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Record Information
Version2.0
Creation Date2009-07-03 22:19:14 UTC
Update Date2014-12-24 20:25:40 UTC
Accession NumberT3D2534
Identification
Common NameBufotenin
ClassSmall Molecule
DescriptionBufotenin (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. The acute toxicity (LD50) of bufotenin in rodents has been estimated at 200 to 300 mg/kg. Death occurs by respiratory arrest.
Compound Type
  • Amine
  • Animal Toxin
  • Frog/Toad Toxin
  • Fungal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1H-Indol-5-ol, {3-[2-(dimethylamino)ethyl]-}
3-(2-(dimethylamino)Ethyl)-1H-indol-5-ol
3-(2-Dimethylaminoethyl)-5-indolol
3-(2-Dimethylaminoethyl)indol-5-ol
3-(beta-Dimethylaminoethyl)-5-hydroxyindole
3-[2-(Dimethylamino)ethyl]-1H-Indol-5-ol
3-[2-(Dimethylamino)ethyl]-5-indolol
3-[2-(Dimethylamino)ethyl]-Indol-5-ol
3-[2-(Dimethylamino)ethyl]indol-5-ol
3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole
5-Hydroxy-N, N-dimethyltryptamine
5-Hydroxy-N,N-dimethyltryptamine
Bufotenine
Cinobufotenine
Cohoba
Dimethylserotonin
DM5-HT
Indol-5-ol, {3-[2-(dimethylamino)ethyl]-}
Mapine
Mappin
Mappine
N, N-Dimethylserotonin
N,N-Dimethyl-5-hydroxytryptamine
N,N-Dimethylserotonin
{3-[(2-Dimethylamino)ethyl]-5-indolol}
{3-[(beta-Dimethylamino)ethyl]-5-hydroxyindole}
Chemical FormulaC12H16N2O
Average Molecular Mass204.268 g/mol
Monoisotopic Mass204.126 g/mol
CAS Registry Number487-93-4
IUPAC Name3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Traditional Namebufotenine
SMILESCN(C)CCC1=CNC2=C1C=C(O)C=C2
InChI IdentifierInChI=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 KeyInChIKey=VTTONGPRPXSUTJ-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point146.5°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.2 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.42 m3·mol-1ChemAxon
Polarizability23.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a4i-9200000000-0af816b35b1e16d258a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-0a4i-9130000000-7bbf336895ab1b156223View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-af3dd65f76ad8654b621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0940000000-8952400d2cb6d011de82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-1900000000-34b8e0879f296431d1e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-59bc27deb381d771d0aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1290000000-c4aa46abeccd608387a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-5900000000-1b322d788e0c55bfa242View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9100000000-3e8c21621c306ca36decView in MoNA
Toxicity Profile
Route of ExposureIngestion (8)
Mechanism of ToxicityBufotenin 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. (6, 7)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBufotenin is a toxin found in some toads (genus Bufo) and mushrooms (genus Amanita). (6)
Minimum Risk LevelNot Available
Health EffectsBufotenin is neurotoxic and can cause hallucinations. (6)
SymptomsBufotenin exposure produces local irritation and causes hallucinations. It may also cause circulation problems peripheral nervous system effects such as flushing and hyperventilation. (6)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01445
HMDB IDHMDB41842
PubChem Compound ID10257
ChEMBL IDCHEMBL416526
ChemSpider ID9839
KEGG IDC08299
UniProt IDNot Available
OMIM ID
ChEBI ID3210
BioCyc IDBUFOTENINE
CTD IDD002027
Stitch IDBufotenin
PDB IDNot Available
ACToR IDNot Available
Wikipedia Linkbufotenin
References
Synthesis ReferenceNot Available
MSDST3D2534.pdf
General References
  1. 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. [10350367 ]
  2. 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. [9468359 ]
  3. 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. [1058643 ]
  4. 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. [8747157 ]
  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. [16732341 ]
  6. Wikipedia. Bufotenin. Last Updated 28 June 2009. [Link]
  7. Wikipedia. Psilocin. Last Updated 22 July 2009. [Link]
  8. Wikipedia. Mollusca. Last Updated 5 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.015 uMNot AvailableBindingDB 50024206
Inhibitory0.145 uMNot AvailableBindingDB 50024206
References
  1. Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K: Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors. Synapse. 2000 Feb;35(2):144-50. [10611640 ]
  2. Wikipedia. Bufotenin. Last Updated 28 June 2009. [Link]
  3. Wikipedia. Psilocin. Last Updated 22 July 2009. [Link]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.07 uMNot AvailableBindingDB 50024206
References
  1. Glennon RA: Central serotonin receptors as targets for drug research. J Med Chem. 1987 Jan;30(1):1-12. [3543362 ]
  2. Wikipedia. Bufotenin. Last Updated 28 June 2009. [Link]
  3. Wikipedia. Psilocin. Last Updated 22 July 2009. [Link]
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
References
  1. Wikipedia. Bufotenin. Last Updated 28 June 2009. [Link]
  2. Wikipedia. Psilocin. Last Updated 22 July 2009. [Link]
General Function:
Serotonin:sodium symporter activity
Specific Function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC501.2 uMNot AvailableBindingDB 50024206
References
  1. Schmitz WD, Denhart DJ, Brenner AB, Ditta JL, Mattson RJ, Mattson GK, Molski TF, Macor JE: Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs). Bioorg Med Chem Lett. 2005 Mar 15;15(6):1619-21. [15745809 ]