N-Oleoyl dopamine (ODA) is a selective, endogenous vanilloid receptor 1 (VR1) agonist isolated from bovine brain.¹ Structurally, it is the amide of oleic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. ODA binds to the human recombinant VR1 with a K_i of 36 nM making it equipotent to capsaicin and slightly more potent than N-arachidonoyl dopamine in this assay.¹ It causes hyperalgesia and nocifensive behavior that is blocked by the VR1 antagonist iodo-resiniferatoxin. ODA is selective for VR1 based on observations that it has weak affinity for the rat CB₁ receptor (K_i of 1.6 µM) and is a very weak inhibitor of FAAH. ODA is also a potent inhibitor of 5-lipoxygenase from rat basophilic leukemia-1 (RBL-1) cells, with a IC₅₀ of 7.5 nM.^2,3

1 Chu, C.J., Huang, S.M., De Petrocellis, L., et al. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. J Biol Chem 278(16) 13633-13639 (2003).

2 Tseng, C., Iwakami, S., Mikajiri, A., et al. Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives. Chem Pharm Bull 40(2) 396-400 (1992).

3 Iwakami, S., Shibuya, M., Tseng, C., et al. Inhibition of arachidonate 5-lipoxygenase by phenolic compounds. Chem Pharm Bull 34 3960-3963 (1986 Jun 30).

Tseng, C., Iwakami, S., Mikajiri, A., et al. Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives. Chem Pharm Bull 40(2) 396-400 (1992).

Chu, C.J., Huang, S.M., De Petrocellis, L., et al. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. J Biol Chem 278(16) 13633-13639 (2003).

Iwakami, S., Shibuya, M., Tseng, C., et al. Inhibition of arachidonate 5-lipoxygenase by phenolic compounds. Chem Pharm Bull 34 3960-3963 (1986 Jun 30).

N-Oleoyl Dopamine is available in the following screening library:

• Bio-active Lipid I Screening Library (96-Well)