dipropyltryptamine
{{Short description|Chemical compound}}
{{Use dmy dates|date=March 2024}}
{{Infobox drug
| Watchedfields = verified
| verifiedrevid = 444963386
| image = DPT.svg
| width = 200px
| image2 = DPT-3d-sticks.png
| width2 = 200px
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| routes_of_administration = Oral, inhalation (smoking), intravenous or intramuscular injection
| class = Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
| legal_AU =
| legal_CA =
| legal_DE = NpSG
| legal_UK = Class A
| legal_US =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| onset = Injection: 10–15 minutes
| elimination_half-life =
| duration_of_action = 2–4 hours
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 61-52-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S7272VWU50
| ATC_prefix = None
| ATC_suffix =
| PubChem = 6091
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5866
| synonyms = DPT; N,N-Dipropyltryptamine
| IUPAC_name = N-[2-(1H-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
| melting_point = 174.5
| melting_high = 178
}}
N,N-Dipropyltryptamine (DPT) is a psychedelic drug and entheogen belonging to the tryptamine family.{{CiteTiHKAL}} Use as a designer drug has been documented by law enforcement officials since as early as 1968.{{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= U.S DOJ, Bureau of Narcotics and Dangerous Drugs|volume=One|issue=Seven|pages=23|access-date=5 April 2021}} However, potential therapeutic use was not investigated until the 1970s.{{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 }} It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine and diethyltryptamine.
Use and effects
Doses ranges of DPT of 100 to 250{{nbsp}}mg (but up to 500{{nbsp}}mg) orally, 100{{nbsp}}mg smoked, 15 to 125{{nbsp}}mg intramuscularly, and 12 to 36{{nbsp}}mg intravenously have been described.{{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. [...] }} Its duration is 2 to 4{{nbsp}}hours orally but can last up to 12{{nbsp}}hours with high doses.
While DPT is chemically similar to dimethyltryptamine (DMT), its psychoactive effects have been said to be markedly different.{{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}} On the other hand, others have reported similarities to DMT, for instance in terms of intensity.
Side effects
Side effects of DPT may include nausea, numbness of the tongue or throat, pupil dilation, increased heart rate, dizziness, anxiety, panic, confusion, paranoia, delusions, and seizures (uncommon).{{Citation needed|date=April 2025}}
The use of DPT has been implicated in at least one death due to seizures,{{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/ }} although details are lacking and the drug has not officially been established as the sole cause of death.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
Pharmacology
Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of this compound strongly suggests 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.{{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 }}
DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.
Chemistry
File:N,N-Dipropyltryptamine.jpg
DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.{{cite journal | title = Analytical Profiles for Five "Designer" Tryptamines
| 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}}
History
DPT was first described in the scientific literature by 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 = 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 = }}{{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 = }}{{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 = }}
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. The Temple believes DPT and other entheogens are physical manifestations of God.{{cite web | url = http://psychede.tripod.com/ | title = Temple of the True Inner Light | work = tripod.com }}
=Legal status=
==Sweden==
DPT is illegal in Sweden as of 26 January 2016.{{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}}
==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,{{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 }} 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.[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]
===Maine===
DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5009 DPT - Isomer Design]
- [https://www.erowid.org/library/books_online/tihkal/tihkal09.shtml TiHKAL entry]
- [http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5009 DPT entry in TiHKAL • info]
- [https://www.erowid.org/chemicals/dpt/dpt_primer.shtml A DPT Primer by Toad]
- [https://www.erowid.org/experiences/subs/exp_DPT.shtml Erowid Experience Vault]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Sigma receptor modulators}}
{{Tryptamines}}
Category:N,N-Dialkyltryptamines
Category:Dipropylamino compounds
Category:Psychedelic tryptamines