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

Use and effects

4-HO-EPT was not included or mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). [2]

Interactions

Pharmacology

Pharmacodynamics

4-HO-EPT activities
TargetAffinity (Ki, nM)
5-HT1A 163
5-HT1B 1,097
5-HT1D 644
5-HT1E 591
5-HT2A 546 (Ki)
3.2 (EC50 Tooltip half-maximal effective concentration)
100% (Emax Tooltip maximal efficacy)
5-HT2B 62 (Ki)
4.3 (EC50)
89% (Emax)
5-HT2C 1,272 (Ki)
129 (EC50)
89% (Emax)
5-HT5A 1,576
5-HT6 284
5-HT7 438
α2A 2,073
α2B, α2C >10,000
D2 3,010
D3 985
D4, D5 >10,000
H1 406
H2 >10,000
M4 >10,000
σ1 1,400
σ2 1,773
KOR Tooltip κ-Opioid receptor>10,000
NR2B 5,947
SERT Tooltip Serotonin transporter1,257
DAT Tooltip Dopamine transporter>10,000
Notes: The smaller the value, the more avidly the drug interacts with the site. Sources: [3] [4]

4-HO-EPT is a potent full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [3] [4] 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. [3] The drug also shows affinity for other serotonin receptors, such as the serotonin 5-HT1A and 5-HT6 receptors. [4] 4-HO-EPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [3]

Pharmacokinetics

The metabolism of 4-HO-EPT has been studied. [5]

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. [6]

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. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  3. 1 2 3 4 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.
  4. 1 2 3 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.
  5. ↑ 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.
  6. ↑ "Misuse of Drugs Act 1971 (Legislation.gov.uk)".
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