An indole is a six-membered benzene ring fused to a five-membered ring that contains one nitrogen. On its own it is C8H7N (PubChem, indole). The same ring system sits in the amino acid tryptophan, which is why so many of the body’s and the mushroom’s signalling molecules share it (PubChem, tryptophan).
Chemists number the ring positions, and that numbering is how the relatives are told apart. DMT’s side chain hangs off position 3 (PubChem, DMT). Psilocin carries a hydroxyl at position 4, and Canada’s Controlled Drugs and Substances Act describes it as a 4-hydroxyindole and psilocybin as a 4-phosphoryloxyindole (CDSA). Serotonin has its hydroxyl at position 5 (PubChem, serotonin).
The term also sorts drugs into families. A 2011 review groups LSD, psilocybin, psilocin and DMT as indoleamines, separate from phenylalkylamines such as mescaline (Halberstadt and Geyer, 2011). A 2018 review calls DMT “the archetype for all indole-containing serotonergic psychedelics” (Cameron and Olson, 2018). Sharing a ring does not mean sharing effects or safety.
Sources
- PubChem: indole (CID 798)
- Halberstadt and Geyer, 2011, Neuropharmacology
- Cameron and Olson, 2018, ACS Chemical Neuroscience: DMT review
- Controlled Drugs and Substances Act, Schedule III (Justice Laws)
Last checked .