Chemistry:4-HO-EPT

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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]

Use and effects

4-HO-EPT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[2] Subsequently however, an assumed prodrug of 4-HO-EPT, 4-AcO-EPT, has emerged as a novel designer drug, and has been said based on online anecdotal reports to have a dose of 20 to 30 mg orally.[3][4]

Interactions

Pharmacology

Pharmacodynamics

4-HO-EPT activities
Target Affinity (Ki, nM)
5-HT1A 163
5-HT1B 1,097
5-HT1D 644
5-HT1E 591
5-HT2A 546 (Ki)
3.2 (EC50)
100% (Emax)
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 >10,000
NR2B 5,947
SERT 1,257
DAT >10,000
Notes: The smaller the value, the more avidly the drug interacts with the site. Sources: [5][6]

4-HO-EPT is a potent full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[5][6] 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.[5] The drug also shows affinity for other serotonin receptors, such as the serotonin 5-HT1A and 5-HT6 receptors.[6] 4-HO-EPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[5]

Pharmacokinetics

The metabolism of 4-HO-EPT has been studied.[7]

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

Canada

4-HO-EPT is not a controlled substance in Canada as of 2025.[8]

United Kingdom

4-HO-EPT is illegal in the United Kingdom as a result of the Psychoactive Substances Act of 2016.[9]

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. ↑ 1.0 1.1 "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 9 October 2025. 
  2. ↑ 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. 
  3. ↑ "4-OH-EPT AC (4-AcO-EPT)" (in ru). https://aipsin.com/newsubstance/227/. 
  4. ↑ "4-HO-EPT AC (4-AcO-EPT)" (in ru). https://aipsin.com/newsubstance/789/. 
  5. ↑ 5.0 5.1 5.2 5.3 "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. 
  6. ↑ 6.0 6.1 6.2 "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science 6 (4): 567–577. April 2023. doi:10.1021/acsptsci.2c00222. PMID 37082754. 
  7. ↑ "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. December 2024. doi:10.1002/dta.3668. PMID 38459837. 
  8. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  9. ↑ "Misuse of Drugs Act 1971 (Legislation.gov.uk)". http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I#reference-M_F_c7632653-ddad-4420-f307-e3da1e36d30e. 



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