Identification of a suspicious drug by using spectroscopic techniques: A forensic analytical chemistry project

Article abstract of DOI:10.1080/00387010.2011.585433

We identified a drug analog by using screening and confirmatory tests. Total ion chromatogram showed a major peak with a molecular ion of 190m/z, but no mass spectrum match from the NIST library. A minor peak was identified as 1-benzylpiperazine (molecular ion = 176m/z). Molecular ions of both peaks differed by 14m/z units, suggesting a -CH₂ - group. Both peaks had the same base peak of 91m/z. Derivatizing the drug analog with trifluoroacetic anhydride confirmed the presence of 1-benzylpiperazine. No reaction occurred with the major peak. We proposed a benzyl-4-methylpiperazine structure, which was confirmed by NMR studies. Copyright

Full text of DOI:10.1080/00387010.2011.585433

This article was downloaded by: [University of Saskatchewan Library]
On: 09 July 2012, At: 09:59
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,
37-41 Mortimer Street, London W1T 3JH, UK
Spectroscopy Letters: An International Journal for
Rapid Communication
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lstl20
Identification of a Suspicious Drug by Using
Spectroscopic Techniques: A Forensic Analytical
Chemistry Project
Huggins Z. Msimanga a & Gregory P. Everhart a
a Department of Chemistry and Biochemistry, Kennesaw State University, Kennesaw, GA
Version of record first published: 28 Mar 2012
To cite this article: Huggins Z. Msimanga & Gregory P. Everhart (2012): Identification of a Suspicious Drug by Using
Spectroscopic Techniques: A Forensic Analytical Chemistry Project, Spectroscopy Letters: An International Journal for Rapid
Communication, 45:3, 161-166
To link to this article: http://dx.doi.org/10.1080/00387010.2011.585433
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to
anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses should
be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims,
proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or indirectly in
connection with or arising out of the use of this material.

Spectroscopy Letters, 45:161–166, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0038-7010 print=1532-2289 online
DOI: 10.1080/00387010.2011.585433
Identification of a Suspicious Drug by
Using Spectroscopic Techniques: A
Forensic Analytical Chemistry Project
Huggins Z. Msimanga,
and Gregory P. Everhart
ABSTRACT We identified a drug analog by using screening and
confirmatory tests. Total ion chromatogram showed a major peak with a
molecular ion of 190 m=z, but no mass spectrum match from the NIST
library. A minor peak was identified as 1-benzylpiperazine (molecular
ion ¼ 176 m=z). Molecular ions of both peaks differed by 14 m=z units,
suggesting a –CH2 – group. Both peaks had the same base peak of
91 m=z. Derivatizing the drug analog with trifluoroacetic anhydride con-
firmed the presence of 1-benzylpiperazine. No reaction occurred with the
major peak. We proposed a benzyl-4-methylpiperazine structure, which
was confirmed by NMR studies.
Department of Chemistry and
Biochemistry, Kennesaw State
University, Kennesaw, GA
KEYWORDS 1-benzyl-4-methylpiperazine, drug analogs, forensic chemistry,
spectroscopy
INTRODUCTION
The Internet abounds in synthetic drugs that are acclaimed to have the
same desired effects on the user as regulated drugs. The misconception is
that these drug analogs are chemically different from the regulated drugs
and thus provide a legal and harmless version of the illegal parent narcotics
while generating similar desired effects. To protect consumers, the Con-
trolled Substance Analog Act of 1986 enacted regulatory laws that deal with
possession and use of designer drugs.[1] Essentially, this act states that pos-
session with the intent to consume any psychoactive substance that has a
chemical structure that is substantially similar to that of a schedule I or II
substance is in violation of the law. A short list of names of drug analogs that
we obtained through conversation with the Georgia Bureau of Investigation
(GBI) staff included sage, crystal, mushroom 2, cloud 9, trip2nite, and—
more recently—k2 and bath salt. Crime labs and law enforcement organiza-
tions across the world are faced with a daunting task of identifying these
recreational drugs because their chemical composition is ever changing.
Unfortunately for the drug user, some of these drugs bring about undesir-
able health issues. In order to educate the community about harmful drugs,
knowledge of the chemical composition of such drugs is paramount. The
Received 18 March 2011;
accepted 30 April 2011.
Address correspondence to Huggins Z.
Msimanga, Department of Chemistry
and Biochemistry, Kennesaw State
University, 1000 Chastain Road,
Kennesaw, GA 30144, USA. E-mail:
hmsimang@kennesaw.edu
161

same knowledge gives law enforcement organiza-
tions some leverage in protecting the community
by regulating harmful drugs. In academia, a need
to provide relevant context for undergraduate
students taking forensic analytical chemistry and
instrumental analysis chemistry classes can be
addressed by analyzing drug analogs that are in
current use.[2,3] There are several advantages to the
student in the instructor’s using such current events
to teach forensic chemistry. The student (investi-
gator) is encouraged to obtain high-quality data
and accurate interpretation, since the final results will
be used to make a ruling on the suspect.[4] There is a
high level of anxiety and motivation to determine the
chemical nature of the drug analog and draw conclu-
sions about whether such a drug is indeed different
from the regulated drug. The student becomes more
familiar with structural interpretation using spectro-
scopy and other techniques. Ultraviolet=Visible
(UV=VIS), attenuated total reflection=fourier trans-
form infrared (ATR=FTIR), gas chromatography
combined with mass spectrometer (GC=MS), and
nuclear magnetic resonance (NMR) instruments are
readily available in undergraduate laboratories now-
adays. These instruments provide useful qualitative
information in analytical spectroscopy that depends
on how matter (drugs) interacts with electromagnetic
radiation. Qualitative information is the basis for
identification of physical evidence in forensic inves-
tigation. Noting that the depth of information pro-
vided by these instruments differs, the Scientific
Working Group on Drug Analysis (SWGDRUG) has
classified analytical methods according to the depth
of information they provide.[5] According to this
group, FTIR, mass spectrometry, and NMR are placed
in category A with maximum potential discriminative
power, while UV=VIS is placed in category C. Uses of
mass spectrometry coupled with GC cover a wide
range of applications, including identification of her-
oin in illicit preparations[6] and determination of illicit
drugs in human hair.[7] Application of GC=MS in inves-
tigating arson cases by Dolan[8] is noteworthy. The use
of FTIR to identify illicit drugs abounds in the litera-
ture.[9,10] In recent years, it has been shown that the
discriminating power of infrared spectroscopy can
be enhanced if coupled with multivariate analysis
techniques.[11–13] We use these instruments to provide
open-ended projects to students as part of their
research experience before they graduate.
In the current study, we analyzed a synthetic drug
whose chemical name on the container was ‘‘6-
triflouro-N-benzyl-methyl piperazine.hcl’’ (TBMP).
This name was suggestive of a class of numerous
synthetic designer drugs that are piperazine deriva-
tives.[14–16] Examples of this class include benzylpi-
perazine (BZP) and 1-(3-trifluoromethyl- piperazine
(TFMPP). Both drugs are harmful to the extent that
in 2002 the U.S. Drug Enforcement Administration
placed them on schedule I of the Controlled Sub-
stance Act.[17] The aim of this study was to use a cur-
rent situation to provide a learning experience for
our forensic chemistry students by having them char-
acterize the chemical structure of TBMP. Students
become more motivated when the subject matter is
current, and they can relate to it. Further, the signifi-
cance of this study lies in the new chemical infor-
mation about TBMP and its disseminating through
the community of scientists. Our first challenge was
the absence of chemical information about TBMP
in the literature, based on the available search
engines (SciFinder, Google.Com). For example, we
could not find a good match of the mass spectrum,
UV spectrum, or infrared spectrum of TBMP in the
literature. This also meant that there was no specific
method in the literature for analyzing TBMP. Thus,
instead of following standard methods as provided
by the American Society for Testing and Materials
(ASTM), we used multiple but independent techni-
ques, starting with presumptive tests (color tests,
TLC, pH measurements) and then employing more
discriminative techniques. This approach provided
flexibility in the identification of TBMP and more
learning experience for the student. The pH measure-
ment gave us some idea about whether we were deal-
ing with an acidic, neutral, or basic molecule. We
then used ultraviolet and midinfrared spectroscopy
to obtain general profile of this drug. We finally used
GC=MS and NMR for confirmatory studies, in accord-
ance with the general protocol used in forensic chem-
istry identification of physical evidence.
MATERIALS AND METHODS
Instrumentation was as follows: Shimadzu
QP-5000 GC=MS (Shimadzu, USA), with electron
ionization energy of 70 eV, was used for acquiring
all spectra. The GC conditions were as follows: A
DB5 capillary column with a 0.25 mm internal
H. Z. Msimanga and G. P. Everhart
162

diameter and 30 m length was used; injection port
temperature was set at 250ꢀC; helium carrier gas flow
was 1 mL=min; oven temperature parameters
included an initial temperature of 60ꢀC maintained
for 1.00 min followed by a temperature gradient of
25ꢀC=min to 259ꢀC, maintained for 4.0 min for a total
run time of 13 min. For the derivatized samples, we
changed the temperature gradient program to
15ꢀC=min in order to maximize separation. Split
mode injection at a ratio of 1:50 was used. Transfer
line temperature between the GC and MS was set
at 280ꢀC. A DPX 300 Bruker NMR instrument (Bru-
ker, USA) was used to acquire the H-NMR and
13C-NMR spectra. For H-NMR, an average of 16 scans
was recorded, while 128 scans were acquired and
averaged for the 13C-NMR spectra.
was measured directly by the Perkin Elmer ATR=
FTIR Spectrometer (USA) on the dry methanol
extract. For GC=MS analysis, about 0.2 g TBMP pow-
der was vortexed for 2 min in 4 mL solvent (water,
methanol, acetone, and ethyl acetate), and the mix-
ture was filtered through a 0.45 mm syringe filter.
The clear solution was extracted with 3 ꢁ 1 mL hex-
ane in the case of water. The methanol, acetone,
and ethyl acetate extracts were preconcentrated by
evaporation under a stream of nitrogen under the
hood. Extractions were performed at pH 3 and 9 to
establish if pH played any role on the efficiency of
extraction. The pH was adjusted using 0.2 M solu-
tions of HCI and NaOH. The prepared sample was
finally injected into the GC=MS using 1 mL injection
volumes. For NMR analysis, about 20–30 mg of drug
powder were dissolved in 0.8 mL CDC13 in the NMR
capillary tubing. This solution was used for both
H-NMR and 13C-NMR.
Procedure was as follows: For pH measurement,
about 20 mg of powder were dissolved in 5 mL of
deionized water by vortexing for 2 min in a I0 mL test
tube. The pH of deionized water was read before
and after the drug powder was added. Test kits were
purchased from Public Safety, Inc. Following the nar-
cotic identification kits (NIK) instructions, about
10 mg portions of the powder were tested for heroin,
morphine, and codeine using test kit B, which con-
tains concentrated nitric acid. Marijuana, hashish,
and THC were tested for by using test kit E. This
reagent contains 2% vanillin and 1% acetaldehyde
in alcohol, chloroform, and concentrated hydro-
chloric acid. We tested for opiates by using test kit
K. This reagent contains a 2% formaldehyde solution
in concentrated sulfuric acid. Cocaine HCL and
cocaine base were tested for by using test kit G,
which contains a 2% cobalt thiocyanate dissolved
in 1:1 water=glycerin, concentrated hydrochloric
acid, and chloroform. Procedures for preparing these
spot test solutions are available in forensic textbooks
and literature as an alternative to buying test
kits.[18,19] For TLC about 20 mg of sample were vor-
texed in 0.50 mL methanol, and the supernatant
was spotted on a silica gel plate. Among several
mobile phases tested, a solvent mixture of 4 mL ethyl
acetate and 0.40 mL methanol gave good separation
as opposed to smears. For UV spectral measurement,
about 10 mg powder was vortexed in 4 mL methanol.
The supernatant, after centrifuging at 2000 rpm for
10 min, was used to measure the UV spectrum using
a Cary 4000 UV=vis Spectrometer (Varian, USA)
against a methanol blank. The infrared spectrum
RESULTS AND DISCUSSION
The roughly 20mg powder changed the pH of
deionized water from pH 6 to 5, indicating slight acid-
ity of the sample. Presumptive color tests were all
negative. For test kit G, a test for cocaine, a pink color-
ation was observed instead of a blue positive color for
cocaine. The TLC experiment showed one single sep-
aration observable under a UV lamp, implying that this
product had one component as shown by the insert in
Fig. 1. The UV spectrum showed maximum absor-
bance around 220 and 258 nm, a typical absorption
of a substituted aromatic ring. The ATR=FTIR spec-
trum measured directly on the dried methanol extract,
showed medium CH stretching at 2950–2847 cmꢂ1
and strong overtones of substituted aromatic rings
around 825–705 cmꢂ1. We could not find spectra in
the literature that compared with our results.
FIGURE 1 Chromatogram of TBMP in ethyl acetate under basic
conditions. The major and minor peaks at 8.14 and 8.46 min are in
the ratio of 64 to 1. The insert is the TLC showing one component.
163
Identification of a Suspicious Drug by Using Spectroscopic Techniques

For GC=MS analysis, extracts that gave well-defined
total ion peaks were those by ethyl acetate around pH
9. Figure 1 shows a major peak at 8.14 min and a
minor one at 8.46 min. The two peaks are in the ratio
of 64 to 1, explaining why the TLC experiment did not
detect the minor component (Fig. 1, insert). For peak
a in Fig. 1, electron ionization (El) measurements
using a GC=MS showed fragments at m=z ¼ 42, 56,
70, 91, 99, 119, 132, 146, and 190. For peak b, intense
fragments at m=z ¼ 42, 56, 91, 134, and 176 and minor
ones at m=z ¼ 118, 120, and 146 were observed Fig. 2.
Both peaks in Fig. 1 have large intensities at 91 m=z,
with 96% and 100% abundances. The 91 m=z intensity
indicates the presence of a benzyl ion that rearranges
to a stable tropylium cation. Assuming 190 and 176 m=
z (Fig. 2) to be molecular ions of peaks a and b in
Fig. 2, the even m=z intensities suggest an even
number of N atoms in both molecules.
FIGURE 3 Structure I proposed for the major peak before deri-
vatization. Structure II proposed after derivatization, showing that
the major peak is 1-benzyl-4-methylpiperazine instead of
4-methylbenzylpiperazine.
we used a temperature gradient of 15ꢀC=min
between 60 and 259ꢀC. The two peaks were sepa-
rated at 12.86 min and 14.50 min as shown by the
chromatogram top of Fig. 4.
While the larger peak was not directly identified
from the NIST Library, the smaller peak was easily
identified by El-MS as 1-benzylpiperazine (BZP),
and its m=z fragments at 42, 56, 91, 134, and 176 have
been reported by Wikstrom and coworkers.[20] Based
on the suggested molecular ion of 190 m=z for the
compound in Fig. 2a, we proposed that the differ-
ence in mass units of 14 m=z was due to a -CH3
substituted to the benzyl ring Fig. 3, Structure 1
Further, the isotopic intensities of 190 m=z (20.4%)
and 191 m=z (2.8%) estimate the number of C atoms
in this molecule to be 12. For further structural eluci-
dation, a dry extract of the TBMP tablet was deriva-
tized by incubation in 100 mL ethyl acetate and
I00 mL trifluoroacetic anhydride (TFAA) at 65–70ꢀC
for 45 min in a sand bath. To maximize separation,
The mass spectrum of peak a did not change from
that obtained prior to derivatization, an indication
that compound a, middle of Fig. 4, did not react with
TFAA. Compound b, bottom of Fig. 4, reacted with
TFAA by replacement of H-atom in the piperazine
moiety, giving intensities at m=z ¼ 43, 57, 91,146,
181, 195, and 272, with 272 m=z as the molecular
FIGURE 4 Top: TBMP chromatogram after derivatization with
TFAA showing (a) the major peak and (b) the minor peak. Middle:
The spectrum of the major peak is unchanged. Bottom: The minor
peak, 1-benzylpiperazine reacted with TFAA.
FIGURE 2 Mass spectrum of (a) the major peak showing a mol-
ecular ion of 190.25 amu and (b) the minor peak showing a mol-
ecular ion of 176.25 amu.
H. Z. Msimanga and G. P. Everhart
164

ion. This pattern of m=z fragments was also reported
for TFAA-derivatized benzylpiperazine.[14] The
observation that compound a did not react with
TFAA indicates that the methyl group in compound
a is not on the benzyl ring as we first proposed,
but it is on the>N-H end of the piperazine moiety.
Thus when -CH3 replaces the H-atom, it prevents this
molecule from reacting with TFAA. In GC=MS
experiments, derivatizing a molecule is often used
to make the molecule thermally stable and to
improve peak shape. In this instance, derivatization
of TBMP enabled us to propose a better structure.
Thus in Fig. 3, Structure II is the preferred one
compared to Structure I. Figure 3 also shows possible
fragments of Structure II leading to the observed
intensities. The name of this compound, via Chem-
Draw software, is ‘‘1-benzyl-4-methylpiperazine.’’ A
compound with identical fragment patterns has been
reported recently by Takahashi and coworkers[21] in
their efforts to build a designer-drugs data library.
This compound is claimed to have similar effects as
those of BZP, but its stimulant effect is slightly
weaker, and it seems to have less negative side
effects such as headaches and nausea.[22]
FIGURE 6 13C-NMR of TBMP, showing five groups of C-atoms
(see text), thus confirming Structure II in Fig. 3.
due to the two -CH2- groups next to the first pipera-
zine moiety. Close to this group are four protons
(d ¼ 2.9 ppm) due to the two -CH2- next to the>N-
CH3 end of the piperazine moiety. The most up-field
intensity with three protons (d ¼ 2.7 ppm) is due to
-CH3 for the proposed structure II in Fig. 3. The
13C-NMR spectrum Fig. 6 indicates five groups of
C-atoms: the aromatic ring group around 130 ppm,
the -CH2- intensity at 61.87 ppm, two intensities at
53.7 and 49.69 ppm belonging to the piperazine
moiety, and a methyl intensity at 43.74 ppm.
H-NMR and 13C-NMR analysis is as follows: Fig. 5 is
H-NMR spectrum obtained directly on the TBMP tab-
let in CDCl3 as a solvent. This spectrum shows five
distinct groups of H- atoms: five protons downfield
belonging to the aromatic ring (d ¼ 7.3 ppm), two
protons (d ¼ 3.6 ppm) due to the benzyl -CH2-
between the aromatic ring and the first N-atom of
the piperazine moiety, and four protons (d ¼ 3.1 ppm)
Both nmr spectra support the structure displayed in
Fig. 3(II). This molecule differs in mass from benzyl
piperazine (m=z ¼ 176) by 14 mass units, well
accounting for m=z ¼ 190 for 1-benzyl-4-methylpiper-
azine. It is possible that 1-benzyl-4-methylpiperazine
was synthesized from benzylpiperazine, which would
account for the minor peak of benzylpiperazine in
Fig. 1 as a residual. We have not been able to link
structure II in Fig. 3 to the name label ‘‘6-triflouro-N-
benzyl-methyl piperazine.hcl ’’ on the container. The
CAS number from Wikipedia encyclopedia[22] is
374898-00-7, and its IUPAC name is 1-benzyl-4-
methylpiperazine, the same name that we obtained
from the ChemDraw software. To date, this compound
is not listed in the SWGDRUG library or SciFinder1
CONCLUSION
The drug TBMP contains one major component
and a minor one. Based on GC=MS and NMR spectra
FIGURE 5 H-NMR of TBMP, showing five groups of H-atoms
(see text), thus confirming Structure II in Fig. 3.
165
Identification of a Suspicious Drug by Using Spectroscopic Techniques

chromatography and mass spectrometry. Anal. Chem. 1972, 44(2),
408–410.
7. Uhl, M. Determination of drugs in hair using GC=MS=MS. Forensic
Science International 1997, 84(1–3), 281–294.
8. Dolan, J. A. Analytical methods for the detection and characterization
of ignitable liquid residues from fire debris. In: Analysis and Interpret-
ation of Fire Scene Evidence; Jose, R. Almirall, Kenneth G. Furton, Ed.;
CRC Press, 2004; 137–164.
9. Wielbo, D.; Tebbett, I. R. Use of microfourier transform infrared spec-
troscopy for the rapid identification of street drugs: Determination of
interference by common diluents. J. Forensic Sci. Soc. 1993, 33,
25–32.
analysis, the major component in TBMP is 1-benzyl-4-
methylpiperazine (Fig. 3, II), and the minor compo-
nent is 1-benzyl piperazine. This drug is soluble in
water and methanol. It was not positive with any of
the color tests we used. A ratio of 64:1 for 1-benzyl-4-
methylpiperazine to 1-benzyl piperazine indicates
that 1-benzyl-4-methylpiperazine was probably pre-
pared from 1-benzyl piperazine. To date there is very
little reported in the literature about 1-benzyl-4-
methylpiperazine in comparison to 1-benzylpipera-
zine. For the student, this project provides a solid
strategy in forensic chemistry for identifying drugs,
starting with presumptive tests (color, pH, TLC, UV,
IR) and ending with confirmation tests (GC=MS,
NMR). Students learn how to use analytical spec-
troscopy to predict the chemical structure of a mol-
ecule.
10. Chalmers, J.; Griffiths, P. R. Handbook of Vibrational Spectroscopy;
John Wiley & Sons: New York, 2002.
´
11. Daeid, N. N.; Waddell, R. J. H. The analytical and chemometric
procedures used to profile illicit drug seizures. Talanta 2005, 67,
280–285.
12. de Peinder, P.; Vredenbregt, M. J.; Visser, T.; de Kaste, D. Detection
of Lipitor counterfeits: A comparison of NIR and Raman spectroscopy
in combination with chemometrics. J. Pharm. Biomed. Anal. 2008,
47, 688–694.
13. Msimanga, H. Z.; Ollis, R. J. Discerning some Tylenol brands
using attenuated total reflection fourier transform infrared data
and multivariate analysis techniques. Appl. Spectrosc. 2010, 64(6),
657–668.
´
14. de Boer, D.; Bosman, I. J.; Hidvegi, E., Manzoni, C.; Benko, A. A.; dos
ACKNOWLEDGMENTS
Reyes, L.; Maes, R. A. A. Piperazine-like compounds: A new group of
designer drugs-of-abuse on the European market. Forensic Science
International 2001, 121, 47–56.
The authors thank Robert Ollis Jr (U.S. Army Crimi-
nal Investigation Laboratory, Forest Park, Georgia),
who has been immensely helpful in shaping our for-
ensic chemistry program; Benjamin Huck for making
certain that our instruments are up and running; and
The Department of Chemistry and Biochemistry for
its financial support and instrumentation.
15. Staak, R.; Fritschi, G.; Maurer, H. New DesignerDdrug 1-(3-trifluoro-
methylphenyl) piperazine (TFMPP): Gas chromatography=mass spec-
trometry and liquid chromatography=mass spectrometry studies on
its Phase I and II metabolism and on its toxicological detection in
rat urine. Journal of Mass Spectrometry 2003, 38, 971–981.
16. Westphal, F.; Junge, T.; Girreser, U.; Stobbe, S.; Perez, S. B. Structure
elucidation of
a new designer benzylpiperazine: 4-Bromo-2,5--
dimethoxy-benzylpiperazine. Forensic Science International 2009,
187(1–3), 87–96.
17. Drug Enforcement Administration, Department of Justice. Controlled
Substance Scheduling Actions. http://www.deadiversion.usdoj.gov/
scheduleslindex.html (accessed on March 10, 2011).
18. Saferstein, R. Criminalistics: An Introduction to Forensic Science,
8th ed.; Pearson Prentice Hall: Upper Saddle River, NJ, 2004,
255–256.
REFERENCES
1. Gregory, K. Flashback to the Federal Analog Act of 1986: Mixing
rules and standards in the cauldron. University of Pennsylvania Law
Review 2008, 156, 1077–1115.
2. Huskins, B.; Dockery, C. R. Detection of psilocybin mushroom analogs
in chocolate: Incorporating current events into the undergraduate
teaching laboratory. Chem. Educator 2009, 14, 1–3.
19. O’Neal, C. L.; Crouch, D. J.; Fatah, A. A. Validation of twelve chemi-
cal spot tests for the detection of drugs of abuse. Forensic Science
International 2000, 109(3), 189–201.
3. Henck, C.; Nally, L. GC=MS analysis of c- hydroxybutyric acid analog:
A forensic chemistry experiment. Journal of Chemical Education
2007, 84(11), 1813–1815.
20. Wikstrom, M.; Holmgren, P.; Ahlner, J. A2 (N-benzylpiperazine),
a new drug of abuse in Sweden. J. Anal. Toxicol. 2004, 28(1),
67–70.
4. Hasan, S.; Bromfield-Lee, D.; Oliver-Hoyo, M.; Cintron-Maidonado, J.
A. Using laboratory chemicals to imitate illicit drugs in a forensic
chemistry activity. J. Chem. Educ. 2008, 85(6), 813–816.
5. Scientific Working Group for the Analysis of Seized Drugs. http://
www.swgdrug.org/ (accessed April 20, 2011).
21. Takahashi, M.; Nagashima, M.; Suzuki, J., Seto, T.; Yasuda, I.;
Yoshida, T. Creation and application of psychoactive designer drugs
data library using liquid chromatography with photodiode array spec-
trometry detector and gas-chromatography-mass spectrometry.
Talanta 2009, 77, 1245–1272.
6. Nakamura, G. R.; Noguchi, T. T.; Jackson, D.; Banks, D. Forensic
identification of heroin in illicit preparations using integrated gas
22. Methylbenzylpiperazine. http://en.wikipedia.org/wiki/Methylbenzyl
piperazine (accessed on March 10, 2011).
H. Z. Msimanga and G. P. Everhart
166