H-D Exchange of Psilocin and Its Analogs
Haruhisa Shirahama, Kazuyo Sogawa, Kimiko Hashimoto
Heterocycles 1999 DOI: 10.3987/com-98-s(h)87 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Citations | 1 |
| Key points | H-D exchange rates of psilocin and its analogs in MeOH-d depend on the C3 substituent, with bufotenine and 5-hydroxyindole exchanging much more slowly than psilocin and its analogs. The text also notes that psilocin is the hallucinogenic principle of Psilocybe mexicana and that air oxidation of psilocin likely produces blue pigments in the mushroom. |
Abstract
H-D exchange experiment?were performed on psilocin (1) and its analogs in MeOH-d,.The various exchange rates depending on their C3- suhstituents were observed.The exchange of bufotenine (5) and 5hydroxyindole ( 7) is much slower than psilocin (1) and its analogs (2 -4).Psilocin ( 1) is a hallucinogenic principle isolated from the poisonous mushroom, Psilocybe rnericanq' and it was recently detected in other Psiloqbe species and also other genera, such as Paneolus, Plureus, and ~o n o c ~b e .' The white fruiting body of this fungi turns blue upon exposure to air, which was probably caused by the air oxidation of psilocin to produce blue pigments.3During the study of the saucture of the blue materials, we synthesized some psilocin derivatives and found that they show various H-D exchange