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
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24650558
Curator's Comment: referenced study was conducted in rat
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q64264 Gene ID: 15550.0 Gene Symbol: Htr1a Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446678 |
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Target ID: P35363 Gene ID: 15558.0 Gene Symbol: Htr2a Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446678 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase. | 1993 Aug |
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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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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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Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. | 2001 Jul-Sep |
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Aphrodisiacs past and present: a historical review. | 2001 Oct |
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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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Sudden death associated with intravenous injection of toad extract. | 2009 Jul 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446678
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2706543
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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Classification Tree | Code System | Code | ||
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DEA NO. |
7433
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WIKIPEDIA |
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
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)