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
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

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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
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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/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Drug Interaction
1,2-Benzodiazepine 中枢神经系统的风险或严重性可以增加抑郁eased when Bufotenine is combined with 1,2-Benzodiazepine.
Acetazolamide 中枢神经系统的风险或严重性可以增加抑郁eased when Acetazolamide is combined with Bufotenine.
Acetophenazine 中枢神经系统的风险或严重性可以增加抑郁eased when Acetophenazine is combined with Bufotenine.
Agomelatine 中枢神经系统的风险或严重性可以增加抑郁eased when Bufotenine is combined with Agomelatine.
Alfentanil 中枢神经系统的风险或严重性可以增加抑郁eased when Alfentanil is combined with Bufotenine.
Alimemazine 中枢神经系统的风险或严重性可以增加抑郁eased when Alimemazine is combined with Bufotenine.
Almotriptan 中枢神经系统的风险或严重性可以增加抑郁eased when Almotriptan is combined with Bufotenine.
Alosetron 中枢神经系统的风险或严重性可以增加抑郁eased when Alosetron is combined with Bufotenine.
Alprazolam 中枢神经系统的风险或严重性可以增加抑郁eased when Alprazolam is combined with Bufotenine.
Alverine 中枢神经系统的风险或严重性可以增加抑郁eased when Bufotenine is combined with Alverine.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
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
或ganic compounds
Super Class
或ganoheterocyclic 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/或ganopnictogen 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
分子框架
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. [文章]
  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. [文章]
  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. [文章]
  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. [文章]
  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. [文章]
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 TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 146.5 °C PhysProp
Predicted Properties
Property Value Source
Water Solubility 3.2 mg/mL ALOGPS
logP 2.04 ALOGPS
logP 1.29 Chemaxon
logS -1.8 ALOGPS
pKa (Strongest Acidic) 9.23 Chemaxon
pKa (Strongest Basic) 9.91 Chemaxon
Physiological Charge 1 Chemaxon
Hydrogen Acceptor Count 2 Chemaxon
Hydrogen Donor Count 2 Chemaxon
Polar Surface Area 39.26 Å2 Chemaxon
Rotatable Bond Count 3 Chemaxon
Refractivity 62.42 m3·mol-1 Chemaxon
Polarizability 23.29 Å3 Chemaxon
Number of Rings 2 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule Yes Chemaxon
MDDR-like Rule No Chemaxon
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 inhibitor Non-inhibitor 0.9218
CYP450 2D6 inhibitor Non-inhibitor 0.5464
CYP450 2C19 inhibitor Non-inhibitor 0.919
CYP450 3A4 inhibitor 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
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Mass Spectrum (Electron Ionization) MS splash10-0a4i-9100000000-3e8c21621c306ca36dec
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Enzymes

Kind
Protein
或ganism
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. [文章]
  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. [文章]

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