220556-74-1

N-Acyl ethanolamines have diverse biological actions that are strongly affected by the associated acyl group. Linoleoyl ethanolamide (LOEA) has potential signaling roles in aging and neurological functioning.^1,2 LOEA has a weak affinity for cannabinoid (CB) receptors (K_i = 10, 25 μM for CB₁, CB₂, respectively). ³ Although hydrolized by fatty acid amide hydrolase (FAAH; K_i = 9 μM) it also inhibits FAAH and inhibits voltage-gated K⁺ channels.^3,4,5,6 (R)-(+)-Linoleyl-1’-hydroxy-2’-propylamide is a homolog of LOEA, characterized by the addition of an (R)-α-methyl group at the methylene carbon adjacent to the amide nitrogen. A similar modification of arachidonoyl ethanolamide to produce R-1 methanandamide imparts higher affinity for the CB receptor as well as improved metabolic stability.⁷ The physiological actions of this compound have not been evaluated.

(R)-(+)-Linoleyl-1'-Hydroxy-2'-Propylamide (Compound 19) is the analogue of endogenous cannabinoid receptor ligand Anandamide (HY-10863). (R)-(+)-Linoleyl-1'-Hydroxy-2'-Propylamide shows weak binding affinity for CB1 and CB2 with Kis of both 21 μM[1].

CB1: 21 μM (Ki); CB2: 21 μM (Ki)

Store at -20°C

1. Lucanic, M., Held, J.M., Vantipalli, M.C., et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans Nature 473(7346),226-229(2011).
2. Watanabe, K., Matsunaga, T., Nakamura, S., et al. Pharmacological effects in mice of anandamide and its related fatty acid ethanolamides, and enhancement of cataleptogenic effect of anandamide by phenylmethylsulfonyl fluoride Biol. Pharm. Bull. 22(4),366-370(1999).
3. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB₁ and CB₂ cannabinoid receptors and metabolic stability J. Med. Chem. 41(27),5353-5361(1998).
4. Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain J. Biol. Chem. 273,32332-32339(1998).
5. Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes J. Biol. Chem. 272,3315-3323(1997).
6. Poling, J.S., Rogawski, M.A., Salem, N., Jr., et al. Anadamide, an endogenous cannabinoid, inhibits shaker-related voltage-gated K⁺ channels Neuropharmacology 35(7),983-991(1996).
7. Abadji, V., Lin, S., Taha, G., et al. (R)-Methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability J. Med. Chem. 37(12),1889-1893(1994).