Group A (2,5-Dimethoxyphenyl type) 25D-NBMe (1) 25B-NBMe (2) 25I-NBMe (3) 25C-NBF () 25B-NBF (5) Group B (Benzofuran-2-yl type) Group C (-Alkoxy-3,5-d
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1 3 * * * * * Analytical data of designer drugs of synthetic phenethylamines Ryosuke SASAKI*, Miho KAT*, Tsuyoshi MATSUMT*, Akira UDAGAWA* and Ryuichi MATSUZAKI* *Tokyo Customs Laboratory , Aomi, Koto-ku, Tokyo Japan In recent years, so-called designer drugs, which are chemicals whose structures are similar to illicit drugs, have been widely distributed and abused in Japan. Synthetic phenethylamines, one group of designer drugs, have similar structures to stimulants, and also stimulate the central nervous system like stimulants. In this study, we classified synthetically produced phenethylamine samples according to their chemical structures, and analyzed them using an infrared spectrometer (IR), gas chromatograph mass spectrometer (GC-MS), liquid chromatograph mass spectrometer coupled with photodiode array detector (LC-PDA-MS) and nuclear magnetic resonance (NMR) spectrometer IR GC-MS LC-PDA-MS NMR Table 1 Fig TFA TFAA *
2 Group A (2,5-Dimethoxyphenyl type) 25D-NBMe (1) 25B-NBMe (2) 25I-NBMe (3) 25C-NBF () 25B-NBF (5) Group B (Benzofuran-2-yl type) Group C (-Alkoxy-3,5-dimethoxyphenyl type) 2-MAPB () 3C-E () 2-EAPB (7) Allylescaline (9) Group D (thers) 3-FPM (10) 5-APDB (11) Prolintane (12) Fig.1 Chemical structures of synthetic phenethylamines used in this study
3 5 Table 1 Synthetic phenethylamines used in this study Sample Number Chemical Name Common Name Mw 1 N-(2-Methoxybenzyl)- 2-(2,5-dimethoxy--methylphenyl)ethanamine 25D-NBMe (-Bromo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine 25B-NBMe (-Iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine 25I-NBMe 27 2-(-Chloro-2,5-dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine 25C-NBF (-Bromo-2,5-dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine 25B-NBF 3 1-(Benzofuran-2-yl)-N-methylpropan-2-amine 2-MAPB (Benzofuran-2-yl)-N-ethylpropan-2-amine 2-EAPB (-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine 3C-E (-Allyloxy-3,5-dimethoxyphenyl)ethanamine Allylescaline (3-Fluorophenyl)-3-methylmorpholine 3-FPM (2,3-Dihydrobenzofuran-5-yl)propan-2-amine 5-APDB (1-Phenylpentan-2-yl)pyrrolidine Prolintane IR Nicolet cm -1 2 cm KBr GC-MS Agilent 790(GC)/5975(MS) DB-5MS 30 m 0.25 mm I.D.,0.25 μm (Agilent) 0 C(1 min) (0 C/min) 320 C(5 min) 320 C 1 μl 50 : C EI 70 V 230 C cm/s LC-PDA-MS Agilent 120 infinity XBridge C1 150 mm 2.1 mm I.D., 3.5 μm (Waters) 0 C A:10 mm B: A/B = 30/ ml/min 1 μl (PDA) PDA nm (Agilent120) 3500 V 70 V ESI 2.2. NMR Varian Mercury-300 (300 MHz) 1 H IR KBr IR GC-MS EI 1 mg 1 mol/l 0.5 ml 1 ml EI TFA mg TFAA 0.2 ml 70 C 30 TFAA 1 ml EI
4 2.3.3 LC-PDA-MS 1 mg 10 ml 2.3. NMR mg 0.7 ml 1. ml 1 H-NMR 3.1 IR cm cm -1 N 1) IR Fig GC-MS EI Group A 2,5- Fig EI Fig Group B -2- Fig.1 7 EI Fig Group C - -3,5- Fig.1 9 EI Fig Group D Fig EI Fig TFA -EI Group A 2,5- Fig TFA EI Fig TFA EI Fig Group B -2- Fig.1 7 TFA EI Fig Group C - -3,5- Fig.1 9 TFA EI Fig Group D Fig TFA EI Fig LC-PDA-MS ESI ESI Fig.5 [M+H] + 25C-NBF () B-NBMe (2) B-NBF (5) Cl 35 Cl 75.77% 37 Cl 2.23% 3 1Br 79 Br 50.9% 1 Br 9.31% 1 1 Cl Br UV UV nm 2) UV Fig Group A 2,5- Fig nm nm , Group B -2- Fig nm 27 nm
5 Group C - -3,5- Fig nm NMR H-NMR Fig H-NMR Fig H-NMR Fig H-NMR Fig H-NMR Fig.7- IR GC-MS LC-PDA-MS NMR IR EI ESI UV 1 H-NMR 1) R. M. Silverstein, F. X. Webster and D. J. Kiemle -MS, IR, NMR - 7, P. 10 (200), ( ) 2) M. Hesse, H. Meier and B. Zeeh-UV, IR, NMR, MS - 2, P. 2 (2010), ( )
6 25D-NBMe (1) 25B-NBMe (2) 25I-NBMe (3) Fig.2-1 IR spectra of 1-3 hydrochloride
7 9 25C-NBF () 25B-NBF (5) 2-MAPB () Fig.2-2 IR spectra of - hydrochloride
8 50 2-EAPB (7) 3C-E () Allylescaline (9) Fig.2-3 IR spectra of 7-9 hydrochloride
9 51 3-FPM (10) 5-APDB (11) Prolintane (12) Fig.2- IR spectra of hydrochloride
10 , H +H Br 150 H N 1 25D-NBMe (1) 230, 25B-NBMe (2) H H H N I-NBMe (3) 1 Cl 13 25C-NBF () F , 232 +H H N 109 Br 13 F 230, B-NBF (5) Fig.3-1 EI-MS spectra of Group A
11 MAPB () EAPB (7) Fig.3-2 EI-MS spectra of Group B H +H C-E () Allylescaline (9) Fig.3-3 EI-MS spectra of Group C H FPM (10) 5-APDB (11) N 17 Prolintane (12) 17 Fig.3- EI-MS spectra of Group D
12 D-NBMe (1) , , 2 229, B-NBMe (2) I-NBMe (3) Fig.-1-1 EI-MS spectra of TFA derivatives of Group A
13 C-NBF () , , , B-NBF (5) Fig.-1-2 EI-MS spectra of TFA derivatives of Group A
14 N CF MAPB () N CF EAPB (7) 299 Fig.-2 EI-MS spectra of TFA derivatives of Group B H 17 3C-E () H H Allylescaline (9) Fig.-3 EI-MS spectra of TFA derivatives of Group C
15 H H FPM (10) APDB (11) Fig.- EI-MS spectra of TFA derivatives of Group D
16 5 Group A 25D-NBMe (1) 25B-NBMe (2) 25I-NBMe (3) [M+H] + [M+H] [M+H] + 25C-NBF () 25B-NBF (5) [M+H] + [M+H] + 32 Group B 2-MAPB () 2-EAPB (7) [M+H] + [M+H] + Group C 3C-E () Allylescaline (9) [M+H] + [M+H] + Group D 3-FPM (10) 5-APDB (11) [M+H] + [M+H] + 11 Prolintane (12) 21 [M+H] + Fig.5 ESI-MS spectra
17 59 Group A 25D-NBMe (1) 25B-NBMe (2) 25I-NBMe (3) nm nm nm 25C-NBF () 25B-NBF (5) Group B MAPB () 2-EAPB (7) 27 Group C 3C-E () Allylescaline (9) nm nm Group D 3-FPM (10) 5-APDB (11) Prolintane (12) nm nm nm Fig. UV spectra
18 0 25D-NBMe (1) 3, Me1-3 1, 2 3, 5, 3, Me 25B-NBMe (2) 3, Me1-3 1, 2 CHCl 3 3 3, 5, 25I-NBMe (3) 3, Me1-3 1, 2 3, 3, 5 Fig H-NMR spectra of Group A
19 1 25C-NBF () 3, Me1, Me2 CHCl 3 3, 5 3, 1, 2 H 2 25B-NBF (5) 3, Me1, Me2 CHCl 3 3, 5 3, 1, 2 H 2 Fig H-NMR spectra of Group A
20 2 2-MAPB () 1 CHCl 3 3, 7 5, H 2 3, 2 2-EAPB (7) 5,, 7 CHCl , 1 H 2 Fig H-NMR spectra of Group B 3C-E () Me1, Me2 CHCl 3 2, Allylescaline (9) Me1, Me2 2, CHCl Fig H-NMR spectra of Group C
21 3 3-FPM (10) 3 5 2,, APDB (11) 3 2 CHCl Prolintane (12) 2, 3, , 2, 5 1 3, Fig.7-1 H-NMR spectra of Group D
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