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Bufotenine

Catalog No. DB01445 Name DrugBank
CAS Number 487-93-4 Website http://www.ualberta.ca/
M. F. C12H16N2O Telephone (780) 492-3111
M. W. 204.26824 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1251

SYNONYMS

IUPAC name
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
IUPAC Traditional name
mappin
Synonyms
Bufotenine

DATABASE IDS

PubChem SID 46507174
CAS Number 487-93-4
PubChem CID 10257

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups illicit; experimental
Description A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.
Pharmacology Bufotenin is a tryptamine related to the neurotransmitter serotonin.
Toxicity Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. The acute toxicity of bufotenin in rodents has been calculated to have an LD50 of between 200 and 300 mg/kg, which by comparison, is comparable to the LD50 for intravenous morphine (200-300 mg/kg) in mice. Death occurs by respiratory arrest.
Affected Organisms
Humans and other mammals
Biotransformation Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.
Absorption Rapidly absorbed following intravenous administration.
References
Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. [Pubmed]
Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [Pubmed]
Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [Pubmed]
Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [Pubmed]
Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. Pubmed
  • Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. Pubmed
  • Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. Pubmed
  • Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. Pubmed
  • Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. Pubmed