| Identification | Back Directory | [Name]
ARACHIDONAMIDE | [CAS]
85146-53-8 | [Synonyms]
Arachidonoyl amide
Arachidonamide (20:4, n-6)
5,8,11,14-Eicosatetraenamide
5(Z),8(Z),11(Z),14(Z)-eicosatetraenamide
5,8,11,14-Eicosatetraenamide, (5Z,8Z,11Z,14Z)- | [Molecular Formula]
C20H33NO | [MDL Number]
MFCD00058606 | [MOL File]
85146-53-8.mol | [Molecular Weight]
303.48 |
| Chemical Properties | Back Directory | [Boiling point ]
462.9±34.0 °C(Predicted) | [density ]
0.908±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide | [form ]
Colorless oil. | [pka]
16.54±0.40(Predicted) |
| Hazard Information | Back Directory | [Uses]
Arachidonamide (20:4, n-6) is a weak cannabinoid CB1 and CB2 agonist. | [Definition]
ChEBI: Arachidonoyl amine is a primary fatty amide resulting from the formal condensation of the carboxy group of arachidonic acid with ammonia. It has a role as a cannabinoid receptor agonist. It is functionally related to an arachidonic acid. | [Biological Activity]
arachidonoyl amide is a cb1 receptor agonist [1]. the cannabinoid receptor type 1, abbreviated as cb1, is a g protein-coupled cannabinoid receptor expressed primarily in the central and peripheral nervous system. cb1 receptor has been implicated in maintaining the homeostasis in health and disease. overexpression of cb1 receptor has been found in human hepatocellular carcinoma tumor samples and other human prostate cancer cells [2].arachidonoyl amide is an analog of anandamide (aea) that lacks the hydroxyethyl moiety. it was hydrolyzed by faah more effectively than aea but exhibited significantly weaker binding to the human cb1 receptor with a ki of 9.6 μm [1]. arachidonoyl amide exhibited similar binding and translocation into cells via the aea transporter compared to aea. arachidonoyl amide inhibited [3h]-aea uptake into human astrocytoma cells with an ic50 of 9 μm [3]. | [storage]
Store at -20°C | [References]
[1] felder c c, briley e m, axelrod j, et al. anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction[j]. proceedings of the national academy of sciences, 1993, 90(16): 7656-7660.
[2] pertwee r g. the diverse cb1 and cb2 receptor pharmacology of three plant cannabinoids: δ9‐tetrahydrocannabinol, cannabidiol and δ9‐tetrahydrocannabivarin[j]. british journal of pharmacology, 2008, 153(2): 199-215.
[3] piomelli, d. ,beltramo, m.,glasnapp, s., et al. structural determinants for recognition and translocation by the anandamide transporter. proceedings of the national academy of sciences of the united states of america 96, 5802-5807 (1999). |
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