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4-HO-DiPT

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
4-HO-DiPT
Clinical data
Other names4-OH-DiPT; 4-Hydroxy-N,N-diisopropyltryptamine; Iprocin
Routes of
administration
Oral[1]
Drug classNon-selectiveserotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action15–20 minutes[1]
Eliminationhalf-life2.7–4.1 h (asluvesilocins.c.Tooltip subcutaneous injection)[2]
Duration of action2–3 hours[1]
Identifiers
  • 3-[2-(diisopropylamino)ethyl]-1H-indol-4-ol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.214.853Edit this at Wikidata
Chemical and physical data
FormulaC16H24N2O
Molar mass260.381 g·mol−1
3D model (JSmol)
  • CC(C)N(CCc1c[nH]c2cccc(O)c12)C(C)C
  • InChI=1S/C16H24N2O/c1-11(2)18(12(3)4)9-8-13-10-17-14-6-5-7-15(19)16(13)14/h5-7,10-12,17,19H,8-9H2,1-4H3 checkY
  • Key:KBRYKXCBGISXQV-UHFFFAOYSA-N checkY
  (verify)

4-HO-DiPT, also known as4-hydroxy-N,N-diisopropyltryptamine or asiprocin, is apsychedelic drug of thetryptamine and4-hydroxytryptamine families related topsilocin (4-HO-DMT).[1][3] It is takenorally.[1] The drug has an unusually fastonset, shortduration, and narrow dose range.[1]

It acts as anon-selectiveserotonin receptor agonist, including of theserotonin5-HT2A receptor.[4][5][6][7] Unlike many other psychedelic tryptamines, the drug appears to have far lowerpotency as an agonist of the serotonin5-HT2C receptor relative to the serotonin 5-HT2A receptor.[4][5][6][7] It is aderivative ofDiPT, a higherhomologue of psilocin (4-HO-DMT) and4-HO-DET, and askeletal isomer of4-HO-DPT.[1]

4-HO-DiPT was first described in thescientific literature by 1977.[3][8][9] It was later described in greater detail byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[3][8][1] The drug was encountered as a noveldesigner drug by 2005.[10] In the 2020s, aprodrug of 4-HO-DiPT known asluvesilocin (RE-104, FT-104; 4-GO-DiPT) was developed and is inclinical trials for the treatment ofpsychiatric disorders such aspostpartum depression.[3][11][12][2]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved) and other publications,Alexander Shulgin reported that 4-HO-DiPT had adose range of 15 to 20 mgorally and aduration of 2 to 3 hours.[1][13][14] However, a wider dose range of 3 to 30 mg or more orally has also been reported.[15] Shulgin has stated that 4-HO-DiPT has an especially steepdose–response curve and narrow dose range, with doses below 10 mg producing few to no effects and doses of more than 20 mg having not been tested due to the intensity of its effects.[1] He personally found that a 20 mg dose produced an intense plus-three experience on theShulgin Rating Scale that "flirted with" the magical plus-four transcendental peak experience.[1] The drug'sonset of action is 15 to 20 minutes and peak effects occur after 20 to 30 minutes.[1] 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."[1]

The effects of 4-HO-DiPT have been reported to includeintrospective changes,insights and realizations, mild object distortion, slight color effects, rainbow halos around objects, very little in the way ofclosed-eye visuals, little in terms ofpsychedelic visuals orsensory changes in general, mildstimulation, mildelation, lighttension,orgasmic enhancement, and powerfulreligious-esque experiences.[1] Other effects included sensations ofmuscle loosening, legtremors,chill-like sensations, and vague bodymalaise.[1] Shulgin has stated that he doubts that 4-HO-DiPT could be distinguished frompsilocin (4-HO-DMT) in anyblindedclinical study.[16] Due to its rapid onset and short duration among other qualities, 4-HO-DiPT has been described as a "good 'novice' introduction to hallucinogens".[1]

Luvesilocin (RE104; 4-GO-DiPT)Drug Effects Questionnaire (DEQ) "feel high" ratings at doses of 5 to 40 mg (equivalent to ~4–32 mg 4-HO-DiPT) viasubcutaneous injection over 6 hours.[2]

The effects of 4-HO-DiPT have been clinically studied in the form of itsprodrugluvesilocin (RE-104; FT-104; 4-GO-DiPT).[2] Luvesilocin was evaluated at doses of 5 to 40 mg (equivalent to ~4–32 mg 4-HO-DiPT) bysubcutaneous injection in this study.[2] It was specifically assessed in terms of modifiedDrug Effects Questionnaire (DEQ) ratings, Mystical Experience Questionnaire (MEQ) ratings, andadverse effects.[2]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]
4-HO-DiPT activities
TargetAffinity (Ki, nM)
5-HT1A5,700–>10,000 (Ki)
1,147–3,900 (EC50Tooltip half-maximal effective concentration)
36–70% (EmaxTooltip maximal efficacy)
5-HT1B>10,000 (Ki)
597–>10,000 (EC50)
95% (
Emax)
5-HT1D1,860 (Ki)
496–8,827 (EC50)
64–124% (
Emax)
5-HT1E>10,000 (Ki)
852–>10,000 (EC50)
79% (
Emax)
5-HT1FND (Ki)
557 (
EC50)
<20–59% (
Emax)
5-HT2A120–922 (Ki)
6.8–334a (EC50)
74–106% (
Emax)
5-HT2B85 (Ki)
5.1–460 (EC50)
55–110% (
Emax)
5-HT2C2.8–>10,000 (Ki)
180–6,442 (EC50)
72–104%a (
Emax)
5-HT3ND
5-HT4ND (Ki)
>10,000 (
EC50)
IA (Emax)
5-HT5A>10,000 (Ki)
243–5,074 (EC50)
56–66% (
Emax)
5-HT6>10,000 (Ki)
697–2,415 (EC50)
55–56% (
Emax)
5-HT7>10,000 (Ki)
ND (EC50)
<20% (
Emax)
α1A>12,000
α1B,α1DND
α2A15,000
α2B,α2C>10,000
β1β3ND
D1D3>25,000
D4,D5>10,000
H19,800–>10,000
H2>10,000
H3,H4ND
M1M3ND
M41,725
M5ND
I1ND
σ1816–1,063
σ22,215
KORTooltip κ-Opioid receptor>10,000
NR2B>10,000
TAAR1Tooltip Trace amine-associated receptor 1>15,000 (Ki) (mouse)
>15,000 (Ki) (rat)
ND (EC50) (human)
SERTTooltip Serotonin transporter419–1,800 (Ki)
163–2,400 (IC50Tooltip half-maximal inhibitory concentration)
IA (EC50)
NETTooltip Norepinephrine transporter11,000 (Ki)
46,000 (IC50)
IA (EC50)
DATTooltip Dopamine transporter>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 ofIP1Tooltip inositol phosphate formation.Refs:[4][5][6][7][17][18][19][20]

4-HO-DiPT acts as anagonist ofserotonin receptors, including theserotonin5-HT2A and5-HT2B receptors.[4][5][6][7][18] It may also act as aserotonin reuptake inhibitor, although itspotency is variable across studies.[4][5][6][7] The drug appears to activate the serotonin5-HT2C receptor with low potency and much lower than for the serotonin 5-HT2A receptor.[4][5][6][7] 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.[19] The drug activates other serotonin receptors with lower potency as well.[19] Unlike many othertryptamines, 4-HO-DiPT is not aligand of the rodenttrace amine-associated receptor 1 (TAAR1).[4][20]

The drug has been found to produce thehead-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3][14][5] In addition, it has fully efficaciousanti-inflammatory effects inpreclinical research.[3][18] 4-HO-DiPT has also been found to produceanxiolytic effects in rodents.[19]

Pharmacokinetics

[edit]

Thepharmacokinetics of 4-HO-DiPT have been studied.[17][2] Theelimination half-life of 4-HO-DiPT in humans when given in the form of itsprodrugluvesilocin (4-GO-DiPT) bysubcutaneous injection has been found to range from 2.7 to 4.1 hours.[2] The average experienceduration was 3.6 hours at a dose of 30 mg in the study.[2]

Chemistry

[edit]

4-HO-DiPT, also known as 4-hydroxy-N,N-diisopropyltryptamine, is asubstituted tryptamine.[1] It is asyntheticanalogue of theneurotransmitterserotonin (5-hydroxytryptamine; 5-HT) and of thenaturally occurringserotonergic psychedelicspsilocin (4-HO-DMT) andpsilocybin (4-PO-DMT).[1][3]

Synthesis

[edit]

Thechemical synthesis of 4-HO-DiPT has been described.[1]

Analogues

[edit]

4-HO-DiPT is closely related toanalogues includingdiisopropyltryptamine (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), and5-HO-DiPT, among others.[1]4-AcO-DiPT (ipracetin),4-PrO-DiPT, andluvesilocin (4-GO-DiPT) areesterprodrugs of 4-HO-DiPT.[3][5][2]

History

[edit]

4-HO-DiPT was first described in thescientific literature byDavid Repke and colleagues in 1977.[3][8][9] Subsequently, its effects in humans were described byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[3][8][1] The drug was encountered as a noveldesigner drug inEurope by 2005.[10]Luvesilocin (4-GO-DiPT), aprodrug of 4-HO-DiPT, was first described in 2021.[3][21]

Society and culture

[edit]

Legal status

[edit]
4-HO-DiPT powder.

Finland

[edit]

Scheduled in government decree on psychoactive substances banned from the consumer market.[22]

Germany

[edit]

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

Sweden

[edit]

Sveriges riksdags health ministryStatens folkhälsoinstitut classified 4-HO-DiPT as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct 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.[23]

United States

[edit]

4-HO-DiPT is not scheduled at the federal level in theUnited States,[24] but it is possible that it could be considered an analog of5-MeO-DiPT, in which case purchase, sale, or possession could be prosecuted under theFederal Analog Act. The United StatesDrug 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.[3]

Florida
[edit]

"4-Hydroxy-N,N-diisopropyltryptamine" is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.[25]

Research

[edit]

Luvesilocin

[edit]
Main article:Luvesilocin
Luvesilocin (RE-104, FT-104; 4-GO-DiPT), aprodrug of 4-HO-DiPT.

Luvesilocin (developmental code names RE-104, FT-104;O-glutaryl-4-HO-DiPT or 4-GO-DiPT), aprodrug of 4-HO-DiPT, has enteredphase 2clinical trials for treatment ofpsychiatric conditions such aspostpartum depression andtreatment-resistant depression.[11][26][27][28]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmnopqrstuShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.https://www.erowid.org/library/books_online/tihkal/tihkal17.shtml
  2. ^abcdefghijLudbrook G, Bryson N, Taylor B, Hocevar-Trnka J, Johnson MW, Hirman J, et al. (2025)."Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study".J Clin Psychopharmacol.45 (5):441–453.doi:10.1097/JCP.0000000000002047.PMC 12379775.PMID 40685873.
  3. ^abcdefghijkl"4-HO-DiPT".Psychedelic Science Review. 23 June 2022. Retrieved8 October 2025.
  4. ^abcdefgRickli A, Moning OD, Hoener MC, Liechti ME (August 2016)."Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens"(PDF).Eur Neuropsychopharmacol.26 (8):1327–1337.doi:10.1016/j.euroneuro.2016.05.001.PMID 27216487.
  5. ^abcdefghKlein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. (April 2021)."Investigation of the Structure-Activity Relationships of Psilocybin Analogues".ACS Pharmacol Transl Sci.4 (2):533–542.doi:10.1021/acsptsci.0c00176.PMC 8033608.PMID 33860183.
  6. ^abcdefKozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (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.385 (1):62–75.doi:10.1124/jpet.122.001454.PMC 10029822.PMID 36669875.
  7. ^abcdefGlatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, et al. (April 2023)."Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice".ACS Pharmacol Transl Sci.6 (4):567–577.doi:10.1021/acsptsci.2c00222.PMC 10111620.PMID 37082754.
  8. ^abcdZamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, et al. (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.12 54.doi:10.3389/fnint.2018.00054.PMC 6235949.PMID 30467466.4-OH-DiPT (4-Hydroxy-diisopropyltryptamine): substituted tryptamine, first synthesized by Repke et al. (1977) and investigated in humans by A. Shulgin (Shulgin and Shulgin, 1997).
  9. ^abRepke DB, Ferguson WJ, Bates DK (1977)."Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols".Journal of Heterocyclic Chemistry.14 (1):71–74.doi:10.1002/jhet.5570140113.ISSN 0022-152X.
  10. ^abhttps://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  11. ^ab"RE 104".AdisInsight. 23 September 2025. Retrieved8 October 2025.
  12. ^Bryson N, Alexander R, Asnis-Alibozek A, Ehlers MD (June 2024)."RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine".ACS Chem Neurosci.15 (12):2386–2395.doi:10.1021/acschemneuro.4c00058.PMC 11191588.PMID 38758589.
  13. ^Shulgin AT (2003)."Basic Pharmacology and Effects". In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137.ISBN 978-0-12-433951-4.
  14. ^abHalberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020)."Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species"(PDF).Neuropharmacology.167 107933.doi:10.1016/j.neuropharm.2019.107933.PMC 9191653.PMID 31917152.Table 4 Human potency data for selected hallucinogens. [...]
  15. ^Luethi D, Liechti ME (October 2018)."Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics".Int J Neuropsychopharmacol.21 (10):926–931.doi:10.1093/ijnp/pyy047.PMC 6165951.PMID 29850881.
  16. ^Shulgin A, Shulgin A (September 1997)."#21. 4-HO-MET".Isomer Design. Transform Press. Retrieved28 November 2023.With [4-HO-MET], some of the original observations suggested that it was more potent than psilocin, certainly more dramatic. But at the bottom line, I doubt that this ethyl homologue, or the isopropyl homologue 4-HO-DIPT for that matter, could be distinguished from the methyl counterpart psilocin in any blind clinical study.
  17. ^abBryson N, Alexander R, Asnis-Alibozek A, Ehlers MD (June 2024)."RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine".ACS Chem Neurosci.15 (12):2386–2395.doi:10.1021/acschemneuro.4c00058.PMC 11191588.PMID 38758589.
  18. ^abcFlanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021)."Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore".ACS Pharmacol Transl Sci.4 (2):488–502.doi:10.1021/acsptsci.0c00063.PMC 8033619.PMID 33860179.
  19. ^abcdKelly TJ, Bonniwell EM, Mu L, Liu X, Hu Y, Friedman V, et al. (April 2024)."Psilocybin analog 4-OH-DiPT enhances fear extinction and GABAergic inhibition of principal neurons in the basolateral amygdala".Neuropsychopharmacology.49 (5):854–863.doi:10.1038/s41386-023-01744-8.PMC 10948882.PMID 37752222.
  20. ^abSimmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016)."In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1"(PDF).J Pharmacol Exp Ther.357 (1):134–144.doi:10.1124/jpet.115.229765.PMID 26791601. Archived fromthe original(PDF) on 9 May 2025.
  21. ^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.
  22. ^"FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".www.finlex.fi. Retrieved8 April 2023.
  23. ^"Svensk författningssamling" [Swedish Code of Statutes](PDF) (in Swedish). Archived fromthe original(PDF) on 29 September 2013. Retrieved25 September 2013.
  24. ^"21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived fromthe original on 27 August 2009. Retrieved17 December 2014.
  25. ^"Statutes & Constitution :View Statutes : Online Sunshine".leg.state.fl.us. Retrieved8 April 2023.
  26. ^"Field Trip Announces First Dosings in Phase I Clinical Study of FT-104" (Press release). 21 July 2022.
  27. ^"An Inside Look into Field Trip's Next-Generation Psychedelic, FT-104". 11 August 2022.
  28. ^"WIPO - Search International and National Patent Collections".patentscope.wipo.int. Retrieved8 April 2023.

External links

[edit]
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