Alkaloids Derived from Tryptophan

Alkaloids Derived from Tryptophan
L-Tryptophan is a neutral heterocyclic amino acid containing essentially an indole ring system. It has been observed that it serves as a precursor for a wide spectrum of indole alkaloids. The various alkaloids derived from tryptophan are conveniently classified into the following categories, namely: (i) Simple Indole Alkaloids; (ii) Simple b-Carboline Alkaloids; (iii) Terpenoid Indole Alkaloids; (iv) Quinoline Alkaloids; (v) Pyrroloindole Alkaloids; (vi) Ergot Alkaloids.
Teonancatl and psilocybin (Simple Indole Alkaloids)
Mushrooms classified to the genus Psilocybe are distributed in the central parts of North America, Central America, the northern part of South America, and Europe. The use of these mushrooms as hallucinogens appears to be limited to Mexico. In these regions, the mushrooms are known as “teonanacatl,” and are used in religious ceremonies.
As hallucinogenic substances of Psilocybe origin, psilocybin was isolated as the main constituent, and psilocin was obtained as a minor constituent.
Psilocybin is a phosphoric acid ester of psilocin, and both of these alkaloids are 4-substituted tryptamine derivatives.