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4-HO-DiPT

Chemical compound

Chemical compound

Luvesilocin: ≤1 hour | elimination_half-life = Luvesilocin (): 2.7–4.1 h (as 4-HO-DiPT) Luvesilocin (s.c.): 3.6hours (range ~3–4hours)

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). 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 (4-HO-DMT) 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 (Tryptamines I Have Known and Loved). The drug was encountered as a novel designer drug by 2005. 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.

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 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[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." However, ASR-3001 (5-MeO-iPALT), 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 (4-HO-DMT) 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".

The effects of 4-HO-DiPT have been clinically studied in the form of its prodrug luvesilocin (RE-104; FT-104; 4-GO-DiPT). Luvesilocin was evaluated at doses of 5 to 40mg (equivalent to ~4–32mg 4-HO-DiPT) by subcutaneous injection in this study. It was specifically assessed in terms of modified Drug Effects Questionnaire (DEQ) ratings, Mystical Experience Questionnaire (MEQ) ratings, and adverse effects.

Interactions

Pharmacology

Pharmacodynamics

TargetAffinity (Ki, nM)
[5-HT1A](5-ht1a-receptor)5,700–10,000 (Ki)
1,147–3,900 ()
36–70% ()
[5-HT1B](5-ht1b-receptor)10,000 (Ki)
597–10,000 (EC50)
95% (Emax)
[5-HT1D](5-ht1d-receptor)1,860 (Ki)
496–8,827 (EC50)
64–124% (Emax)
[5-HT1E](5-ht1e-receptor)10,000 (Ki)
852–10,000 (EC50)
79% (Emax)
[5-HT1F](5-ht1f-receptor)ND (Ki)
557 (EC50)
maxmaximal efficacy}})
[5-HT2A](5-ht2a-receptor)120–922 (Ki)
6.8–334a (EC50)
74–106% (Emax)
[5-HT2B](5-ht2b-receptor)85 (Ki)
5.1–460 (EC50)
55–110% (Emax)
[5-HT2C](5-ht2c-receptor)2.8–10,000 (Ki)
180–6,442 (EC50)
72–104%a (Emax)
[5-HT3](5-ht3-receptor)ND
[5-HT4](5-ht4-receptor)ND (Ki)
10,000 (EC50)
IA (Emax)
[5-HT5A](5-ht5a-receptor)10,000 (Ki)
243–5,074 (EC50)
56–66% (Emax)
[5-HT6](5-ht6-receptor)10,000 (Ki)
697–2,415 (EC50)
55–56% (Emax)
[5-HT7](5-ht7-receptor)10,000 (Ki)
ND (EC50)
maxmaximal efficacy}})
α1A12,000
α1B, α1DND
α2A15,000
α2B, α2C10,000
β1–β3ND
D1–D325,000
D4, D510,000
H19,800–10,000
H210,000
H3, H4ND
M1–M3ND
M41,725
M5ND
I1ND
σ1816–1,063
σ22,215
10,000
NR2B10,000
15,000 (Ki) (mouse)
15,000 (Ki) (rat)
ND (EC50) (human)
419–1,800 (Ki)
163–2,400 ()
IA (EC50)
11,000 (Ki)
46,000 (IC50)
IA (EC50)
26,000 (Ki)
100,000 (IC50)
IA (EC50)
**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 formation. **Refs:**

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 (TAAR1).

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 (4-GO-DiPT) 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 (5-hydroxytryptamine; 5-HT) and of the naturally occurring serotonergic psychedelics psilocin (4-HO-DMT) and psilocybin (4-PO-DMT).

Synthesis

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

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. 4-AcO-DiPT (ipracetin), 4-PrO-DiPT, and luvesilocin (4-GO-DiPT) 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 (Tryptamines I Have Known and Loved). The drug was encountered as a novel designer drug in Europe by 2005. Luvesilocin (4-GO-DiPT), a prodrug of 4-HO-DiPT, was first described in 2021.

Society and culture

4-HO-DiPT powder.

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 (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.

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 (4-HO-DMT) 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 (DEA) 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

Main article: 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.

References

References

  1. {{CiteTiHKAL https://www.erowid.org/library/books_online/tihkal/tihkal17.shtml
  2. (23 June 2022). "4-HO-DiPT".
  3. {{CitePiHKAL
  4. https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  5. (23 September 2025). "RE 104".
  6. (June 2024). "RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine". ACS Chem Neurosci.
  7. (2025). "Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study". J Clin Psychopharmacol.
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  9. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
  10. (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol.
  11. (10 July 2023). "Pioneering Psychedelics Scientist Alexander "Sasha" Shulgin's Legacy Lives On Via New Compounds And Research".
  12. (2 November 2023). "The Heirs to a Vault of Novel Psychedelics Take a Trip Into the Unknown".
  13. (30 March 2025). "What Happens When You Inherit 500 Psychedelic Compounds?".
  14. (2 April 2024). "Shulgin Farm and the Future of Psychedelic Drug Development (Featuring: Paul F. Daley, Ph.D.)". Psychedelics Today.
  15. (September 1997). "#21. 4-HO-MET". Transform Press.
  16. (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens". Eur Neuropsychopharmacol.
  17. (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci.
  18. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". J Pharmacol Exp Ther.
  19. (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacol Transl Sci.
  20. (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacol Transl Sci.
  21. (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther.
  22. (April 2024). "Psilocybin analog 4-OH-DiPT enhances fear extinction and GABAergic inhibition of principal neurons in the basolateral amygdala". Neuropsychopharmacology.
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  24. (2018). "The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines". Front Integr Neurosci.
  25. (1977). "Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols". Journal of Heterocyclic Chemistry.
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  27. "Controlled Drugs and Substances Act".
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