Precursor of anandamide
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Glycerophospho-N-Arachidonoyl Ethanolamine

Item No. 10011347

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
mono(2,3-dihydroxypropyl)-mono[2-[[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]ethyl]ester phosphoric acid
CAS Number
201738-25-2
Synonyms
  • Glycerophosphoanandamide
  • Glycerophospho-Arachidonoyl Ethanolamide
  • GP-NArE
Molecular Formula
C25H44NO7P
Formula Weight
501.6
Purity
≥97%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCOP(=O)(O)OCC(O)CO
InChi Code
InChI=1S/C25H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(29)26-20-21-32-34(30,31)33-23-24(28)22-27/h6-7,9-10,12-13,15-16,24,27-28H,2-5,8,11,14,17-23H2,1H3,(H,26,29)(H,30,31)/b7-6-,10-9-,13-12-,16-15-
InChi Key
PAGKVQGBMADPCS-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    N-Acylated ethanolamines (NAE) are naturally-occurring lipids that have diverse bioactivities. The different types of NAE can be derived from glycerophospho-linked precursors by the activity of glycerophosphodiesterase 1 (GDE1).1 Glycerophospho-N-arachidonoyl ethanolamine is the precursor of arachidonoyl ethanolamide (AEA), also known as anandamide. AEA is an endogenous cannabinoid neurotransmitter that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.2 It 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.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Simon, G.M., and Cravatt, B.F. Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. The Journal of Biological Chemisty 283, 9341-9349 (2008).

    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. 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).