Norpsilocin – A Newly Discovered Psilocybin Derivative

Magic mushrooms may be synthesizing this newly-discovered compound from baeocystin.

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When it comes to what causes the psychedelic effects of psychedelic mushrooms (aka psilocybin mushrooms or magic mushrooms), the focus is usually on psilocybin. However, this is an incorrect assumption and causes confusion when trying to discuss the chemistry of the mushroom and understanding the physiological effects it has.

The human body metabolizes psilocybin to psilocin which is currently regarded by scientists to be the active psychoactive component.1 Further, there are other derivatives of psilocybin such as baeocystin, norbaeocystin, and aeruginascin whose chemistry, effects, and interactions are virtually unknown and receive little attention in the scientific arena.

The Discovery of Norpsilocin

Recently, another psilocybin derivative called norpsilocin was isolated from Psilocybe cubensis by researchers at the Hans-Knöll Institute in Jena, Germany.2 Using 1D and 2D NMR spectroscopy, the researchers defined the structure of norpsilocin as shown in Figure 1. This can be compared with the chemical structure of psilocin shown in Figure 2.

Figure 1: The chemical structure of norpsilocin.

Figure 2: The chemical structure of psilocin.

In this work, the researchers also developed a new extraction method that prevents dephosphorylation of the mushroom chemicals so the true metabolic profile of Psilocybe can be determined. From this, the researchers call norpsilocin a “natural product” of the Psilocybe mushroom and go on to say,

It likely represents the actual psychotropic agent liberated from its 4-phosphate ester derivative, the known natural product baeocystin.

In other words, the researchers propose that norpsilocin is made from baeocystin when it is dephosphorylated in the body. The structure of baeocystin is shown in Figure 3.

Figure 3: The chemical structure of baeocystin.

It is not known if norpsilocin has any psychotropic activity or how it may work in conjunction with other magic mushroom compounds.

Magic Mushrooms Contain a Mixture of Compounds

This important research work adds to the understanding of the complex chemistry and variability of the natural compounds in psilocybin mushrooms. Norpsilocin is just the latest compound to be identified. There may be more, perhaps many more.

Additional research will lead to a better understanding of the molecules in magic mushrooms and how they interact with receptors and each other (aka the entourage effect). Studying and understanding all of the compounds found in magic mushrooms and how they work together may result in formulations that have different properties (and therefore different effects) than pure psilocybin or magic mushrooms.

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