Psilocin is the Active Component in Magic Mushrooms – Not Psilocybin
So-called “magic mushrooms” (aka shrooms) are known to cause a psychoactive effect on people. Archeological evidence supports the use of these magic mushrooms dating all the way back to 3000 BC. Some known effects of consuming quantities of mushrooms include altered perceptions, hallucinations, disorganized thinking, anxiety, and an altered perception of time. For the most part, all of these effects are attributed to the molecule psilocybin. However, technically speaking, psilocin is the molecule responsible for most of the psychoactive properties in magic mushrooms.
Psilocybin refers to the molecule (4-phosphoryloxy-N,N-dimethyltryptamine, aka, [3-(2-trimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate).
Psilocin refers to the molecule 4-hydroxy-N, N-dimethyltryptamine.
These two molecules are pictured below.
Psilocybin is a Means for Ingesting Psilocin
Although psilocybin receives most of the credit for affecting mood and perception, psilocin is probably the molecule actually responsible for producing the psychoactive effects. The most reasonable explanation is as follows:
- Psilocin is psychoactive. But psilocin is not stable. Psilocin degrades quickly in the presence of air, heat, and/or light. This makes sense because the 4-hydroxy group on the tryptamine is susceptible to oxidation.
- Psilocybin is not psychoactive. But, it is far more stable that psilocin. Unlike psilocin (which has 4-hydroxy group on the tryptamine ring system), psilocybin has a phosphate ester in this position. That phosphate ester protects the molecule from degradation (e.g., oxidation), making psilocybin more stable than psilocin.
- Psilocybin is easily converted into psilocin. When psilocybin is ingested (e.g., by eating mushrooms or mushroom preparations) it gets rapidly converted into psilocin. The conversion of psilocybin into psilocin can occur under either acidic conditions and/or enzymatic dephosphorylation by alkaline phosphatase enzymes.
Overall, the most reasonable theory is that a person ingests psilocybin (e.g., by eating mushrooms containing psilocybin) as a means of administering psilocin. In other words, a person takes psilocybin, which is converted into psilocin, which produces the observed psychoactive effects.
No One Talks About Psilocin.
Although the distinction between psilocin and psilocybin seems like a technicality, it could have important implications. For example, a group called the “California Psilocybin Legalization Initiative” recently made headway towards decriminalizing psilocybin. As a result, California residents may have the opportunity to vote on the decriminalization of Psilocybin.
According to the California Secretary of State’s website, the proposed initiative (if passed) would “Decriminalize use, possession, sale, transport, or cultivation of psilocybin (a hallucinogenic compound) by persons at least 21 years of age.” (emphasis added).
Notably, none of the proposed legislation mentions psilocin. None of the reports on California Psilocybin Legalization Initiative mention it either. What does this mean? Does it really matter?
Psilocin is Different From Psilocybin
Practically speaking, taking psilocybin provides a means for administering a psilocin equivalent. A user takes one molecule of psilocybin and (after some metabolism and chemistry) receives one molecule of psilocin, which provides the majority of the psychoactive effects.
However, although psilocybin can be viewed as a psilocin equivalent, the two are not exactly the same. To be clear, they are different molecules. Accordingly, the effects of administering psilocybin will not be exactly the same as administering psilocin.
One critical difference is that administering psilocybin requires the subject to wait for the dephosphorylation reaction to take place. That means that the pharmacokinetics for psilocybin are necessarily different than for psilocin. Anecdotal evidence (comparing subjective effects from mushrooms differing in their relative amounts of psilocybin vs psilocin) supports the notion that these two molecules may produce different effects. How different? No one knows.
Would decriminalizing psilocybin result in the decriminalization of psilocin? What about other psilocybin derivatives, like baeocystin? See Psilocybin Chemistry.