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GC/MS Library of Various Over the Counter Drugs

Grace Dauer
Organic Chemistry II Laboratory: Spring 2015
Department of Science, Our Lady of the Lake College
March 6, 2015
In Partial Fulfillment of the Independent Project Component

Problem Statement:
As mentioned by the Organic II Laboratory instructor and Chemistry Coordinator,
Daphne Olendorf, at Our Lady of the Lake College (OLOLC), OLOLC is primarily a
medical-based college that offers classes such as pharmacology, toxicology, and
biochemistry; yet, the college has no Gas Chromatography/Mass Spectroscopy (GC/MS)
drug-specific library for those pre-med and pre-graduate school students wanting to
conduct research in pharmacology or drug analysis (D. Olendorf, personal
communication, February 23, 2015). The proposed project aims to complete a GC/MS
library to contribute to the education of students at this college. Students enrolled in the
Fall 2014 Organic I laboratory course, used the GC/MS to identify the active ingredients
in various over the counter drugs such as Advil and Tylenol. The class had difficultly
reading the mass spectrums because students had no information for comparison. This
project will provide comparison spectrums for future chemistry labs at OLOLC. GC/MS
is used in forensic toxicology laboratories to identify drugs in human tissue or separately.
Identifying the mass spectrums of various drugs is a good way to learn about practical
applications of forensic toxicology. Research has been done to create the most efficient
GC/MS libraries for drugs in toxicology laboratories. Some studies have been conducted
to create procedures that yield more precise mass spectrums for better results as opposed
to just inserting the extracted drug into the instrument. I believe that the colleges
chemistry laboratory has a gap in materials needed to teach students about these
disciplines specific to toxicology, and propose that this issue be resolved via a GC/MS
drug library.

Literature Review:
An important role of a clinical toxicology laboratory is to test human specimens and
tissues for the presence of drugs. Forensic toxicologists do not have a complete
memorization of every spectroscopy or chromatography pattern of every drug or
chemical they work with. They use libraries (often already programs into their devices) to
compare their results to in order to get an accurate observation. Previous research has
been done to find new ways to create accessible libraries to make these comparisons. To
meet these needs, one groups of researchers developed a new Gas Chromatography-Mass
Spectrometry (GC/MS) procedure that facilitates routine screening and automated
reporting of 212 drugs by laboratory technologists around the clock without the need to
sign out by an on-site mass spectrometry-trained toxicologist (Nair et al, 2013). Another
device was created for analyzing spectrometry data to identify and Quantify Individual
Components in a Sample, (QUICS), allows creation of chemical library entries from
known samples from unknown metabolites present in experimental samples but without a
corresponding library entry. According to Corey DeHaven, creator of QUICS, this
method accounts for all ions in a sample spectrum, performs library matches, and allows
review of the data to quality check library entries (Dehaven et al., 2010). The QUICS
method is a way to identify metabolites in a sample, and when new metabolites that are

not yet included in the reference library are observed, this method creates a library entry
to identify that metabolite in future studies.
An example of what a forensic toxicologist might do is test human plasma for simple
over the counter drugs. One research study found a way to determine the presence of
ibuprofen in human plasma and urine using gas chromatography/mass spectroscopy. This
study explains how a liquid-liquid extraction was performed to obtain the samples from
the three healthy male volunteers all given 600 mg of ibuprofen. This study also explains
the importance of creation of the standard solutions and graphs for comparison. After
complete testing, the researchers found that the GC/MS was not sensitive enough to
observe ibuprofen is plasma and urine. MSTFA was added as a reagent to increase
sensitivity to allow for observance of ibuprofen in these samples (Yilmaz and Erdem,
2010). Without a comparison graph of what the GC/MS of ibuprofen looks like, these
researchers would not have been able to tell that the GC/MS was not picking up the drug
in the samples.
Knowledge of GC/MS drug-specific libraries and how to create and use them is essential
in understanding the basics of forensic toxicology. I am proposing a gap in Our Lady of
the Lakes references related to educating students who are interested in conducting
research in pharmacology or drug analysis. Chemists and scholars are finding new and
better ways to analyze drugs using various chemical instruments. Procedures are
available to explain how to identify drugs using GC/MS but Our Lady of the Lake should
acquire its own drug-specific library for future labs.
Accurate observance of qualitative chemical data is made easier by the use of chemical
libraries. A large volume of data is typically produced in a mass spectroscopy experiment

and requires computers for data storage. Manufacturers of mass spectrometers and a
number of researchers have developed data formats for handling the amount of data that
needs to be observed in these types of experiments. Chemdata.NIST has a variety of
chemical libraries available for use such as spectra for environmentally relevant
compounds and spectra for glycan, to name a few (Chemdata.NIST).
Methodology and Procedure:
Based on the difference in polarities and molecular weights of the various drugs tested,
each drug should have different mass spectrums. GC/MS is one instrument used for
qualitative testing, or testing to identify the species or compound present. GC, or gas
chromatography, separates compounds based on retention time and polarity. The mobile
phase that will be used for the duration of this project is helium gas, and the stationary
phase is a column packed with silica gel. The gas chromatograph shows different sized
peaks, where each peak represents a different molecule. MS, or mass spectroscopy, will
remove an electron from the molecule, causing it to fragment fragment the molecule in a
predictable way. The mass spectrum shows lines of different heights based on molecular
weight. An FTIR (Fourier Transform Infrared Spectroscoper) will be used to help confirm
the identification of any compounds present. In infrared spectroscopy, IR radiation is
passed through a sample and some is absorbed by the sample andsome of it is
transmitted. The resulting spectrum represents the molecular absorption and transmission,
creating a molecular fingerprint of the sample.
Part A

1. Crush one tablet of ibuprofen using a clean mortar and pestle and transfer the
powder to a labeled centrifuge tube. Add 2 mL of diethyl either and to the tube,
cap, and shake vigorously. Allow undissolved fractions to settle at the bottom of
the tube.
2. After the powder settles after 2 minutes, transfer the supernatant liquid to a new
centrifuge tube. Centrifuge the mixture for about 2 minutes. Repeat process of
adding diethyl either until the supernatant is clear.
3. Evaporate the solvent by placing the beaker in a hot water bath. When all of the
solvent has evaporated, cool the beaker to room temperature.
4. Repeat steps 1-3 using dichloromethane (DCM ) in place of diethyl either.
5. Run both samples (from diethyl either and from DCM) on the GC/MS and the
FTIR. Whichever solvent yields the best GC peaks will be used for the other
drugs tested.
Part B
1. Repeat steps 1-3 in part A for each drug listed using the solvent that yielded the
best GC peaks.

Nair, H., Woo, F., Hoofnagle, A. N., & Baird, G. S. (2013). Clinical Validation of a
Highly Sensitive GC-MS Platform for Routine Urine Drug Screening and RealTime Reporting of up to 212 Drugs. Journal Of Toxicology, 1-7.
%3d#db=a9h&AN=95008529 (Accessed Feb 27, 2015).

DeHaven, C. D., Evans, A. M., Hongping, D., & Lawton, K. A. (2010). Organization of
GC/MS and LC/MS metabolomics data into chemical libraries. Journal Of
Cheminformatics, 2(1), 1-12. doi:10.1186/1758-2946-2-9.
%3d#db=a9h&AN=64933347 (Accessed Feb 27, 2015).

Yilmaz, B.; Erdem, A. Determination of Ibuprofen in Human Plasma and Urine by Gas
Chromatography/Mass Spectrometry. AOAC. Inter. [Online] 2014, 97, 415-420.

2ZQ%3d%3d#db=a9h&AN=95633969 (Accessed Feb 5, 2015).
Chemdata. Mass Spectral Library and Other Tools: Libraries. (Accessed March
4, 2015).