Chemistry:4-HO-DPT

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4-HO-DPT, also known as 4-hydroxy-N,N-dipropyltryptamine or as deprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT).[1][2] It is taken orally.[1][2]

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[3] It produces psychedelic-like effects in animals.[3] The drug is closely structurally related to other psychedelic tryptamines such as dipropyltryptamine (DPT), 5-MeO-DPT, and psilocin (4-HO-DMT), among others.[1]

4-HO-DPT was first described in the scientific literature by David Repke and colleagues in 1977.[4][5][3][6] It was encountered as a novel designer drug in 2012.[7][8][9][3] A presumed prodrug, 4-AcO-DPT, is also known, and has likewise been encountered as a designer drug.[3]

Use and effects

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, the dose and duration of 4-HO-DPT are unknown.[1] At a dose of 20 mg orally, there were possibly threshold effects and nothing more.[1][10] Per Shulgin, there were not enough observations to know what dose would result in activity or what the effects would be.[1] However, the occurrence of threshold effects at a dose of 20 mg was suggestive that "something is nearby".[1]

Subsequently, 4-HO-DPT and its presumed prodrug 4-AcO-DPT have been encountered as novel designer drugs, substantiating the notion that more significant effects do indeed occur with 4-HO-DPT at sufficiently high doses.[7][8][9][3] Based on user reports, 4-HO-DPT has an onset of 15 to 45 minutes, a duration of 5 to 8 hours, and produces hallucinogenic effects including psychedelic visuals among others.[2]

Interactions

Pharmacology

Pharmacodynamics

4-HO-DPT activities
Target Affinity (Ki, nM)
5-HT2A 1.6 (EC50)
103% (Emax)
5-HT2B 2.2 (EC50)
94% (Emax)
5-HT2C 212 (EC50)
83% (Emax)
Notes: The smaller the value, the more avidly the drug interacts with the site. Sources: [3]

4-HO-DPT acts as a high-efficacy partial agonist to full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3] It has more than two orders of magnitude greater potency as an agonist of the serotonin 5-HT2A and 5-HT2B receptors than as an agonist of the serotonin 5-HT2C receptor.[3] Hence, it shows considerable selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[3]

Compared to psilocin (4-HO-DMT), 4-HO-DPT has about the same potency and efficacy as a serotonin 5-HT2A receptor agonist, has about the same potency but is much more efficacious as a serotonin 5-HT2B receptor agonist (Emax = 39% vs. 94%, respectively), and has about the same efficacy but approximately 10-fold lower potency as a serotonin 5-HT2C receptor agonist.[3]

4-HO-DPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3] Its potency for inducing the head-twitch response in mice is about 4- or 5-fold lower than that of psilocin.[3]

Pharmacokinetics

The metabolism of 4-HO-DPT has not been studied.[11][12]

Chemistry

4-HO-DPT, also known as 4-hydroxy-N,N-dipropyltryptamine, is a substituted tryptamine and 4-hydroxytryptamine derivative related to psilocin (4-HO-DMT).[1]

Synthesis

The chemical synthesis of 4-HO-DPT has been described.[1][4] It is said to be difficult to make.[1]

Crystal structure

In 2019, Chadeayne and colleagues solved the crystal structure of the fumarate salt of 4-HO-DPT.[13] The authors describe the structure as follows: "The asymmetric unit contains one 4-HO-DPT cation, protonated at the dipropylamine N atom. There are also two independent water molecules, and half of a fumarate ion present."[13]

Analogues

Analogues of 4-HO-DPT include dipropyltryptamine (DPT), 5-MeO-DPT, psilocin (4-HO-DMT), 4-HO-DET, 4-HO-DiPT, 4-HO-MPT, 4-HO-EPT, 4-HO-PiPT, and 5-HO-DPT, among others.[1] 4-AcO-DPT is a presumed prodrug of 4-HO-DPT.[3]

History

4-HO-DPT was first described in the scientific literature by David Repke and colleagues in 1977.[4][5][3][6] Subsequently, it was described in further detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe in 2012.[7][8][9][3]

Society and culture

Canada

4-HO-DPT is not a controlled substance in Canada as of 2025.[14]

Germany

4-HO-DPT is controlled in Germany under the Neue-psychoaktive-Stoffe-Gesetz (NpSG; New Psychoactive Substances Act) as of July 2019.[15][16][17][18]

Sweden

4-HO-DPT is classified as a "dangerous substance" Sweden, which means that it cannot be legally bought or sold without a special permit, though it is still not yet an illegal drug.[19]

Switzerland

4-HO-DPT is a controlled substance in Switzerland as of 2020.[20]

United Kingdom

4-HO-DPT is a Class A drug in the United Kingdom, as a result of the tryptamine catch-all clause.[21]

United States

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  "4-HO-DPT". https://erowid.org/library/books_online/tihkal/tihkal20.shtml. 
  2. ↑ 2.0 2.1 2.2 "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences 21 (23): 9279. December 2020. doi:10.3390/ijms21239279. PMID 33291798. "4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].". 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science 4 (2): 533–542. April 2021. doi:10.1021/acsptsci.0c00176. PMID 33860183. "Repke synthesized several other psilocin homologues, including 4-hydroxy-N-methyl-N-ethyltryptamine (4-HO-MET), 4-hydroxy-N-methyl-N-isopropyltryptamine (4-HO-MIPT), 4-hydroxy-N,N-dipropyltryptamine (4-HO-DPT), and 4-hydroxy-N,N-diisopropyltryptamine (4-HO-DIPT).63,64". 
  4. ↑ 4.0 4.1 4.2 "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. 1977. doi:10.1002/jhet.5570140113. ISSN 0022-152X. 
  5. ↑ 5.0 5.1 "Scientists Solve the Crystal Structure of the Psilocbyin Derviative 4-HO-DPT". 2 January 2020. https://psychedelicreview.com/scientists-solve-the-crystal-structure-of-the-psilocbyin-derviative-4-ho-dpt/. 
  6. ↑ 6.0 6.1 "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. 1977. doi:10.1002/jhet.5570140113. ISSN 0022-152X. 
  7. ↑ 7.0 7.1 7.2 "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)". 2 July 2024. https://www.euda.europa.eu/publications/implementation-reports/2012_en. 
  8. ↑ 8.0 8.1 8.2 "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Human Psychopharmacology 35 (1). January 2020. doi:10.1002/hup.2719. PMID 31909513. 
  9. ↑ 9.0 9.1 9.2 "Identification of six tryptamine derivatives as designer drugs in illegal products". Forensic Toxicology 39 (1): 248–258. 2021. doi:10.1007/s11419-020-00556-5. ISSN 1860-8965. http://link.springer.com/10.1007/s11419-020-00556-5. Retrieved 16 October 2025. 
  10. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. 
  11. ↑ "4-Hydroxy-N,N-methylpropyltryptamine (4-OH-MPT) in vitro human metabolism". Toxicologie Analytique et Clinique 34 (3): S96. 2022. doi:10.1016/j.toxac.2022.06.147. Bibcode: 2022ToxAC..34Q..96B. 
  12. ↑ "Biomarkers of 4-hydroxy-N,N-methylpropyltryptamine (4-OH-MPT) intake identified from human hepatocyte incubations". Expert Opinion on Drug Metabolism & Toxicology 18 (12): 831–840. December 2022. doi:10.1080/17425255.2022.2166826. PMID 36609205. 
  13. ↑ 13.0 13.1 "Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate tetrahydrate". IUCrData 4 (11). 2019-11-28. doi:10.1107/S241431461901469X. ISSN 2414-3146. Bibcode: 2019IUCrD...491469C. http://scripts.iucr.org/cgi-bin/paper?S241431461901469X. 
  14. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  15. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (in de). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27. Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf. 
  16. ↑ "§ 4 NpSG" (in de). Bundesamt für Justiz [Federal Office of Justice]. https://www.gesetze-im-internet.de/npsg/__4.html. 
  17. ↑ "§ 3 NpSG" (in de). Bundesamt für Justiz [Federal Office of Justice]. https://www.gesetze-im-internet.de/npsg/__3.html. 
  18. ↑ "Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (in de). Deutscher Bundestag. May 30, 2016. pp. 20. http://dip21.bundestag.de/dip21/btd/18/085/1808579.pdf. 
  19. ↑ "Tio nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten [Public Health Agency of Sweden]. February 14, 2018. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2018/februari/tio-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/. 
  20. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in de). Bundeskanzlei [Federal Chancellery of Switzerland]. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  21. ↑ "Schedule 2: Part I: Class A Drugs". Misuse of Drugs Act 1971. UK Government. http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I. 



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