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Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase (FAAH). Arachidonoyl amide is an analog of AEA that lacks the hydroxyethyl moiety. It is hydrolyzed by FAAH more effectively than AEA but exhibits significantly weaker binding to the human CB1 receptor with a Ki of 9.6 µM.1,2 Arachidonoyl amide and AEA exhibit similar binding and translocation into cells via the AEA transporter. It inhibits [3H]-AEA uptake into human astrocytoma cells with an IC50 of 9 µM.3 Arachidonoyl amide also inhibits rat glial gap junction cell-cell communication by 90% at a concentration of 20 µM.4
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. Proc Natl Acad Sci USA907656-7660(1993).
2
Lang, W., Qin, C., Lin, S., et al. Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase. J Med Chem42896-902(1999).
3
Piomelli, D., Beltramo, M., Glasnapp, S., et al. Structural determinants for recognition and translocation by the anandamide transporter. Proc Natl Acad Sci USA965802-5807(1999).
4
Boger, D.L., Sato, H., Lerner, A.E., et al. Arachidonic acid amide inhibitors of gap junction cell-cell communication. Bioorg Med Chem Lett91151-1154(1999).
Synonyms
Arachidonamide
Arachidonic Acid amide
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
85146-53-8
Molecular Formula
C20H33NO
Formula Weight
303.5
Formulation
A solution in methyl acetate
Purity
>98%
Stability
1 year
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N
Background Reading
Lang, W., Qin, C., Lin, S., et al. Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase. J Med Chem42896-902(1999).
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. Proc Natl Acad Sci USA907656-7660(1993).
Piomelli, D., Beltramo, M., Glasnapp, S., et al. Structural determinants for recognition and translocation by the anandamide transporter. Proc Natl Acad Sci USA965802-5807(1999).
Boger, D.L., Sato, H., Lerner, A.E., et al. Arachidonic acid amide inhibitors of gap junction cell-cell communication. Bioorg Med Chem Lett91151-1154(1999).