An internal standard for the quantification of arachidonoyl ethanolamide
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Alternative(s)
10011178Arachidonoyl Ethanolamide-d4
Unlabeled Version(s)
90050Arachidonoyl Ethanolamide
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Arachidonoyl Ethanolamide-d8

Item No. 390050

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide-5,6,8,9,11,12,14,15-d8
CAS Number
924894-98-4
Synonyms
  • AEA-d8
  • Anandamide-d8
Molecular Formula
C22H29D8NO2
Formula Weight
355.6
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
1 mg/ml EtOH:PBS pH 7.2: can dilute 1:1.6 (>380 µg/ml)10 mg/ml EtOH:PBS pH 7.2: can dilute 1:1 (>5 mg/ml)100 ¿g/ml EtOH:PBS pH 7.2: can dilute 1:1.6 (>38 µg/ml)DMF: >10 mg/mlDMSO: >30 mg/mlEthanol: >100 mg/mlPBS pH 7.2: <100 µg/ml (from AEA)
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-/i6D,7D,9D,10D,12D,13D,15D,16D
InChi Key
LGEQQWMQCRIYKG-FBFLGLDDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    Arachidonoyl ethanolamide-d8 (AEA-8) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of AEA by GC- or LC-mass spectrometry. AEA is the ethanolamine amide of arachidonic acid, first isolated from porcine brain.1 It is an endogenous cannabinoid neurotransmitter that binds to both CB1 and CB2 receptors.2 AEA inhibits the specific binding of [3H]-HU-243 to synaptosomal membranes with a Ki value of 52 nM, compared to 46 nM for Δ9-THC.1

    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).

    Product Citations

    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).

    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).

    Lee, H.-C., Simon, G.M., and Cravatt, B.F. ABHD4 regulates multiple classes of N-acyl phospholipids in the mammalian central nervous system. Biochemistry 54(15), 2539-2549 (2015).

    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).