Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for their psychoactive effects, which tend to be psychedelic in nature. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. ayahuasca). Many synthetic tryptamines have also been made, including the migrainedrugsumatriptan and its relatives. The table below lists some commonly encountered substituted tryptamines.
The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: ergoline alkaloids, LSD, ibogaine and yohimbine.
A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.
However, the effects produced by consuming preparations of dried or brewed mushrooms are far less predictable and largely depend on the particular mushrooms used and the age and preservation of the extract.
There are many species of "magic" mushrooms that contain varying amounts of these tryptamines, as well as uncertain amounts of other chemicals.
As a consequence, the hallucinogenic activity, as well as the extent of toxicity produced by various plant samples, are often unknown.
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