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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2O
Molecular Weight 204.2682
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFOTENINE

SMILES

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

InChI

InChIKey=VTTONGPRPXSUTJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Bufotenine is a hallucinogenic serotonin analog found in frog and toad skins, mushrooms, plants and some mammals (especially in the brains, plasma, and urine of schizophrenics). It

CNS Activity

Curator's Comment: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q64264
Gene ID: 15550.0
Gene Symbol: Htr1a
Target Organism: Mus musculus (Mouse)
Target ID: P35363
Gene ID: 15558.0
Gene Symbol: Htr2a
Target Organism: Mus musculus (Mouse)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders.
1995 Nov 27
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
1997 Apr-May
Altered consciousness states and endogenous psychoses: a common molecular pathway?
1997 Dec 19
Molecular basis of partial agonism: orientation of indoleamine ligands in the binding pocket of the human serotonin 5-HT2A receptor determines relative efficacy.
2003 Jan
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.
2003 Jul
Urinary excretion of dietary contaminants in horses.
2006 Aug
New indole N-oxide alkaloids from Evodia fargesii.
2006 Feb
Lack of bufadienolides in the skin secretion of red bellied toads, Melanophryniscus spp. (Anura, Bufonidae), from Uruguay.
2007 Jan
Liquid chromatography-tandem mass spectrometry method for the simultaneous analysis of multiple hallucinogens, chlorpheniramine, ketamine, ritalinic acid, and metabolites, in urine.
2007 Oct
Indolealkylamines: biotransformations and potential drug-drug interactions.
2008 Jun
Early onset muscarinic manifestations after wild mushroom ingestion.
2008 Sep
Sudden death associated with intravenous injection of toad extract.
2009 Jul 1
Elevated urine levels of bufotenine in patients with autistic spectrum disorders and schizophrenia.
2010
Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics.
2010 Jul 1
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: referenced study was conducted on mice.
Age-matched wild-type FVB/N and Tg-CYP2D6 mice were given an intraperitoneal dose of either harmaline 90, 2, 5, or 15 mg/kg) or bufotenine (0, 2, 10 0r 20 mg/kg). Wild-type and Tg-CYP2D6 mice exhibited hyperthermia with high doses of bufotenine ( 10 and 20 mg/kg).
Route of Administration: Intraperitoneal
In Vitro Use Guide
To determine if serotonin is involved in associative conditioning-produced changes of Type B photo-receptors, isolated nervous systems were exposed to a conditioning procedure in the absence or presence of drugs that alter normal serotonergic neurotransmission. Nervous systems were dissected, mounted and treated with protease before washing with artificial seawater (ASW), or ASW containing 100 microM bufotenine. When treated bufotenine clearly reduced the pairing specific cumulative depolarization and changes in input resistance. Treatment involving bufotenine suggests that serotonin modulates Type B photoreceptor excitability during associative conditioning.
Name Type Language
BUFOTENINE
MART.   MI  
Common Name English
MAPPINE
Common Name English
5-HYDROXY-N,N-DIMETHYLTRYPTAMINE
Systematic Name English
N,N-dimethyl-5-HT
Common Name English
BUFOTENINE [MI]
Common Name English
3-(2-DIMETHYLAMINOETHYL)-5-INDOLOL
Systematic Name English
N,N-DIMETHYLSEROTONIN
Common Name English
5-OH-DMT
Common Name English
BUFOTENINE [MART.]
Common Name English
NSC-89593
Code English
dimethylserotonin
Common Name English
DM5-HT
Common Name English
BUFOTENIN
Common Name English
Classification Tree Code System Code
DEA NO. 7433
Created by admin on Fri Dec 15 18:48:41 GMT 2023 , Edited by admin on Fri Dec 15 18:48:41 GMT 2023
WIKIPEDIA TiHKAL
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Code System Code Type Description
NSC
89593
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DRUG BANK
DB01445
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PUBCHEM
10257
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WIKIPEDIA
BUFOTENIN
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FDA UNII
0A31347TZK
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EPA CompTox
DTXSID0048894
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MERCK INDEX
m2753
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PRIMARY Merck Index
ECHA (EC/EINECS)
207-667-9
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CHEBI
3210
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CAS
487-93-4
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