“Magic” (psilocybin-containing) mushrooms contain many molecules aside from psilocybin. For the most part, these psilocybin derivatives (aka “psilocybin analogs”) 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.
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.
Other examples of psilocybin derivatives include:
- Psilocin (sometimes spelled psilocyn)
- [3-(2-trimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate (aka Aeruginascin)
- Baeocystin (aka [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate)
- Norbaeocystin (aka [3-(aminoethyl)-1H-indol-4-yl] dihydrogen phosphate), and
- 4-hydroxytryptamine (serotonin)
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.
Now, consider the structural difference between psilocybin and baeocystin.
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.