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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassNot Available
SubclassNot Available
Direct parentAlkaloids and Derivatives
Alternative parentsSerotonins; Indoles; Phenols and Derivatives; Substituted Pyrroles; Tertiary Amines; Polyamines; Enols
Substituentsphenol derivative; substituted pyrrole; benzene; pyrrole; tertiary amine; enol; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
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
Property Value Probability
Human Intestinal Absorption + 0.9957
Blood Brain Barrier + 0.9604
Caco-2 permeable + 0.5521
P-glycoprotein substrate Substrate 0.7363
P-glycoprotein inhibitor I Non-inhibitor 0.9844
P-glycoprotein inhibitor II Non-inhibitor 0.6343
Renal organic cation transporter Inhibitor 0.6362
CYP450 2C9 substrate Non-substrate 0.7941
CYP450 2D6 substrate Substrate 0.5684
CYP450 3A4 substrate Substrate 0.6268
CYP450 1A2 substrate Inhibitor 0.6444
CYP450 2C9 substrate Non-inhibitor 0.9218
CYP450 2D6 substrate Non-inhibitor 0.5464
CYP450 2C19 substrate Non-inhibitor 0.919
CYP450 3A4 substrate Non-inhibitor 0.8388
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7531
Ames test Non AMES toxic 0.6702
Carcinogenicity Non-carcinogens 0.9596
Biodegradation Not ready biodegradable 0.9933
Rat acute toxicity 2.5986 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7984
hERG inhibition (predictor II) Non-inhibitor 0.7167
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 Solubility3.2ALOGPS
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
Spectra
Spectra
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
ResourceLink
KEGG CompoundC08299
PubChem Compound10257
PubChem Substance46507174
ChemSpider9839
ChEBI3210
ChEMBL
IUPHAR144
Guide to Pharmacology144
WikipediaBufotenine
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