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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
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
1993 Aug
Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization.
1993 Mar
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.
1995 Dec 27
Mapping the binding site pocket of the serotonin 5-Hydroxytryptamine2A receptor. Ser3.36(159) provides a second interaction site for the protonated amine of serotonin but not of lysergic acid diethylamide or bufotenin.
1996 Jun 21
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
1997 Apr-May
Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine.
2001 Jul-Sep
Aphrodisiacs past and present: a historical review.
2001 Oct
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity.
2001 Sep
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.
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 Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
WIKIPEDIA TiHKAL
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
Code System Code Type Description
NSC
89593
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
PRIMARY
DRUG BANK
DB01445
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PUBCHEM
10257
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
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WIKIPEDIA
BUFOTENIN
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
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FDA UNII
0A31347TZK
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
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EPA CompTox
DTXSID0048894
Created by admin on Sat Dec 17 01:14:07 UTC 2022 , Edited by admin on Sat Dec 17 01:14:07 UTC 2022
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MERCK INDEX
M2753
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PRIMARY Merck Index
ECHA (EC/EINECS)
207-667-9
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PRIMARY
CHEBI
3210
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CAS
487-93-4
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