Joint Research Centre. The European Commission's in-house science service

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1 ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 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 1/03/201 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 2000 Received on 1 ebruary 201 PACKAGIG 1 * glass vial white powder ame of customer Service commun des laboratoires rance Customer's identification The following structure(s) was/were identified in the sample: H Data of identified compound(s) IUPAC ame ethyl (-fluorophenyl)(piperidin-2-yl)acetate AME -Ethylphenidate SYYMS -EPH ormula C 1 H 20 2 W Monoisotopic Mass 2.10 InChI InChI=1S/C1H202/c1-2--1(1)1( )---(1)--/h-,-1,1H,2-,H2,1H3 InChI Key RKXQYWDJDYSE-UHAYSA- SMILES c1ccc(cc1)c(c(=)cc)c2cccc2 Claude Guillou, abiano Reniero, Hubert Chassaigne, Joana Lobo Vicente, Veronica Holland, Kamil Kolar European Commission, Joint Research Centre Institute for Health and Consumer Protection (IHCP) via E. ermi, 2 TP 21 I-22 Ispra (VA) - Italy Phone: ax: claude.guillou@ec.europa.eu ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page 1 of

2 ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page 2 of Processing and interpretation based on data provided by: Service commun des laboratoires rance Title 21 ile ame \\.1..2\ihcp$\I01\BI_CHEMICAL_ITERACTI_METABMICS\CLE2SAD\!PRPSED-STRUCTURE\CLE _AS\2000_201-21\201-21\201-21\IR.SPA Date Stamp 2 Jan 201 :33:3 Date 2 Jan 201 :3:0 Technique Infrared Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Reflectance Spectrum Range Points Count Data Spacing _201-21_IR.esp Wavenumber (cm-1) %Reflectance H 3 C H

3 2000_201-21_EI3.0min.esp.0 Joint Research Centre Processing and interpretation based on data provided by: Service commun des laboratoires rance Count 1 Data Type Condensed Date :2:2 AM Date Stamp 2 Jan 1 0:30 am ile ame \\.1..2\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLE2SAD\!proposed-structure\_SAD-DB\Results\2 000_201-21\2000_201-21_EI_3.min Ion Mode EI Mass Spec Model GCMS Pyro Plot Type Stick Retention Time 3.0 Sample ds CH2Cl2/MeH : Scan Scan Mode Centroid Spectrum Assigned.2% [33-21/0-0] Spectrum Type MS TIC 23. Total Signal H EI M m/z ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page 3 of

4 Table of fragments o. ragment Structure ormula Label m/z Calc. TIC Calc. (%) Difference (Da) m/z Exp. RI Exp. (%) TIC Exp. (%) 1 - H CH CH M - CH ,-(H) CH M - CH ,(-H) CH 2 C3H M - CH H 1-,-(H) H 31 C 2 3 CH CH2 M - CH ,- CH CH M - CH ,-(-H2) H H C CH M - CH H 2 C -,-(-H) CH M - C3H H 2 C 1 -,-(-H) C 1 1 CH M - CH ,- 3 H 2 C CH2 M - C3H M H 31 C 2 H C1H202 M ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

5 Processing and interpretation based on data provided by: Service commun des laboratoires rance Count 022 Data Type ull Date ::2 AM Date Stamp 0 eb 201 3:3 pm Estimated Molecular Ion 20. ile ame C:\Windows\system32\LCQT-mrm_1_21mrm_Compressed (Centroid) Mass Spec Model impact H perator alex Retention Time.0 Sample 21mrm Scan Mode Compressed (Centroid) Spectrum Assigned.% [1-21/0-0] Spectrum Type MS TIC 2.3 Total Signal _201-21_LCQT-mrm_1_21mrm.esp.0 H H 3 C m/z ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

6 Data from BCIM group at JRC, IHCP Ispra r.1H.esp Joint Research Centre MR spectra Acquisition Time (sec) 2.23 Comment SCL Paris D D1 1 DE DS 2 Date eb 201 :2:1 Date Stamp eb 201 :2:1 ile ame \\.1..2\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLE2SAD\!proposed-structure\BCIM_AS\BCIM_ 00\2000_201-21\1\PDATA\1\1r requency (MHz) GB 0 ISTRUM <spect> LB 0 S 2 ucleus 1H umber of Transients 2 rigin spect riginal Points Count 32 wner nmrsu PC 1 PRBHD < mm CPQCI 1H/-C/1/D Z-GRD Z03/00 > PULPRG <zg30> Points Count 3 Pulse Sequence zg30 Receiver Gain 1.1 S 00. S SI 3 SSB 0 SW(cyclical) (Hz) 0.23 SWH Solvent DMS-d Spectrum ffset (Hz) Spectrum Type standard Sweep Width (Hz) 0.0 TD 3 TD0 1 TE 2.3 Temperature (degree C) 2. UC1 <1H> WDW 0 M01(t, 1) 1 H 2 H 3 C 2 1 M0(m, 1,1) M0(t,,1) M0(m, 2,) Water M(m,,) M0(br s, ) M(br s, ) M0(br dd, ) M03(q, ) M0(br d, ) DMS M02(m, ) M(m, ) Chemical Shift (ppm) 1 H MR (00 MHz, DMS-d ) d ppm 1. (t, J=.1 Hz, 3 H) (m, 2 H) (m, 1 H) (m, 3 H) 2. (q, J=. Hz, 1 H) 3.2 (br d, J=.2 Hz, 1 H) 3. (br dd, J=.0, 3.3 Hz, 1 H) (m, 3 H) (m, 2 H).3 (t, J=.0 Hz, 2 H).01 (br s, 1 H).1 (br s, 1 H) ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

7 Table of assignments and zoomed parts: o. Atom Exp. Shift (ppm) Multiplet M M M 1 1. M 1. M 2. M M0 3. M0 2.1 M0.1 M0 H 3 C 2 1 H 2 M0(m, 1,1) 1.2 M0 1.2 M0.3 M M M0 1.1 M M(br s, ) M0(br s, ) M0(t,,1) Chemical Shift (ppm) M01(t, 1) M0(m, 2,) Water M0(br dd, ) M0(br d, ) M03(q, ) DMS M(m,,) M02(m, ) M(m, ) Chemical Shift (ppm) ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

8 r.C.esp Joint Research Centre Acquisition Time (sec) 0.0 Comment mm CPQCI 1H/-C/1/D Z-GRD Z03/00 D D1 2 DE 1 DS Date eb 201 :0:3 Date Stamp eb 201 :0:3 ile ame \\.1..2\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLE2SAD\!proposed-structure\BCIM_AS\BCIM_ 00\2000_201-21\2\PDATA\1\1r requency (MHz) GB 0 ISTRUM <spect> LB 1 S 2 ucleus C umber of Transients 2 rigin spect riginal Points Count 32 wner nmrsu PC 1 PRBHD < mm CPQCI 1H/-C/1/D Z-GRD Z03/00 > PULPRG <jmod> Points Count 32 Pulse Sequence jmod Receiver Gain.0 S S SI 32 SSB 0 SW(cyclical) (Hz) SWH Solvent DMS-d Spectrum ffset (Hz) 0.33 Spectrum Type APT Sweep Width (Hz) TD 3 TD0 1 TE 2. Temperature (degree C) 2. UC1 <C> WDW 1 M(br d,,1) M0(br d, 1,1)..2 M0(s, ) M0(s, ). 2. M01(s, 1) M1(s, ).1. M1(d, 1) 0.0 M(d, ) H M0(s, ) M02(s, ) M03(s, ) M0(s, ) H 3 C M0(s, 2) DMS Chemical Shift (ppm) C MR (11 MHz, DMS-d ) d ppm 1.21 (s, 1 C) 21. (s, 1 C) 21. (s, 1 C) 2.02 (s, 1 C). (s, 1 C) 2. (s, 1 C). (s, 1 C) 1. (s, 1 C).3 (br d, J=22. Hz, 1 C) 0. (d, J=3.32 Hz, 1 C) 1.1 (br d, J=. Hz, 1 C).32 (d, J=2.3 Hz, 1 C). (s, 1 C) ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

9 Table of assignments and zoomed parts: o. Atom Exp. Shift (ppm) Multiplet M M M M0. M0 2. M0. M M0 1.3 M0 1.3 M0 H M 1.1 M M H 3 C M1 1. M1 M(br d,,1) M0(br d, 1,1)..2. M1(s, )..1 M1(d, 1) 0.0 M(d, ) Chemical Shift (ppm) M0(s, ) M0(s, ) M01(s, 1) M0(s, 2) M0(s, ) DMS M0(s, ) M02(s, ) M03(s, ) Chemical Shift (ppm) ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of

10 ragmentation of the observed molecule and the virtual MS (EI) spectrum predicted by Thermo Scientific Mass rontier.00 H H. H H H ADMIISTRATIVE ARRAGEMET JRC-r 33-CLE2SAD-DG TAXUD-r TAXUD/201/DE/31 Page of