Advances in psychedelics: Structure of synthetic DMT analogue solved

Remember that episode of The Simpsons in which Homer is sent to the South Pacific and eventually finds himself hallucinating after licking a toad?

The substance responsible for Homer’s hallucination (if, of course, The Simpsons wasn’t an animated sitcom) is 5-MeO-DMT, or 5-methoxy-N,N-dimethyltraptamine, a naturally occurring psychedelic substance of the tryptamine class. It’s known for its rapid onset and can induce powerful yet short psychedelic experiences. Preliminary research shows that just a single inhalation can increase “satisfaction with life, mindfulness and psychopathological symptoms”.

In addition to being found in at least one species of toad (Incilius alvarius, the Colorado River toad, seen above), it is present in a wide variety of plant species, including the yopo tree, the seeds from which it was first isolated in 1959. It is a close relative of the more well-known DMT (N,N-dimethyltryptamine), the active ingredient in ayahuasca.

An analogue of 5-MeO-DMT was first synthesized in 2004 by Dr. Alexander Shulgin and his wife, Ann, and the novel psychedelic, 5-MeO-DALT, or N,N-diallyl-5-methoxytryptamine, was the result. (The chemist and pharmacologist claims that over the last 50 years, he’s created more psychedelic drugs than any other person to date.) What separates the two substances is their structure: in 5-MeO-DALT, allyl groups are substituted for the methyl groups in 5-MeO-DMT.

Although there are anecdotal reports of its use as a recreational psychedelic (on the street, it’s often referred to as “Foxtrot” or “Foxy”), there is almost no scientific literature on the pharmacological and physiological effects of its use. But those who’ve dabbled with 5-MeO-DALT have reported effects similar to that of DMT. Early reports from Shuglin describe a rapid onset after taking a relatively small dose, and a trip typically lasting two to four hours.

Earlier this year, a team of scientists from the University of Massachusetts Dartmouth and CaaMTech, a drug company focused on psychedelics based in Issaquah, Washington, successfully synthesized and solved the structure of crystalline 5-MeO-DALT freebase. Their work was recently published in the journal Acta Crystallographica.

“We were interested in studying 5-MeO-DALT because it combines oral activity, a rapid onset time, and a short duration of action,” said Dr. Andrew Chadeayne, lead author of the paper and the CEO at CaaMTech, in a news release. Where 5-MeO-DMT is not orally active and typically inhaled, the appeal of the synthesized analogue is that it can be taken as an oral supplement.

By successfully mapping the crystal structure of “Foxtrot”, scientists will be able to examine the properties and effects of the substance at a molecular level. Although 5-MeO-DALT is a synthetic compound, the idea is that this work will help provide researchers with new insights into the way similar compounds act in the natural world.

“Although some of these compounds have been available on the grey market for over a decade, they have not been rigorously characterized, which is necessary for understanding their potential as pharmaceutical products,” said Chadeayne.

While previous reports on the substance described the freebase as a residue of brown solids suggesting unknown impurities, Chedeayne said the compound has been isolated by his team as “clear, colourless crystals in virtually 100 per cent purity”.