BETWEE DG TAXATI AD CUSTMS UI (DG TAXUD) AD THE JIT RESEARCH CETRE (JRC) for fast recognition of ew Psychoactive Substances (PS) and identification of unknown chemicals This report was generated on 13/1/2 based on data from the European Customs laboratories and the Joint Research Centre. This report includes sample and molecular information, spectral data and associated tables and figures. The chemical structure(s) was/were identified by Bio-chemical interactions & metabolomics (BCIM) group chemists on the basis of analytical data available. MR assignments proposed below were performed by ACD labs tools in agreement with the chemical structure identified by analytical experts. Reported data are related to the sample in the following table: Eurodat number 3 Received on 7 ctober 2 Weight [mg] 1 PACKAGIG 1mg in glass vial Colour pink-orange ame of customer Belgian Customs laboratory Customer's identification BD-57-1A Customer's information Confirmation of 5-MDMB-PICA Customer's comments ew synthetic cannabinoid - 5-MDMB-PICA -to be confirmed The following structure(s) was/were identified in the sample: Data of identified compound(s) Chemicalize IUPAC name methyl 2-{[1-(5-fluoropentyl)-1H-indol-3-yl]formamido}-3,3-dimethylbutanoate AME 5-MDMB-PICA ormula C 21 H 29 2 3 W 376.465 Monoisotopic Mass 376.2221 InChI InChI=1/C21H2923/c1-21(2,3)1(2(26)27-4)23-19(25)-14-(13-9-5--12-22)17-11-7-6-1-15()17/h6-7,1-11,14,1H,5,-9,12-13H2,1-4H3,(H,23,25) SMILES =C(C)C(C(=)c2cn(CCCCC)c1ccccc12)C(C)(C)C Claude Guillou, abiano Reniero, Hubert Chassaigne, Margaret Holland European Commission, DG Joint Research Centre Directorate via E. ermi, 2749 TP 21 I-2127 Ispra (VA) - Italy Phone: +39 332 7567 claude.guillou@ec.europa.eu Page 1 of 9
Page 2 of 9 BD-57-1A_P Wavenumber (cm-1) 4 3 36 34 32 3 2 26 22 2 1 14 12 %Transmittance 32 4 4 56 64 72 Processing and interpretation based on data provided by: Belgian Customs laboratory Comment PEDER ile ame \\139.191.6.2\ihcp$\I1\BI_CHEMICAL_ITERACTI_METABMICS\CLE2SAD\!PRPSED-STRUCTURE\CLE _AS\3_BD-57-1A\BD-57-1A_P.SP Date Stamp wed sep 2 11:7:5 2 Date wed sep 2 11:7:5 2 Technique Infrared Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range 65. - 4. Points Count 3351 Data Spacing 1.
Processing and interpretation based on data provided by: Belgian Customs laboratory Comment EVAPRATED SLUTI I DCM/MTH ile ame \\139.191.6.2\ihcp$\I1\BI_CHEMICAL_ITERACTI_METABMICS\CLE2SAD\!PRPSED-STRUCTURE\CLE _AS\3_BD-57-1A\BD-57-1A_.SP Date Stamp wed oct 5 9:14:5 2 Date wed oct 5 9:14:5 2 Technique Infrared Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range 65. - 4. Points Count 3351 Data Spacing 1. %Transmittance 72 64 56 4 4 BD-57-1A_ 335 3443 353 319 2957 271 9 1734 29 1465 154 1535 1372 133 1212 3 77 777 935 99 113 164 13 112 747 32 4 3 36 34 32 3 2 26 22 2 1 14 12 Wavenumber (cm-1) Page 3 of 9
Processing and interpretation based on data provided by: Belgian Customs laboratory Comment DCM/MeH Count 471 Data Type Centroided Mass Spectrum Date 12 ct 2 17:4: Date Stamp 2 Sep 2 :14:4 Estimated Molecular Ion 376.2 ile ame BD-57-1A_292_4_1_Centroided Mass Spectrum_EI+ Inlet Model ther Probe Ion Mode EI+ perator Admin Plot Type Stick Retention Time 15.3 Sample BD-57-1A Scan 4573 Separation Type Gas-Solid Chromatography Spectrum Title DCM/MeH Spectrum Type MS TIC 361.92 Total Signal 7964221 22 3_BD-57-1A.lnk 232. 29 19 17 176 CH 3 5 154 132 12 1 99 77 66 55 144. 44 41.5 233.15 32.15 376.2 33 22 1 EI+ 57.51. 26. 2.15 5 1 15 2 25 3 35 m/z Page 4 of 9
Table of fragments o. ragment Structure ormula Label m/z Calc. TIC Calc. (%) m/z Exp. RI Exp. (%) TIC Exp. (%) 1 1-7,15(+H) C6H11(+) M - C15H13 1.7 2.752 1.1 9.275 2.752 2 1-27 C7H142(+) M - C14H15 144.12 7.34 144.1 25.94 7.34 3 1-17 C14H15(+) M - C7H142 232.113 32.49 232.1 1. 32.49 C + 4 7-27(+H) CH223(+) M - C5H9 2.147 2.5 2.15.525 2.5 5 1-23(+H) C17H2123(+) M - C4H 32.153 5.13 32.15 17.149 5.13 CH + 6 M + C H 3 M 376.2 6.94 376.2 17.14 5.95 C21H2923(+) C H 3 Page 5 of 9
Data from BCIM group at JRC, IHCP Ispra Joint Research Centre MR spectra Acquisition Time (sec) 2.7263 Date 7 ct 2 11:57:52 Date Stamp 7 ct 2 11:57:52 ile ame \\139.191.6.2\ihcp$\I1\Bio_Chemical_Interaction_Metabonomics\CLE2SAD\!proposed-structure\BCIM_AS\BCIM_6 \3\1\PDATA\1\1r requency (MHz) 6.13 ucleus 1H umber of Transients 64 riginal Points Count 3276 wner nmrsu Points Count 65536 Pulse Sequence zg3 Receiver Gain 23.55 SW(cyclical) (Hz) 1219.23 Solvent DMS-d6 Spectrum ffset (Hz) 376.515 Spectrum Type standard Sweep Width (Hz) 1219.5 Temperature (degree C) 37.1 1..9..7 3.1.1.1r.spectrus 22 2 23 19 25 12 11 13 27 14 15 6 7 5 21 1 26 9 1 17 Water M2(m) 27,26,25(m) 1.5.6 4 3 DMS-d6.5 2 1 23(s).4 3.67 3(m) 5(m).3 DMS-d6*.2 (s).39 11(d) 13(t) 12(t) 14(m) 6,1(m) 2,19(m) DMS-d6* 4(m).1.45.44.42.42.11.1 7.56 7.55 7.54 7.53 7.21 7.2 7.2 7. 7.14 4.52 4.5 4.47 4.46 4.39 4.3 4.23 4.23 4.1 1.9 1. 1.7 1.6 1.72 1.69 1.41 1.39 1.3 1.3.9.94.96 1.1 1.96 1.9 2.92.9 2.7 1.912.9 2.1.7.35 9 7 6 5 4 3 Chemical Shift (ppm) 1 H MR (6 MHz, DMS-d 6 ) δ ppm.9-1.6 (m, H) 1.7-1.26 (m, 1 H) 1.29-1.44 (m, 2 H) 1.62-1. (m, 2 H) 1.1-1.9 (m, 2 H) 3.67 (s, 3 H) 4.1-4.29 (m, 2 H) 4.34-4.52 (m, 3 H) 7.13-7. (m, 1 H) 7.21 (t, J=7.5 Hz, 1 H) 7.55 (t, J=6.7 Hz, 2 H).11 (d, J=7.9 Hz, 1 H).39 (s, 1 H) Page 6 of 9
Table of assignments and zoomed parts: Joint Research Centre o. Atom Exp. Shift (ppm) Multiplet 1 27 1.5 M1 2 26 1.5 M1 3 25 1.5 M1 26 25 27 4 4 1.39 M3 5 3 1.7 M4 6 5 1.7 M5 7 23 3.67 M6 6 4.22 M7 9 1 4.22 M7 1 2 4.46 M 11 19 4.46 M 12 14 7.14 M9 13 13 7.21 M13 14 12 7.55 M1 15 11.11 M11.39 M12 23 22 2 21 19 17 1 9 3 1 1 7 5 2 11 4 6 15 12 14 13 Page 7 of 9
Acquisition Time (sec).944 Comment 5 mm CPQCI 1H/19-13C/15/D Z-GRD Z11473/12 Date 7 ct 2 12:13:2 Date Stamp 7 ct 2 12:13:2 ile ame \\139.191.6.2\ihcp$\I1\Bio_Chemical_Interaction_Metabonomics\CLE2SAD\!proposed-structure\BCIM_AS\BCIM_6 \3\2\PDATA\1\1r requency (MHz) 15.92 ucleus 13C umber of Transients 256 Pulse Sequence jmod Receiver Gain 13.5 SW(cyclical) (Hz) 36231. Solvent DMS-d6 Spectrum ffset (Hz) 11.3359 Spectrum Type APT Sweep Width (Hz) 3623.7 Temperature (degree C) 37.1 3_BD-57-1A.lnk M3(s, 27,26,25).7.6.5.4.3.2.1 27 26 23 22 25 19 2 1 21 1 17 3 9 2 5 4 7 1 6 11 12 15 14 13 M2(s, ) 132.9 M(s, 11) M17(s, 13) M1(s, 12) M15(s, 14) 122.44 121.62 121. 11.79 M1(s, 23) M11(s, 19) 6.43 51.3 M(s) 4.63 27.25 -.1 -.2 -.3 -.4 -.5 -.6 172.43 4.2 M23(s, 2) M22(s, ) 136.59 127.1 M21(s, 15) M19(s, 1) 19.27 M14(s, 9) 3.57 4.63 M12(s) M13(s) 46.31 M9(s, 6) 22.62 22.65 29.75 29.7 29.91 34.31 M6(s) M5(s) M4(s, 5) M2(s) -.7 M7(s, ) -. M1(s, 4) -.9-1. DMS-d6 1 14 12 1 6 4 Chemical Shift (ppm) Page of 9
Table of assignments and zoomed parts: Joint Research Centre o. Atom Exp. Shift (ppm) Multiplet 1 4 22.62 M1 2 27 27.25 M3 3 26 27.25 M3 4 25 27.25 M3 5 5 29.75 M4 6 34.31 M7 7 6 46.31 M9 23 51.3 M1 9 19 6.43 M11 1 9 19.27 M14 11 14 11.79 M15 12 11 121. M 13 13 121.62 M17 14 12 122.44 M1 15 1 127.1 M19 132.9 M2 17 15 136.59 M21 1 4.2 M22 19 2 172.43 M23 23 22 26 2 21 25 19 17 27 1 9 3 1 1 7 5 2 11 4 6 15 12 14 13 Page 9 of 9