Bufotenine

Identification

Name
Bufotenine
Accession Number
DB01445
Type
Small Molecule
Groups
Experimental, 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
Categories
UNII
0A31347TZK
CAS number
487-93-4
Weight
Average: 204.2682
Monoisotopic: 204.126263144
Chemical Formula
C12H16N2O
InChI Key
VTTONGPRPXSUTJ-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics

Bufotenin is a tryptamine related to the neurotransmitter serotonin.

Mechanism of action
Not Available
Absorption

Rapidly absorbed following intravenous administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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

Route of elimination
Not Available
Half life
Not Available
Clearance
Not 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not 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
Human Metabolome Database
HMDB41842
KEGG Compound
C08299
PubChem Compound
10257
PubChem Substance
46507174
ChemSpider
9839
BindingDB
50024206
ChEBI
3210
ChEMBL
CHEMBL416526
IUPHAR
144
Guide to Pharmacology
GtP Drug Page
Wikipedia
Bufotenine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9100000000-3e8c21621c306ca36dec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organoheterocyclic compounds
Sub Class
Indoles and derivatives
Direct Parent
Serotonins
Alternative Parents
Hydroxyindoles / 3-alkylindoles / Alkaloids and derivatives / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Substituted pyrroles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Serotonin / Hydroxyindole / 3-alkylindole / Indole / Alkaloid or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Substituted pyrrole / Benzenoid / Pyrrole
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary 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...
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...
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 October 02, 2017 04:58