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4-HO-DiPT

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4-HO-DiPT
Clinical data
Routes of
administration		Oral
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled
Pharmacokinetic data
Duration of action2–3 hours[1]
Identifiers
  • 3-[2-(diisopropylamino)ethyl]-1H-indol-4-ol
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.214.853 Edit 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
 ☒NcheckY (what is this?)  (verify)

4-HO-DiPT, also known as 4-hydroxy-N,N-diisopropyltryptamine or as iprocin, is a synthetic psychedelic drug of the tryptamine family. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT.

Dosage

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In TiHKAL, Alexander Shulgin reported that 4-HO-DiPT had a dose range of 15 to 20 mg orally and a duration of 2 to 3 hours.[1][2] However, a wider recreational dose range of 3 to 30 mg or more orally has also been reported.[3] The drug is active at around 3 mg and above, and its effects last for 2 to 3 hours.[4] Higher doses, such as those above 30 mg, can increase the duration of its effects significantly.

Effects

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The effects of 4-HO-DiPT are broadly comparable to those of other serotonergic psychedelics such as LSD and psilocin, but they are distinguished by their relative brevity. Shulgin "doubt[s] that there is another psychedelic drug, anywhere, that can match this one for speed, for intensity, for brevity, and sensitivity to dose, at least one that is active orally." An idiosyncratic effect of the drug, also noted by Shulgin, is its tendency to induce tremors.[1][5][6]

Some users have reported a minor audio distortion with lower dosages. Higher dosages increase the polarity of the distortion. It is defined as being slightly lower in pitch and creating several different effects, such as pitch bend, volume distortion, and rate distortion. As with most DiPT psychedelics, music can become more dissonant and less harmonious. Users have also reported a visual distortion widely comparable to the hallucinogen LSD.

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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4-HO-DiPT activities
Target Affinity (Ki, nM)
5-HT1A 5,700–>10,000
3,900 (EC50Tooltip half-maximal effective concentration)
36% (EmaxTooltip maximal efficacy)
5-HT1B >10,000
5-HT1D 1,860
5-HT1E >10,000
5-HT1F ND
5-HT2A 120–922 (Ki)
6.82–334 (EC50)
74–106% (Emax)
5-HT2B 85 (Ki)
5.12–460 (EC50)
55–110% (Emax)
5-HT2C 2.8–>10,000 (Ki)
1,080–6,442 (EC50)
72–104% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A >10,000
5-HT6 >10,000
5-HT7 >10,000
α1A >12,000
α1B, α1D ND
α2A 15,000
α2B, α2C >10,000
β1–β3 ND
D1–D3 >25,000
D4, D5 >10,000
H1 9,800–>10,000
H2 >10,000
H3, H4 ND
M1–M3 ND
M4 1,725
M5 ND
I1 ND
σ1 816–1,063
σ2 2,215
TAAR1Tooltip Trace amine-associated receptor 1 >15,000 (Ki) (mouse)
>15,000 (Ki) (rat)
ND (EC50) (human)
SERTTooltip Serotonin transporter 419–1,800 (Ki)
163–2,400 (IC50Tooltip half-maximal inhibitory concentration)
IA (EC50)
NETTooltip Norepinephrine transporter 11,000 (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. Refs: [7][8][9][10][11][12][13]

4-HO-DiPT acts as an agonist of serotonin receptors, including the serotonin 5-HT2A and 5-HT2B receptors.[7][8][9][10][12] It may also act as a serotonin reuptake inhibitor, although its potency is variable across studies.[7][8][9][10] The drug appears to activate the serotonin 5-HT2C receptor with low potency and much lower than for the serotonin 5-HT2A receptor.[7][8][9][10] Unlike many other tryptamines, 4-HO-DiPT is not a ligand of the rodent trace amine-associated receptor 1 (TAAR1).[7][13]

Pharmacokinetics

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The pharmacokinetics of 4-HO-DiPT have been studied.[11]

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4-HO-DiPT Powder
4-HO-DiPT powder.

Finland

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Scheduled in government decree on psychoactive substances banned from the consumer market.[14]

Germany

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

Sweden

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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.[15]

United States

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4-HO-DiPT is not scheduled at the federal level in the United States,[16] 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.

Florida

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"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.[17]

Research

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FT-104 [https://pubchem.ncbi.nlm.nih.gov/compound/162510634

FT-104 (O-glutaryl-4-HO-DiPT), a prodrug to 4-HO-DiPT, has entered double blind, randomized, placebo controlled, phase 1 clinical trials in healthy volunteers at the Royal Adelaide Hospital in Australia for the treatment of postpartum depression and treatment-resistant depression. [18][19][20]

References

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  1. ^ a b c Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ Halberstadt 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. [...]
  3. ^ 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.
  4. ^ "Erowid 4-HO-DiPT Vault : Dosage". www.erowid.org. Retrieved 8 April 2023.
  5. ^ "4-Hydroxy-DIPT". Erowid.
  6. ^ "Tihkal 4-HO-DIPT entry".
  7. ^ a b c d e Rickli 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.
  8. ^ a b c d Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt 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.
  9. ^ a b c d Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter" (PDF). J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  10. ^ a b c d Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice" (PDF). ACS Pharmacol Transl Sci. 6 (4): 567–577. doi:10.1021/acsptsci.2c00222. PMC 10111620. PMID 37082754.
  11. ^ a b 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.
  12. ^ a b Flanagan 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" (PDF). ACS Pharmacol Transl Sci. 4 (2): 488–502. doi:10.1021/acsptsci.0c00063. PMC 8033619. PMID 33860179.
  13. ^ a b Simmler 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". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601.
  14. ^ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014". www.finlex.fi. Retrieved 8 April 2023.
  15. ^ "Svensk författningssamling" [Swedish Code of Statutes] (PDF) (in Swedish). Archived from the original (PDF) on 29 September 2013. Retrieved 25 September 2013.
  16. ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 27 August 2009. Retrieved 17 December 2014.
  17. ^ "Statutes & Constitution :View Statutes : Online Sunshine". leg.state.fl.us. Retrieved 8 April 2023.
  18. ^ "Field Trip Announces First Dosings in Phase I Clinical Study of FT-104" (Press release). 21 July 2022.
  19. ^ "An Inside Look into Field Trip's Next-Generation Psychedelic, FT-104". 11 August 2022.
  20. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int. Retrieved 8 April 2023.
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