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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
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
Aphrodisiacs past and present: a historical review.
2001 Oct
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
[Urine peptide patterns in children with milder types of autism].
2006 May 25
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:47:20 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:47:20 GMT 2023
PRIMARY
NSC
95093
Created by admin on Fri Dec 15 15:47:20 GMT 2023 , Edited by admin on Fri Dec 15 15:47:20 GMT 2023
PRIMARY
PUBCHEM
18078
Created by admin on Fri Dec 15 15:47:20 GMT 2023 , Edited by admin on Fri Dec 15 15:47:20 GMT 2023
PRIMARY
CAS
2963-79-3
Created by admin on Fri Dec 15 15:47:20 GMT 2023 , Edited by admin on Fri Dec 15 15:47:20 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY