Sains Malaysiana 46(1)(2017): 149–156

http://dx.doi.org/10.17576/jsm-2017-4601-19

Impurity Profiling of Amphetamine and Methamphetamine Using Gas Chromatography Mass Spectrometry (GCMS) Harmonised Methods

(Pemprofilan Bendasing Amfetamin dan Metamfetamin Menggunakan Kaedah Pengharmonian Analisis Kromatografi Gas Spektrometri (GCMS))

WAN NUR SYUHAILA MAT DESA* & DZULKIFLEE ISMAIL

Forensic Science Programme, School of Health Sciences, Universiti Sains Malaysia

16150 Kubang Kerian, Kelantan Darul Naim, Malaysia

Diserahkan: 23 Februari 2016/Diterima: 9 Mei 2016

ABSTRACT

Impurity profiling of drug seizures is a scientific approach employed to understand drug trafficking networks thus has becoming increasingly important in criminal investigation. This paper presents the feasibility of using the Collaborative Harmonisation of Methods for the Profiling of AmphetamineType Stimulants (CHAMP) established by the European Commission authority for impurity profiling of amphetamine and methamphetamine samples. Both drugs were analysed using similar extraction procedure and analytical conditions. The impurities were extracted from an alkaline buffer solution (pH8.1) using toluene prior to gas chromatography-mass spectrometry (GC-MS) analyses. The results showed that the reproducibility of the method for detecting amphetamine and methamphetamine ranged between 7.4-8.9 and 6.2-8.4 %RSD, respectively. Identification of impurities was performed by referencing against the available MS databases as well as to previous reported impurity profiling studies. Phenyl-2-propanone (P2P), also known as benzyl-methyl-ketone (BMK), as well as other specific impurities such as 4-methyl-5-phenylpyrimidine, bis-(1-phynelisopropyl) amine, N-formylamphetamine and N,N-di (b-phenylisopropyl) amines were identified in the amphetamine samples, indicating Leuckart’s pathway as the route of synthesis. Because P2P was also detected in the methamphetamine samples, the possible route of synthesis of the methamphetamine samples being Leuckart’s, nitrostyrene synthesis or reductive amination could not be ruled out.

Keywords: Amphetamine; chromatographic profiles; impurities; mass spectrum; methamphetamine

ABSTRAK

Pemprofilan bendasing bagi rampasan dadah merupakan pendekatan saintifik yang diguna pakai bagi memahami jaringan penyeludupan dadah yang menjadi semakin penting dalam penyiasatan jenayah. Kertas ini membentangkan kebolehlaksanaan Kaedah Pengharmonian Kolaboratif untuk Pemprofilan Amfetamin (CHAMP) yang diwujudkan oleh Suruhanjaya Eropah bagi pemprofilan dadah amfetamin dan metamfetamin. Sampel telah dianalisa dengan melalui proses pengekstrakan dan analisis yang sama. Pengekstrakan bendasing dilakukan menggunakan larutan penimbal beralkali (pH8.1) dengan toluen sebelum analisis kromatografi gas-spektrometri (GC-MS) dijalankan. Kebolehulangan pengesanan yang direkodkan bagi amfetamin dan metamfetamin masing-masing ialah 7.4-8.9 dan 6.2-8.4% RSD. Pengenalpastian bendasing telah dilakukan dengan merujuk kepada pengkalan data MS dan kajian yang telah dijalankan sebelum ini. Fenil-2-propanon(P2P) atau juga dikenali sebagai benzil-metil-keton (BMK) telah dikenal pasti dalam sampel amfetamin selain bendasing seperti 4-metil-5-fenilpirimidina,bis-(1-fenilisopropil) amina, N-formilamfetamina dan N, N-di (b-isopropil) amina yang menunjukkan penggunaan kaedah sintesis Leuckart. P2P telah dikesan di dalam sampel metamfetamin yang menunjukkan laluan sintesis bagi dadah ini adalah berkemungkinan Leuckart, nitrostirena atau reduktif aminasi.

Kata kunci: Amfetamin; bendasing; metamfetamin; pemprofilan kromatografi; spektrum jisim

RUJUKAN

Aalberg, L., Andersson, K., Bertler, C., Cole, M.D., Finnon, Y., Huizer, H., Jalava, K., Kaa, E., Lock, E., Lopes, A., Meer, A.P.-v. d., Sippola, E. & Dahlén, J. 2005a. Development of a harmonised method for the profiling of amphetamines: II. Stability of impurities in organic solvents. Forensic Science International 149(2-3): 231-241.

Aalberg, L., Andersson, K., Bertler, C., Boren, H., Cole, M.D., Dahlen, J., Finnon, Y., Huizer, H., Jalava, K., Kaa, E., Lock, E., Lopes, A., van der Meer, A.P. & Sippola, E. 2005b. Development of a harmonised method for the profiling of amphetamines, I. Synthesis of standards and compilation of analytical data. Forensic Science International 149(2-3): 219-229.

Abdullah, A.F.L., Haw, C.K., MatDesa, W., Sulaiman, M., Hamdan, R. & Kunalan, V. 2014. Clandestine drug laboratory: Emergence, types, factors and problems. Health and the Environment Journal 5(2): 11-27.

Allan, A. & Ely, R. 2011. In Crime Scene, Northwestern Association of Forensic Scientist (NWAFS) Newsletter Vol. 37, Washington, USA. pp. 15-25.

Allen, A. & Cantrell, T.S. 1989. Synthetic reductions in clandestine amphetamines and methamphetamines laboratories: A review. Forensic Science International 42(1): 183-199.

Andersson, K., Jalava, K., Lock, E., Finnon, Y., Huizer, H., Kaa, E., Lopes, A., van der Meer, A.P., Cole, M.D., Dahlén, J. & Sippola, E. 2007a. Development of a harmonised method for the profiling of amphetamines: III. Development of the gas chromatographic method. Forensic Science International 169(1): 50-63.

Andersson, K., Jalava, K., Lock, E., Huizer, H., Kaa, E., Lopes, A., van der Meer, A.P., Cole, M.D., Dahlén, J. & Sippola, E. 2007b. Development of a harmonised method for the profiling of amphetamines: IV. Optimisation of sample preparation. Forensic Science International 169(1): 64-76.

Andersson, K., Lock, E., Jalava, K., Huizer, H., Jonson, S., Kaa, E., Lopes, A., van der Meer, A.P., Sippola, E., Dujourdy, L. & Dahlén, J. 2007c. Development of a harmonised method for the profiling of amphetamines VI: Evaluation of methods for comparison of amphetamine. Forensic Science International 169(1): 86-99.

Bachs, S. & Woo, F. 2007. A detailed mechanistic fragmentation analysis of methamphetamine and select regioisomers by GC/ MS. Journal of Forensic Sciences 52(2): 308-319.

Baharudin, A., Anuar, L., Saini, S., Bakar, O.C., Razali, R. & Jaafar, N.R.N. 2013. Psychiatric comorbidity among community-based, treatment seeking opioid dependents in Klang Valley. Sains Malaysiana 42(3): 417-421.

Ballany, J., Caddy, B., Cole, M.D., Finnon, Y., Aalberg, L. & Janhunen, K. 2001. Developement of a harmonised pan- European method for the profiling of amphetamines. Science and Justice 41(3): 193-196.

Cole, M.D. 2003. The Analysis of Controlled Substances. West Sussex: John Wiley & Sons.

Daeid, N.N., Cresswell, S. & Ismail, D. 2003. Variations in the organic impurity profile in Leuckart synthesised amphetamine sulphate made by the same chemist. Forensic Science International 136(suppl. 1): 89-90.

Hamdan, R., Hassan, N.F.N., Desa, W.N.S.M., Kunalan, V., Sulaiman, M. & Abdullah, A.F.L. 2015. Characterisation of seized clandestine methamphetamine in Malaysia. Malaysian Journal of Forensic Sciences 6(1): 20-29.

Inohue, H., Iwata, Y.T. & Kuyama, K. 2008. Characterization and profiling of methamphetamine seizures. Journal of Health and Sciences 54(6): 615-622.

Isa, M.F.M., Guan, N.C., Rashid, R.A., Habil, M.H., Sidi, H., Said, M.A. & Sulaiman, A.H. 2013. Sexual behaviour among male methamphetamine and heroin dependents in selected areas in Malaysia. Sains Malaysiana 42(12): 1819-1826.

Kunalan, V., NicDaeid, N., Kerr, W.J., Buchanan, H.A.S. & McPherson, A.R. 2009. Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart route and reductive amination methods. Analytical Chemistry 81(17): 7342-7348.

Lock, E., Aalberg, L., Andersson, K., Dahlén, J., Cole, M.D., Finnon, Y., Huizer, H., Jalava, K., Kaa, E., Lopes, A., van der Meer, A.P. & Sippola, E. 2007. Development of a harmonised method for the profiling of amphetamines V: Determination of the variability of the optimised method. Forensic Science International 169(1): 77-85.

NIST. 2008. Mass spectral ibrary (NIST 08) and NIST mass spectral earch programe (version 2.0f).

Power, J.D., O’Brien, J., Talbot, B., Barry, M. & Kavanagh, P. 2014. The identification of an impurity product, 4,6-dimethyl- 3,5-diphenylpyridin-2-one in an amphetamine importation seizure, a potential route specific by-product for amphetamine synthesized by the APAAN to P2P, Leuckart route. Forensic Science International 241: e13-e19.

Puthaviriyakorn, N., Siriviriyasomboon, J., Phorachata, W., Pan-ox, W., Sasaki, T. & K.Tanaka (2002). Identification of impurities and statistical classification of methamphetamine tablets (Ya-Ba) seized in Thailand. Forensic Science International 1(2): 105-113.

Qi, Y., Evans, I.D. & McCluskey, A. 2006. Australian federal police seizures of illicit crystalline methamphetamine (‘ice’) 1998-2002: Impurity analysis. Forensic Science International 164(2-3): 201-210.

Qi, Y., Evans, I.D. & McCluskey, A. 2007. New impurity profiles of recent Australian imported ‘ice’: methamphetamine impurity profiling and the identification of (pseudo)ephedrine and Leuckart specific marker compounds. Forensic Science International 169: 173-180.

Stojanovska, N., Fu, S., Tahtouh, M., Kelly, T., Beavis, A. & Kirkbride, K.P. 2013. A review of impurity profiling and synthetic route of manufacture of methylamphetamine, 3,4-methylenedioxymethylamphetamine, amphetamine, dimethylamphetamine and p-methoxyamphetamine Forensic Science International 224(1-3): 8-26.

United Nations Office on Drugs and Crime (UNODC), United Nations. 2014. New York.

Verweij, A.M.A. 1989. Impurities in illicit drug preparations: Amphetamine and Methamphetamines. Forensic Science Review 1(1): 1-11.

*Pengarang untuk surat-menyurat; email: wannurs@usm.my