4-HO-DPT

4-Hydroxy-N,N-dipropyltryptamine5

4-HO-DPT is a synthetic compound that is not known to occur in nature. However, in 1990, mushroom researcher Jochen Gartz patented a method for adding DPT to mushroom growth medium which resulted in the mushroom fruiting bodies containing 4-HO-DPT.1

The Chemistry of 4-HO-DPT

4-HO-DPT is a psilocybin derivative and a structural homolog of psilocin. Repke et al. were first to report the synthesis of 4-HO-DPT  in 1977.2

In October 2019, researchers solved the crystal structure of 4-HO-DPT.3 They describe the structure as “…a singly protonated DPT cation, one half of a fumarate dianion (completed by a crystallographic centre of symmetry) and two water molecules of crystallization in the asymmetric unit.”

The Pharmacology of 4-HO-DPT

Little is known about the pharmacology of 4-HO-DPT. Alexander and Ann Shulgin documented their synthesis of 4-HO-DPT (#20 in TiHKAL), and describe a 20 mg oral dose as, “Possible threshold, nothing more.” 4

The new crystal structure of 4-HO-DPT discussed earlier opens to door to understanding its physical properties. This discovery also allows scientists to test its activity at biological receptors.

The Applications and Potential of 4-HO-DPT

Prior to the current work to solve its crystal structure, virtually nothing was known about 4-HO-DPT. Characterizing this fundamental structure is essential for all downstream research, such as structure-activity relationships that define the biological and clinical properties of the molecule. Understanding these relationships is key to developing effective drugs.

    References
  1. Gartz J. Process for obtaining tryptophane derivatives by culturing higher mushrooms. May 1990. https://patents.google.com/patent/DD278600A1/en?oq=DD278600A1.
  2. Repke DB, Ferguson WJ, Bates DK. Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols. Journal of Heterocyclic Chemistry. 1977;14(1):71-74. doi:10.1002/jhet.5570140113
  3. Chadeayne AR, Pham DNK, Golen JA, Manke DR. Bis(4-hy­droxy-N,N-di-n-propyl­tryptammonium) fumarate tetrahydrate. IUCrData. 2019;4(11):x191469. doi:10.1107/S241431461901469X
  4. Shulgin A, Shulgin A. TIHKAL: The Continuation. Transform Press Berkeley; 1997.
  5. PubChem. Dipropyl-4-hydroxytryptamine. https://pubchem.ncbi.nlm.nih.gov/compound/21854223.