N-Oleoyl Dopamine

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

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

2. Tseng, C.F., 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. (Tokyo) 40(2), 396-400 (1992).

3. Iwakami, S., Shibuya, M., Tseng, C.F., et al. Inhibition of arachidonate 5-lipoxygenase by phenolic compounds. Chem. Pharm. Bull. (Tokyo) 34(9), 3960-3963 (1986).

Matsumoto, G., Inobe, T., Amano, T., et al. N-Acyldopamine induces aggresome formation without proteasome inhibition and enhances protein aggregation via p62/SQSTM1 expression. Sci. Rep. 8(1), 9585 (2018).