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THE EFFECT OF 4‐HYDROXYINDOLES ON THE METABOLISM OF 5‐HYDROXYTRYPTAMINE (SEROTONIN) *
Author(s) -
WisemanDistler M. H.,
Sourkes T. L.
Publication year - 1962
Publication title -
annals of the new york academy of sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.712
H-Index - 248
eISSN - 1749-6632
pISSN - 0077-8923
DOI - 10.1111/j.1749-6632.1962.tb50109.x
Subject(s) - library science , annals , citation , gerontology , medicine , sociology , classics , computer science , history
Psilocybin has been shown to be the active component of the Mexican mushroom, Psitocybe mexicana.l I t belongs to the category of hydroxylated indoles showing hallucinogenic and vasopressor properties. Chemically it is the 0-phosphoryl ester of psilocin (4-hydroxy-N-dimethyltryptamine) (FIGURE 1). Psilocin in turn is the 4-hydroxy analogue of bufotenine (5-hydroxy-N-dimethyltryptamine) . Thus psilocin and bufotenine are the dimethyl derivatives of 4-hydroxytryplamine (4HT) and 5-hydroxytryptamine (serotonin, 5HT) respectively. Serotonin, the decarboxylation product of 5-liydroxytryptophan, is oxidized to its aldehyde by the action of monoamine oxidase (MAO) and then further metabolized to 5-hydroxyindoleacetic acid (5HIAA). In an analogous fashion 4-hydroxytryptophan, which may be the natural precursor of psilocybin, is metabolized to 4 hydroxyindoleacetic acid (4HIAA).2 These pathways of metabolism are catalyzed by the same enzymes, that is, 4HT is a substrate for MAO. However, psilocybin resists oxidation by MAC) Liz vitro.3 This may be due to interference by the phosphate ester group, although the phosphate ester is readily hydrolyzed by alkaline phosphatase (unpublished data) and intestinal pho~phatase,~ giving rise to psilocin. Both psilocin and bufotenine are substrates for MAO, although poor ones. Because of the similarity in chemical structure and pathways of metabolism between the 4and 5-hydroxyindoles it was of interest to study the effect of the 4-hydroxyindoles on the catabolism of 5HT.