N-Arachidonoylserotonin
Based on 1 Customer Validation
N-Arachidonoylserotonin (Arachidonyl serotonin) is a dual FAAH inhibitor and TRPV1 antagonist. N-Arachidonoylserotonin blocks Anandamide (HY-10863) hydrolysis, increases brain Anandamide levels, and promotes CB1 receptor signaling in the dorsal hippocampus. N-Arachidonoylserotonin normalizes HPA axis dysregulation, reduces plasma corticosterone levels, and induces anxiolytic-like effects in mice. N-Arachidonoylserotonin reverses behavioral despair, inhibits contextual fear memory retrieval, and produces dose-dependent antinociceptive effects in rodents. N-Arachidonoylserotonin inhibits intestinal motility. N-Arachidonoylserotonin can be used to study stress-related disorders, traumatic memory and related psychiatric disorders, pain, and intestinal motility disorders.
For research use only. We do not sell to patients.
- Purity: 99.11%
- CAS No.: 187947-37-1
- Formula: C30H42N2O2
- Molecular Weight:462.67
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Storage:
Solution, -20°C, 2 years
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Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
IC50 & Target
[3]|
CB1 |
hTRPV1 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HEK293 | IC50 |
0.27 μM
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Antagonism of capsaicin-induced intracellular Ca2+ elevation in HEK293 cells overexpressing human recombinant TRPV1 assessed by Fluo-3 fluorescence measurement.
Antagonism of capsaicin-induced intracellular Ca2+ elevation in HEK293 cells overexpressing human recombinant TRPV1 assessed by Fluo-3 fluorescence measurement.
|
18027904 |
In Vitro
N-Arachidonoylserotonin (30 min) inhibits FAAH in rat brain membranes with an IC50 of 8 μM[3].
N-Arachidonoylserotonin (2 h) is a potent antagonist of hTRPV1 in HEK293 cells, with an IC50 of 0.27 μM[3].
N-Arachidonoylserotonin (50 μM) does not inhibit MAGL in cell-free homogenates even at concentrations up to 50 μM[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
N-Arachidonoylserotonin (0.1-1 mg/kg; i.p.; 30 min before testing) inhibits the retrieval of contextual fear memory in mice[2].
N-Arachidonoylserotonin (1-20 mg/kg; i.p.; single dose; 30 min before labeling) inhibits intestinal motility in mice, with significant inhibition observed at doses of 10 mg/kg and above, and its effect is partially mediated by CB1 receptors[4].
N-Arachidonoylserotonin (15 mg/kg; i.p.; single dose) significantly inhibits intestinal motility in CB1 receptor-deficient mice, although this effect partially depends on CB1 receptors (42% inhibition in wild-type vs. 22% inhibition in mutant mice)[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Wistar rats (male, 220-240 g, 4 h restraint stress model)[1]
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Dosage:2.5 mg/kg; 5 mg/kg
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Administration:i.p.; three times at 24 h, 5 h, and 1 h prior to FST test or sacrifice
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Result:Reversed behavioral despair at 5 mg/kg, significantly decreasing immobility time and increasing climbing time.
Completely reversed stress-induced elevation of plasma corticosterone levels at 5 mg/kg.
Significantly increased BDNF mRNA and protein levels in the hippocampus at 2.5 mg/kg.
Increased BDNF mRNA levels and showed a trend for increase in protein levels at 5 mg/kg.
Significantly elevated anandamide (AEA) levels in the medial PFC at 2.5 mg/kg.
Did not significantly alter BDNF levels in non-stressed animals except for a decrease in mRNA expression at 5 mg/kg.
Caused a significant elevation of corticosterone levels in non-stressed rats at 2.5 mg/kg.
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Animal Model:Swiss mice (male, 25-30 g)[2]
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Dosage:0.1, 0.3, and 1.0 mg/kg (i.p.); 0.125, 0.25, and 0.5 nmol (intra-hippocampal)
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Administration:i.p. (30 min before test); intra-hippocampal (10 min before test)
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Result:Decreased freezing responses at all i.p. doses (0.1, 0.3, 1 mg/kg) during the expression of contextual fear memory.
Did not affect freezing when administered before conditioning at 0.3 mg/kg.
Decreased freezing at intra-hippocampal doses of 0.125 and 0.25 nmol, but the 0.5 nmol dose was ineffective.
Did not interfere with basal motor activity in the open field test.
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Animal Model:ICR mice (Male, 20-22 g)[4]
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Dosage:1, 2.5, 5, 10, 15, 20 mg/kg
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Administration:i.p.; single dose; 30 min before marker
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Result:Inhibited intestinal motility in a dose-dependent manner, with significant effects starting at 10 mg/kg.
Was significantly reduced by rimonabant (0.1 mg/kg) when combined with a 15 mg/kg dose.
Increased the inhibitory effect of anandamide and PEA at 5 mg/kg.
Increased small intestine levels of anandamide (1.85 pmol/mg lipid at 10 mg/kg vs. control 1.08 pmol/mg lipid) and 2-AG (2.30 nmol/mg lipid at 10 mg/kg vs. control 1.23 nmol/mg lipid) starting from 10 mg/kg.
Increased PEA levels at 15 mg/kg (9.36 pmol/mg lipid vs. control 6.60 pmol/mg lipid).
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Animal Model:CB1 receptor-deficient mice and wild-type littermates (Female, 19-22 g)[4]
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Dosage:15 mg/kg
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Administration:i.p.; single dose; 30 min before marker
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Result:Significantly reduced intestinal motility in CB1 receptor-deficient mice.
Induced a larger reduction in motility in wild-type mice (42% inhibition) compared to CB1 receptor-deficient mice (22% inhibition).
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Animal Model:FAAH-deficient mice (Female, 19-22 g)[4]
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Dosage:15 mg/kg
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Administration:i.p.; single dose; 30 min before marker
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Result:Significantly reduced intestinal motility in FAAH-deficient mice.
Chemical Information
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CAS No. 187947-37-1
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Appearance Liquid
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Molecular Weight 462.67
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Formula C30H42N2O2
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Color Colorless to light yellow
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SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCC1=CNC2=C1C=C(O)C=C2)=O
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Synonyms
Arachidonyl serotonin; AA-5-HT
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Solution, -20°C, 2 years
Purity & Documentation
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Data Sheet (272 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
[1]. Navarria A, et al. The dual blocker of FAAH/TRPV1 N-arachidonoylserotonin reverses the behavioral despair induced by stress in rats and modulates the HPA-axis. Pharmacological research. 2014 Sep;87:151-9. [Content Brief]
[3]. Ortar G, et al. New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. J Med Chem. 2007 Dec 27;50(26):6554-69. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
N-Arachidonoylserotonin Related Classifications
HY-103337 Related Classifications
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Keywords
- N-Arachidonoylserotonin
- 187947-37-1
- Arachidonyl serotonin
- AA-5-HT
- FAAH
- TRP Channel
- Cannabinoid Receptor
- human TRPV1
- dorsal hippocampus
- intestinal motility
- TRPV1 antagonist
- anandamide hydrolysis
- FAAH inhibitor
- rat FAAH
- plasma corticosterone levels
- HPA-axis deregulation
- CB1 receptor signaling
- Inhibitor
- inhibitor
- inhibit