What are Psilocybin Derivatives?

What are Psilocybin Derivatives?

Magic Mushrooms contain many molecules (aside from psilocybin). For the most part, these psilocybin derivatives can be described as a group (aka genus) of tryptamine compounds. In that context, the term “psilocybin derivatives” refers to a collection of molecules sharing a common chemical structure with psilocybin.  Psilocybin derivatives share a tryptamine core with a pendant ethylamino group, as illustrated by the General structure in Figure 1.  The groups defined with “R” groups can be varied as needed to define specific molecules falling within the genus.

 

Figure 1: General structure defining a set of psilocybin derivatives.

For example, the most famous psilocybin derivative (psilocybin itself) can be described by the making the following selections:
R7 = R6 = R4 = R8 =R3 = R9 = H
R5 = Phosphate ester (i.e., OPO(OH)2)
R1 = R2 = CH3

Applying those selections would provide the molecule psilocybin:

Chemical structure of psilocybin. Psilocybin is one (of many possible) psilocybin derivatives.

Other examples of psilocybin derivatives include the following:

Why Are Psilocybin Derivatives Important?

Psilocybin derivatives are important because “minor” chemical differences can make a big difference in the body. For example, consider the difference between amphetamine and methamphetamine.  The difference is one methyl group on the amine.

Amphetamine and Methamphetamine differ by ONE methyl group. This “minor” structural difference results in a major difference in the properties of the drug.

 

 

 

 

 

 

 

Now, consider the structural difference between psilocybin and baeocystin.

Psilocybin differs from baeocystin by one methyl group. For the non-chemist, each of the straight lines coming off of the “N” represents a CH3 group, which is called a methyl group. (For the hardcore chemists, we apologize for the inconsistency in showing the quaternary ammonium form on the left but not the right).

The above illustrated “minor” structural difference could potentially have dramatic effects at a cellular level.

Path Forward – Study these Molecules

To be clear, we are not suggesting that baeocystin and psilocybin have pharmacological differences akin to those known for amphetamine and methamphetamine.  Our real point is that we have absolutely no idea how baeocystin’s pharmacology differs from psilocybin’s pharmacology.  The same holds true for the other psilocybin derivatives, like aeruginascin.

Not all “magic mushrooms” are created equal.  There are over 200 known species of psychoactive mushrooms.  Anecdotal evidence suggests that the subjective effects of these mushrooms differ considerably.  Those differences can be understood by (1) studying the chemotype (aka molecular composition) of each species and (2) correlating the chemotype with the observed effects.  In other words, invest in psilocybin chemistry. Ultimately, developing a better understanding of the molecules in magic mushrooms will pave the way for formulated products.

 

 

 

4 thoughts on “What are Psilocybin Derivatives?

  1. tomi

    “R7 = R6 = R5 = R8 =R3 = H
    R4 = Phosphate ester (i.e., OPO(OH)2)
    R1 = R2 = CH3”

    Get your shit together. Phosphate ester group should be labelled as R5. Oh, and where is R9….

    • Staff Scientist Post author

      Tomi – Thank you for catching the typos. They should be fixed now. Please let us know if you catch anything else that needs correction. We appreciate your help.

  2. Jeroen

    I understand that psilocybin is commonly used to describe the principal active chemical of ”magic mushrooms” but I still don’t understand why even in clinical trials it is stated to be that principle chemical, when it is known that psilocybin is actually a prodrug of psilocin, and that the latter is the actually active molecule. Despite the fact that there is a big upside to having psilocybin in pill or other extract form due to its stability compared to oxidation prone psilocin, there is still a source of confusion here. I’d very much appreciate your take on this.

    • Staff Scientist Post author

      100% agree.
      The popular language for describing the active molecules in magic mushrooms is in direct contrast to the accepted scientific terminology.
      That creates signifiant communication problems because we use the same word to mean very different (and contradictory) things. That creates all sorts of unnecessary confusion on the topic. For what it’s worth, we’ve noticed several new outlets cleaning up their language over the past couple of months. Still, it’s probably going to be a long road to fixing this issue.

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