4-HO-EPT

4-HO-EPT
Clinical data
Other names4-OH-EPT; 4-Hydroxy-N-ethyl-N-propyltryptamine; Eprocin
Routes of
administration		Oral
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
IUPAC name
  • 3-{2-[ethyl(propyl)amino]ethyl}-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
SMILES
  • CCCN(CC)CCC1=CNC2=CC=CC(O)=C12
InChI
  • 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]

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]

Chemistry

Analogues

Analogues of 4-HO-EPT include ethylpropyltryptamine (EPT), 5-MeO-EPT, 5-fluoro-EPT, 4-HO-MPT, 4-HO-PiPT, 4-HO-DET, and 4-HO-DPT, among others.

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.

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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