An endogenous anandamide metabolite
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Labeled Version(s)
9001413Prostaglandin D2 Ethanolamide-d4
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Prostaglandin D2 Ethanolamide

Item No. 12012

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-11-oxo-9α,15S-dihydroxy-prosta-5Z,13E-dien-1-amide
CAS Number
398138-28-8
Synonyms
  • PGD2-EA
  • Prostamide D2
Molecular Formula
C22H37NO5
Formula Weight
395.5
Purity
≥96%
Formulation (Request formulation change)
A 5 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 8.3 mg/mlDMSO: 8.3 mg/mlEthanol: 12.5 mg/mlPBS (7.2): 2.5 mg/ml
SMILES
O[C@@H](C1)[C@H](C/C=C\CCCC(NCCO)=O)[C@@H](/C=C/[C@@H](O)CCCCC)C1=O
InChi Code
InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-20,24-26H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-/m0/s1
InChi Key
KEYDJKSQFDUAGF-YIRKRNQHSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    500 µg

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    5 mg

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    Product Description

    Prostaglandin D2 ethanolamide (PGD2-EA) is a bioactive lipid produced by the sequential metabolism of anandamide (arachidonoyl ethanolamide) by cyclooxygenase (COX) enzymes, in particular by COX-2, and PGD synthase.1,2,3 The biosynthesis of PGD2-EA from anandamide can also be increased when anandamide metabolism is diminished by deletion of fatty acid amide hydrolase.4 PGD2-EA is inactive against recombinant prostanoid receptors, including the D prostanoid receptor.5 It increases the frequency of miniature inhibitory postsynaptic currents in primary cultured hippocampal neurons, an effect which is the opposite of that induced by anandamide.3. PGD2-EA also induces apoptosis in colorectal carcinoma cell lines.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

    2. Patsos, H.A., Hicks, D.J., Dobson, R.R.H., et al. The endogenous cannabinoid, anandamide, induces cell death in colorectal carcinoma cells: A possible role for cyclooxygenase 2. Gut 54(12), 1741-1750 (2005).

    3. Sang, N., Zhang, J., and Chen, C. PGE2 glycerol ester, a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neurons. J. Physiol. 572(Pt 3), 735-745 (2006).

    4. Weber, A., Ni, J., Ling, K.H.J., et al. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J. Lipid. Res. 45(4), 757-763 (2004).

    5. Matias, I., Chen, J., De Petrocellis, L., et al. Prostaglandin ethanolamides (prostamides): In vitro pharmacology and metabolism. J. Pharmacol. Exp. Ther. 309(2), 745-757 (2004).