Psilocin indole ring

Determination of the indole alkaloids psilocin and psilocybin in fungi has been the most popular application of EC in the analysis of alkaloids in a plant matrix. This research has primarily been done by two groups Christiansen and co-workers in Norway, and Kysilka and Wurst in the Czech Republic. Especially psilocin is well suited for EC, due to its hydroxy substituent on the indole ring, essentially a phenol, whereas in psilocybin this group is phosphorylated. Since the pH of the mobile phase is not critical to the oxidation of either the phenolic group or indole nucleus, it has been possible to use different separation techniques. 

If the alkyl side chain at the 3 position of the indole nucleus is shortened (e.g., gramine) or lengthened (e.g., 3-(3-dimethylamino)-propyl indole) activity seems to decrease strikingly. Also, as the substituents are moved around the benzene ring of indole, activity decreases greatly in the order 4,5,6,7. For example, whereas 4-OH-DMT(psilocin) is active at about 5 mg orally (i.e., about as active as STP), 5-OH-DMT(bufotenin) is not psychedelic at all. 

This compound cluster exhibits a two-ring, "open-chained, indolic chemical structure, and in contrast to other psychedelics it is all but inactive when taken orally unless accompanied by certain other compounds. Shortacting tryptamines are closely related to neurotransmitters (such as bufotenine), to MDA (a major botanical source of the snuffs belongs to the nutmeg family), to tryptophan (an essential amino acid produced in human digestion of proteins) and to psilocybin and psilocin (which are tryptamines of longer duration). DMT, the simplest member, occurs normally in the blood, brain and (in higher concentrations) in the cerebrospinal fluid. 

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