Both Psilocin and the phosporylated version Psilocybin are present in Liberty Cap. Psilocybin is a Zwitterion, where there are separated internal charges but overall the molecule is neutral. Psilocybin is unstable, readily decomposing into Psilocin. They are indole alkaloids based on Tryptamine and very similar to the monoamine neurotransmitter
Serotonin which Psilocin can partially substitute for. Both are mildly poisonous, ingestion of which can lead to a wide range of sometimes opposite effects such as dis-orientation, hallucination, altered time perspectives, tachycardia, elation, depression, dilation of pupils, restlessness, euphoria, auditory distortions, kaleidoscopic visions with eyes closed, synaesthesia, fever, headache and nausea; the effects lasting anything from 3 to 8 hours, but they are highly variable depending upon the individual. Psilocybin is readily de-phosphorylated within mammalian bodies after ingestion into Psilocin, which is the psychactive component. The de-phosphorylation process occurs either under strongly acidic conditions (such as occur within the stomach) or by the action of enzymes called phosphatases. Psilocybin is therefore a 'prodrug'. The resulting Psilocin is thought to be a partial agonist of the serotonin receptors (specifically the 5-HT 2A receptors) in the pre-frontal cortex of the brain.
The fatal dose of Psilocybin is estimated to be 6g, whereas the dose required for intoxication is just 6mg.
Two other minor constituents of the mushroom, thought to be the pre-cursors of Psilocybin nd Psilocin, are
Norbaeocystin both of which are phosphorylated indole compounds and zwitterions (dipolar - possessing separated opposite charges but overall having a net zero charge). Whereas Psilocybin has two methyl groups, Baeocystin has but one and Norbaeocystin none. Both are metabolised to Psilocin within the human body.
The stems of the mushroom turn a bluish hue when bruised, a characteristic (which is not unique) of Liberty Cap. This is due to the formation of oxidation products of Psilocin. (Other mushrooms can bruise to a blue colour without containing any Psilocin or Psilocybin). The blue colour results from the action of an enzyme contained within the mushrooms themselves (but only released when the cell walls are disrupted) called hydroxyindole oxidase. The resultant enzymatic reaction on Psilocin yields, it is said, the highly coloured
1,2-benzoquinone). Unfortunately, the same source which says that the resulting ortho-quinone is blue, in another section of the encylopaedia contrarily says that ortho-quinone is red! This can only mean that blue is red! (Your Author is inclined to believe that ortho-quinone is indeed red). Thus your author has been unsuccessful in finding the true structural formula of the blue degradation compound, which your author finds much more interesting than whether or not it gives the imbiber hallucinations. Your author notes that para-quinone is yellow and was therefore pondering if the blue substance could instead be meta-quinone. But on further investigation your Author discovered that meta-quinone, somewhat surprisingly, cannot exist, which explains why he could not find it on the internet. When your Author tried drawing meta-quinone, it became immediately obvious that two non-contiguous double bonds could not fit into the proposed chemical. So the mystery remains: red is blue according to Wikipedia (and several other sources on the internet).