The Lipid Library

Analysis of Anandamide and other Biologically Active Amides

Anandamide and other biologically active amides are currently attracting great interest because of their important biological functions. The following references were collected as part of our regular literature reviews for our own research purposes, and therefore reflect our personal research interests. We are sure that we have not covered the subject exhaustively, but we have done our best. We hope that this will be a good starting point at least. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. The survey covers the years 1990 onwards, and will be updated at approximately six-monthly intervals.

• Arai,Y., Fukushima,T., Shirao,M., Yang,X.J. and Imai,K. Sensitive determination of anandamide in rat brain utilizing a coupled-column HPLC with fluorimetric detection. Biomed. Chromatogr., 14, 118-124 (2000).
• Bazinet,R.P., Lee,H.J., Felder,C.C., Porter,A.C., Rapoport,S.I. and Rosenberger,T.A. Rapid high-energy microwave fixation is required to determine the anandamide (N-arachidonoylethanolamine) concentration of rat brain. Neurochem. Res., 30, 597-601 (2005).
• Bilyk,A., Piazza,G.J., Bistline,R.G. and Haas,M.J. Separation of cholesterol, and fatty acylglycerols, acids and amides by TLC. Lipids, 26, 405-406 (1991).
• Carbonare,M.D., Tonidandel,L., Berto,F., Luise,D., Mardegan,A., Giordano,G., Da Dalt,L., Guiotto,A., Battistin,L., Leon,A. and Traldi,P. Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determination. Rapid Commun. Mass Spectrom., 20, 353-360 (2006).
• Carpenter,T., Poore,D.D., Gee,A.J., Deshpande,P., Merkler,D.J. and Johnson,M.E. Use of reversed phase HP liquid chromatography to assay conversion of N-acylglycines to primary fatty acid amides by peptidylglycine-alpha-amidating monooxygenase. J. Chromatogr. B, 809, 15-21 (2004).
• Chapman,K.D., Venables,B.J., Diana,E.E. and Gross,G.W. Identification and quantification of neuroactive acylethanolamines in cottonseed processing fractions. J. Am. Oil Chem. Soc., 80, 223-229 (2003).
• Chou,H.J. Determination of diethanolamine and N-nitrosodiethanolamine in fatty acid diethanolamides. J. Ass. Off. Anal. Chem. Int., 81, 943-947 (1998).
• Cravatt,B.F., Lerner,R.A. and Boger,D.L. Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): a synthetic approach to the chemical analysis of trace quantities of a natural product. J. Am. Chem. Soc., 118, 580-590 (1996).
• Fontana,A., Dimarzo,V., Cadas,H. and Piomelli,D. Analysis of anandamide, an endogenous cannabinoid substance, and of other natural N-acylethanolamines. Prostaglandins Leukotrienes Essential Fatty Acids, 53, 301-308 (1995).
• Gee,A.J., Groen,L.A. and Johnson,M.E. Ion trap mass spectrometry of trimethylsilylamides following gas chromatography. J. Mass Spectrom., 35, 305-310 (2000).
• Gee,A.J., Groen,L.A. and Johnson,M.E. Determination of fatty acid amides as trimethylsilyl derivatives by gas chromatography with mass spectrometric detection. J. Chromatogr. A, 849, 541-552 (1999).
• Giuffrida,A. and Piomelli,D. Isotope dilution GC/MS determination of anandamide and other fatty acylethanolamides in rat blood plasma. FEBS Letts, 422, 373-376 (1998).
• Giuffrida,A., de Fonseca,F.R. and Piomelli,D. Quantification of bioactive acylethanolamides in rat plasma by electrospray mass spectrometry. Anal. Biochem., 280, 87-93 (2000).
• Glass,M., Hong,J.W., Sato,T.A. and Mitchell,M.D. Misidentification of prostamides as prostaglandins. J. Lipid Res., 46, 1364-1368 (2005).
• Gonthier,M.-P., Hoareau,L., Festy,F., Matias,I., Valenti,M., Bes-Houtmann,S., Rouch,C., Silva,C.R.-D., Chesne,S., d'Hellencourt,C.L.), Cesari,M., Di Marzo,V. and Roche,R. Identification of endocannabinoids and related compounds in human fat cells. Obesity, 15, 837-845 (2007).
• Gunstone,F.D. High-resolution 13C NMR spectra of long-chain acids, methyl esters, glycerol esters, nitriles, amides, alcohols and acetates. Chem. Phys. Lipids, 66, 189-193 (1993).
• Hamberger,A. and Stenhagen,G. Erucamide as a modulator of water balance: New function of a fatty acid amide. Neurochem. Res., 28, 177-185 (2003).
• Han,B.N., McPhail,K.L., Ligresti,A., Di Marzo,V. and Gerwick,W.H. Semiplenamides A-G, fatty acid amides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. J. Nat. Prod., 66, 1364-1368 (2003).
• Hanus,L.O., Fales,H.M., Spande,T.F. and Basile,A.S. A gas chromatographic-mass spectral assay for the quantitative determination of oleamide in biological fluids. Anal. Biochem., 270, 159-166 (1999).
• Hardison,S., Weintraub,S.T. and Giuffrida,A. Quantification of endocannabinoids in rat biological samples by GC/MS: Technical and theoretical considerations. Prostaglandins Other Lipid Mediators, 81, 106-112 (2006).
• Kaphalia,B.S.and Ansari,G.A.S. Single step thin-layer chromatographic method for quantitation of enzymatic formation of fatty acid anilides. J. Chromatogr. B, 705, 269-275 (1998).
• Kasai,H.F., Tsubuki,M. and Honda,T. Studies on high-energy collision-induced dissociation of endogenous cannabinoids: 2-arachidonoylglycerol and N-arachidonoylethanolamide in FAB-mass spectrometry. Anal. Sci., 22, 921-930 (2006).
• Kasai,H.F., Tsubuki,M., Takahashi,K., Honda,T. and Ueda,H. Analyses of anandamide and endocannabinoid-like compounds using collision-induced dissociation in fast atom bombardment ionization-mass spectrometry and gas chromatography/chemical ionization-mass spectrometry. Anal. Sci., 19, 1593-1598 (2003).
• Kingsley,P.J. and Marnett,L.J. Analysis of endocannabinoids by Ag+ coordination tandem mass spectrometry. Anal. Biochem., 314, 8-15 (2003).
• Kingsley,P.J. and Marnett,L.J. LC-MS-MS analysis of neutral eicosanoids. Methods Enzymol., 433, 91-112 (2007).
• Koga,D., Santa,T., Fukushima,T., Homma,H. and Imai,K. Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric determination of anandamide and its analogs in rat brain and peripheral tissues. J. Chromatogr. B, 690, 7-13 (1997).
• Koga,D., Santa,T., Hagiwara,K., Imai,K., Takizawa,H., Nagano,T., Hirobe,M., Ogawa,M., Sato,T., Inoue,K. and Kudo,I. High-performance liquid chromatography and fluorometric detection of arachidonylethanolamide (anandamide) and its analogs, derivatized with 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCL). Biomed. Chromatogr., 9, 56-57 (1995).
• Madl,T. and Mittelbach,M. Quantification of primary fatty acid amides in commercial tallow and tallow fatty acid methyl esters by HPLC-APCI-MS. Analyst, 130, 565-570 (2005).
• Markey,S.P., Dudding,T. and Wang,T.C.L. Base- and acid-catalyzed interconversions of O-acyl-and N-acyl-ethanolamines: a cautionary note for lipid analyses. J. Lipid Res., 41, 657-662 (2000).
• McIlhinney,R.A. Acylated proteins: identification of the attached fatty acids and their linkages. In: 'CRC Handbook of Chromatography. Analysis of Lipids'. (ed. K.D. Mukherjee & N. Weber, CRC Press, Boca Raton), pp. 241-248 (1993).
• Moldovan,Z., Maldonado,C. and Bayona,J.M. Electron ionization and positive-ion chemical ionization mass spectra of N-(2-hydroxyethyl)alkylamides. Rapid Commun. Mass Spectrom., 11, 1077-1082 (1997).
• Muccio,G.G. and Stella,N. An optimized GC-MS method detects nanomolar amounts of anandamide in mouse brain. Anal. Biochem., 373, 220-228 (2008).
• Nichols,K.K., Ham,B.M., Nichols,J.J., Ziegler,C. and Green-Church,K.B. Identification of fatty acids and fatty acid amides in human meibomian gland secretions. Invest. Ophthalmol. Vis. Sci., 48, 34-39 (2007).
• Obata,T., Sakurai,Y., Kase,Y., Tanifuji,Y. and Horiguchi,T. Simultaneous determination of endocannabinoids (arachidonylethanolamide and 2-arachidonylglycerol) and isoprostane (8-epiprostaglandin F2 alpha) by gas chromatography-mass spectrometry-selected ion monitoring for medical samples. J. Chromatogr. B, 792, 131-140 (2003).
• Richardson,D., Ortori,C.A., Chapman,V., Kendall,D.A. and Barrett,D.A. Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Anal. Biochem., 360, 216-226 (2007).
• Rubino,F.M., Zecca,L. and Sonnino,S. Characterization of a complex mixture of ceramides by fast atom bombardment and precursor and fragment analysis mass spectrometry. Biol. Mass Spectrom., 23, 82-90 (1994).
• Saghatelian,A., Trauger,S.A., Want,E.J., Hawkins,E.G., Siuzdak,G. and Cravatt,B.F. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry, 43, 14332-14339 (2004).
• Sarchielli,P., Pini,L.A., Coppola,F., Rossi,C., Baldi,A., Mancini,M.L. and Calabresi,P. Endocannabinoids in chronic migraine: CSF findings suggest a system failure. Neuropsychopharmacology, 32, 1384-1390 (2007).
• Schmid,P.C., Krebsbach,R.J., Perry,S.R., Dettmer,T.M., Maasson,J.L. and Schmid,H.H.O. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Letts, 375, 117-120 (1995).
• Schmid,P.C., Schwartz,K.D., Smith,C.N., Krebsbach,R.J., Berdyshev,E.V. and Schmid,H.H.O. A sensitive endocannabinoid assay. The simultaneous analysis of N-acylethanolamines and 2-monoacylglycerols. Chem. Phys. Lipids, 104, 185-191 (2000).
• Schmid,P.C., Wold,L.E., Krebsbach,R.J., Berdyshev,E.V. and Schmid,H.H.O. Anandamide and other N-acylethanolamines in human tumorsLipids, 37, 907-912 (2002).
• Schmidt,A., Brune,K. and Hinz,B. Determination of the endocannabinoid anandamide in human plasma by high-performance liquid chromatography. Biomed. Chromatogr., 20, 336-342 (2006).
• Schreiber,D., Harlfinger,S., Nolden,B.M., Gerth,C.W., Jaehde,U., Schoemig,E., Klosterkoetter,J., Giuffrida,A., Astarita,G., Piomelli,D and Leweke,F.M. Determination of anandamide and other fatty acyl ethanolamides in human serum by electrospray tandem mass spectrometry. Anal. Biochem., 361, 162-168 (2007).
• Serhan,C.N. Mediator lipidomics. Prostaglandins Other Lipid Mediators, 77, 4-14 (2005).
• Sultana,T. and Johnson,M.E. Sample preparation and gas chromatography of primary fatty acid amides. J. Chromatogr. A, 1101, 278-285 (2006).
• Tan,B., Bradshaw,H.B., Rimmerman,N., Srinivasan,H., Yu,Y.W., Krey,J.F., Monn,M.F., Chen,J..S.-C., Hu,S..S.-J., Pickens,S.R. and Walker,J.M. Targeted lipidomics: discovery of new fatty acyl amides. AAPS J., 8, E461-E465 (2006).
• Thumser,A.E.A., Voysey,J. and Wilton,D.C. A fluorescence displacement assay for the measurement of arachidonoyl ethanolamide (anandamide) and oleoyl amide (octadecenoamide) hydrolysis. Biochem. Pharmacol., 53, 433-435 (1997).
• Vietzke,J.P., Strassner,M. and Hintze,U. Separation and identification of ceramides in the human stratum corneum by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry and electrospray multiple-stage mass spectrometry profiling. Chromatographia, 50, 15-20 (1999).
• Vogeser,M., Hauer,D., Azad,S.C., Huber,E., Storr,M. and Schelling,G. Release of anandamide from blood cells. Clin. Chem. Lab. Med., 44, 488-491 (2006).
• Vosmann,K., Klein,E. and Weber,N. Reaction of fatty acid amides and ethanolamides with trimethylsulfonium hydroxide. J. Chromatogr. A, 773, 239-247 (1997).
• Walker,J.M., Krey,J.F., Chen,J.S., Vefring,E., Jahnsen,J.A., Bradshaw,H. and Huang,S.M. Targeted lipidomics: fatty acid amides and pain modulation. Prostaglandins Other Lipid Mediators, 77, 35-45 (2005).
• Wang,Y., Liu,Y., Ito,Y., Hashiguchi,T., Kitajima,I., Yamakuchi,M., Shimizu,H., Matsuo,S., Imaizumi,H. and Maruyama,I. Simultaneous measurement of anandamide and 2-arachidonoylglycerol by polymyxin B-selective adsorption and subsequent high-performance liquid chromatography analysis: Increase in endogenous cannabinoids in the sera of patients with endotoxic shock. Anal. Biochem., 294, 73-82 (2001).
• Weber,A., Ni,J.S., Ling,K.H.J., Acheampong,A., Tang-Liu,D.D.S., Burk,R., Cravatt,B.F. and Woodward,D. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J. Lipid Res., 45, 757-763 (2004).
• Williams,J., Pandarinathan,L., Wood,J., Vouros,P. and Makriyannis,A. Endocannabinoid metabolomics: A novel liquid chromatography-mass spectrometry reagent for fatty acid analysis. AAPS J., 8, E655-E660 (2006).
• Williams,J., Wood,J., Pandarinathan,L., Karanian,D.A., Bahr,B.A., Vouros,P. and Makriyannis,A. Quantitative method for the profiling of the endocannabinoid metabolome by LC-atmospheric pressure chemical ionization-MS. Anal. Chem., 79, 5582-5593 (2007).
• Yagen,B. and, Burstein,S. Novel and sensitive method for the detection of anandamide by the use of its dansyl derivative. J. Chromatogr. B, 740, 93-99 (2000).
• Yang,H.Y.T., Karoum,F., Felder,C., Badger,H., Wang,T.C.L. and Markey,S.P. GC/MS analysis of anandamide and quantification of N-arachidonoylphosphatidylethanolamides in various brain regions, spinal cord, testis, and spleen of the rat. J. Neurochem., 72, 1959-1968 (1999).

Updated: 1/3/2008 Credits/disclaimer	Scottish Crop Research Institute (and MRS Lipid Analysis Unit), Invergowrie, Dundee (DD2 5DA), Scotland