The Mass Spectrum of Cocaine

The current literature allows an analysis of the electron impact mass spectral fragmentations of cocaine (I). Using published high-resolution mass measurements as a reference, the mass spectra of several cocaine derivatives were examined—specifically those having individual functional group modifications at the nitrogen, alkyl ester group, aromatic ring and two-carbon bridge. Previously proposed major fragmentation pathways are supported by these data, and structures and mechanisms for lesser fragmentations are proposed. The relative intensities of the m/z 152 ions in the mass spectra of the cocaine diasteromers are rationalized based on these proposals.