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
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q64264 Gene ID: 15550.0 Gene Symbol: Htr1a Target Organism: Mus musculus (Mouse) |
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Target ID: P35363 Gene ID: 15558.0 Gene Symbol: Htr2a Target Organism: Mus musculus (Mouse) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization. | 1993 Mar |
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| Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization. | 1995 Dec 27 |
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| Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. | 1995 Nov 27 |
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| 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 |
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| 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 |
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| Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. | 1997 Apr-May |
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| Altered consciousness states and endogenous psychoses: a common molecular pathway? | 1997 Dec 19 |
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| Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. | 2001 |
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| 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 |
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| Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. | 2001 Jul-Sep |
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| RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity. | 2001 Sep |
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| Indolealkylamines: biotransformations and potential drug-drug interactions. | 2008 Jun |
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| Elevated urine levels of bufotenine in patients with autistic spectrum disorders and schizophrenia. | 2010 |
Sample Use Guides
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
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.
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DEA NO. |
7433
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TiHKAL
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89593
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DB01445
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10257
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BUFOTENIN
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0A31347TZK
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DTXSID0048894
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m2753
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207-667-9
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3210
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487-93-4
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ACTIVE MOIETY
METABOLITE (PARENT)
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
