An irreversible COX-2 inhibitor
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N-(3-hydroxyphenyl)-Arachidonoyl amide

Item No. 10007704

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(3-hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
183718-75-4
Synonyms
  • 3-HPA
  • 3-HPAA
Molecular Formula
C26H37NO2
Formula Weight
395.6
Purity
≥98%
Formulation
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.3 mg/ml
λmax
246, 282 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)Nc1cccc(O)c1
InChi Code
InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-26(29)27-24-20-19-21-25(28)23-24/h6-7,9-10,12-13,15-16,19-21,23,28H,2-5,8,11,14,17-18,22H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-
InChi Key
ZWSMMQKRRVRXBA-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $43

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    10 mg

    $81

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    50 mg

    $333

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    100 mg

    $580

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    Product Description

    N-(3-hydroxyphenyl)-Arachidonoyl amide (3-HPA) is an analog of AM404 (N-(4-hydroxyphenyl)-arachidonoyl amide), which is a selective inhibitor of carrier-mediated transport of arachidonoyl ethanolamide (AEA).1 3-HPA is metabolized by both cyclooxygenase-1 (COX-1) and COX-2 and was found to selectively and irreversibly inhibit COX-2 with an IC50 value of 2 µM.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beltramo, M., Stella, N., Calignano, A., et al. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 277(5329), 1094-1097 (1997).

    2. Turman, M.V., Kinsgley, P.J., and Marnet, L.J. 9th International conference on eicosanoids and other bioactive lipids in cancer, inflammation, and related diseases. (2005).