ethylpropyltryptamine, N-ethyl-N-propyltryptamine, N-Ethyl-N-[2-(1H-indol-3-yl)ethyl]-1-propanamine

EPT is an unsubstituted tryptamine compound. Structurally, it is the N-ethyl analog of DPT (N,N-dipropyltryptamine) and the N-propyl analog of DET (N,N-diethyltryptamine). There is no entry for EPT in Alexander and Ann Shulgin’s book TiHKAL.1

The Chemistry of EPT

Until recently, there was only scattered mention of EPT in the scientific literature.2–4 In 2020, Chadeayne et al. published the crystal structure of the fumarate salts of EPT and another DMT analog, MALT (N-methyl-N-allyltryptamine).5 The authors explain that their reasoning for studying these two compounds centers on understanding the structure-activity relationships between similar compounds, as well as their “cooperative biological activity.” They added that “The preparation of pure crystalline forms of these compounds is essential to conducting meaningful biological studies and ultimately developing drug products.”

The Pharmacology of EPT

Although nothing is known about the pharmacology of EPT, based solely on its chemical structure, it may be an agonist at the serotonin 5-HT2A receptor.

The Applications and Potential of EPT

Studying the applications and potential for EPT is a wide-open area for research.

  1. Shulgin A, Shulgin A. TIHKAL: The Continuation. First Edition, Eighth Printing. Transform Press Berkeley; 2017.
  2. Brandt SD, Freeman S, Fleet IA, Alder JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Analyst. 2005;130(9):1258-1262. doi:10.1039/B504001A
  3. Brandt SD, Freeman S, Fleet IA, McGagh P, Alder JF. Analytical chemistry of synthetic routes to psychoactive tryptamines : Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. The Analyst. 2005;130(3):330. doi:10.1039/b413014f
  4. Ascic E, Hansen CL, Quement STL, Nielsen TE. Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet–Spengler theme. Chem Commun. 2012;48(27):3345-3347. doi:10.1039/C2CC17704H
  5. Chadeayne AR, Pham DNK, Golen JA, Manke DR. DMT analogues: N-ethyl-N-propyl­tryptamine and N-allyl-N-methytryptamine as their hydro­fumarate salts. Acta Cryst E. 2020;76(8):1201-1205. doi:10.1107/S2056989020008683