4-HO-DiPT
Template:Short description Template:Cs1 config Template:Use dmy dates Template:Drugbox
4-HO-DiPT, also known as 4-hydroxy-N,N-diisopropyltryptamine or as iprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT).<ref name="TiHKAL">Template:CiteTiHKAL https://www.erowid.org/library/books_online/tihkal/tihkal17.shtml</ref><ref name="PSR2022">Template:Cite web</ref> It is taken orally.<ref name="TiHKAL" /> The drug has an unusually fast onset, short duration, and narrow dose range.<ref name="TiHKAL" />
It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.<ref name="Rickli_2016" /><ref name="Klein_2021" /><ref name="Kozell_2023" /><ref name="Glatfelter_2023" /> Unlike many other psychedelic tryptamines, the drug appears to have far lower potency as an agonist of the serotonin 5-HT2C receptor relative to the serotonin 5-HT2A receptor.<ref name="Rickli_2016" /><ref name="Klein_2021" /><ref name="Kozell_2023" /><ref name="Glatfelter_2023" /> It is a derivative of DiPT, a higher homologue of psilocin (4-HO-DMT) and 4-HO-DET, and a skeletal isomer of 4-HO-DPT.<ref name="TiHKAL" />
4-HO-DiPT was first described in the scientific literature by 1977.<ref name="PSR2022" /><ref name="Zamberlan_2018" /><ref name="Repke_1977" /> It was later described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).<ref name="PSR2022" /><ref name="Zamberlan_2018" /><ref name="TiHKAL" /> The drug was encountered as a novel designer drug by 2005.<ref name="EMCDDA2005">https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005</ref> In the 2020s, a prodrug of 4-HO-DiPT known as luvesilocin (RE-104, FT-104; 4-GO-DiPT) was developed and is in clinical trials for the treatment of psychiatric disorders such as postpartum depression.<ref name="PSR2022" /><ref name="AdisInsight-Luvesilocin">Template:Cite web</ref><ref name="Bryson_2024">Template:Cite journal</ref><ref name="Ludbrook_2025">Template:Cite journal</ref>
Use and effects
In his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, Alexander Shulgin reported that 4-HO-DiPT had a dose range of 15 to 20Template:Nbspmg orally and a duration of 2 to 3Template:Nbsphours.<ref name="TiHKAL" /><ref name="Shulgin2003">Template:Cite book</ref><ref name="Halberstadt_2020">Template:Cite journal</ref> However, a wider dose range of 3 to 30Template:Nbspmg or more orally has also been reported.<ref name="Luethi_2018">Template:Cite journal</ref> Shulgin has stated that 4-HO-DiPT has an especially steep dose–response curve and narrow dose range, with doses below 10Template:Nbspmg producing few to no effects and doses of more than 20Template:Nbspmg having not been tested due to the intensity of its effects.<ref name="TiHKAL" /> He personally found that a 20Template:Nbspmg dose produced an intense plus-three experience on the Shulgin Rating Scale that "flirted with" the magical plus-four transcendental peak experience.<ref name="TiHKAL" /> The drug's onset of action is 15 to 20Template:Nbspminutes and peak effects occur after 20 to 30Template:Nbspminutes.<ref name="TiHKAL" /> Shulgin has stated that he "truly doubt[s] that there is another psychedelic drug, anywhere, that can match [4-HO-DiPT] for speed, for intensity, for brevity, and [sensitivity] to dose, at least one that is active orally."<ref name="TiHKAL" />
The effects of 4-HO-DiPT have been reported to include introspective changes, insights and realizations, mild object distortion, slight color effects, rainbow halos around objects, very little in the way of closed-eye visuals, little in terms of psychedelic visuals or sensory changes in general, mild stimulation, mild elation, light tension, orgasmic enhancement, and powerful religious-esque experiences.<ref name="TiHKAL" /> Other effects included sensations of muscle loosening, leg tremors, chill-like sensations, and vague body malaise.<ref name="TiHKAL" /> Shulgin has stated that he doubts that 4-HO-DiPT could be distinguished from psilocin (4-HO-DMT) in any blinded clinical study.<ref name="Shulgin_1997">Template:Cite web</ref> Due to its rapid onset and short duration among other qualities, 4-HO-DiPT has been described as a "good 'novice' introduction to hallucinogens".<ref name="TiHKAL" />
The effects of 4-HO-DiPT have been clinically studied in the form of its prodrug luvesilocin (RE-104; FT-104; 4-GO-DiPT).<ref name="Ludbrook_2025" /> Luvesilocin was evaluated at doses of 5 to 40Template:Nbspmg (equivalent to ~4–32Template:Nbspmg 4-HO-DiPT) by subcutaneous injection in this study.<ref name="Ludbrook_2025" /> It was specifically assessed in terms of modified Drug Effects Questionnaire (DEQ) ratings, Mystical Experience Questionnaire (MEQ) ratings, and adverse effects.<ref name="Ludbrook_2025" />
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 5,700–>10,000 (Ki) 1,147–3,900 (Template:Abbrlink) 36–70% (Template:Abbrlink) |
| 5-HT1B | >10,000 (Ki) 597–>10,000 (Template:Abbr) 95% (Template:Abbr) |
| 5-HT1D | 1,860 (Ki) 496–8,827 (Template:Abbr) 64–124% (Template:Abbr) |
| 5-HT1E | >10,000 (Ki) 852–>10,000 (Template:Abbr) 79% (Template:Abbr) |
| 5-HT1F | Template:Abbr (Ki) 557 (Template:Abbr) <20–59% (Template:Abbr) |
| 5-HT2A | 120–922 (Ki) 6.8–334a (Template:Abbr) 74–106% (Template:Abbr) |
| 5-HT2B | 85 (Ki) 5.1–460 (Template:Abbr) 55–110% (Template:Abbr) |
| 5-HT2C | 2.8–>10,000 (Ki) 180–6,442 (Template:Abbr) 72–104%a (Template:Abbr) |
| 5-HT3 | Template:Abbr |
| 5-HT4 | Template:Abbr (Ki) >10,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| 5-HT5A | >10,000 (Ki) 243–5,074 (Template:Abbr) 56–66% (Template:Abbr) |
| 5-HT6 | >10,000 (Ki) 697–2,415 (Template:Abbr) 55–56% (Template:Abbr) |
| 5-HT7 | >10,000 (Ki) Template:Abbr (Template:Abbr) <20% (Template:Abbr) |
| α1A | >12,000 |
| α1B, α1D | Template:Abbr |
| α2A | 15,000 |
| α2B, α2C | >10,000 |
| β1–β3 | Template:Abbr |
| D1–D3 | >25,000 |
| D4, D5 | >10,000 |
| H1 | 9,800–>10,000 |
| H2 | >10,000 |
| H3, H4 | Template:Abbr |
| M1–M3 | Template:Abbr |
| M4 | 1,725 |
| M5 | Template:Abbr |
| I1 | Template:Abbr |
| σ1 | 816–1,063 |
| σ2 | 2,215 |
| Template:Abbrlink | >10,000 |
| NR2B | >10,000 |
| Template:Abbrlink | >15,000 (Ki) (mouse) >15,000 (Ki) (rat) Template:Abbr (Template:Abbr) (human) |
| Template:Abbrlink | 419–1,800 (Ki) 163–2,400 (Template:Abbrlink) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | 11,000 (Ki) 46,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | >26,000 (Ki) >100,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Footnotes: a = Stimulation of Template:Abbrlink formation. Refs: <ref name="Rickli_2016">Template:Cite journal</ref><ref name="Klein_2021">Template:Cite journal</ref><ref name="Kozell_2023">Template:Cite journal</ref><ref name="Glatfelter_2023">Template:Cite journal</ref><ref name="Bryson_2024a" /><ref name="Flanagan_2021">Template:Cite journal</ref><ref name="Kelly_2024" /><ref name="Simmler_2016">Template:Cite journal</ref> | |
4-HO-DiPT acts as an agonist of serotonin receptors, including the serotonin 5-HT2A and 5-HT2B receptors.<ref name="Rickli_2016" /><ref name="Klein_2021" /><ref name="Kozell_2023" /><ref name="Glatfelter_2023" /><ref name="Flanagan_2021" /> It may also act as a serotonin reuptake inhibitor, although its potency is variable across studies.<ref name="Rickli_2016" /><ref name="Klein_2021" /><ref name="Kozell_2023" /><ref name="Glatfelter_2023" /> The drug appears to activate the serotonin 5-HT2C receptor with low potency and much lower than for the serotonin 5-HT2A receptor.<ref name="Rickli_2016" /><ref name="Klein_2021" /><ref name="Kozell_2023" /><ref name="Glatfelter_2023" /> However, in another study, it was only about 2.5-fold more potent as an agonist of the serotonin 5-HT2A receptor relative to the serotonin 5-HT2C receptor.<ref name="Kelly_2024" /> The drug activates other serotonin receptors with lower potency as well.<ref name="Kelly_2024" /> Unlike many other tryptamines, 4-HO-DiPT is not a ligand of the rodent trace amine-associated receptor 1 (TAAR1).<ref name="Rickli_2016" /><ref name="Simmler_2016" />
The drug has been found to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.<ref name="PSR2022" /><ref name="Halberstadt_2020" /><ref name="Klein_2021" /> In addition, it has fully efficacious anti-inflammatory effects in preclinical research.<ref name="PSR2022" /><ref name="Flanagan_2021" /> 4-HO-DiPT has also been found to produce anxiolytic effects in rodents.<ref name="Kelly_2024">Template:Cite journal</ref>
Pharmacokinetics
The pharmacokinetics of 4-HO-DiPT have been studied.<ref name="Bryson_2024a">Template:Cite journal</ref><ref name="Ludbrook_2025" /> The elimination half-life of 4-HO-DiPT in humans when given in the form of its prodrug luvesilocin (4-GO-DiPT) by subcutaneous injection has been found to range from 2.7 to 4.1Template:Nbsphours.<ref name="Ludbrook_2025" /> The average experience duration was 3.6Template:Nbsphours at a dose of 30Template:Nbspmg in the study.<ref name="Ludbrook_2025" />
Chemistry
4-HO-DiPT, also known as 4-hydroxy-N,N-diisopropyltryptamine, is a substituted tryptamine.<ref name="TiHKAL" /> It is a synthetic analogue of the neurotransmitter serotonin (5-hydroxytryptamine; 5-HT) and of the naturally occurring serotonergic psychedelics psilocin (4-HO-DMT) and psilocybin (4-PO-DMT).<ref name="TiHKAL" /><ref name="PSR2022" />
Synthesis
The chemical synthesis of 4-HO-DiPT has been described.<ref name="TiHKAL" />
Analogues
4-HO-DiPT is closely related to analogues including diisopropyltryptamine (DiPT), 5-MeO-DiPT, psilocin (4-HO-DMT), 4-HO-DET (ethocin), 4-HO-MET (metocin), 4-HO-MiPT (miprocin), 4-HO-DPT (deprocin), 4-HO-MPT (meprocin), 4-HO-DALT (dalocin), 4-HO-MALT (malocin), and 5-HO-DiPT, among others.<ref name="TiHKAL" /> 4-AcO-DiPT (ipracetin), 4-PrO-DiPT, and luvesilocin (4-GO-DiPT) are ester prodrugs of 4-HO-DiPT.<ref name="PSR2022" /><ref name="Klein_2021" /><ref name="Ludbrook_2025" />
History
4-HO-DiPT was first described in the scientific literature by David Repke and colleagues in 1977.<ref name="PSR2022" /><ref name="Zamberlan_2018">Template:Cite journal</ref><ref name="Repke_1977">Template:Cite journal</ref> Subsequently, its effects in humans were described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).<ref name="PSR2022" /><ref name="Zamberlan_2018" /><ref name="TiHKAL" /> The drug was encountered as a novel designer drug in Europe by 2005.<ref name="EMCDDA2005" /> Luvesilocin (4-GO-DiPT), a prodrug of 4-HO-DiPT, was first described in 2021.<ref name="PSR2022" /><ref name="US11292765">Bryson N. Tryptamine prodrugs. US 2021/0403425 A1, Field Trip Psychedelics, Inc0. Published online April 5, 2022. Accessed May 27, 2022. https://patents.google.com/patent/US11292765B2/en?q=field+trip+health&assignee=Field+Trip+Psychedelics+Inc.</ref>
Society and culture
Legal status
Finland
Scheduled in government decree on psychoactive substances banned from the consumer market.<ref>Template:Cite web</ref>
Germany
Scheduled in New Psychoactive Substances Act (NpSG). Use of covered substances is permitted only for industrial and scientific purposes.
Sweden
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-HO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 4-hydroxi-N,N-diisopropyltryptamin (4-HO-DIPT), making it illegal to sell or possess.<ref>Template:Cite web</ref>
United States
4-HO-DiPT 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 is possible that it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act. The United States Drug Enforcement Administration (DEA) proposed scheduling 4-HO-DiPT in January 2022, but due to an effective public response, it withdrew its proposal in July 2022.<ref name="PSR2022" />
Florida
"4-Hydroxy-N,N-diisopropyltryptamine" 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">Template:Cite web</ref>
Research
Luvesilocin
Luvesilocin (developmental code names RE-104, FT-104; O-glutaryl-4-HO-DiPT or 4-GO-DiPT), a prodrug of 4-HO-DiPT, has entered phase 2 clinical trials for treatment of psychiatric conditions such as postpartum depression and treatment-resistant depression.<ref name="AdisInsight-Luvesilocin" /><ref name="GlobeNewswire2022">Template:Cite press release</ref><ref name="PsychedelicSpotlight2022">Template:Cite web</ref><ref name="US346005716">Template:Cite web</ref>
See also
References
External links
- 4-HO-DIPT - Isomer Design
- 4-HO-DiPT - PsychonautWiki
- 4-HO-DIPT - Erowid
- 4-HO-DIPT - TiHKAL - Erowid
- 4-HO-DIPT - TiHKAL - Isomer Design
- The Big & Dandy 4-HO-DiPT Thread - Bluelight
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