Dipropyltryptamine
Template:Short description Template:Cs1 config Template:Use dmy dates Template:Infobox drug
Dipropyltryptamine (DPT), also known as N,N-dipropyltryptamine or as "The Light", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).<ref name="TiHKAL">Template:CiteTiHKAL</ref><ref name="MalacaLoFaroTamborra2020">Template:Cite journal</ref> It is taken orally or by other routes.<ref name="TiHKAL" />
The drug acts as a serotonin receptor modulator, including as a serotonin 5-HT2A receptor agonist.<ref name="Ray_2010">Template:Cite journal</ref><ref name="Kozell_2023">Template:Cite journal</ref><ref name="Blough_2014">Template:Cite journal</ref><ref name="Nagai_2007">Template:Cite journal</ref><ref name="Nelson_1993" /> It is a close structural homologue of DMT and diethyltryptamine (DET).<ref name="TiHKAL" /> Derivatives 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">Template:Cite journal</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">Template:Cite book</ref><ref name="Kaplan1987">Template:Cite journal</ref>
Use and effects
In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists DPT's dose range as 100 to 250Template:Nbspmg orally and its duration as 2 to 4Template:Nbsphours.<ref name="TiHKAL" /><ref name="TittarelliManocchiPantano2015" /> A 500Template:Nbspmg dose was also reported, which was described as "exhausting" and as lasting 12Template:Nbsphours.<ref name="TiHKAL" /> The 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 100Template:Nbspmg, by intramuscular injection at low doses of 15 to 30Template:Nbspmg, moderate doses of 30 to 70Template:Nbspmg, and "peak experience" doses of 75 to 125Template:Nbspmg, and by intravenous injection at 12 to 36Template:Nbspmg.<ref name="TiHKAL" /><ref name="Halberstadt_2020">Template:Cite journal</ref>
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.<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">Template:Cite book</ref>
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.<ref name="TittarelliManocchiPantano2015">Template:Cite journal</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">Template:Cite journal</ref><ref name="RichardsRheadDileo1977">Template:Cite journal</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">Template:Cite journal</ref>
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.<ref name="Araujo_2015">Template:Cite journal</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 agitation, tachycardia, hyperthermia, and serotonergic crisis, particularly in combination with monoamine oxidase inhibitors or other serotonergic substances.<ref name="Araujo_2015" />
A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT2A receptor modulation but have not identified persistent neurotoxicity.<ref name="Castelhano_2021">Template:Cite journal</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
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) | Species |
|---|---|---|
| 5-HT1A | 31.8–1,641 (Ki) 274–>10,000 (Template:Abbrlink) 99% (Template:Abbrlink) |
Human Human Human |
| 5-HT1B | 854–8,081 (Ki) 1,210 (Template:Abbr) |
Human Human |
| 5-HT1D | 619 | Human |
| 5-HT1E | 2,338 | Human |
| 5-HT2A | 3.0–2,579 (Ki) 26.1–943a (Template:Abbr) 85a–97% (Template:Abbr) |
Human Human Human |
| 5-HT2B | 42 | Human |
| 5-HT2C | 281–3,500 (Ki) 444a (Template:Abbr) 93%a (Template:Abbr) |
Human Human Human |
| 5-HT3 | >10,000 | Human |
| 5-HT4 | Template:Abbr | Template:Abbr |
| 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 | Template:Abbr | Template:Abbr |
| 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 |
| Template:Abbrlink | 157–480 (Ki) 157–23,000 (Template:Abbrlink) >100,000 (Template:Abbr) |
Human Human Rat |
| Template:Abbrlink | >10,000 (Ki) 2,900–3,202 (Template:Abbr) >100,000 (Template:Abbr) |
Human Human Rat |
| Template:Abbrlink | 1,500 (Ki) 2,218–9,100 (Template:Abbr) >100,000 (Template:Abbr) |
Human Human Rat |
| Notes: The smaller the value, the more avidly the drug binds to the site. Footnotes: a = Stimulation of Template:Abbrlink formation. Refs: <ref name="Ray_2010" /><ref name="Kozell_2023" /><ref name="Blough_2014" /><ref name="Nagai_2007" /><ref name="Nelson_1993">Template:Cite journal</ref><ref name="KiDatabase">Template:Cite web</ref><ref name="Tyagi_2023">Template:Cite journal</ref> | ||
DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.<ref name="Halberstadt_2020" /><ref name="Fantegrossi_2008" /> 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.<ref name="Fantegrossi_2008">Template:Cite journal</ref>
Chemistry
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 or as an oily or crystalline base. The drug is synthetic and has not been found to occur endogenously.<ref name="Pinchbeck2003" />
Detection
DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.<ref name="Spratley_2004">Template:Cite journal</ref>
Synthesis
The chemical synthesis of DPT has been described.<ref name="TiHKAL" />
Analogues
Analogues 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">Template:Cite journal</ref><ref name="Barlow_1959a">Template:Cite journal</ref><ref name="Vane_1959">Template:Cite journal</ref> Use of DPT as a designer drug has been documented by law enforcement officials since as early as 1968.<ref name="Microgram1968">Template:Cite journal</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">Template:Cite journal</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">Template:Cite journal</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 entheogens are physical manifestations of God.<ref name="TiHKAL" /><ref>Template:Cite web</ref>
Legal status
Sweden
DPT is illegal in Sweden as of 26 January 2016.<ref>Template:Cite web</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">Template:Cite web</ref> 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.<ref name="Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL">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 audiogenic seizures in mouse models of fragile X syndrome (FXS) at a 10Template:Nbspmg/kg dose, with its mechanism of action appearing to be independent of serotonin and sigma σ1 receptor activation.<ref name="TyagiSarafCanal2023" /> 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.<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 proconvulsant action, indicating complex interactions.<ref name="TyagiSarafCanal2023">Template:Cite journal</ref>
See also
References
External links
- DPT - Isomer Design
- DPT - PsychonautWiki
- DPT - Erowid
- DPT - TiHKAL - Erowid
- DPT - TiHKAL - Isomer Design
- The Big & Dandy DPT Thread - Bluelight
- A DPT Primer by Toad - Erowid
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