An inhibitor of AEA uptake
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OMDM-2

Item No. 10179

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1R)-2-hydroxy-1-[(4-hydroxyphenyl)methyl]ethyl]-9Z-octadecenamide
CAS Number
616884-63-0
Synonyms
  • (R)-N-oleoyl Tyrosinol
Molecular Formula
C27H45NO3
Formula Weight
431.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: MiscibleDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 30 mg/ml
λmax
225, 279 nm
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)N[C@@H](CO)Cc1ccc(O)cc1
InChi Code
InChI=1S/C27H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(31)28-25(23-29)22-24-18-20-26(30)21-19-24/h9-10,18-21,25,29-30H,2-8,11-17,22-23H2,1H3,(H,28,31)/b10-9-/t25-/m1/s1
InChi Key
ICDMLAQPOAVWNH-HAAQQRBASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Numerous analogs of arachidonoyl ethanolamide (AEA, anandamide; Item No. 90050) potentiate its biological activity.1 This potentiation is ascribed either to inhibition of AEA reuptake into neurons, or inhibition of fatty acid amide hydrolase (FAAH) within the neurons.2 OMDM-2 is an endocannabinoid analog specifically designed to be a potent and selective inhibitor of the cellular uptake of AEA.3 Structurally, OMDM-2 is the amide of (R)-tyrosinol with oleic acid. In RBL-2H3 cells, OMDM-2 inhibits the cellular uptake of tritiated AEA with an IC50 of 3 µM, with negligible effects on the CB1 receptor and VR1.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci. 65(6-7), 607-616 (1999).

    2. Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. The Journal of Biological Chemisty 276(10), 6967-6973 (2001).

    3. Ortar, G., Ligresti, A., De Petrocellis, L., et al. Novel selective and metabolically stable inhibitors of anandamide cellular uptake. Biochem. Pharmacol. 65(9), 1473-1481 (2003).