View source for Dipropyltryptamine

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

<!-- Clinical data -->
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category = 
| 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]]
| ATC_prefix = None
| ATC_suffix =

<!-- Legal status -->
| legal_AU = 
| legal_CA = 
| legal_DE = NpSG
| legal_UK = Class A
| legal_US = 
| legal_status =

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

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 61-52-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S7272VWU50
| PubChem = 6091
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5866
| synonyms = DPT; ''N'',''N''-Dipropyltryptamine; "The Light"

<!-- Chemical data -->
| IUPAC_name = ''N''-[2-(1''H''-indol-3-yl)]ethyl-''N''-propylpropan-1-amine
| C=16 | H=24 | N=2
| SMILES = CCCN(CCC)CCC1=CNC2=C1C=CC=C2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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,3-4,9-12H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BOOQTIHIKDDPRW-UHFFFAOYSA-N

<!-- Physical data -->
| melting_point = 174.5
| melting_high = 178
}}

'''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|author=Jim DeKorne|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 |last=Kaplan |first=Eric |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==
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>

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="RichardsRheadDileo1977">{{cite journal | last1=Richards | first1=William A. | last2=Rhead | first2=John C. | last3=Dileo | first3=Francesco B. | last4=Yensen | first4=Richard | last5=Kurland | first5=Albert A. | title=The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients | journal=Journal of Psychedelic Drugs | volume=9 | issue=1 | date=1977 | issn=0022-393X | doi=10.1080/02791072.1977.10472020 | pages=1–10 | url=https://www.tandfonline.com/doi/full/10.1080/02791072.1977.10472020 | access-date=8 November 2025| url-access=subscription }}</ref><ref name="RichardsRheadGrof1980" /> However, it is also said to have a rapid onset that can be psychologically overwhelming.<ref name="Dutta2012" /><ref name="RichardsRheadGrof1980">{{cite journal | last1=Richards | first1=William A. | last2=Rhead | first2=John C. | last3=Grof | first3=Stanislav | last4=Goodman | first4=Louis E. | last5=Di Leo | first5=Francesco | last6=Rush | first6=Lockwood | title=DPT as an Adjunct in Brief Psychotherapy with Cancer Patients | journal=OMEGA - Journal of Death and Dying | volume=10 | issue=1 | date=1980 | issn=0030-2228 | doi=10.2190/NGUB-V4RM-T7DC-XTH3 | pages=9–26 | url=https://journals.sagepub.com/doi/10.2190/NGUB-V4RM-T7DC-XTH3 | access-date=8 November 2025| url-access=subscription }}</ref>

==Side effects==
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" />

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

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatleft" style="font-size:small;"
|+ DPT activities
|-
! [[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<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-HT1D receptor|5-HT<sub>1D</sub>]] || 619 || 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<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-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-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || 4,373 || Human
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || 4,543 || Human
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || 284 || Human
|-
| [[D1 receptor|D<sub>1</sub>]] || >10,000 || Human
|-
| [[D2 receptor|D<sub>2</sub>]] || 9,249 || Human
|-
| [[D3 receptor|D<sub>3</sub>]] || 1,361 || Human
|-
| [[D4 receptor|D<sub>4</sub>]] || 2,014 || Human
|-
| [[D5 receptor|D<sub>5</sub>]] || >10,000 || Human
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 881 || Human
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]] || 443 || Human
|-
| [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}} || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 458 || Human
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || 339 || Human
|-
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 514 || Human
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-2 adrenergic receptor|β<sub>2</sub>]] || >10,000 || Human
|-
| [[H1 receptor|H<sub>1</sub>]] || 125 || Human
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || >10,000 || Human
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || >10,000 || Human
|-
| [[I1 receptor|I<sub>1</sub>]] || 340 || Human
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]] || 397 || Human
|-
| [[Sigma-2 receptor|σ<sub>2</sub>]] || 2,917 || Human
|-
| {{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|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"
| 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>
|}

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>

==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>

===Synthesis===
The [[chemical synthesis]] of DPT has been described.<ref name="TiHKAL" />

===Analogues===
[[Structural analog|Analogue]]s of DPT include [[dimethyltryptamine]] (DMT), [[diethyltryptamine]] (DET), [[diisopropyltryptamine]] (DiPT), [[diallyltryptamine]] (DALT), [[methylethyltryptamine]] (MET), [[methylpropyltryptamine]] (MPT), [[ethylpropyltryptamine]] (EPT), [[propylisopropyltryptamine]] (PiPT), [[4-HO-DPT]], [[5-HO-DPT]], and [[5-MeO-DPT]], among others.<ref name="TiHKAL" />

==History==
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==
===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]].<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===
====Sweden====
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====
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,<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=====
"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.<ref name="Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL">[http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL]</ref>

=====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 [[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}}

== External links ==
* [https://isomerdesign.com/pihkal/explore/5009 DPT - Isomer Design]
* [https://psychonautwiki.org/wiki/DPT DPT - PsychonautWiki]
* [https://www.erowid.org/chemicals/dpt/dpt.shtml DPT - Erowid]
* [https://www.erowid.org/library/books_online/tihkal/tihkal09.shtml DPT - TiHKAL - Erowid]
* [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}}
{{Serotonin receptor modulators}}
{{Sigma receptor modulators}}
{{Monoamine reuptake inhibitors}}
{{Tryptamines}}

[[Category:5-HT1A agonists]]
[[Category:5-HT1B agonists]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2C agonists]]
[[Category:Designer drugs]]
[[Category:N,N-Dialkyltryptamines]]
[[Category:Dipropylamino compounds]]
[[Category:Entheogens]]
[[Category:Psychedelic-assisted therapy]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin reuptake inhibitors]]
[[Category:Sigma receptor modulators]]