4-HO-EPT

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]

4-HO-EPT

Clinical data
Other names	4-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
IUPAC name 3-{2-[ethyl(propyl)amino]ethyl}-1H-indol-4-ol
CAS Number	2595431-59-5 N[PubChem]
PubChem CID	138454310
ChemSpider	129433801
UNII	Y3J8M5UX6G
CompTox Dashboard (EPA)	DTXSID801336292
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image
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

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

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

Pharmacology

Pharmacodynamics

4-HO-EPT is a potent full agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[3][4] It has one to two orders of magnitude greater potency as a serotonin 5-HT_2A and 5-HT_2B receptor agonist than as a serotonin 5-HT_2C receptor agonist.^[3] The drug also shows affinity for other serotonin receptors, such as the serotonin 5-HT_1A 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

Legal status

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

• Substituted tryptamine