487-93-4CN(C)CCc1c[nH]c2ccc(O)cc12VTTONGPRPXSUTJ-UHFFFAOYSA-NBufotenin 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 tertiary amine and a tryptamine alkaloid. It is functionally related to a N,N-dimethyltryptamine.
487-93-4DTXSID0048894CHEMBL416526CHEBI:3210DEA Schedule I Controlled Substance -> Hallucinogenic substances
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
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Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Bufotenin is present in the skin of some common species of frogs, and its ingestion (such as from licking or kissing a frog) can result in vivid hallucinations.
Bufotenin (5-hydroxy-N,N-dimetyltryptamine) is a tryptamine alkaloid widely present in frogs as a component of their chemical defense system. It is a potent hallucinogen, with activity similar activity to LSD from interacting with the 5HT2 human receptor.
Bufotenin is a neurotoxin similar to the mushroom toxin psilocin. Thus it likely acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is likely also a 5-HT1A and 5-HT2A/2C agonist. (L1081, L1673)
Upon oral administration, bufotenine is extensively metabolized by monoamine oxidase enzymes.
Bufotenine is a known human metabolite of n,n-dimethyl-5-methoxytryptamine.
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.
HistoryBufotenin 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.
VerwendenControlled 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.
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DefinitionChEBI: 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.