Identification
NameBufotenine
Accession NumberDB01445
TypeSmall Molecule
GroupsExperimental, Illicit
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.

Structure
Thumb
Synonyms
3-[2-(dimethylamino)ethyl]-5-indolol
3-[2-(dimethylamino)ethyl]indol-5-ol
3-[β-(dimethylamino)ethyl]-5-hydroxyindole
5-hydroxy-N,N-dimethyltryptamine
Bufotenin
DM5-HT
N,N-dimethylserotonin
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII0A31347TZK
CAS number487-93-4
WeightAverage: 204.2682
Monoisotopic: 204.126263144
Chemical FormulaC12H16N2O
InChI KeyVTTONGPRPXSUTJ-UHFFFAOYSA-N
InChI
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
IUPAC Name
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
SMILES
CN(C)CCC1=CNC2=C1C=C(O)C=C2
Pharmacology
IndicationNot Available
Structured Indications Not Available
Pharmacodynamics

Bufotenin is a tryptamine related to the neurotransmitter serotonin.

Mechanism of actionNot Available
Related Articles
Absorption

Rapidly absorbed following intravenous administration.

Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16732341 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)146.5 °CPhysProp
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 RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9957
Blood Brain Barrier+0.9604
Caco-2 permeable+0.5521
P-glycoprotein substrateSubstrate0.7363
P-glycoprotein inhibitor INon-inhibitor0.9844
P-glycoprotein inhibitor IINon-inhibitor0.6343
Renal organic cation transporterInhibitor0.6362
CYP450 2C9 substrateNon-substrate0.7941
CYP450 2D6 substrateSubstrate0.5684
CYP450 3A4 substrateSubstrate0.6268
CYP450 1A2 substrateInhibitor0.6444
CYP450 2C9 inhibitorNon-inhibitor0.9218
CYP450 2D6 inhibitorNon-inhibitor0.5464
CYP450 2C19 inhibitorNon-inhibitor0.919
CYP450 3A4 inhibitorNon-inhibitor0.8388
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7531
Ames testNon AMES toxic0.6702
CarcinogenicityNon-carcinogens0.9596
BiodegradationNot ready biodegradable0.9933
Rat acute toxicity2.5986 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7984
hERG inhibition (predictor II)Non-inhibitor0.7167
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-9100000000-3e8c21621c306ca36decView in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as serotonins. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentSerotonins
Alternative ParentsHydroxyindoles / 3-alkylindoles / Alkaloids and derivatives / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Substituted pyrroles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
SubstituentsSerotonin / Hydroxyindole / 3-alkylindole / Indole / Alkaloid or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Substituted pyrrole / Benzenoid / Pyrrole
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorstertiary amine, tryptamine alkaloid (CHEBI:3210 ) / Indole alkaloids (C08299 )

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Uniprot Name:
Amine oxidase [flavin-containing] A
Molecular Weight:
59681.27 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Uniprot Name:
Amine oxidase [flavin-containing] B
Molecular Weight:
58762.475 Da
Drug created on July 31, 2007 07:09 / Updated on September 01, 2017 10:39