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Anion Identification via Complexation with meso-octamethylcalix(4)pyrrole and Detection Using Electrospray Ionization Mass Spectrometry

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Abstract: 

The routine identification of controlled substances and adulterants during forensic chemistry analysis often involves the identification of counter ions or salt forms present in an exhibit. Here, the use of the compound meso-octamethylcalix(4)pyrrole (C4P) during salt-form identification analysis is presented. C4P is a commercially-available, anion-binding agent that can be reacted with a controlled substance or adulterant, resulting in the sequestration of anionic species, usually present as counter ions to the active ingredient. Formation of noncovalent complexes between the cyclic host C4P compound and anionic guests is investigated using electrospray ionization–mass spectrometry (ESI–MS). Complexes with chloride, bromide, iodide, nitrate, and acetate are readily observed and mass spectrometry analysis provides identification via molecular weight characterization. Chloride and bromide complexes are also characterized by the isotopic distribution of their molecular ions. Formation of host–guest complexes is not observed for sulfate and phosphate salts, presumably due to steric hindrance and energetically unfavorable conditions.
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Keywords: anion identification; drug analysis; electrospray ionization–mass spectrometry; forensic chemistry; forensic science; meso-octamethylcalix(4)pyrrole; noncovalent complex

Document Type: Research Article

Affiliations: U.S. Drug Enforcement Administration, Southwest Laboratory, 2815 Scott Street, Vista, CA 92081.

Publication date: March 1, 2010

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