4-HO-EPT

Last updated

4-HO-EPT
4-Hydroxy-N-ethyl-N-propyltryptamine.svg
4-HO-EPT 3D BS.png
Clinical data
Other names4-OH-EPT; 4-Hydroxy-N-ethyl-N-propyltryptamine; Eprocin
Routes of
administration 		Oral
Drug class Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-{2-[ethyl(propyl)amino]ethyl}-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H22N2O
Molar mass 246.354 g·mol−1
3D model (JSmol)
  • CCCN(CC)CCC1=CNC2=CC=CC(O)=C12
  • InChI=1S/C15H22N2O/c1-3-9-17(4-2)10-8-12-11-16-13-6-5-7-14(18)15(12)13/h5-7,11,16,18H,3-4,8-10H2,1-2H3
  • Key:JQELEPKHBXEAHR-UHFFFAOYSA-N

4-HO-EPT, also known as 4-hydroxy-N-ethyl-N-propyltryptamine or as eprocin, is a psychedelic drug of the tryptamine family, which is structurally related to psilocin (4-HO-DMT). [1] It was encountered as a novel designer drug in Japan by 2021. [1]

Contents

Interactions

Pharmacology

Pharmacodynamics

4-HO-EPT is a potent full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [2] [3] It has one to two orders of magnitude greater potency as a serotonin 5-HT2A and 5-HT2B receptor agonist than as a serotonin 5-HT2C receptor agonist. [2] The drug also shows affinity for other serotonin receptors, such as the serotonin 5-HT1A and 5-HT6 receptors. [3] 4-HO-EPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2]

Pharmacokinetics

The metabolism of 4-HO-EPT has been studied. [4]

Society and culture

United Kingdom

4-HO-EPT is illegal in the United Kingdom as a result of the Psychoactive Substances Act of 2016. [5]

United States

4-HO-EPT may be considered an analogue of psilocin, which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption would be illegal under the Federal Analogue Act.[ citation needed ]

See also

References

  1. 1 2 Tanaka R, Kawamura M, Hakamatsuka T, Kikura-Hanajiri R (2021). "Identification of six tryptamine derivatives as designer drugs in illegal products". Forensic Toxicology. 39 (1): 248–258. doi:10.1007/s11419-020-00556-5. ISSN   1860-8965 . Retrieved 9 October 2025.
  2. 1 2 3 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.
  3. 1 2 Glatfelter 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 Pharmacology & Translational Science. 6 (4): 567–577. doi:10.1021/acsptsci.2c00222. PMC   10111620 . PMID   37082754.
  4. ↑ Bergh MS, Bogen IL, Grafinger KE, Huestis MA, Øiestad ÅM (December 2024). "Metabolite markers for three synthetic tryptamines N-ethyl-N-propyltryptamine, 4-hydroxy-N-ethyl-N-propyltryptamine, and 5-methoxy-N-ethyl-N-propyltryptamine". Drug Testing and Analysis. 16 (12): 1544–1557. doi:10.1002/dta.3668. PMC   11635065 . PMID   38459837.
  5. ↑ "Misuse of Drugs Act 1971 (Legislation.gov.uk)".
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