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Arachidonoyl amide

Cayman Chemical Item Number 10007295

Arachidonamide; Arachidonic Acid amide (CAS 85146-53-8)

Arachidonoyl amide (CAS 85146-53-8)

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Description

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 USA 90 7656-7660 (1993).

2 Lang, W., Qin, C., Lin, S., et al. Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase. J Med Chem 42 896-902 (1999).

3 Piomelli, D., Beltramo, M., Glasnapp, S., et al. Structural determinants for recognition and translocation by the anandamide transporter. Proc Natl Acad Sci USA 96 5802-5807 (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 Lett 9 1151-1154 (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
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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 Chem 42 896-902 (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 USA 90 7656-7660 (1993).

Piomelli, D., Beltramo, M., Glasnapp, S., et al. Structural determinants for recognition and translocation by the anandamide transporter. Proc Natl Acad Sci USA 96 5802-5807 (1999).

Boger, D.L., Sato, H., Lerner, A.E., et al. Arachidonic acid amide inhibitors of gap junction cell-cell communication. Bioorg Med Chem Lett 9 1151-1154 (1999).

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Arachidonoyl amide is available in the following screening library:

Size Price Quantity Subtotal
5 mg $33.00 $0.00
10 mg $63.00 $0.00
25 mg $149.00 $0.00
50 mg $264.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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Arachidonoyl-N-methyl amide
Arachidonoyl-N,N-dimethyl amide
Arachidonoyl Serinol
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