Date of Award

Spring 2013

Degree Name

Bachelor of Science

Major

Neurochemistry

First Advisor

Janet Morrison

Second Advisor

David Henderson

Third Advisor

William Church

Abstract

The recent emergence and widespread abuse of new classes of compounds on the designer drug market as “legal” alternatives to scheduled drugs such as Ecstasy has prompted interest in the development of analytical methods for their detection and characterization. Synthetic cathinones, which are structurally similar to amphetamines, are commonly advertised as a “legal highs” or “herbal highs,” and are marketed under names such as “bath salts” and “plant food.” To avoid drug abuse legislation, a “not for human consumption” warning is typically printed on the label. Their ready availability on the Internet and in “head” shops, convenience stores, and even gas stations has spurred the popularity and abuse of these drugs for their euphoric/stimulant effects. The dramatic increase since 2009 in U.S. drug seizures involving cathinones, coupled with a significant rise in calls to poison control centers, emergency room visits, and even deaths due to synthetic cathinone intoxication, have prompted 37 states to ban these substances. In October 2011 the U.S. Drug Enforcement Agency exercised its emergency scheduling authority to temporarily designate three synthetic cathinones as Schedule I substances under the Controlled Substances Act.

The current study explores the development of an analytical method based on headspace and direct immersion solid-phase microextraction (HS-SPME and DI-SPME, respectively) coupled with gas chromatography-mass spectrometry (GC-MS) for the rapid laboratory confirmation of synthetic cathinones in oral fluid. Target analytes included butylone, diethylpropion, flephedrone, mephedrone, methedrone, MDPV, methylone, and naphyrone. Results of method optimization experiments designed to maximize SPME recoveries of cathinones from oral fluid are presented. Parameters investigated include incubation/extraction temperature, sample pH and salting out effects. In-matrix derivatization with ethylchloroformate and 2,2,2-trichloroethylchloroformate was explored. The mass spectrometric fragmentation of the alkylchloroformate derivatives was characterized and selectivity advantages were summarized. An internal standard calibration method was developed using matrix-matched calibrators and deuterated analogs of the target drugs as internal standards. Validation data including limit of detection, limit of quantification, and accuracy of quantification in oral fluid are presented.

Comments

Senior thesis completed at Trinity College for the degree of Bachelor of Science in Neurochemistry.

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