BUFOTENINE

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 1A 58	Agonist 2,752
5-hydroxytryptamine receptor 2A 73	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275	Primary		Basic research	Unknown

PubMed

Show entries

Title	Date	PubMed
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.	1993 Aug	8394987
Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization.	1993 Mar	8450829
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.	1995 Dec 27	8549774
Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders.	1995 Nov 27	8747157
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	8967979

Showing 1 to 5 of 15 entries

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Patents

Sample Use Guides

In Vivo Use Guide

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.