DrugBank: Bufotenine (DB01445)

enzymes (2)

Identification

Name

Bufotenine

Accession Number

DB01445

Type

small molecule

Groups

illicit, experimental

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Serotonin Antagonists
Hallucinogens

CAS number

487-93-4

Weight

Average: 204.2682
Monoisotopic: 204.126263144

Chemical Formula

C₁₂H₁₆N₂O

InChI Key

InChIKey=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

Plain Text

IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

SMILES

CN(C)CCC1=CNC2=C1C=C(O)C=C2

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

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

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	146.5 °C	PhysProp

Predicted Properties

Property	Value	Source
water solubility	3.20e+00 g/l	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	ChemAxon
rotatable bond count	3	ChemAxon
refractivity	62.42	ChemAxon
polarizability	23.29	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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
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
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
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
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

Resource	Link
KEGG Compound	C08299
PubChem Compound	10257
PubChem Substance	46507174
ChemSpider	9839
ChEBI	3210
ChEMBL	3210
IUPHAR	144
Guide to Pharmacology	144
Wikipedia	http://en.wikipedia.org/wiki/Bufotenine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Enzymes
1. Amine oxidase [flavin-containing] A 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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine UniProt ID: P21397 Gene: MAOA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 2. Amine oxidase [flavin-containing] B 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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine UniProt ID: P27338 Gene: MAOB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report

Enzymes

1. Amine oxidase [flavin-containing] A

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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine

UniProt ID: P21397 Link_out

Gene: MAOA Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

2. Amine oxidase [flavin-containing] B

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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine

UniProt ID: P27338 Link_out

Gene: MAOB Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

Comments

Drug created on July 31, 2007 07:09 / Updated on February 08, 2013 16:20