An endogenous cannabinoid
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Arachidonoyl Ethanolamide

Item No. 90050

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
94421-68-8
Synonyms
  • AEA
  • Anandamide
Molecular Formula
C22H37NO2
Formula Weight
347.5
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 30 mg/mlEthanol: 100 mg/mlEthanol:PBS (1:2): 5 mg/mlPBS pH 7.2: Slightly soluble*
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChi Code
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChi Key
LGEQQWMQCRIYKG-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $50

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    10 mg

    $95

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    50 mg

    $347

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    100 mg

    $644

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    Product Description

    Arachidonoyl ethanolamide (AEA) is the ethanolamine amide of arachidonic acid, originally isolated from porcine brain.1 AEA is an endogenous cannabinoid neurotransmitter that binds to both cannabinoid 1 (CB1) and CB2 receptors.2 AEA has Ki values ranging from 61 to 543 nM for CB1 receptors and from 279 to 1,940 nM for CB2 receptors.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090), 1946-1949 (1992).

    2. 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(16), 7656-7660 (1993).

    3. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 6(8), 635-664 (1999).

    Product Citations

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Sachdev, S., Vemuri, K., Banister, S.D., et al. In vitro determination of the CB1 efficacy of illicit synthetic cannabinoids. (2019).

    Drori, A., Permyakova, A., Hadar, R., et al. Cannabinoid-1 receptor regulates mitochondrial dynamics and function in renal proximal tubular cells. Diabetes Obes. Metab. 21(1), 146-159 (2019).

    Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS. J. Lipid. Res. 58(3), 615-624 (2017).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

    Karlsson, J., and Fowler, C.J. Inhibition of endocannabinoid metabolism by the metabolites of ibuprofen and flurbiprofen. PLoS One 9(7), e103589 (2014).

    Ribeiro, R., Wen, J., Li, S., et al. Involvement of ERK1/2, cPLA2 and NF-κB in microglia suppression by cannabinoid receptor agonists and antagonists. Prostaglandins Other Lipid Mediat. 100-101, (2013).

    Endsley, M.P., Thill, R., Choudhry, I., et al. Expression and function of fatty acid amide hydrolase in protstate cancer. Int. J. Cancer 123(6), 1318-1326 (2008).

    Horswill, J.G., Bali, U., Shaaban, S., et al. PSNCBAM-1, a novel allosteric antagonist at cannabinoid CB1 receptors with hypophagic effects in rats. Br. J. Pharmacol. 152(5), 805-814 (2007).

    Goparaju, S.K., Ueda, N., Yamaguchi, H., et al. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett. 422, 69-73 (1998).

    Deutsch, D.G., and Chin, S.A. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 46, 791-796 (1993).