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General chemical structure of N-acylethanolamines

An N-acylethanolamine (NAE) is a type of fatty acid amide formed when one of several types of acyl group is linked to the nitrogen atom of ethanolamine. These amides conceptually can be formed from a fatty acid and ethanolamine with the release of a molecule of water, but the known biological synthesis uses a specific phospholipase D to cleave the phospholipid unit from N-acylphosphatidylethanolamines.[1] Another route relies on the transesterification of acyl groups from phosphatidylcholine by an N-acyltransferase (NAT) activity.[citation needed] The suffixes -amine and -amide in these names each refer to the single nitrogen atom of ethanolamine that links the compound together: it is termed "amine" in ethanolamine because it is considered as a free terminal nitrogen in that subunit, while it is termed "amide" when it is considered in association with the adjacent carbonyl group of the acyl subunit. Names for these compounds may be encountered with either "amide" or "amine" varying by author.[2]

Examples of N-acylethanolamines include:[3]

These bioactive lipid amides are generated by the membrane enzyme NAPE-PLD, and natural bile acids regulate this essential process.[16]


  1. ^ Okamoto, Y.; Morishita, J.; Tsuboi, K.; Tonai, T.; Ueda, N. (2004). "Molecular characterization of a phospholipase D generating anandamide and its congeners". The Journal of Biological Chemistry. 279 (7): 5298–5305. doi:10.1074/jbc.M306642200. PMID 14634025.
  2. ^ For example, note synonyms in PubChem for oleoylethanolamine.
  3. ^ The list and references provided are based on background discussion in Okamoto Y, Morishita J, Tsuboi K, Tonai T, Ueda N (February 2004). "Molecular characterization of a phospholipase D generating anandamide and its congeners". J. Biol. Chem. 279 (7): 5298–305. doi:10.1074/jbc.M306642200. PMID 14634025.
  4. ^ WA Devane, L Hanus, A Breuer, RG Pertwee, LA Stevenson, G Griffin, D Gibson, A Mandelbaum, A Etinger, and R Mechoulam; Hanus; Breuer; Pertwee; Stevenson; Griffin; Gibson; Mandelbaum; Etinger; Mechoulam (1992). "Isolation and structure of a brain constituent that binds to the cannabinoid receptor". Science. 258 (5090): 1946–1949. Bibcode:1992Sci...258.1946D. doi:10.1126/science.1470919. PMID 1470919.CS1 maint: Multiple names: authors list (link)
  5. ^ Di Marzo (1998). "'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: biochemistry and possible physiopathological relevance". Biochimica et Biophysica Acta. 1392 (2–3): 153–75. doi:10.1016/s0005-2760(98)00042-3. PMID 9630590.
  6. ^ Di Marzo; De Petrocellis, L; Fezza, F; Ligresti, A; Bisogno, T (2002). "Anandamide receptors". Prostaglandins, Leukotrienes, and Essential Fatty Acids. 66 (2–3): 377–91. doi:10.1054/plef.2001.0349. PMID 12052051.
  7. ^ a b Calignano; La Rana, G; Giuffrida, A; Piomelli, D (1998). "Control of pain initiation by endogenous cannabinoids". Nature. 394 (6690): 277–81. Bibcode:1998Natur.394..277C. doi:10.1038/28393. PMID 9685157.
  8. ^ Lambert; Vandevoorde, S; Jonsson, KO; Fowler, CJ (2002). "The palmitoylethanolamide family: a new class of anti-inflammatory agents?". Current Medicinal Chemistry. 9 (6): 663–74. doi:10.2174/0929867023370707. PMID 11945130.
  9. ^ Rahman, Iffat Ara Sonia; Tsuboi, Kazuhito; Uyama, Toru; Ueda, Natsuo (2014-08-01). "New players in the fatty acyl ethanolamide metabolism". Pharmacological Research. Lipid amide signaling: regulation, physiological roles and pathological implications. 86: 1–10. doi:10.1016/j.phrs.2014.04.001. PMID 24747663.
  10. ^ a b Chapman, Kent; Venables, Barney; Markovic, Robert; Blair Jr, Raymond; Bettinger, Chris (1999). "N-Acylethanolamines in Seeds. Quantification of Molecular Species and Their Degradation upon Imbibition". Plant Physiology. 120 (4): 1157–1164. doi:10.1104/pp.120.4.1157. PMC 59349. PMID 10444099.
  11. ^ Motes, Christy M.; Pechter, Priit; Yoo, Cheol Min; Wang, Yuh-Shuh; Chapman, Kent D.; Blancaflor, Elison B. (2005-12-12). "Differential effects of two phospholipase D inhibitors, 1-butanol and N-acylethanolamine, on in vivo cytoskeletal organization and Arabidopsis seedling growth". Protoplasma. 226 (3–4): 109–123. doi:10.1007/s00709-005-0124-4. ISSN 0033-183X. PMID 16333570.
  12. ^ a b Rodríguez De Fonseca; Navarro, M; Gómez, R; Escuredo, L; Nava, F; Fu, J; Murillo-Rodríguez, E; Giuffrida, A; Loverme, J (2001). "An anorexic lipid mediator regulated by feeding". Nature. 414 (6860): 209–12. Bibcode:2001Natur.414..209R. doi:10.1038/35102582. PMID 11700558.
  13. ^ Kilaru, Aruna; Tamura, Pamela; Isaac, Giorgis; Welti, Ruth; Venables, Barney J.; Seier, Edith; Chapman, Kent D. (2012-06-07). "Lipidomic analysis of N-acylphosphatidylethanolamine molecular species in Arabidopsis suggests feedback regulation by N-acylethanolamines". Planta. 236 (3): 809–824. doi:10.1007/s00425-012-1669-z. ISSN 0032-0935. PMC 3579225. PMID 22673881.
  14. ^ Brown I, Cascio MG, Wahle KW, Smoum R, Mechoulam R, Ross RA, et al. (2010). "Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines". Carcinogenesis. 31 (9): 1584–91. doi:10.1093/carcin/bgq151. PMC 2930808. PMID 20660502.
  15. ^ Kim HY, Spector AA, Xiong ZM (2011). "A synaptogenic amide N-docosahexaenoylethanolamide promotes hippocampal development". Prostaglandins Other Lipid Mediat. 96 (1–4): 114–20. doi:10.1016/j.prostaglandins.2011.07.002. PMC 3215906. PMID 21810478.
  16. ^ Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G (Dec 2014). "Structure of Human N-Acylphosphatidylethanolamine-Hydrolyzing Phospholipase D: Regulation of Fatty Acid Ethanolamide Biosynthesis by Bile Acids". Structure. 23 (3): 598–604. doi:10.1016/j.str.2014.12.018. PMC 4351732. PMID 25684574.