Substituted tryptamines (or simply tryptamines) are a group of organic compounds that are based upon the tryptamine core structure. The class is composed of all the derivative compounds which can be formed by substituting one or more hydrogen atoms in the tryptamine core structure with other substituents. Natural tryptamines are found in most plants and animals, forming from the decarboxylation of the amino acid tryptophan.
The chemical class encompasses a variety of biologically important compounds such as hormones like melatonin and the neurotransmitter serotonin (5-hydroxytryptamine). Many psychoactive tryptamines have been found to occur in nature, although a large number of synthetic variants have been discovered in recent years. Notably, the dimethyltryptamine (DMT) and 5-MeO-DMT have been found to occur in the human body, although their function is unclear. Most of the known substituted tryptamines act as psychedelics (e.g. psilocybin, DMT, ibogaine), although there are some that have entactogenic properties (e.g. aMT, 5-MeO-MiPT). Lysergamides can technically be classified as complex tryptamines, like Ibogaine.
In terms of subjective effects, psychedelic tryptamines are generally regarded as producing a significantly stronger and "deeper" psychedelic effect than the other major class of psychedelics, the substituted phenethylamines (e.g. mescaline or the 2C-x family). Users tend to report greater amounts of ego dissolution, time distortion, conceptual thinking, and transpersonal effects such as unity and interconnectedness with substituted tryptamines. The reason for this is unknown. The subcategory of hallucinogens known as entheogens predominantly consist of tryptamines such as DMT (including ayahuasca), 5-MeO-DMT, and psilocybin.
The tryptamine core structure consists of an indole ring with attached amino group via a two-carbon sidechain (monoamine chain) at R3. Ring unsubstituted tryptamines, or so called "base tryptamines", can have various substitutions at the nitrogen (RN1 and RN2) and at Rα. Ring substituted tryptamines can be further substituted at the R4 and R5 positions on the indole ring.
The psychedelic effects of tryptamines are believed to come from their efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience is the subject of on-going research.
List of substituted tryptamines
This table does not include the following groups of substituted tryptamines:
Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"
|DMT||Dimethyltryptamine, Dmitri, "The Spirit Molecule"||CH3||CH3||H||H||H|
Ring substituted tryptamines
- "Tryptamines". ScienceDirect. Archived from the original on January 11, 2020. Retrieved January 11, 2020.