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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-13 11:42:12 UTC
Update Date2019-07-23 06:35:07 UTC
HMDB IDHMDB0041842
Secondary Accession Numbers
  • HMDB41842
Metabolite Identification
Common NameBufotenin
DescriptionA 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. Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America.
Structure
Data?1563863707
Synonyms
ValueSource
3-[2-(Dimethylamino)ethyl]-5-indololChEBI
3-[2-(Dimethylamino)ethyl]indol-5-olChEBI
3-[beta-(Dimethylamino)ethyl]-5-hydroxyindoleChEBI
5-Hydroxy-N,N-dimethyltryptamineChEBI
BufotenineChEBI
DM5-HTChEBI
N,N-DimethylserotoninChEBI
3-[b-(Dimethylamino)ethyl]-5-hydroxyindoleGenerator
3-[Β-(dimethylamino)ethyl]-5-hydroxyindoleGenerator
1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}HMDB
3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)HMDB
3-(2-Dimethylaminoethyl)-5-indololHMDB
3-(2-Dimethylaminoethyl)indol-5-olHMDB
3-(beta-Dimethylaminoethyl)-5-hydroxyindoleHMDB
3-[2-(Dimethylamino)ethyl]-1H-indol-5-olHMDB
3-[2-(Dimethylamino)ethyl]-indol-5-olHMDB
5-Hydroxy-N, N-dimethyltryptamineHMDB
CinobufotenineHMDB
CohobaHMDB
DimethylserotoninHMDB
indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}HMDB
MapineHMDB
MappinHMDB
MappineHMDB
N, N-DimethylserotoninHMDB
N,N-Dimethyl-5-hydroxytryptamineHMDB
{3-[(2-dimethylamino)ethyl]-5-indolol}HMDB
{3-[(beta-dimethylamino)ethyl]-5-hydroxyindole}HMDB
N,N Dimethyl 5 hydroxytryptamineHMDB
5 Hydroxy N,N dimethyltryptamineHMDB
BufoteninKEGG
Chemical FormulaC12H16N2O
Average Molecular Weight204.2682
Monoisotopic Molecular Weight204.126263144
IUPAC Name3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Traditional Namebufotenine
CAS Registry Number487-93-4
SMILES
CN(C)CCC1=CNC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
InChI KeyVTTONGPRPXSUTJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Alkaloid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.2 g/LALOGPS
logP2.04ALOGPS
logP1.29ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area39.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.42 m³·mol⁻¹ChemAxon
Polarizability23.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-0af816b35b1e16d258a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9130000000-7bbf336895ab1b156223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-af3dd65f76ad8654b621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0940000000-8952400d2cb6d011de82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-1900000000-34b8e0879f296431d1e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-59bc27deb381d771d0aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1290000000-c4aa46abeccd608387a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-5900000000-1b322d788e0c55bfa242Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9100000000-3e8c21621c306ca36decSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01445
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001402
Chemspider ID9839
KEGG Compound IDC08299
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBufotenin
METLIN IDNot Available
PubChem Compound10257
PDB IDNot Available
ChEBI ID3210
Food Biomarker OntologyNot Available
VMH IDM01408
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:1058643 ]
  2. 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:8747157 ]
  3. 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:9468359 ]
  4. 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:10350367 ]
  5. 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:16732341 ]