The use of cyclohexanone as a “derivatizing” reagent for the GC–MS detection of amphetamines and ephedrines in seizures and the urine B.M. El-Haj, A.M.

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The use of cyclohexanone as a “derivatizing” reagent for the GC–MS detection of amphetamines and ephedrines in seizures and the urine B.M. El-Haj, A.M. Al-Amri, M.H. Hassan, H.S. Ali, R.K. Bin Khadem Forensic Science International Volume 135, Issue 1, Pages 16-26 (July 2003) DOI: 10.1016/S0379-0738(03)00101-4

Fig. 1 The mass spectra of the acetyl derivative of methamphetamine (A) and the diacetyl derivative of pseudoephedrine (B), as obtained from PMW_TOX2 mass-spectra library. The significant similarity of the two mass spectra together with the very low abundance of the molecular ion (M) in (A) at m/z=191 and the absence of M in (B) should be noted. Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 2 Reactions of primary amines (A) and secondary amines (B) with carbonyl compounds. Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 3 Reactions of the ephedrines and the amphetamines with cyclohexanone at high temperatures. Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 4 EI mass spectra of the cyclohexanone derivatives of amphetamine (A), methamphetamine (B), ephedrine (C), pseudoephedrine (D) and phenylpropanolamine (norephedrine) (E). Molecular ion (M). Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 4 EI mass spectra of the cyclohexanone derivatives of amphetamine (A), methamphetamine (B), ephedrine (C), pseudoephedrine (D) and phenylpropanolamine (norephedrine) (E). Molecular ion (M). Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 5 Amphetamine as an impurity in a methamphetamine seizure. Extracted-ion chromatogram obtained from the GC–MS analysis of a methamphetamine seizure, upon using cyclohexanone as “derivatizing” reagent. The ratio m/z of 124 (base peak ion for amphetamine-CXCP) and 138 (base peak ion for methamphetamine-CXCP) were used in the extraction of the ion-chromatogram. The retention times and EI mass spectral ions for the two compounds (a) amphetamine-CXCP and (b) methamphetamine-CXCP are the same as those for the corresponding reference substances in Fig. 4(A) and (B). Cyclohexanone condensation product (CXCP). Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 6 Amphetamine as a metabolite of methamphetamine. Extracted-ion chromatogram obtained from the GC–MS analysis of the urine of a methamphetamine user, upon using cyclohexanone as “derivatizing” reagent. The ratio m/z of 124 (base peak ion for amphetamine-CXCP) and 138 (base peak ion for methamphetamine-CXCP) were used in the extraction of the ion-chromatogram. The retention times and EI mass spectral ions for the two compounds (a) amphetamine-CXCP and (b) methamphetamine-CXCP, are the same as those for the corresponding reference substances in Fig. 4(A) and (B). Cyclohexanone condensation product (CXCP). Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 7 Norpseudoephedrine as metabolite of pseudoephedrine extracted-ion chromatogram obtained from the GC–MS analysis of the urine of a pseudoephedrine user, upon using cyclohexanone as “derivatizing” reagent. The ratio m/z of 125 (base peak ion of norpseudoephedrine-CXCP) and 202 (base peak ion of pseudoephedrine-CXCP) were used in the extraction of the ion chromatogram. The retention times and EI mass spectral ions for the two compounds (a) norpseudoephedrine-CXCP (norpseudoephedrine is also known as phenylpropanolamine) and (b) pseudoephedrine-CXCP, are the same as those for the corresponding reference substances in Fig. 4(E) and (D). Cyclohexanone condensation product (CXCP). Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)

Fig. 8 Demonstration of Khat use. Extracted-ion chromatogram and EI mass spectrum ions (table) obtained from the GC–MS analysis of the urine of a Khat user, upon using cyclohexanone as “derivatizing” reagent. The ratio m/z of 125 (base peak ion for the two cyclohexanone derivatives), was used in the extraction of the ion-chromatograms. Forensic Science International 2003 135, 16-26DOI: (10.1016/S0379-0738(03)00101-4)