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Arachidonoyl Ethanolamide Phosphate

Cayman Chemical Item Number 10180

AEA-P; Anandamide Phosphate (CAS 183323-26-4)

Arachidonoyl Ethanolamide Phosphate (CAS 183323-26-4)

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Description

Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid (CB) to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as Δ9-THC.1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).2 The phosphate ester of AEA, AEA-P, has been tested as a water soluble prodrug version of AEA in the treatment of C6 glioma cells in vivo. Here it acts with essentially the same potency as AEA.3 However, when tested for inhibition of AEA binding to isolated rat brain CB1 receptors, AEA-P is about 5-fold less potent as an agonist with a Ki of about 200 nM.4 The phosphate esters of AEA and its analogs are also structural variants of lysophosphatidic acid (LPA). However, the effects of AEA-P on the various LPA receptors have not been tested.

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 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 7656-7660 (1993).

3 Fowler, C.J., Jonsson, K., Andersson, A., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochem Pharmacol 66 757-767 (2003).

4 Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).

Synonyms
  • AEA-P
  • Anandamide Phosphate
Formal Name N-​(2-​(phosphonooxy)ethyl)-​5Z,​8Z,​11Z,​14Z-​eicosatetraenamide
CAS Number 183323-26-4
Molecular Formula C22H38NO5P
Formula Weight 427.5
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​NCCOP(=O)​(O)​O

Background Reading

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

Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).

Fowler, C.J., Jonsson, K., Andersson, A., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochem Pharmacol 66 757-767 (2003).

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 7656-7660 (1993).

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Arachidonoyl Ethanolamide Phosphate is available in the following screening library:

Size Price Quantity Subtotal
250 µg $19.00 $0.00
500 µg $36.00 $0.00
1 mg $68.00 $0.00
5 mg $304.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

1-Oleoyl Lysophosphatidic Acid (sodium salt)
Arachidonoyl Ethanolamide
Arachidoyl Ethanolamide Exclusive
R-1 Methanandamide Phosphate
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