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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2O.C2H2O4
Molecular Weight 294.3031
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFOTENINE MONOOXALATE

SMILES

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

InChI

InChIKey=DYESHNNFAFXIKV-UHFFFAOYSA-N
InChI=1S/C12H16N2O.C2H2O4/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12;3-1(4)2(5)6/h3-4,7-8,13,15H,5-6H2,1-2H3;(H,3,4)(H,5,6)

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

Molecular Formula C2H2O4
Molecular Weight 90.0349
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
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
Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders.
1995 Nov 27
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
1996 Dec
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
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
Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS.
2001
The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry.
2001 Jan
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity.
2001 Sep
Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin.
2002 Apr 5
Composition of indolealkylamines of Bufo rubescens cutaneous secretions compared to six other Brazilian bufonids with phylogenetic implications.
2003 Apr
New indole N-oxide alkaloids from Evodia fargesii.
2006 Feb
[Urine peptide patterns in children with milder types of autism].
2006 May 25
Lack of bufadienolides in the skin secretion of red bellied toads, Melanophryniscus spp. (Anura, Bufonidae), from Uruguay.
2007 Jan
Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds.
2010
Elevated urine levels of bufotenine in patients with autistic spectrum disorders and schizophrenia.
2010
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 Fri Dec 15 15:47:20 UTC 2023
Edited
by admin
on Fri Dec 15 15:47:20 UTC 2023
Record UNII
4494BFP9LU
Record Status Validated (UNII)
Record Version
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Name Type Language
BUFOTENINE MONOOXALATE
Common Name English
BUFOTENINE HYDROGEN OXALATE
Common Name English
N,N-DIMETHYL-5-HYDROXYTRYPTAMINE MONOOXALATE
Systematic Name English
NSC-95093
Code English
INDOL-5-OL, 3-(2-(DIMETHYLAMINO)ETHYL)-, OXALATE (1:1) (SALT)
Systematic Name English
BUFOTENINE OXALATE (1:1)
Common Name English
Code System Code Type Description
FDA UNII
4494BFP9LU
Created by admin on Fri Dec 15 15:47:20 UTC 2023 , Edited by admin on Fri Dec 15 15:47:20 UTC 2023
PRIMARY
NSC
95093
Created by admin on Fri Dec 15 15:47:20 UTC 2023 , Edited by admin on Fri Dec 15 15:47:20 UTC 2023
PRIMARY
PUBCHEM
18078
Created by admin on Fri Dec 15 15:47:20 UTC 2023 , Edited by admin on Fri Dec 15 15:47:20 UTC 2023
PRIMARY
CAS
2963-79-3
Created by admin on Fri Dec 15 15:47:20 UTC 2023 , Edited by admin on Fri Dec 15 15:47:20 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY