nh f o - policija · joint research centre the european commission's in-house science service...

Joint Research CentreThe European Commission's in-house science service

ADMINISTRATIVE ARRANGEMENT JRC-Nr 33619-CLEN2SAND-DG TAXUD-Nr TAXUD/2014/DE/315

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ADMINISTRATIVE ARRANGEMENT JRC-Nr 33619-CLEN2SAND-DG TAXUD-Nr TAXUD/2014/DE/315BETWEEN DG TAXATION AND CUSTOMS UNION (DG TAXUD) AND THE JOINT RESEARCH CENTRE (JRC)for fast recognition of New Psychoactive Substances (NPS) and identification of unknown chemicalsThis report was generated on 18/03/2016 based on data from the European Customs laboratories and the JointResearch Centre. This report includes sample and molecular information, spectral data and associated tables andfigures. The chemical structure(s) was/were identified by Bio-chemical interactions & metabolomics (BCIM) groupchemists on the basis of analytical data available. NMR assignments proposed below were performed by ACD labstools in agreement with the chemical structure identified by analytical experts. Reported data are related to thesample in the following table:

Eurodat number 16020005 Received on 18 February 2016PACKAGING 1 * glass vial white powderName of customer Service commun des laboratoires FranceCustomer's identification 2016-24417

The following structure(s) was/were identified in the sample:

OO

NH

F

Data of identified compound(s)IUPAC Name ethyl (4-fluorophenyl)(piperidin-2-yl)acetateNAME 4F-Ethylphenidate SYNONYMS 4F-EPHFormula C15H20FNO2 FW 265.3232Monoisotopic Mass 265.147807InChI InChI=1S/C15H20FNO2/c1-2-19-15(18)14(13-5-3-4-10-17-13)11-6-8-12(16)9-7-11/h6-9,13-14,17H,2-5,10H2,1H3InChI Key RKXQYWFDJDYSEN-UHFFFAOYSA-NSMILES Fc1ccc(cc1)C(C(=O)OCC)C2CCCCN2

Claude Guillou, Fabiano Reniero, Hubert Chassaigne, Joana Lobo Vicente, Veronica Holland, Kamil Kolar

European Commission, Joint Research CentreInstitute for Health and Consumer Protection (IHCP)via E. Fermi, 2749TP 281 I-21027 Ispra (VA) - ItalyPhone: +39 0332 785678Fax: +39 0332 [email protected]://ec.europa.eu/jrc/en/institutes/ihcp



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Processing and interpretation based on data provided by:Service commun des laboratoires FranceTitle 24417File Name \\139.191.6.82\ihcp$\I01\BIO_CHEMICAL_INTERACTION_METABONOMICS\CLEN2SAND\!PROPOSED-STRUCTURE\CLEN

_NAS\16020005_2016-24417\2016-24417\2016-24417\IR.SPADate Stamp 29 Jan 2016 11:33:53 Date 29 Jan 2016 12:34:06Technique Infrared Spectral Region IRX Axis Wavenumber (cm-1) Y Axis %ReflectanceSpectrum Range 525.0251 - 3500.1670 Points Count 6172Data Spacing 0.4821

16020005_2016-24417_IR.esp

Wavenumber (cm-1)3500 3000 2500 2000 1500

%R

efle

ctan

ce

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

85

3463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043463.043434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63434.63390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.733390.73

3368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073368.073334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323334.323270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.683270.68

3172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.813172.81

3107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.723107.72 3065.3

3065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.33065.3

3010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.343010.34

2965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.982965.98

2928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.382928.38

2867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.152867.15

2791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462791.462775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.062775.06

2706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122706.122680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.092680.09 2629.95

2629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.952629.95

2589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.932589.93

2558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.112558.11

2489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.652489.65

2425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.532425.53

2402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.392402.39

2197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492197.492164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.222164.22

2099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.622099.62

1980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051980.051941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481941.481921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721921.721888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.451888.45

1867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.241867.24

1809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871809.871779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.491779.49

1747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.191747.19 1737.07

1737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.071737.07

1720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.191720.19

1688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.851688.85

1683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.071683.07

1635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.341635.34

1580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.381580.38

1569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.291569.29

1503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.241503.24

1445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.871445.87

1434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.31434.3

1375137513751375137513751375137513751375137513751375137513751375137513751375137513751375

1330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.641330.64

1314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.251314.25

1294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.481294.48

1224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.581224.58

1198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.061198.06

1162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.381162.38

1135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.381135.38

1100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.671100.67

1054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.871054.87

1020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.641020.64

990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75990.75

964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72964.72

920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36920.36

864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44864.44

843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22843.22

810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92810.92

763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67763.67

752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1752.1

720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28720.28

629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16629.16

599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75599.75 542.86

542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86542.86

CH3

O

O

NH

F



of 10

16020005_2016-24417_EI+3.760min.esp

m/z260240220200180160140120100806040

M263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100263.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100236.100207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000207.000

182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100182.100

162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000162.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000135.000

109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000109.000

84.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.100

63.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.00063.000

55.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.10055.100

EI+

Processing and interpretation based on data provided by:Service commun des laboratoires FranceCount 166 Data Type CondensedDate 9:42:28 AM Date Stamp 25 Jan 16 09:30 amFile Name \\139.191.6.82\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\_SAND-DB\Results\1602

0005_2016-24417\16020005_2016-24417_EI+_3.76minIon Mode EI+ Mass Spec Model GCMS PyroPlot Type Stick Retention Time 3.760Sample ds CH2Cl2/MeOH : 2016-24417Scan 419 Scan Mode CentroidSpectrum Assigned 69.2% [33-281/0-100] Spectrum Type MSTIC 253.78 Total Signal 3335484

1 2

O3

4

O5

6

7

8

910

11

NH12 13

14 15

16 F17

1819



of 10

Table of fragmentsNo. Fragment Structure Formula Label m/z Calc. TIC Calc.

(%)Difference

(Da)m/z Exp. RI Exp.

(%)TIC Exp.

(%)

1 7-12NH12

11

10 9

8

CH+

7

C5H10N M - C10H10FO2 84.081 41.842 0.019 84.100 100.000 41.842

2 6,13-19(+H) C7H6F M - C8H14NO2 109.045 18.925 -0.045 109.000 44.424 18.925

3 7-9,12(-H)

NH12

CH2+

98

7 C3H5N M - C12H15FO2 55.042 3.938 0.058 55.100 9.628 3.938

4 1-6,13-19(+H)CH+6

4O3

2CH31

13

14 15

16

1819

O5

F17 C10H11FO2 M - C5H9N 182.074 2.014 0.026 182.100 4.550 2.002

5 6-8,13-19

CH2+

87

6 13

14 15

16

1819

F17

C9H8F M - C6H12NO2 135.060 1.121 -0.060 135.000 2.574 1.121

6 6-7,11-19(-H2)

NH12CH2

+

117

613

1415

16

1819

F17

C9H7FN M - C6H13O2 148.056 0.702 -0.056 148.000 1.606 0.702

7 4-10,13-19(-H)

CH2+

109 8

76

413

14 15

16

1819O5

F17

C12H11FO M - C3H9NO 190.079 0.324 0.021 190.100 0.717 0.324

8 4-8,13-19(-H)CH28

7

6

C+

4

13

14 15

16

1819

O5

F17 C10H7FO M - C5H13NO 162.048 0.262 -0.048 162.000 0.593 0.262

9 2-9,13-19

98

7

6

4O3

CH2+

2

13

14 15

16

1819

O5

F17 C12H12FO2 M - C3H8N 207.082 0.081 -0.082 207.000 0.178 0.081

10 MNH

+

12

11

10 9

8

7

6

4O3

2CH31

13

14 15

16

1819

O5

F17

C15H20FNO2 M 265.147 0.006 -0.147 265.000 0.013 0.005



of 10

Processing and interpretation based on data provided by:Service commun des laboratoires FranceCount 19022 Data Type Full Date 7:46:52 AMDate Stamp 04 Feb 2016 3:43 pm Estimated Molecular Ion 1920.8File Name C:\Windows\system32\LCQTOF-mrm_1_24417mrm_Compressed (Centroid)Mass Spec Model impact H Operator alex Retention Time 6.085Sample 24417mrm Scan Mode Compressed (Centroid)Spectrum Assigned 47.6% [1-1921/0-100] Spectrum Type MSTIC 132.39 Total Signal 12921917

CH3

O

O

NH

F

16020005_2016-24417_LCQTOF-mrm_1_24417mrm.esp

m/z2602402202001801601401201008060

266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150266.150

238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100238.100221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150221.150

192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100192.100

175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100175.100147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050147.050

133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050133.050107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650107.650

84.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.10084.100

56.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.05056.050



of 10

16020005.001.001.1r.1H.esp

Chemical Shift (ppm)9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0

3.05

1.92

1.14

3.08

1.00

1.01

1.01

3.05

2.02

2.01

0.97

0.96

DMSO

WaterM08(t, 19,14)

M04(br d, 11)

M07(m, 18,15)

M05(br dd, 7)

M01(t, 1)

M03(q, 11) M02(m, 8)

M13(m, 9)

M06(m, 2,6)

M10(br s, 12)

M09(br s, 12)

M12(m, 10,9)

Data from BCIM group at JRC, IHCP IspraNMR spectraAcquisition Time (sec) 2.7263 Comment 2016-24417 SCL ParisD 0.0002 D1 1 DE 10DS 2 Date 19 Feb 2016 11:52:41Date Stamp 19 Feb 2016 11:52:41File Name \\139.191.6.82\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_6

00\16020005_2016-24417\1\PDATA\1\1rFrequency (MHz) 600.1300 GB 0 INSTRUM <spect>LB 0 NS 256 Nucleus 1HNumber of Transients 256 Origin spect Original Points Count 32768Owner nmrsu PC 1PROBHD <5 mm CPQCI 1H/19F-13C/15N/D Z-GRD Z114073/0012 >PULPROG <zg30> Points Count 65536 Pulse Sequence zg30Receiver Gain 1.91 SF 600.13 SFO1 600.133706048414SI 65536 SSB 0 SW(cyclical) (Hz) 12019.23SWH 12019.2307692308 Solvent DMSO-d6Spectrum Offset (Hz) 3706.0515 Spectrum Type standard Sweep Width (Hz) 12019.05TD 65536 TD0 1 TE 299.9993Temperature (degree C) 26.999 UNC1 <1H> WDW 0

1H NMR (600 MHz, DMSO-d6) d ppm 1.13 (t, J=7.15 Hz, 3 H) 1.27 - 1.36 (m, 2 H) 1.36 - 1.47 (m, 1 H)1.58 - 1.73 (m, 3 H) 2.94 (q, J=10.94 Hz, 1 H) 3.26 (br d, J=12.29 Hz, 1 H) 3.76 (br dd, J=9.08, 3.39 Hz, 1H) 4.08 - 4.20 (m, 3 H) 7.21 - 7.28 (m, 2 H) 7.34 (t, J=6.70 Hz, 2 H) 9.01 (br s, 1 H) 9.41 (br s, 1 H)

CH3 12

O

O

6

7

8

910

11

NH2

+

12

14 15

F

1819



of 10

Table of assignments and zoomed parts:

Chemical Shift (ppm)9.5 9.0 8.5 8.0 7.5

2.02

2.01

0.97

0.96

M08(t, 19,14)

M07(m, 18,15)

M10(br s, 12) M09(br s, 12)

Chemical Shift (ppm)4.0 3.5 3.0 2.5 2.0 1.5

3.05

1.92

1.14

3.08

1.00

1.01

1.01

3.05

DMSO

Water

M04(br d, 11)M05(br dd, 7)

M01(t, 1)

M03(q, 11)M02(m, 8)

M13(m, 9)

M06(m, 2,6)

M12(m, 10,9)

No. Atom Exp. Shift(ppm)

Multiplet

1 1 1.13 M012 8 1.33 M023 9 1.41 M134 10 1.66 M125 9 1.66 M126 11 2.94 M037 11 3.26 M048 7 3.76 M059 2 4.14 M0610 6 4.14 M0611 18 7.24 M0712 15 7.24 M0713 19 7.34 M0814 14 7.34 M0815 12 9.01 M0916 12 9.41 M10

CH3 12

O

O

6

7

8

910

11

NH2

+

12

14 15

F

1819



of 10

16020005.002.001.1r.13C.esp

Chemical Shift (ppm)170 160 150 140 130 120 110 100 90 80 70 60 50 40

M01(s, 1)

M05(s, 11)M02(s, 9)

M03(s, 10)

M04(s, 8)

M06(s, 6)

M07(s, 7)

M08(s, 2)

M17(s, 4)M12(d, 13)

M13(br d, 19,14)

M09(br d, 18,15)

DMSO

M16(d, 16)

171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13

163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12

161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44 11

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2961.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.88

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

44.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.98

26.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0221.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.99

21.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.78

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

Acquisition Time (sec) 0.9044 Comment 5 mm CPQCI 1H/19F-13C/15N/D Z-GRD Z114073/0012D 0.0002 D1 2 DE 18DS 4 Date 19 Feb 2016 12:05:36Date Stamp 19 Feb 2016 12:05:36File Name \\139.191.6.82\ihcp$\I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_6

00\16020005_2016-24417\2\PDATA\1\1rFrequency (MHz) 150.9028 GB 0 INSTRUM <spect>LB 1 NS 256 Nucleus 13CNumber of Transients 256 Origin spect Original Points Count 32768Owner nmrsu PC 1PROBHD <5 mm CPQCI 1H/19F-13C/15N/D Z-GRD Z114073/0012 > PULPROG <jmod>Points Count 32768 Pulse Sequence jmod Receiver Gain 183.05SF 150.902809 SFO1 150.92091733708SI 32768 SSB 0 SW(cyclical) (Hz) 36231.88SWH 36231.884057971 Solvent DMSO-d6Spectrum Offset (Hz) 18108.3359 Spectrum Type APT Sweep Width (Hz) 36230.78TD 65536 TD0 1 TE 299.9986Temperature (degree C) 26.999 UNC1 <13C> WDW 1

13C NMR (151 MHz, DMSO-d6) d ppm 14.21 (s, 1 C) 21.78 (s, 1 C) 21.99 (s, 1 C) 26.02 (s, 1 C) 44.98 (s, 1C) 52.76 (s, 1 C) 57.11 (s, 1 C) 61.88 (s, 1 C) 116.36 (br d, J=22.11 Hz, 1 C) 130.79 (d, J=3.32 Hz, 1 C)131.16 (br d, J=8.85 Hz, 1 C) 162.32 (d, J=244.36 Hz, 1 C) 171.13 (s, 1 C)

CH3 12

O 4

O

6

7

8

910

11

NH2

+

13

14 15

16 F

1819



of 10

Table of assignments and zoomed parts:No. Atom Exp. Shift

(ppm)Multiplet

1 1 14.21 M012 9 21.78 M023 10 21.99 M034 8 26.02 M045 11 44.98 M056 6 52.76 M067 7 57.11 M078 2 61.88 M089 18 116.36 M0910 15 116.36 M0911 13 130.79 M1212 19 131.16 M1313 14 131.16 M1314 16 162.32 M1615 4 171.13 M17

CH3 12

O 4

O

6

7

8

910

11

NH2

+

13

14 15

16 F

1819

Chemical Shift (ppm)170 165 160 155 150 145 140 135 130 125

M17(s, 4)M12(d, 13)

M13(br d, 19,14)M09(br d, 18,15)

M16(d, 16)

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

2911

6.29

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

116.

4411

6.44

130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80130.80

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1313

1.13

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

131.

1913

1.19

161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51161.51

163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12163.12

171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13171.13

Chemical Shift (ppm)60 55 50 45 40 35 30 25 20

M01(s, 1)

M05(s, 11) M02(s, 9)M04(s, 8)

M07(s, 7)

M08(s, 2)

M06(s, 6)

M03(s, 10)DMSO

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

14.2

114

.21

21.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.7821.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.9921.99

26.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.0226.02

44.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.9844.98

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

52.7

652

.76

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

57.1

157

.11

61.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.8861.88



of 10

Fragmentation of the observed molecule and the virtual MS (EI+) spectrum predicted byThermo Scientific Mass Frontier

3040

5060

7080

9010

011

012

013

014

015

016

017

018

019

020

021

022

023

024

025

026

027

028

0

013253850637588100

109.

00

84.1

0

83.1

055

.10

182.

00

110.

0010

7.00

41.1

063

.00

135.

1014

8.00

207.

0075

.00

125.

0019

0.10

162.

0026

3.00

NH

OO

F

•

OO

H

F

•O

HO

F

O•

F

NF

F

NH

NH

•

F

O

•

F

nh f o - policija · joint research centre the european commission's in-house science service...

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