A hydrolysis-resistant endocannabinoid analog that inhibits AEA cellular uptake
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AM1172

Item No. 10005223

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-5Z,8Z,11Z,14Z-eicosatetraenyl-4-hydroxy-benzamide
CAS Number
251908-92-6
Molecular Formula
C27H39NO2
Formula Weight
409.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 0.15 mg/ml
λmax
209, 253 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNC(=O)c1ccc(O)cc1
InChi Code
InChI=1S/C27H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-28-27(30)25-20-22-26(29)23-21-25/h6-7,9-10,12-13,15-16,20-23,29H,2-5,8,11,14,17-19,24H2,1H3,(H,28,30)/b7-6-,10-9-,13-12-,16-15-
InChi Key
XCWBOAHOJHPWLA-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $98

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    10 mg

    $186

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    50 mg

    $686

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    100 mg

    $1,077

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    Product Description

    Numerous analogs of arachidonoyl ethanolamide (AEA) potentiate its biological activity.1 This potentiation is ascribed either to inhibition of AEA reuptake into neurons, or inhibition of fatty acid amide hydrolase (FAAH) within the neurons.2 AM1172 is an endocannabinoid analog specifically designed to be a potent and selective inhibitor of AEA uptake that is resistant to FAAH hydrolysis.3 Structurally, AM1172 is the “reversed” isomer of AM404, constructed using arachidonyl amine; this may account for its metabolic stability. In mouse cortical neurons, AM1172 blocked the uptake of tritiated AEA with an EC50 of about 1.5 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci. 65(6-7), 607-616 (1999).

    2. Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. The Journal of Biological Chemisty 276(10), 6967-6973 (2001).

    3. Fegley, D., Kathuria, S., Mercier, R., et al. Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172. Proc. Natl. Acad. Sci. USA 101(23), 8756-8761 (2004).