4-HO-DiPT


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. It is taken orally. The drug has an unusually fast onset, short duration, and narrow dose range. Among orally administered psychedelics, it is one of the shortest-acting compounds known.
It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. 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. It is a derivative of DiPT, a higher homologue of psilocin and 4-HO-DET, and a skeletal isomer of 4-HO-DPT.
4-HO-DiPT was first described in the scientific literature by 1977. It was later described in greater detail by Alexander Shulgin in his 1997 book
TiHKAL''. The drug was encountered as a novel designer drug by 2005. In the 2020s, a prodrug of 4-HO-DiPT known as luvesilocin was developed and is in clinical trials for the treatment of psychiatric disorders such as postpartum depression.

Use and effects

In his book TiHKAL and other publications, Alexander Shulgin reported that 4-HO-DiPT had a dose range of 15 to 20mg orally and a duration of 2 to 3hours. However, a wider dose range of 3 to 30mg or more orally has also been reported. Shulgin has stated that 4-HO-DiPT has an especially steep dose–response curve and narrow dose range, with doses below 10mg producing few to no effects and doses of more than 20mg having not been tested due to the intensity of its effects. He personally found that a 20mg dose produced an intense plus-three experience on the Shulgin Rating Scale that "flirted with" the magical plus-four transcendental peak experience. The drug's onset of action is 15 to 20minutes and peak effects occur after 20 to 30minutes. Shulgin has stated that he "truly doubt that there is another psychedelic drug, anywhere, that can match for speed, for intensity, for brevity, and to dose, at least one that is active orally." However, ASR-3001, a more recent psychedelic, may be slightly faster than 4-HO-DiPT.
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. Other effects included sensations of muscle loosening, leg tremors, chill-like sensations, and vague body malaise. Shulgin has stated that he doubts that 4-HO-DiPT could be distinguished from psilocin in any blinded clinical study. Due to its rapid onset and short duration among other qualities, 4-HO-DiPT has been described as a "good 'novice' introduction to hallucinogens".
File:Effects of luvesilocin at different doses on the Drug Effects Questionnaire over 6 hours.png|thumb|left|250px|class=skin-invert-image|Luvesilocin Drug Effects Questionnaire "feel high" ratings at doses of 5 to 40mg via subcutaneous injection over 6hours.
The effects of 4-HO-DiPT have been clinically studied in the form of its prodrug luvesilocin. Luvesilocin was evaluated at doses of 5 to 40mg by subcutaneous injection in this study. It was specifically assessed in terms of modified Drug Effects Questionnaire ratings, Mystical Experience Questionnaire ratings, and adverse effects.

Interactions

Pharmacology

Pharmacodynamics

4-HO-DiPT acts as an agonist of serotonin receptors, including the serotonin 5-HT2A and 5-HT2B receptors. It may also act as a serotonin reuptake inhibitor, although its potency is variable across studies. The drug appears to activate the serotonin 5-HT2C receptor with low potency and much lower than for the serotonin 5-HT2A receptor. 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. The drug activates other serotonin receptors with lower potency as well. Unlike many other tryptamines, 4-HO-DiPT is not a ligand of the rodent trace amine-associated receptor 1.
The drug has been found to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. In addition, it has fully efficacious anti-inflammatory effects in preclinical research. 4-HO-DiPT has also been found to produce anxiolytic effects in rodents.

Pharmacokinetics

The pharmacokinetics of 4-HO-DiPT have been studied. The elimination half-life of 4-HO-DiPT in humans when given in the form of its prodrug luvesilocin by subcutaneous injection has been found to range from 2.7 to 4.1hours. The average experience duration was 3.6hours at a dose of 30mg in the study.

Chemistry

4-HO-DiPT, also known as 4-hydroxy-N,''N''-diisopropyltryptamine, is a substituted tryptamine. It is a synthetic analogue of the neurotransmitter serotonin and of the naturally occurring serotonergic psychedelics psilocin and psilocybin.

Synthesis

The chemical synthesis of 4-HO-DiPT has been described.

Analogues

4-HO-DiPT is closely related to analogues including diisopropyltryptamine, 5-MeO-DiPT, psilocin, 4-HO-DET, 4-HO-MET, 4-HO-MiPT, 4-HO-DPT, 4-HO-MPT, 4-HO-DALT, 4-HO-MALT, and 5-HO-DiPT, among others. 4-AcO-DiPT, 4-PrO-DiPT, and luvesilocin are ester prodrugs of 4-HO-DiPT.

History

4-HO-DiPT was first described in the scientific literature by David Repke and colleagues in 1977. Subsequently, its effects in humans were described by Alexander Shulgin in his 1997 book TiHKAL. The drug was encountered as a novel designer drug in Europe by 2005. Luvesilocin, a prodrug of 4-HO-DiPT, was first described in 2021.

Society and culture

Legal status

Canada

4-HO-DiPT is not a controlled substance in Canada as of 2025.

Finland

Scheduled in government decree on psychoactive substances banned from the consumer market.

Germany

Scheduled in New Psychoactive Substances Act. Use of covered substances is permitted only for industrial and scientific purposes.

Sweden

health ministry Statens folkhälsoinstitut classified 4-HO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 4-hydroxi-N,N-diisopropyltryptamin, making it illegal to sell or possess.

United States

4-HO-DiPT is not scheduled at the federal level in the United States, but it is possible that it could be considered an analogue of psilocin or 5-MeO-DiPT, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act. The United States Drug [Enforcement Administration] proposed scheduling 4-HO-DiPT in January 2022, but due to an effective public response, it withdrew its proposal in July 2022.
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.

Research

Luvesilocin

, 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.