Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative, more specifically, a DMT analog, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin. The name bufotenin originates from the toad genus Bufo, which includes several species of psychoactive toads, most notably Incilius alvarius, that secrete bufotoxins from their parotoid glands. Bufotenin is similar in chemical structure to the psychedelics psilocin (4-HO-DMT), 5-MeO-DMT and DMT, chemicals which also occur in some of the same fungus, plant and animal species as bufotenin. Nomenclature Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT), N,N-dimethyl-5-hydroxytryptamine, dimethyl serotonin, and mappine. 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. Sources Toads Bufotenin is found in the poison and eggs of several species of toads belonging to the genus Bufo, but is most concentrated in the Colorado River toad (formerly Bufo alvarius, now Incilius alvarius), the only toad species with enough bufotenin for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines such as ch'an su (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. The toad was "recurrently depicted in Mesoamerican art", which some authors have interpreted as indicating that the effects of ingesting Bufo secretions have been known in Mesoamerica for many years; however, others doubt that this art provides sufficient "ethnohistorical evidence" to support the claim. In addition to bufotenin, Bufo venoms also contain digoxin-like cardiac glycosides, and ingestion of the venom can be fatal. Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. A court case in Spain, involving a physician who dosed people with smoked Mexican Toad poison, one of his customers died after inhaling three doses, instead of the usual of only one, had images of intoxicated with this smoke suffering obvious hypocalcemic hand muscular spasms. Reports in the mid-1990s indicated that bufotenin-containing toad venom had appeared as a street drug, supposedly but in fact not an aphrodisiac, ingested orally in the form of