Bufotenine

Identification

Generic Name
Bufotenine
DrugBank Accession Number
DB01445
Background

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.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Thumb
Weight
Average: 204.2682
Monoisotopic: 204.126263144
Chemical Formula
C12H16N2O
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

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Upon oral administration, bufotenine is extensively metabolized by monoamine oxidase enzymes.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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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. Respiratory arrest may occur, possibly leading to death.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Bufotenine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Bufotenine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Bufotenine.
AclidiniumBufotenine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Bufotenine is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Bufotenine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Bufotenine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Bufotenine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Bufotenine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Bufotenine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds 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
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines 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
1-hydroxy-2-unsubstituted benzenoid / 3-alkylindole / Alkaloid or derivatives / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amine, tryptamine alkaloid (CHEBI:3210) / Indole alkaloids (C08299)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0A31347TZK
CAS number
487-93-4
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

References

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0041842
KEGG Compound
C08299
PubChem Compound
10257
PubChem Substance
46507174
ChemSpider
9839
BindingDB
50024206
ChEBI
3210
ChEMBL
CHEMBL416526
ZINC
ZINC000000001070
Guide to Pharmacology
GtP Drug Page
Wikipedia
Bufotenin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
References
  1. Jiang XL, Shen HW, Mager DE, Yu AM: Pharmacokinetic interactions between monoamine oxidase A inhibitor harmaline and 5-methoxy-N,N-dimethyltryptamine, and the impact of CYP2D6 status. Drug Metab Dispos. 2013 May;41(5):975-86. doi: 10.1124/dmd.112.050724. Epub 2013 Feb 7. [Article]
  2. Fuller RW, Snoddy HD, Perry KW: Tissue distribution, metabolism and effects of bufotenine administered to rats. Neuropharmacology. 1995 Jul;34(7):799-804. doi: 10.1016/0028-3908(95)00049-c. [Article]

Drug created on July 31, 2007 13:09 / Updated on January 07, 2021 03:10