Bufotenine

Chemical Properties

Bufotenine is an indole alkaloid obtained from the seeds and leaves of Piptadenia peregrine and P. macrocarpa. It has also been isolated from the skin glands of toads (Bufo species). The base is typically seen as white crystalline powder and the oxalate hydrate as a lavender to brown powder. The oxalate hydrate is slightly soluble in chloroform and can be separated from chloroform insoluble material for analysis.

History

Bufotenin was isolated from toad skin, and named by the Austrian chemist Handovsky at the University of Prague during World War I.The structure of bufotenine was confirmed in 1934 by Heinrich Wieland's laboratory in Munich, and the first reported synthesis of bufotenine was by Toshio Hoshino and Kenya Shimodaira in 1935.

Uses

Controlled substance (hallucinogen).
Bufotenine is a hallucinogenic serotonin analog found in frog and toad skins, mushrooms, plants and some mammals (especially in the brains, plasma, and urine of schizophrenics). It is a potent hallucinogen used in its natural state by several shaman sects and in some drug abuse situations in the United States and Australia. It causes schizophrenia and other psychotic symptoms.

Definition

ChEBI: Bufotenine is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tryptamine alkaloid and a tertiary amine. It derives from a N,N-dimethyltryptamine.