Joint Research Centre

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1 ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ 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 /1/ 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 11 Received on January PACKAGIG 1 glass vial white powder ( mg) Registration date January ame of customer Service commun des laboratoires France Customer's identification -77 The following structure(s) was/were identified in the sample: Data of identified compound(s) Formula C H FW 6. Monoisotopic Mass 6. Chemicalize IUPAC name -phenyl--[1-(-phenylethyl)piperidin--yl]pentanamide InChI (v.1.) InChI=1S/CH/c1---1-()(------)--1-(--) /h-, H,-,1-H,1H InChI Key (v.1.) VCCPXHWAJYWQMR-UHFFFAYSA- SMILES (v.1.1) CCCCC(=)(CCC(CCc1ccccc1)CC)cccccc Claude Guillou, Fabiano Reniero, Hubert Chassaigne, Joana Lobo Vicente, Veronica Holland, Salvatore Tirendi, Kamil Kolar European Commission, Joint Research Centre Institute for Health and Consumer Protection (IHCP) via E. Fermi, TP I- Ispra (VA) - Italy Phone: 767 Fax: 7 claude.guillou@ec.europa.eu ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page 1 of

2 ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of Processing and interpretation based on data provided by: Service commun des laboratoires France Title 77 File ame \\.11.6.\ihcp I1\BI_CHEMICAL_ITERACTI_METABMICS\CLESAD\!PRPSED-STRUCTURE\CLE _AS\11_-77\77.SPA Date Stamp ov :1: Date ov 1:1: Technique Infrared Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Reflectance Spectrum Range Points Count 6 Data Spacing. Wavenumber (cm-1) %Reflectance HC

3 Processing and interpretation based on data provided by: Service commun des laboratoires France Combine <-6> Count Data Source ame -77_Centroid_EI Data Type Condensed Date ov 1:: Date Stamp ov 6: pm File ame -77_Centroid_EI Ion Mode EI Mass Spec Model GCMS Plot Type Stick Retention Time 6. Sample Ds CHCl/MeH : -77 Scan Scan Mode Centroid Spectrum Assigned.% [-/-1] TIC.1 Total Signal 71. Relative Intensity (%) Retention Time: 6.. Ion Mode: EI 7 7 HC EI ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ m/z Page of

4 6 Table of fragments Joint Research Centre o. Fragment Structure Formula Label m/z Calc. TIC Calc. (%) 1 -,-(-H) H C 11 1 CH Difference (Da) m/z Exp. RI Exp. (%) TIC Exp. rigin (%) C6H1 M - C1H Manual CH M - CH Manual CH -,7,-(H) 7 H C C CH M - CH Manual 7-,- CH 7 CH1 M - CH Manual 1-1(-H) C1H M - C1H Manual 6 -,- CH 7 C1H1 M - C1H Manual 6 H C 11 CH 7 -,11-,-(H) 7 C11H M - CH Manual 6 C -, C C1H M - C1H Manual 1-,- CH CH M - C7H Manual C H M H 1 C 7 CH M Manual ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of

5 Data from BCIM group at JRC, IHCP Ispra Joint Research Centre MR spectra Acquisition Time (sec).7 Comment mg in 6 ul DMS-d6 Paris 1/ Date Jan ::1 Date Stamp Jan ::1 File ame \\.11.6.\ihcp I1\Bio_Chemical_Interaction_Metabonomics\CLESAD\!proposed-structure\BCIM_AS\BCIM_6 \11\1\PDATA\1\1r Frequency (MHz) 6. ucleus 1H umber of Transients rigin spect riginal Points Count 6 wner nmrsu Points Count 66 Pulse Sequence zg Receiver Gain 1.1 SW(cyclical) (Hz) 1. Solvent DMS-d6 Spectrum ffset (Hz) 76. Spectrum Type standard Sweep Width (Hz) 1. Temperature (degree C). ormalized Intensity r.esp M(m, 1,,,,) M1(t, 1) H 11a H C 1. M(m, 1,) M(m,,) 1 1 M(t, ). M(br d,,1)...1 M1(m, ) M11(m, ) M(br s, 11a) M1(br s) M7(m, ) M(quin, ) DMS M(m, ) M(m, ) M6(br d,,) M(m,,1) M(qd,,) Chemical Shift (ppm) δ H (DMS-d 6 ): 1. (1H, br s, M), (H, m, M), (1H, m, M1), (H, m, M), (H, m, M), (1H, m, M11),. (H, br s, M1),. (H, br d, J=11 Hz, M),.-. (H, m, M),.-. (H, m, M),.6-. (H, m, M7), 1. (H, br d, J= Hz, M6), 1. (H, t, J=7 Hz, M), 1.6 (H, qd, J= and Hz, M), 1.1 (H, quin, J=7 Hz, M), (H, m, M),.7 (H, t, J=7 Hz, M1) ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of

6 Table of assignments and zoomed parts: o. Atom Exp. Shift (ppm) Multiplet o. Atom Exp. Shift (ppm) M1 1. M 1.1 M 1.6 M M 6 1. M 7 1. M M6. M7 1. M M.1 M. M a 1. ormalized Intensity. M(m,,) M(m, 1,,,,) M(m, 1,) H 11a 1 H C 1. M1(m, ) Chemical Shift (ppm) ormalized Intensity M1(t, 1) M11(m, ) M1(br s) M(br d,,1) M7(m, ) M(m, ) M(m,,1) DMS M(t, ) M(quin, ) M6(br d,,) M(m, ) M(qd,,) Chemical Shift (ppm) ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page 6 of

7 ormalized Intensity Joint Research Centre Acquisition Time (sec). Comment mm CPQCI 1H/1F-C//D Z-GRD Z117/ Date Jan :: Date Stamp Jan :: File ame \\.11.6.\ihcp I1\Bio_Chemical_Interaction_Metabonomics\CLESAD\!proposed-structure\BCIM_AS\BCIM_6 \11_-77\\PDATA\1\1r Frequency (MHz). ucleus C umber of Transients 6 rigin spect riginal Points Count 6 wner nmrsu Points Count 6 Pulse Sequence jmod Receiver Gain. SW(cyclical) (Hz) 61. Solvent DMS-d6 Spectrum ffset (Hz) 11. Spectrum Type APT Sweep Width (Hz) 6.7 Temperature (degree C) r.esp M(s, 1,) M1(s,,) M1(s,,) M(s, ) M(s, ) H H C 1 M11(s, ) M1(s, 1) M(s, ) M(s, ) M(s, 1) M(s, ) M6(s, ) M(s, ) M(s, ) M(s,,) -. M(s,,1) M(s, ) DMS Chemical Shift (ppm) δ C (DMS-d 6 ): 1. (C-),.7 (C-), 7.6 (C-1),. (C-, ),. (C-, ),.1 (C-, 1),.1 (C-),. (C-), 7. (C-, 1), 6. (C-), 1. (C-1, ),. (C-),. (C-),. (C-),. (C-, ),. (C-),.1 (C-), 1.1 (C-1) ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page 7 of

8 Zoomed parts: ormalized Intensity 1 M(s, 1,) H H C 1 M1(s,,) M1(s,,) M(s, ) M(s, ) M1(s, 1,) M(s, ) M(s, 1) Chemical Shift (ppm) ormalized Intensity M11(s, ) M1(s, 1) M6(s, ) M(s, ) M(s,,) M(s, ) M(s, ) M(s, ) M(s,,1) DMS 6 Chemical Shift (ppm) ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of

9 MS spectra Joint Research Centre Combine <-> Count 1 Data Source ame 11_-77_MS_-_1_Centroided Mass Spectrum_ES Data Type Centroided Mass Spectrum Date 1 Jan :: Date Stamp 1 Jan :: Estimated Molecular Ion 6.1 File ame \\.11.6.\ihcp I1\Bio_Chemical_Interaction_Metabonomics\CLESAD\!proposed-structure\BCIM_AS\BCIM_ QTF\11_-77\11_-77_MS_-.CDF Inlet Model Electrospray Inlet Ion Mode ES Plot Type Stick Retention Time. Scan Separation Type o Chromatography Spectrum Assigned.% [-/-1] TIC 7.6 Total Signal 11.6 Relative Intensity (%) Retention Time:. Ion Mode: ES HC ES m/z ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of

10 Combine <-> Count 1 Data Source ame 11_-77_MSMS_6_EV_-_1_Centroided Mass Spectrum_ES Data Type Centroided Mass Spectrum Date 1 Jan :: Date Stamp 1 Jan :7: Estimated Molecular Ion 66.1 File ame \\.11.6.\ihcp I1\Bio_Chemical_Interaction_Metabonomics\CLESAD\!proposed-structure\BCIM_AS\BCIM_ QTF\11_-77\11_-77_MSMS_6_EV_-.CDF Inlet Model Electrospray Inlet Ion Mode ES Plot Type Stick Retention Time. Scan Separation Type o Chromatography Spectrum Assigned 7.% [-/-1] TIC.77 Total Signal 7. Relative Intensity (%) Retention Time:. 1. Ion Mode: ES HC ES ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ m/z Page 1 of

11 Table of fragments o. Fragment Structure Formula Label m/z Calc. TIC Calc. (%) Difference (Da) m/z Exp. RI Exp. (%) TIC Exp. (%) rigin C H C 6 CH M - C1H Manual CH M - CH Manual CH -,-(H) H C 7 6 CH M - CH Manual 7-1,- H C 1 7 C1H M - C1H Manual 1-7,-(H) C11H M - CH Manual CH CH1 M - C11H Manual H C 1 CH 7 1-1,-(H) 7 C1H M - C1H Manual 6 H C 1 CH 1 1-1,-(-H) 7 CH M - CH Manual C H (H) C1H M - CH Manual M(H) H H 1 C 7 CH M H Manual ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page 11 of

12 Fragmentation of the observed molecule and the virtual MS (EI) spectrum predicted by Thermo Scientific Mass Frontier H 16.1 H ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of

13 Fragmentation of the observed molecule and the virtual MS and MSMS spectra predicted by Thermo Scientific Mass Frontier H H H H 6. H ADMIISTRATIVE ARRAGEMET JRC-r 61-CLESAD-DG TAXUD-r TAXUD/1/DE/ Page of