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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
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Bufotenine
  • Serotonin
  • Tryptamine
  • Alkaloid or derivatives
  • Hydroxyindole
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsBufotenin is a tryptamine related to the neurotransmitter serotonin.
Mechanism of actionNot Available
AbsorptionRapidly 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
ToxicityIngestion 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9218
CYP450 2D6 substrateNon-inhibitor0.5464
CYP450 2C19 substrateNon-inhibitor0.919
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point146.5 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
References
Synthesis ReferenceNot Available
General Reference
  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
  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
  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
  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
  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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

2. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details
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Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14