What Are Psilocybin Derivatives?

There are many compounds closely resembling psilocybin from a chemical structure standpoint, but pharmacological information about these psilocybin derivatives is few and far between.

January 09, 2019 -

“Magic” (psilocybin-containing) mushrooms contain many molecules aside from psilocybin. For the most part, these psilocybin derivatives can be described as a group of tryptamine compounds. In that context, the term “psilocybin derivatives” refers to a collection of molecules (i.e., a genus) sharing a common chemical structure with psilocybin.  Psilocybin derivatives share a tryptamine core with a pendant ethylamino group, as illustrated in Figure 1.  The groups defined with “R” 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 = Hydrogen atom (H)
  • R5 = Phosphate ester (i.e., OPO(OH)2)
  • R1 = R2 = methyl group (CH3)

Applying those selections would provide the molecule psilocybin as shown in Figure 2.

Figure 2: Chemical structure of psilocybin. Psilocybin is one of many possible psilocybin derivatives.

Other examples of psilocybin derivatives include:

Why Are Psilocybin Derivatives Important?

Psilocybin derivatives are important because what are considered to be 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.

Figure showing the differences between Amphetamine and Methamphetamine

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.

Figures showing 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 or 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 (by one methyl group) could potentially have dramatic effects at a cellular level.

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 the 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.