Solved: The Crystal Structure of the Iodide Salts of DMPT and DMALT

The catalog of compounds for use in psychedelic drug research continues to grow.

-

The psychedelic research company CaaMTech has published in Acta Crystallographic E, the crystal structures of the iodide salts of the quaternary tryptammonium compounds DMPT and DMALT.1 This study adds to the growing body of scientific work on structurally related tryptamine compounds that the company has published since early 2019.2–10

DMPT and DMALT are structural analogs of the quaternary tryptammonium toad secretion bufotenidine and the magic mushroom compound aeruginascin. The latter two compounds have recently entered the psychedelic research arena due to their natural occurrence in living organisms alongside other psychedelic tryptamines, including bufotenin and psilocybin.

Chemically, the compounds are known as N,N-dimethyl-N-propyltryptammonium iodide (DMPT iodide), and N,N-dimethyl-N-allyltryptammonium iodide (DMALT iodide). Each crystal structure comprises one cation of the compound and one iodide anion (Figure 1).

Figure 1: The chemical structures of the salts DMPT iodide and DMALT iodide.1

In the press release, CaaMTech says these are “the world’s first crystal structures of unsubstituted quaternary tryptammonium salts.”

Why Solve the Crystal Structures of these Salts?

Dr. Andrew Chadeayne, CEO of CaaMTech and lead author of the study, explained that “In nature, quaternary tryptammonium compounds are present alongside their better-known tertiary amine analogs, like psilocybin or psilocin; but their pharmacology has not been studied. Adding DMPT and DMALT to CaaMTech’s library of unique tryptamines creates new opportunities for drug development and personalized medicine.”

As part of this study, Dr. Chadeayne and his team also published the synthesis methods for making DMPT iodide and DMALT iodide. This advancement in psychedelic chemistry lets labs synthesize the compounds themselves for use in research studies.

Crystal Structures in the Big Picture of Psychedelic Research

Crystal structures are essential for helping researchers ‘see’ what’s going on at a molecular level. This view gives them a better understanding of how receptors and compounds look and act in nature. Making small changes at the molecular level can translate into significant changes in the effects. Therefore, working with compounds at the molecular level is essential for understanding the mechanisms of how drugs work and how other compounds affect them.

0 Comments
Inline Feedbacks
View all comments
    References
  1. Chadeayne AR, Pham DNK, Golen JA, Manke DR. Quaternary tryptammonium salts: N,N-dimethyl-N-n-propyl­tryptammonium (DMPT) iodide and N-allyl-N,N-di­methyl­tryptammonium (DMALT) iodide. Acta Cryst E. 2020;76(8):1357-1360. doi:10.1107/S2056989020010014
  2. Chadeayne AR, Golen JA, Manke DR. The Crystal Structure of 4-AcO-DMT Fumarate. Published online 2019. https://psychedelicreview.com/wp-content/uploads/2019/03/The-Crystal-Structure-of-4-AcO-DMT-Fumarate.pdf
  3. Chadeayne AR, Golen JA, Manke DR. Bis(4-acetoxy-N,N -dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug. Acta Crystallographica Section E Crystallographic Communications. 2019;75(6):900-902. doi:10.1107/S2056989019007370
  4. Chadeayne AR, Pham DNK, Golen JA, Manke DR. The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin. Acta Crystallographica Section E Crystallographic Communications. 2019;75(9):1316-1320. doi:10.1107/S2056989019011253
  5. 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
  6. Chadeayne AR, Golen JA, Manke DR. N-Methyl-N-propyltryptamine (MPT). IUCrData. 2019;4(7):x190962. doi:10.1107/S2414314619009623
  7. Chadeayne AR, Pham DNK, Golen JA, Manke DR. Bis(4-hy­droxy-N-isopropyl-N-methyl­trypt­ammo­nium) fumarate: a new crystalline form of miprocin. Acta Cryst E. 2020;76(4):514-517. doi:10.1107/S2056989020002923
  8. Chadeayne AR, Pham DNK, Golen JA, Manke DR. Norpsilocin: freebase and fumarate salt. Acta Crystallographica Section E Crystallographic Communications. 2020;76(4):589-593. doi:10.1107/S2056989020004077
  9. Chadeayne AR, Pham DNK, Golen JA, Manke DR. 5-MeO-DALT: the freebase of N,N-diallyl-5-methoxytryptamine. IUCrData. 2020;5(4):x200498. doi:10.1107/S2414314620004988
  10. 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