Psilocybin

October 02, 2017
My psychedelic properties may lead to new drugs.
What molecule am I?

Psilocybin is a psychoactive prodrug that is found primarily in so-called “magic” mushrooms of the Psilocybe genus. In the body, it converts to psilocin, which has psychedelic properties similar to those of LSD mescaline.

In 1958, Swiss chemist Albert Hofmann and co-workers isolated psilocybin and smaller amounts of psilocin from the mushroom P. mexicana. (More than 20 years earlier, Hofmann began to study LSD, including ingesting it himself. Because of this work, he became known as the “father of LSD”.)

Hofmann and Franz Troxler reported the synthesis of psilocybin in a 1963 patent. Forty years later, Osamu Shirota and colleagues at the National Institute of Health Sciences (Tokyo) developed an efficient large-scale synthesis.

But until recently, the biosynthesis of psilocybin was a mystery. Because the hallucinogen is of interest to pharmaceutical researchers as a basis for useful drugs, Dirk Hoffmeister and colleagues at Friedrich Schiller University (Jena, Germany) delved into the biosynthesis and identified four enzymes that mushrooms use to make the compound. They then sequenced the genomes of two mushroom species to find the genes that cause the fungi to produce psilocybin.

Finally, the researchers used three of the enzymes to synthesize psilocybin from 4-hydroxy-L-tryptophan in one pot. One natural-products researcher commented, “This work clearly sets the stage for bioengineered psilocybin production and/or for analogues that may serve as compelling alternatives to existing synthetic strategies.”

Psilocybin fast facts

CAS Reg. No. 520-52-5
Molar mass 284.25 g/mol
Formula C12H17N2O4P
Appearance White crystals
Melting point 224 ºC
Water solubility 2 g/L (est.)
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