Mass spectral similarity mapping applied to fentanyl analogs

Silverstein, 1962, Spectrometric identification of organic compounds, J. Chem. Educ., 39, 546, 10.1021/ed039p546 Creek, 2014, Metabolite identification: are you sure? And how do your peers gauge your confidence?, Metabolomics, 10, 350, 10.1007/s11306-014-0656-8 Rivier, 2003, Criteria for the identification of compounds by liquid chromatography-mass spectrometry and liquid chromatography-multiple mass spectrometry in forensic toxicology and doping analysis, Anal. Chim. Acta, 492, 69, 10.1016/S0003-2670(03)00889-4 Schymanski, 2014, Identifying small molecules via high resolution mass spectrometry: communicating confidence, Environ. Sci. Technol., 48, 2097, 10.1021/es5002105 Stein, 1994, Optimization and testing of mass spectral library search algorithms for compound identification, J. Am. Soc. Mass Spectrom., 5, 859, 10.1016/1044-0305(94)87009-8 Moorthy, 2017, Combining fragment-ion and neutral-loss matching during mass spectral library searching: a new general purpose algorithm applicable to illicit drug identification, Anal. Chem., 89, 13261, 10.1021/acs.analchem.7b03320 Burke, 2017, The hybrid search: a mass spectral library search method for discovery of modifications in proteomics, J. Proteome Res., 16, 1924, 10.1021/acs.jproteome.6b00988 Kim, 2012, A method of finding optimal weight factors for compound identification in gas chromatography–mass spectrometry, Bioinformatics, 28, 1158, 10.1093/bioinformatics/bts083 Koo, 2013, Comparative analysis of mass spectral matching-based compound identification in gas chromatography-mass spectrometry, J. Chromatogr. A, 1298, 132, 10.1016/j.chroma.2013.05.021 Stein, 1999, An integrated method for spectrum extraction and compound identification from gas chromatography/mass spectrometry data, J. Am. Soc. Mass Spectrom., 10, 770, 10.1016/S1044-0305(99)00047-1 Stein, 1994, Estimating probabilities of correct identification from results of mass spectral library searches, J. Am. Soc. Mass Spectrom., 5, 316, 10.1016/1044-0305(94)85022-4 Mclafferty, 1998, Comparison of algorithms and databases for matching unknown mass spectra, J. Am. Soc. Mass Spectrom., 9, 92, 10.1016/S1044-0305(97)00235-3 Wei, 2014, Compound identification in GC-MS by simultaneously evaluating the mass spectrum and retention index, Analyst, 139, 2507, 10.1039/C3AN02171H Remoroza, 2018, Creating a mass spectral reference library for oligosaccharides in human milk, Anal. Chem., 90, 8977, 10.1021/acs.analchem.8b01176 Blaženović, 2018, Effects of gut bacteria depletion and high-Na + and low-K + intake on circulating levels of biogenic amines, Mol. Nutr. Food Res., 63, 1801184, 10.1002/mnfr.201801184 Barupal, 2018, Integrating bioinformatics approaches for a comprehensive interpretation of metabolomics datasets, Curr. Opin. Biotechnol., 54, 1, 10.1016/j.copbio.2018.01.010 Blaženović, 2018, Software tools and approaches for compound identification of LC-MS/MS data in metabolomics, Metabolites, 8, 31, 10.3390/metabo8020031 Jang, 2019, LC–MS/MS software for screening unknown erectile dysfunction drugs and analogs: artificial neural network classification, peak-count scoring, simple similarity search, and hybrid similarity search algorithms, Anal. Chem., 91, 9119, 10.1021/acs.analchem.9b01643 Burke, 2019, FDR estimation for hybrid mass spectral library search identifications in bottom-up proteomics, J. Proteome Res., 18, 3233, 10.1021/acs.jproteome.8b00863 Cooper, 2019, Hybrid search: a method for identifying metabolites absent from tandem mass spectrometry libraries, Anal. Chem., 91, 13924, 10.1021/acs.analchem.9b03415 Humphreys, 2018, Opiate of the masses: stopping an American epidemic from going global, Foreign Aff., 97, 118 Cooper, 1986, Identification of fentanyl derivatives, J. Forensic Sci., 31, 511, 10.1520/JFS12283J Misailidi, 2018, Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil, Forensic Toxicol., 36, 12, 10.1007/s11419-017-0379-4 Morrow, 2019, The opioid epidemic: moving toward an integrated, holistic analytical response, J. Anal. Toxicol., 43, 1, 10.1093/jat/bky049 Federal Register, Vol. 83, No. 25, February 6, 2018, pp. 5188–5192. SWGDRUG Mass Spectral Library Version 3.3, URL https://swgdrug.org. Borg, 2013 Kearsley, 1998, The solution of the metric STRESS and SSTRESS problems in multidimensional scaling using Newton’s method, Comput. Stat., 13, 369 Buja, 2008, Data visualization with multidimensional scaling, J. Comput. Graph. Stat., 17, 444, 10.1198/106186008X318440 Agarwal, 2007, Generalized non-metric multidimensional scaling, J. Mach. Learn. Res., 2, 11 Wallace, 2017, Mass spectral library quality assurance by inter-library comparison, J. Am. Soc. Mass Spectrom., 733, 10.1007/s13361-016-1589-4 Venables, 2002 R Core Team, 2018 Bodnar Willard, 2014, Statistical approach to establish equivalence of unabbreviated mass spectra, Rapid Commun. Mass Spectrom., 28, 83, 10.1002/rcm.6759 Bodnar Willard, 2017, Statistical comparison of mass spectra for identification of amphetamine-type stimulants, Forensic Sci. Int., 270, 111, 10.1016/j.forsciint.2016.11.013 Bonetti, 2018, Mass spectral differentiation of positional isomers using multivariate statistics, Forensic Chem., 9, 50, 10.1016/j.forc.2018.06.001 Harris, 2014, Fragmentation differences in the EI spectra of three synthetic cannabinoid positional isomers: JWH-250, JWH-302, and JWH-201, Int. J. Mass Spectrom., 368, 23, 10.1016/j.ijms.2014.05.005 Mayer, 2016, Chemiacl attribution of fentanyl using multivariate statistical analysis of orthogonal mass spectral data, Anal. Chem., 88, 4303, 10.1021/acs.analchem.5b04434 Davidson, 2019, The differentiation of 2,5-dimethoxy-N-N(N-methoxybenzyl)phenethylamine (NBOMe) isomers using GC retention indicies and multivariate analysis of ion abundances in electron ionization mass spectra, Forensic Chem., 14, 10.1016/j.forc.2019.100160