N-Oleoyl Glycine

N-Oleoyl glycine is an endogenous lipoamino acid.^1,2 It increases triglyceride levels in 3T3-L1 adipocytes, an effect that can be reversed by SR141716 (rimonabant; Item No. 9000484), and selectively induces the expression of mRNA encoding the cannabinoid 1 (CB₁) receptor over mRNA encoding the CB₂ receptor in the same cells when used at a concentration of 50 µM.² N-Oleoyl glycine (1 µM) potentiates glycine-induced chloride currents in Xenopus oocytes expressing α1-, α1β-, α2-, α2β-, or α3 subunit-containing glycine receptors but not those expressing α3β subunit-containing glycine receptors.³ It increases c-Fos protein levels, intracellular calcium levels, and Agouti-related protein (AgRP) secretion in mHypoE-38 hypothalamic cells, effects that can be reversed by AM251 (Item No. 71670).⁴ N-Oleoyl glycine (60 mg/kg) reduces binge-like ethanol intake in alcohol-preferring mice without affecting total fluid intake and does not affect sucrose intake in the sucrose preference test in mice.⁵ It reduces balance impairments, thermal hyperalgesia, mechanical allodynia, aggressiveness, and immobility time in the tail suspension test, indicating antidepressant-like activity, in a mouse model of traumatic brain injury when administered at a dose of 50 mg/kg.⁶

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1. Bradshaw, H.B., Rimmerman, N., Hu, S.S.-J., et al. Chapter 8 Novel endogenous N-acyl glycines: Identification and characterization. Vitam. Horm. 81, 191-205 (2009).

2. Wang, S., Xu, Q., Shu, G., et al. N-Oleoyl glycine, a lipoamino acid, stimulates adipogenesis associated with activation of CB₁ receptor and Akt signaling pathway in 3T3-L1 adipocyte. Biochem. Biophys. Res. Commun. 466(3), 438-443 (2015).

3. Gallagher, C.I., Sheipouri, D., Shimmon, S., et al. Identification of N-acyl amino acids that are positive allosteric modulators of glycine receptors. Biochem. Pharmacol. 180, 114117 (2020).

4. Wu, J., Zhu, C., Yang, L., et al. N-oleoylglycine-induced hyperphagia is associated with the activation of agouti-related protein (AgRP) neuron by cannabinoid receptor type 1 (CB1R). J. Agric. Food. Chem. 65(5), 1051-1057 (2017).

5. Shahen-Zoabi, S., Smoum, R., Bingor, A., et al. N-oleoyl glycine and N-oleoyl alanine attenuate alcohol self-administration and preference in mice. Transl. Psychiatry 13(1), 273 (2023).

6. Piscitelli, F., Guida, F., Luongo, L., et al. Protective effects of N-oleoylglycine in a mouse model of mild traumatic brain injury. ACS Chem. Neurosci. 11(8), 1117-1128 (2020).

Gallagher, C.I., Sheipouri, D., Shimmon, S., et al. Identification of N-acyl amino acids that are positive allosteric modulators of glycine receptors. Biochem. Pharmacol. 180, 114117 (2020).