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OMDM-2

Cayman Chemical Item Number 10179

(R)-N-oleoyl Tyrosinol

OMDM-2

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Description

Numerous analogs of arachidonoyl ethanolamide1 (AEA, anandamide) potentiate its biological activity. 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

1 Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci 65 607-616 (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. J Biol Chem 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 1473-1481 (2003).

Synonyms
  • (R)-N-oleoyl Tyrosinol
Formal Name (R)-​N-​(1-​(4-​hydroxyphenyl)-​2-​hydroxyethyl)oleamide
Molecular Formula C27H45NO3
Formula Weight 431.7
Formulation A crystalline solid
Purity ≥98%
λmax 225, 279 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCC/C=C\CCCCCCCC(=O)​N[C@@H]​(CO)​Cc1ccc(O)​cc1

Background Reading

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. J Biol Chem 276(10) 6967-6973 (2001).

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

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

OMDM-2 is available in the following screening library:

Size Price Quantity Subtotal
1 mg $14.00 $0.00
5 mg $63.00 $0.00
10 mg $112.00 $0.00
50 mg $490.00 $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

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