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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

Molecular Formula C12H16N2O
Molecular Weight 204.2682
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
A test of the transmethylation hypothesis in acute schizophrenic patients.
1975 Oct
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
Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia.
1999 Apr
Occurrence of bufotenin in the Osteocephalus genus (Anura: Hylidae).
2005 Sep 15
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
Sudden death associated with intravenous injection of toad extract.
2009 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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:21:43 GMT 2025
Edited
by admin
on Mon Mar 31 19:21:43 GMT 2025
Record UNII
0A31347TZK
Record Status Validated (UNII)
Record Version
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Name Type Language
BUFOTENINE
MART.   MI  
Common Name English
NSC-89593
Preferred 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
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 Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
WIKIPEDIA TiHKAL
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
Code System Code Type Description
NSC
89593
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
DRUG BANK
DB01445
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
PUBCHEM
10257
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
WIKIPEDIA
BUFOTENIN
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
FDA UNII
0A31347TZK
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
SMS_ID
300000056850
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID0048894
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
MERCK INDEX
m2753
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
207-667-9
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
CHEBI
3210
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
CAS
487-93-4
Created by admin on Mon Mar 31 19:21:43 GMT 2025 , Edited by admin on Mon Mar 31 19:21:43 GMT 2025
PRIMARY
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