheogen]]s are physical manifestations of [[God]].<ref>{{cite web | url = http://psychede.tripod.com/ | title = Temple of the True Inner Light | work = tripod.com }}</ref>
DPT is used as a [[religious]] [[sacrament]] by the [[Temple of the True Inner Light]], a [[New York City]] offshoot of the [[Native American Church]].<ref name="TiHKAL" /> The Temple believes DPT and other [[entheogen]]s are physical manifestations of [[God]].<ref name="TiHKAL" /><ref>{{cite web | title = Temple of the True Inner Light | url = http://psychede.tripod.com/ | work = tripod.com }}</ref>


===Legal status===
===Legal status===
====Sweden====
====Sweden====
DPT is illegal in Sweden as of 26 January 2016.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | title=31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=sv | date=November 2015}}</ref>
DPT is illegal in Sweden as of 26 January 2016.<ref>{{cite web | title = 31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | date = November 2015 | url = http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | publisher = Folkhälsomyndigheten | language = sv }}</ref>


====United Kingdom====
====United Kingdom====
Line 174: Line 190:


====United States====
====United States====
DPT is not scheduled at the federal level in the United States,<ref name="PART 1308 – SCHEDULES OF CONTROLLED SUBSTANCES – 1308.11 Schedule I">{{cite web | url = http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | work = CFR | title = SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. | access-date = 17 December 2014 | archive-date = 27 August 2009 | archive-url = https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | url-status = dead }}</ref> but it could be considered an analog of [[5-MeO-DiPT]], [[dimethyltryptamine|DMT]], or [[diethyltryptamine|DET]], in which case purchase, sale, or possession could be prosecuted under the [[Federal Analogue Act]].
DPT is not scheduled at the federal level in the United States,<ref name="PART 1308 – SCHEDULES OF CONTROLLED SUBSTANCES – 1308.11 Schedule I">{{cite web | title = SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. | url = http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | work = CFR | access-date = 17 December 2014 | archive-date = 27 August 2009 | archive-url = https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | url-status = dead }}</ref> but it could be considered an analog of [[5-MeO-DiPT]], [[dimethyltryptamine|DMT]], or [[diethyltryptamine|DET]], in which case purchase, sale, or possession could be prosecuted under the [[Federal Analogue Act]].


=====Florida=====
=====Florida=====
Line 182: Line 198:
DPT is a Schedule I [[controlled substance]] in the state of [[Maine]] making it illegal to buy, sell, or possess in Maine.
DPT is a Schedule I [[controlled substance]] in the state of [[Maine]] making it illegal to buy, sell, or possess in Maine.


==References==
==Research==
=== Fragile X syndrome ===
DPT has been found to completely prevent [[sound|audiogenic]] [[seizure]]s in [[animal model|mouse model]]s of [[fragile X syndrome]] (FXS) at a 10{{nbsp}}mg/kg dose, with its [[mechanism of action]] appearing to be independent of [[serotonin receptor|serotonin]] and [[sigma receptor|sigma]] [[sigma-1 receptor|σ<sub>1</sub> receptor]] activation.<ref name="TyagiSarafCanal2023" /> While DPT is an [[agonist]] at several serotonin receptors [[In vitro|''in vitro'']], its [[anticonvulsant]] effects were not blocked by [[binding selectivity|selective]] [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT1A receptor|5-HT<sub>1A</sub>]], or [[5-HT1B receptor|5-HT<sub>1B</sub> receptor]] [[receptor antagonist|antagonist]]s nor by a selective sigma σ<sub>1</sub> receptor antagonist [[In vivo|''in vivo'']].<ref name="TyagiSarafCanal2023" /> The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation.<ref name="TyagiSarafCanal2023" /> At higher doses, DPT switched from [[anticonvulsant]] to [[convulsant|proconvulsant]] action, indicating complex interactions.<ref name="TyagiSarafCanal2023">{{cite journal | vauthors = Tyagi R, Saraf TS, Canal CE | title = The Psychedelic <i>N</i>,<i>N</i>-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 10 | pages = 1480–1491 | date = October 2023 | pmid = 37854624 | pmc = 10580393 | doi = 10.1021/acsptsci.3c00137 }}</ref>
 
== See also ==
* [[Substituted tryptamine]]
 
== References ==
{{Reflist}}
{{Reflist}}


==External links==
== External links ==
* [https://isomerdesign.com/pihkal/explore/5009 DPT - Isomer Design]
* [https://isomerdesign.com/pihkal/explore/5009 DPT - Isomer Design]
* [https://www.erowid.org/library/books_online/tihkal/tihkal09.shtml TiHKAL entry]
* [https://psychonautwiki.org/wiki/DPT DPT - PsychonautWiki]
* [http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5009 DPT entry in TiHKAL • info]
* [https://www.erowid.org/chemicals/dpt/dpt.shtml DPT - Erowid]
* [https://www.erowid.org/chemicals/dpt/dpt_primer.shtml A DPT Primer by Toad]
* [https://www.erowid.org/library/books_online/tihkal/tihkal09.shtml DPT - TiHKAL - Erowid]
* [https://www.erowid.org/experiences/subs/exp_DPT.shtml Erowid Experience Vault]
* [http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5009 DPT - TiHKAL - Isomer Design]
* [https://www.bluelight.org/xf/threads/59257 The Big & Dandy DPT Thread - Bluelight]
* [https://www.erowid.org/chemicals/dpt/dpt_primer.shtml A DPT Primer by Toad - Erowid]


{{Psychedelics}}
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Serotonin receptor modulators}}
{{Sigma receptor modulators}}
{{Sigma receptor modulators}}
{{Monoamine reuptake inhibitors}}
{{Tryptamines}}
{{Tryptamines}}


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[[Category:Dipropylamino compounds]]
[[Category:Dipropylamino compounds]]
[[Category:Entheogens]]
[[Category:Entheogens]]
[[Category:Psychedelic-assisted therapy]]
[[Category:Psychedelic tryptamines]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin reuptake inhibitors]]
[[Category:Serotonin reuptake inhibitors]]
[[Category:Sigma receptor modulators]]
[[Category:TiHKAL]]

Latest revision as of 08:50, 27 November 2025

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| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=16242CCCN(CCC)CCC1=CNC2=C1C=CC=C21S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3BOOQTIHIKDDPRW-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite174.5178 | _combo_data= | _physiological_data= | _clinical_data= Oral, smoking, intramuscular injection, intravenous injection[1]Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; HallucinogenNone | _legal_data=NpSGClass A

| _other_data=N-[2-(1H-indol-3-yl)]ethyl-N-propylpropan-1-amine

| _image_0_or_2 = DPT.svgDPT-3d-sticks.png | _image_LR =

| _datapage = Dipropyltryptamine (data page) | _vaccine_target=_type_not_vaccine | _legal_all=Class A | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=61-52-9 | PubChem=6091 | ChemSpiderID=5866 | ChEBI= | ChEMBL= | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=S7272VWU50 | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

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Dipropyltryptamine (DPT), also known as N,N-dipropyltryptamine or as "The Light", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).[1][2] It is taken orally or by other routes.[1]

The drug acts as a serotonin receptor modulator, including as a serotonin 5-HT2A receptor agonist.[3][4][5][6][7] It is a close structural homologue of DMT and diethyltryptamine (DET).[1] Derivatives of DPT include 4-HO-DPT and 5-MeO-DPT, among others.[1]

DPT was first described in the literature by 1959.[8][9][10] It was encountered as a novel designer drug by 1968[11] and was reported as a possible treatment for alcoholism in 1973.[12][2][13] The drug is the sacrament of the Temple of the True Inner Light, a New York City-based religious group.[1][14][15]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists DPT's dose range as 100 to 250Script error: No such module "String".mg orally and its duration as 2 to 4Script error: No such module "String".hours.[1][12] A 500Script error: No such module "String".mg dose was also reported, which was described as "exhausting" and as lasting 12Script error: No such module "String".hours.[1] The onset and time to peak effects were not given, but it was implied to have a fast onset.[1] In addition to oral administration, DPT has been assessed by smoking at a dose of 100Script error: No such module "String".mg, by intramuscular injection at low doses of 15 to 30Script error: No such module "String".mg, moderate doses of 30 to 70Script error: No such module "String".mg, and "peak experience" doses of 75 to 125Script error: No such module "String".mg, and by intravenous injection at 12 to 36Script error: No such module "String".mg.[1][16]

The effects of DPT have been reported to include visuals, being intensely visual at high doses, changes in time perception, feeling like one is in a different place like on a mountain in clouds or in a big castle, enhanced recall of memories and experiences, enhanced emotional expressiveness and self-exploration, entity encounters, and religious feelings.[1][17][13] Other effects included trouble talking, feeling uncomfortable, nervousness, feeling light, and body rush.[1] Given at a high dose intravenously, it was described as every bit as powerful as a psychedelic as DMT.[1] According to one account however, DPT and DMT, despite their chemical similarity, "reveal completely different worlds".[17]

Other reports have stated effects of DPT including visual and auditory hallucinations, increased color intensity, flashes of light and sparkles, apparitions of faces, increased music appreciation, ego dissolution, stimulation, euphoria, relaxation, paranoia, psychosis, anxiety, nausea, dizziness, muscle tremors, and increased heart rate, among others.[12] Its duration is described as much shorter than those of certain other psychedelics like LSD, which can be advantageous in a clinical setting.[18][19][20] However, it is also said to have a rapid onset that can be psychologically overwhelming.[18][20]

Side effects

Although tryptamines such as psilocybin and dimethyltryptamine (DMT) have relatively well‑characterized safety, synthetic analogues like DPT lack thorough toxicological evaluation and are mainly associated with anecdotal reports of intoxication and a few cases of fatal outcomes when used recreationally.[21] The pharmacological similarity of DPT to DMT suggests a generally low intrinsic toxicity at controlled doses but a pronounced risk of acute adverse reactions, including agitation, tachycardia, hyperthermia, and serotonergic crisis, particularly in combination with monoamine oxidase inhibitors or other serotonergic substances.[21]

A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT2A receptor modulation but have not identified persistent neurotoxicity.[22] The main safety concerns are acute psychophysiological and behavioral disturbances rather than long‑term organ toxicity. Overall, DPT is a potent, short‑acting serotonergic hallucinogen with limited safety data and a toxicity profile comparable to related tryptamines such as DMT and 5-MeO-DMT.[21][22]

Interactions

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Pharmacology

Pharmacodynamics

DPT activities
Target Affinity (Ki, nM) Species
5-HT1A 31.8–1,641 (Ki)
274–>10,000 (EC50Tooltip half-maximal effective concentration)
99% (EmaxTooltip maximal efficacy)		 Human
Human
Human
5-HT1B 854–8,081 (Ki)
1,210 (EC50)		 Human
Human
5-HT1D 619 Human
5-HT1E 2,338 Human
5-HT2A 3.0–2,579 (Ki)
26.1–943a (EC50)
85a–97% (Emax)		 Human
Human
Human
5-HT2B 42 Human
5-HT2C 281–3,500 (Ki)
444a (EC50)
93%a (Emax)		 Human
Human
Human
5-HT3 >10,000 Human
5-HT4 ND ND
5-HT5A 4,373 Human
5-HT6 4,543 Human
5-HT7 284 Human
D1 >10,000 Human
D2 9,249 Human
D3 1,361 Human
D4 2,014 Human
D5 >10,000 Human
α1A 881 Human
α1B 443 Human
α1D ND ND
α2A 458 Human
α2B 339 Human
α2C 514 Human
β1–β2 >10,000 Human
H1 125 Human
H2–H4 >10,000 Human
M1–M5 >10,000 Human
I1 340 Human
σ1 397 Human
σ2 2,917 Human
SERTTooltip Serotonin transporter 157–480 (Ki)
157–23,000 (IC50Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)		 Human
Human
Rat
NETTooltip Norepinephrine transporter >10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (EC50)		 Human
Human
Rat
DATTooltip Dopamine transporter 1,500 (Ki)
2,218–9,100 (IC50)
>100,000 (EC50)		 Human
Human
Rat
Notes: The smaller the value, the more avidly the drug binds to the site. Footnotes: a = Stimulation of IP1Tooltip inositol phosphate formation. Refs: [3][4][5][6][7][23][24]

DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[16][25] Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of DPT strongly suggests that the 5-HT2A receptor is an important site of action for the drug, but the modulatory actions of a serotonin 5-HT1A receptor antagonist also imply a serotonin 5-HT1A receptor-mediated component to the actions of DPT.[25] Unusually among most psychedelics, DiPT did not show evidence of behavioral tolerance in rodents.[26]

Chemistry

DPT HCl Powder
DPT hydrochloride powder.

DPT, also known as N,N-dipropyltryptamine, is a substituted tryptamine related to dimethyltryptamine (DMT).[1] It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. The drug is synthetic and has not been found to occur endogenously.[17]

Detection

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.[27]

Synthesis

The chemical synthesis of DPT has been described.[1]

Analogues

Analogues of DPT include dimethyltryptamine (DMT), diethyltryptamine (DET), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), methylethyltryptamine (MET), methylpropyltryptamine (MPT), ethylpropyltryptamine (EPT), propylisopropyltryptamine (PiPT), propylallyltryptamine (PALT), 4-HO-DPT, 5-HO-DPT, and 5-MeO-DPT, among others.[1]

History

DPT was first described in the scientific literature by 1959.[8][9][10] Use of DPT as a designer drug has been documented by law enforcement officials since as early as 1968.[11] It was described as a treatment for alcoholism by Stanislav Grof and colleagues in 1973.[2][12][13][28] It was also studied for treatment of anxiety associated with terminal cancer in the late 1970s.[28] However, it was not further studied for such purposes after 1980.[29]

Society and culture

Religious use

DPT is used as a religious sacrament by the Temple of the True Inner Light, a New York City offshoot of the Native American Church.[1] The Temple believes DPT and other entheogens are physical manifestations of God.[1][30]

Legal status

Sweden

DPT is illegal in Sweden as of 26 January 2016.[31]

United Kingdom

DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.

United States

DPT is not scheduled at the federal level in the United States,[32] but it could be considered an analog of 5-MeO-DiPT, DMT, or DET, in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act.

Florida

"DPT (N,N-Dipropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[33]

Maine

DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.

Research

Fragile X syndrome

DPT has been found to completely prevent audiogenic seizures in mouse models of fragile X syndrome (FXS) at a 10Script error: No such module "String".mg/kg dose, with its mechanism of action appearing to be independent of serotonin and sigma σ1 receptor activation.[34] While DPT is an agonist at several serotonin receptors in vitro, its anticonvulsant effects were not blocked by selective serotonin 5-HT2A, 5-HT1A, or 5-HT1B receptor antagonists nor by a selective sigma σ1 receptor antagonist in vivo.[34] The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation.[34] At higher doses, DPT switched from anticonvulsant to proconvulsant action, indicating complex interactions.[34]

See also

References

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  1. ↑ a b c d e f g h i j k l m n o p q r Script error: No such module "citation/CS1".
  2. ↑ a b c Script error: No such module "Citation/CS1".
  3. ↑ a b Script error: No such module "Citation/CS1".
  4. ↑ a b Script error: No such module "Citation/CS1".
  5. ↑ a b Script error: No such module "Citation/CS1".
  6. ↑ a b Script error: No such module "Citation/CS1".
  7. ↑ a b Script error: No such module "Citation/CS1".
  8. ↑ a b Script error: No such module "Citation/CS1".
  9. ↑ a b Script error: No such module "Citation/CS1".
  10. ↑ a b Script error: No such module "Citation/CS1".
  11. ↑ a b Script error: No such module "Citation/CS1".
  12. ↑ a b c d Script error: No such module "Citation/CS1".
  13. ↑ a b c Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ a b Script error: No such module "Citation/CS1".
  17. ↑ a b c Script error: No such module "citation/CS1".
  18. ↑ a b Script error: No such module "Citation/CS1".
  19. ↑ Script error: No such module "Citation/CS1".
  20. ↑ a b Script error: No such module "Citation/CS1".
  21. ↑ a b c Script error: No such module "Citation/CS1".
  22. ↑ a b Script error: No such module "Citation/CS1".
  23. ↑ Script error: No such module "citation/CS1".
  24. ↑ Script error: No such module "Citation/CS1".
  25. ↑ a b Script error: No such module "Citation/CS1".
  26. ↑ Script error: No such module "Citation/CS1".
  27. ↑ Script error: No such module "Citation/CS1".
  28. ↑ a b Script error: No such module "Citation/CS1".
  29. ↑ Script error: No such module "Citation/CS1".
  30. ↑ Script error: No such module "citation/CS1".
  31. ↑ Script error: No such module "citation/CS1".
  32. ↑ Script error: No such module "citation/CS1".
  33. ↑ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
  34. ↑ a b c d Script error: No such module "Citation/CS1".

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External links

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