Some pyridine derivatives as “route-specific markers” in 4-methoxyamphetamine (PMA) prepared by the Leuckart method  Dariusz Błachut, Krystyna Wojtasiewicz, Zbigniew Czarnocki  Forensic Science International  Volume 152, Issue 2, Pages 157-173 (September 2005) DOI: 10.1016/j.forsciint.2004.07.018 Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 1 The chemical structures of 2,4-dimethyl-3,5-diphenylpyridine 1, 2,4-dimethyl-3,5-di-(4′-methoxyphenyl)pyridine 2, 2,6-dimethyl-3,5-diphenylpyridine 3 and 2,6-dimethyl-3,5-di-(4′-methoxyphenyl)pyridine 4. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 2 The selected fragment of TIC chromatogram from crude PMA showing newly identified pyridines 2 and 4. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 3 The EI mass spectra of pyridines 2 and 4. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 4 The selected fragment of TIC chromatogram from impurity extract of amphetamine sulfate obtained by the Leuckart method. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 5 The mass spectra of pyridines 1 and 3. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 6 Typical TIC chromatograms of crude PMA samples obtained by the Leuckart method using different reagents: A—formamide, B—formamide/HCOOH, C—ammonium formate. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 7 The “pyridine region” of extracted ion chromatograms of crude PMA samples obtained by the Leuckart method using different reagents. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 8 The TIC chromatogram of PMA sulfate impurity extracts: A—crude salt, B—salt obtained after vacuum distillation. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Fig. 9 The “pyridine region” of extracted ion chromatograms (m/z 319) of crude PMA samples obtained from 4-methoxyphenylacetone mixed with formalin. The amount of formalin: A—15μl, B—50μl. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Scheme 1 a: H2SO4/AcOH, 140°C, 2h; b: POCl3, 140°C, 24h; c: H2/Pd, 20°C, 24h. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Scheme 2 a: PPA, AcOH, 1.5h, 120–130°C; b: NH3, EtOH, 105°C, 190h; c: POCl3, 140°C, 16h; d: H2/Pd, 20°C, 24h. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Scheme 3 a: NH3, 20°C, 48h; b: Br2/H2O, 0°C, 2h; c: POCl3, 135°C, 8h; d: HVP(red), reflux, 12h; e: (4-MeO-C2H4)B(OH)2, Pd(PPh3)4, NaHCO3, benzene/H2O/EtOH, 80°C, 24h. Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Scheme 4 Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions

Scheme 5 Forensic Science International 2005 152, 157-173DOI: (10.1016/j.forsciint.2004.07.018) Copyright © 2004 Elsevier Ireland Ltd Terms and Conditions