Notice: file_put_contents(): Write of 533317 bytes failed with errno=28 No space left on device in /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php on line 36

Warning: http_response_code(): Cannot set response code - headers already sent (output started at /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php:36) in /opt/frankenphp/design.onmedianet.com/app/src/Models/Response.php on line 17

Warning: Cannot modify header information - headers already sent by (output started at /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php:36) in /opt/frankenphp/design.onmedianet.com/app/src/Models/Response.php on line 20
4-HO-DPT - Wikipedia Jump to content

4-HO-DPT

From Wikipedia, the free encyclopedia

4-HO-DPT
Clinical data
Other names4-OH-DPT; 4-Hydroxy-N,N-dipropyltryptamine; Deprocin
Routes of
administration		Oral[1]
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
Identifiers
  • 3-[2-(dipropylamino)ethyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H24N2O
Molar mass260.381 g·mol−1
3D model (JSmol)
  • CCCN(CCC)CCc2c[nH]c1cccc(O)c12
  • InChI=1S/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-12-17-14-6-5-7-15(19)16(13)14/h5-7,12,17,19H,3-4,8-11H2,1-2H3 checkY
  • Key:MZLRMPTVOVJXLW-UHFFFAOYSA-N checkY
  (verify)

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.[1] It is the 4-hydroxyl analogue of dipropyltryptamine (DPT).[1] The drug is taken orally.[1]

It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[2] It produces psychedelic-like effects in animals.[2]

4-HO-DPT was first described in the scientific literature by David Repke and colleagues in 1977.[3][4][2][5] It was encountered as a novel designer drug in Europe by 2013.[6]

Use and effects

[edit]

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 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] Per Shulgin, there are not enough observations to know what dose will result in activity or what the effects will be.[1] However, the occurrence of threshold effects at a dose of 20 mg is suggestive that "something is nearby".[1]

Interactions

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

Pharmacology

[edit]

Pharmacodynamics

[edit]

4-HO-DPT acts as a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2] It has around two orders of magnitude greater potency or more as an agonist of the serotonin 5-HT2A and 5-HT2B receptors than as an agonist of the serotonin 5-HT2C receptor.[2] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2]

Chemistry

[edit]

Synthesis

[edit]

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

Crystal structure

[edit]

In 2019, Chadeayne and colleagues solved the crystal structure of the fumarate salt of 4-HO-DPT.[7] 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."

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. https://erowid.org/library/books_online/tihkal/tihkal20.shtml
  2. ^ a b c d e f Klein 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 Pharmacology & Translational Science. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. 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
  3. ^ Repke 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.
  4. ^ Bauer BE (2 January 2020). "Scientists Solve the Crystal Structure of the Psilocbyin Derviative 4-HO-DPT". Psychedelic Science Review. Retrieved 8 October 2025.
  5. ^ Ferguson WJ, Bates DK, Repke DB (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.
  6. ^ "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)". www.euda.europa.eu. 2 July 2024. Retrieved 9 October 2025.
  7. ^ Chadeayne AR, Pham DN, Golen JA, Manke DR (2019-11-28). "Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate tetrahydrate". IUCrData. 4 (11) x191469. Bibcode:2019IUCrD...491469C. doi:10.1107/S241431461901469X. ISSN 2414-3146.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=4-HO-DPT&oldid=1316044014"