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
| 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 |
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. | 2010-10 |
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| Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics. | 2010-07-01 |
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| Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds. | 2010 |
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| Elevated urine levels of bufotenine in patients with autistic spectrum disorders and schizophrenia. | 2010 |
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| Sudden death associated with intravenous injection of toad extract. | 2009-07-01 |
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| Early onset muscarinic manifestations after wild mushroom ingestion. | 2008-09 |
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| Indolealkylamines: biotransformations and potential drug-drug interactions. | 2008-06 |
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| Liquid chromatography-tandem mass spectrometry method for the simultaneous analysis of multiple hallucinogens, chlorpheniramine, ketamine, ritalinic acid, and metabolites, in urine. | 2007-10 |
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| Lack of bufadienolides in the skin secretion of red bellied toads, Melanophryniscus spp. (Anura, Bufonidae), from Uruguay. | 2007-01 |
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| Urinary excretion of dietary contaminants in horses. | 2006-08 |
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| Identification of 5-hydroxy-tryptamine (bufotenine) in takini (Brosimumacutifolium Huber subsp. acutifolium C.C. Berg, Moraceae), a shamanic potion used in the Guiana Plateau. | 2006-06-30 |
|
| [Urine peptide patterns in children with milder types of autism]. | 2006-05-25 |
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| New indole N-oxide alkaloids from Evodia fargesii. | 2006-02 |
|
| Occurrence of bufotenin in the Osteocephalus genus (Anura: Hylidae). | 2005-09-15 |
|
| Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues. | 2005 |
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| Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys. | 2003-07 |
|
| Composition of indolealkylamines of Bufo rubescens cutaneous secretions compared to six other Brazilian bufonids with phylogenetic implications. | 2003-04 |
|
| Molecular basis of partial agonism: orientation of indoleamine ligands in the binding pocket of the human serotonin 5-HT2A receptor determines relative efficacy. | 2003-01 |
|
| 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. | 2002-04-05 |
|
| Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. | 2001-11-23 |
|
| Aphrodisiacs past and present: a historical review. | 2001-10 |
|
| RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity. | 2001-09 |
|
| 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. | 2001-01 |
|
| Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. | 2001 |
|
| Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. | 1999-04 |
|
| Altered consciousness states and endogenous psychoses: a common molecular pathway? | 1997-12-19 |
|
| Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. | 1997-04-01 |
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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. | 1996-12 |
|
| 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. | 1996-06-21 |
|
| Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization. | 1995-12-27 |
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| Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. | 1995-11-27 |
|
| Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase. | 1993-08 |
|
| Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization. | 1993-03 |
|
| A test of the transmethylation hypothesis in acute schizophrenic patients. | 1975-10 |
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.
| Substance Class |
Chemical
Created
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admin
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Mon Mar 31 19:21:43 GMT 2025
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Mon Mar 31 19:21:43 GMT 2025
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| Record UNII |
0A31347TZK
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| Record Status |
Validated (UNII)
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7433
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TiHKAL
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DB01445
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10257
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BUFOTENIN
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m2753
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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PARENT -> METABOLITE ACTIVE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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