Protons I Have Known and Loved. Fifty Shades of Grey-Market Spectra

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Supplementary Data for PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Page Analyte. Alleged. Found. Acquired. 4 P0.
PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra Stephen J. Chapman* and Arabo A. Avanes Supplementary Data: http://dx.doi.org/10.16889/isomerdesign-1-supp

“Once you get a serious spectrum collection, the tendency is to push it as far as you can.” pace Hunter S. Thompson

*

Correspondence to: Isomer Design, 4103-210 Victoria St, Toronto, ON, Canada, M5B 2R3. E-mail: [email protected]

Supplementary Data for PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra Page Analyte

Alleged

Found

Acquired

4 P0

PEA HCl

PEA HCl

2014-08-19

7 P1

2C-H

2C-H

10 P1 as HCl

2C-H

13 P2

Page Analyte

Alleged

Found

Acquired

70 B1

25B-NBOMe

25B-NBOMe

2013-01-16

2013-01-16

73 B2

25C-NBOMe

25C-NBOMe

2013-01-16

2C-H HCl

2013-11-08

76 B3

25I-NBOMe

25I-NBOMe

2013-01-16

2C-D

2C-D

2012-11-20

79 B4

25I-NBOH

25I-NBOH

2013-01-16

16 P3

2C-E

2C-E

2012-11-24

82 B5

25I-NBMD

25I-NBMD

2013-05-07

19 P4

2C-P

2C-P

2012-11-24

85 B6

25D-NBOMe

25D-NBOMe

2013-01-16

22 P4 in DMF-d7 2C-P

2C-P

2013-05-07

88 B7

25E-NBOMe

25E-NBOMe

2013-01-16

25 P5

2C-IP

2C-IP

2012-11-24

91 B8

25IP-NBOMe

25IP-NBOMe

2013-03-26

28 P6a

2C-C

2C-E

2012-11-24

94 B9

25G-NBOMe

25G-NBOMe

2013-05-07

31 P6b

2C-C

2C-C

2013-03-26

97 B10

M-NBOMe

M-NBOMe

2013-01-16

34 P7

2C-I

2C-I

2012-11-24

100 IM1

25H-NBOMe imine 25H-NBOMe imine 2013-11-08

37 P8

2C-T

2C-T

2012-11-24

104 IM2

25I-NBOMe imine

40 P9

2C-T-2

2C-T-2

2012-11-24

43 P10

2C-T-4

2C-T-4

2012-11-24

46 P11

2C-T-7

2C-T-7

2012-11-24

49 P12

Escaline

Escaline

2013-01-16

52 P13a

Proscaline

Proscaline

2012-11-24

55 P13b

Proscaline

Proscaline

2013-03-26

58 P14

AL

AL

2012-11-24

61 P15

MAL

MAL

2012-11-24

64 P16

BOD

BOD

2012-11-24

67 P17

bk-2C-B

bk-2C-B

2013-11-29

25I-NBOMe imine

2013-11-08

(blank)

Page 4 of 105 1H

NMR (700 MHz, DMSO-d6) δ 8.29 (s , 3H), 7.34 – 7.21 (m, 5H), 3.02 – 2.97 (m, 2H), 2.95 – 2.89 (m, 2H). 1

8.30

8.28

8.26

8.24

7.36

7.34

7.32

7.30

7.28

11 (m) 2.92

1.92

10 (m) 3.00

4.83

2,3,4,5,6 (m) 7.28

3.35 8.32

11

NH3 12

2

12 (s) 8.29

8.34

+

10

7.26

7.24

7.22

7.20

7.18 3.04

3.02

3.00

1.90

Ana lyte P0: PEA; 2-Phenyletha n-1-a mine HCl Acquis i on Da te 2014-08-19T02:01:52 Solvent dms o 6 Tempera ture 27 5 Number of Sca ns 64 4 Rela xa on Dela y 5 3 Spectrometer Frequency 699.81 Spectra l Width 11160.7 Nucleus 1H Acquired Size 50223

2.98

2.96

2.94

2.92

2.90

2.88

2.86

Page 5 of 105

Ana lyte P0: PEA; 2-Phenyletha n-1-a mine HCl Acquis i on Da te 2014-08-19T02:01:52 Solvent dms o 6 Tempera ture 27 5 Number of Sca ns 64 4 Rela xa on Dela y 5 3 Spectrometer Frequency 699.81 Spectra l Width 11160.7 Nucleus 1H Acquired Size 50223

1H

NMR (700 MHz, DMSO-d6) δ 8.29 (s , 3H), 7.34 – 7.21 (m, 5H), 3.02 – 2.97 (m, 2H), 2.95 – 2.89 (m, 2H). +

10 1

11

NH3 12

2

11 (m) 2.92

9.0

8.5

8.0

7.5

1.92 1.90

10 (m) 3.00

4.83

2,3,4,5,6 (m) 7.28

3.35

12 (s) 8.29

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 6 of 105

2-Phenyletha n-1-a mine H+ Modgra ph NMRPredict Des ktop DMSO-d6 Bes t 50 12489 700.00 1H

8.0

5

1

4

+

10 11

NH3 12

2 3

7.26

7.25

10 (t) 3.66

7.24

7.23

7.22

7.21

7.20

7.19

7.18

7.17

7.16

7.5

7.0

6.5

6.0

5.5

5.0

4.5

11 (t) 3.13

7.15

5.22

3.00 8.5

6

2,3,4,5,6 (m) 7.21

7.27

9.0

NMR (700 MHz, DMSO-d6) δ 8.10 (s , 3H), 7.26 – 7.15 (m, 5H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (t, J = 7.6 Hz, 2H).

4.0

1.76

12 (s) 8.10

1H

2.01

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 7 of 105

Ana l yte P1: 2C-H freeba s e Acqui s i on Da te 2013-01-17T02:00:25 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 6.88 – 6.81 (m, 1H), 6.76 – 6.68 (m, 2H), 3.71 (s , 3H), 3.68 (s , 3H), 2.73 – 2.66 (m, 2H), 2.63 – 2.55 (m, 2H), 1.32 (s , 2H).

75 O 65

6 5 4

NH2 12

10 1

11

2 3

O 62 72

MeO (s) 3.68

6.90

6.85

6.80

6.75

6.70

6.65

3.75

3.70

3.65

3.60

2.75

2.70

2.65

2.60

2.14

12 (s) 1.32

1.93

10 (m) 2.59

1.85

11 (m) 2.69

2.90

3.10

MeO (s) 3.71

2.06

ArH (m) 6.71

1.03

ArH (m) 6.84

2.55

1.40

1.35

1.30

1.25

Page 8 of 105

Ana l yte P1: 2C-H freeba s e Acqui s i on Da te 2013-01-17T02:00:25 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 6.88 – 6.81 (m, 1H), 6.76 – 6.68 (m, 2H), 3.71 (s , 3H), 3.68 (s , 3H), 2.73 – 2.66 (m, 2H), 2.63 – 2.55 (m, 2H), 1.32 (s , 2H).

75 O 65

6 5

10 1

4

11

NH2 12

2 3

O 62 72

MeO (s) 3.68

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

12 (s) 1.32

1.85 1.93

11 (m) 2.69

3.10 2.90

MeO (s) 3.71

1.03 2.06

ArH (m) 6.84

10 (m) 2.59

3.5

3.0

2.5

2.14

ArH (m) 6.71

2.0

1.5

1.0

0.5

0.0

Page 9 of 105

2C-H freeba s e Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 6.76 (d, J = 7.9 Hz, 1H), 6.71 – 6.65 (m, 2H), 3.80 (s , 3H), 3.72 (s , 3H), 2.80 – 2.69 (m, 4H), 2.70 (s , 2H).

75 O 65

6 5

10 1

4

11

NH2 12

2 3

O 62 72

4,6 (m) 6.68

75 (s) 3.72

9.0

8.5

8.0

7.5

7.0

10,11 (m) 2.75

3.00 3.00

72 (s) 3.80

0.99 1.96

3 (d) 6.76

12 (s) 2.70

6.5

6.0

5.5

5.0

4.5

4.0

4.00 2.06

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 10 of 105

6 5

8.15

6.95

6.90

1

4

+

10 11

NH3 12

2 O 62

3

72

6.85

6.80

6.75

3.70

10 (m) 2.85

3.65

2.95

1.97

3.75

11 (m) 2.94

1.99

MeO (s) MeO (s) 3.74 3.69

2.02

ArH (m) 6.79

3.06

8.20

NMR (500 MHz, DMSO-d6) δ 8.19 (s , 3H), 6.94 – 6.87 (m, 1H), 6.82 – 6.76 (m, 2H), 3.74 (s , 3H), 3.69 (s , 3H), 2.98 – 2.91 (m, 2H), 2.88 – 2.81 (m, 2H).

3.06

8.25

1H

1.01

2.90

Ana l yte P1 HCl : 2C-H H+ 75 Acqui s i on Da te 2013-11-08T20:55:22 Sol vent dms o O 65 Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 1 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058 12 (s) ArH (m) 8.19 6.90

2.90

2.85

2.80

Page 11 of 105

Ana l yte P1 HCl : 2C-H H+ Acqui s i on Da te 2013-11-08T20:55:22 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 1 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058 ArH (m) 6.79

9.0

8.5

NMR (500 MHz, DMSO-d6) δ 8.19 (s , 3H), 6.94 – 6.87 (m, 1H), 6.82 – 6.76 (m, 2H), 3.74 (s , 3H), 3.69 (s , 3H), 2.98 – 2.91 (m, 2H), 2.88 – 2.81 (m, 2H).

O 65

6 5

1

4

+

10 11

NH3 12

2 O 62

3

72

MeO (s) 3.69

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

10 (m) 2.85 11 (m) 2.94

1.99 1.97

3.06 3.06

MeO (s) 3.74

1.01 2.02

ArH (m) 6.90

2.90

12 (s) 8.19

1H

75

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 12 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-H H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 7.00 (d, J = 7.2 Hz, 1H), 6.86 (d, J = 7.0 Hz, 2H), 3.80 (s , 3H), 3.72 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.7, 0.9 Hz, 2H).

75 O 65

6 5

1

4

+

10 11

NH3 12

2 O 62

3

72

4,6 (d) 6.86 12 (s) 8.10

75 (s) 3.72

3 (d) 7.00

72 (s) 3.80

10 (td) 3.13

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.97

3.05 3.05 2.04

0.96 1.88

3.05

11 (t) 3.66

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 13 of 105

Ana lyte P2: 2C-D H+ Acquis i on Da te 2012-11-20T16:56:00 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

8.15

8.10

6.85

5

2 3

O 62 72

6.780

11 (m) 2.93

2.140

6.775

2.135

6.75

3.80

3.75

10 (m) 2.83

2.130

2.125

3.70

3.65

2.95

40 (d) 2.13

2.120

2.115

2.90

2.85

2.86

72,75 (s) 3.73

1.88

ArH (s) 6.78

6.785

6.80

NH3 12

11

1

4 40

+

10

6

1.90

6.815

O 65

0.93

6.820

0.94

6.825

3.76

6.830

ArH (d) 6.82

NMR (500 MHz, DMSO-d6) δ 8.15 (s , 3H), 6.82 (d, J = 0.8 Hz, 1H), 6.78 (s , 1H), 3.73 (s , 6H), 2.97 – 2.89 (m, 2H), 2.87 – 2.80 (m, 2H), 2.13 (d, J = 0.7 Hz, 3H).

5.73

12 (s) 8.15

1H

75

2.80

2.15

2.10

Page 14 of 105

Ana lyte P2: 2C-D H+ Acquis i on Da te 2012-11-20T16:56:00 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

1H

NMR (500 MHz, DMSO-d6) δ 8.15 (s , 3H), 6.82 (d, J = 0.8 Hz, 1H), 6.78 (s , 1H), 3.73 (s , 6H), 2.97 – 2.89 (m, 2H), 2.87 – 2.80 (m, 2H), 2.13 (d, J = 0.7 Hz, 3H).

75 O 65

5

11

1

4 40

+

10

6

NH3 12

2 O 62

3

72

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 2.93

40 (d) 2.13

1.90 1.88

5.73

72,75 (s) 3.73

0.94 0.93

ArH (d) 6.82

3.76

12 (s) 8.15

10 (m) 2.83

3.5

3.0

2.86

ArH (s) 6.78

2.5

2.0

1.5

1.0

0.5

0.0

Page 15 of 105

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

2C-D H+ Modgra ph NMRPredict Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.75 (s , 2H), 3.71 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.12 (d, J = 1.1 Hz, 3H).

75 O 65

5

11

1

4 40

+

10

6

NH3 12

2 3

O 62 72

11 (t) 3.66

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

40 (d) 2.12

3.5

3.06

10 (td) 3.13

1.98

6.11 2.02

72,75 (s) 3.71

1.76

3,6 (s) 6.75

3.07

12 (s) 8.10

3.0

2.5

2.0

1.5

1.0

Page 16 of 105

Ana lyte P3: 2C-E H+ Acquis i on Da te 2012-11-24T13:37:16 Solvent dms o Tempera ture 25 Number of Sca ns 1 Rela xa on Dela y 1 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

8.05

8.00

6.80

O 65

6 5

1

4

42 41

+

10 11

NH3 12

2 3

O 62 72

MeO (s) 3.74

6.75 3.80

3.75

3.70

3.00

2.95

2.90

2.85

42 (t) 1.11

2.80

2.75

2.70

2.65

2.60

2.55

3.07

41 (q) 2.54

2.06

10 (m) 2.82

2.00

11 (m) 2.95

3.08

2.98

MeO (s) 3.74

1.08

ArH (s) 6.81

1.04

3.01

12 (s) 8.02

NMR (500 MHz, DMSO-d6) δ 8.02 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.74 (s , 3H), 3.74 (s , 3H), 3.00 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.54 (q, J = 7.5 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

1.98

ArH (s) 6.79

1H

75

2.50

1.15

1.10

Page 17 of 105

Ana lyte P3: 2C-E H+ Acquis i on Da te 2012-11-24T13:37:16 Solvent dms o Tempera ture 25 Number of Sca ns 1 Rela xa on Dela y 1 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

9.0

8.5

8.0

NMR (500 MHz, DMSO-d6) δ 8.02 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.74 (s , 3H), 3.74 (s , 3H), 3.00 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.54 (q, J = 7.5 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

O 65

6 5

1

4

42 41

+

10 11

NH3 12

2 3

O 62 72

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

42 (t) 1.11

2.5

3.07

11 (m) 41 (q) 2.95 2.54

2.06

MeO (s) 3.74

10 (m) 2.82

2.00 1.98

ArH (s) 6.81

2.98 3.08

MeO (s) 3.74

1.04 1.08

ArH (s) 6.79

3.01

12 (s) 8.02

1H

75

2.0

1.5

1.0

0.5

0.0

Page 18 of 105

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

2C-E H+ Modgra ph NMRPredict Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.80 (d, J = 1.2 Hz, 2H), 3.71 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.50 (qd, J = 6.6, 1.0 Hz, 2H), 1.12 (t, J = 6.6 Hz, 3H).

75 O 65 42

6 5

11

1

4 41

+

10

NH3 12

2 O 62

3

72

11 (t) 3.66

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

42 (t) 1.12

3.0

2.5

2.95

41 (qd) 2.50

1.93

10 (td) 3.13

1.98

6.09 1.99

72,75 (s) 3.71

1.99

3,6 (d) 6.80

3.06

12 (s) 8.10

2.0

1.5

1.0

0.5

Page 19 of 105

Ana l yte P4: 2C-P H+ Acqui s i on Da te 2012-11-24T13:58:43 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 8.04 (s , 3H), 6.79 (s , 2H), 3.74 (s , 3H), 3.73 (s , 3H), 2.99 – 2.90 (m, 2H), 2.86 – 2.79 (m, 2H), 2.51 – 2.45 (m, 2H), 1.60 – 1.45 (m, 2H), 0.89 (t, J = 7.4 Hz, 3H).

75 O 65 44 45

6 5

1

4 43

+

10 11

NH3 12

2 O 62

3

72

MeO (s) 3.73 12 (s) 8.04

3,6 (s) 6.79

MeO (s) 3.74

11 (m) 2.95

10 (m) 2.82

43 (m) 2.48

44 (m) 1.52

45 (t) 0.89

8.1

8.0

6.8

3.8

3.7

3.0

2.9

2.8

2.7

2.6

2.5

1.6

3.04

2.05

1.78

2.01

2.07

3.03

3.11

2.07

2.83

1.58 1.57 1.56 1.55 1.54 1.53 1.52 1.51 1.50 1.49 1.48

1.5

0.9

Page 20 of 105 1H

NMR (500 MHz, DMSO-d6) δ 8.04 (s , 3H), 6.79 (s , 2H), 3.74 (s , 3H), 3.73 (s , 3H), 2.99 – 2.90 (m, 2H), 2.86 – 2.79 (m, 2H), 2.51 – 2.45 (m, 2H), 1.60 – 1.45 (m, 2H), 0.89 (t, J = 7.4 Hz, 3H).

75 O 65 44 45

6 5

1

4 43

+

10 11

NH3 12

2 3

O 62 72

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

43 (m) 2.48

44 (m) 1.52

2.5

2.0

1.5

45 (t) 0.89

3.04

11 (m) 2.95

2.07 2.01

3.11 3.03

MeO (s) 3.74

2.07

3.6 (s) 6.79

2.83

12 (s) 8.04

10 (m) 2.82

2.05

MeO (s) 3.73

1.78

Ana l yte P4: 2C-P H+ Acqui s i on Da te 2012-11-24T13:58:43 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1.0

0.5

Page 21 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-P H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.80 (t, J = 1.0 Hz, 2H), 3.71 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.63 (td, J = 7.9, 1.1 Hz, 2H), 1.64 (ddt, J = 14.4, 7.8, 6.6 Hz, 2H), 0.94 (t, J = 6.6 Hz, 3H).

75 O 65 44 45

6 5

1

4 43

+

10 11

NH3 12

2 3

O 62 72

11 (t) 3.66

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

45 (t) 0.94

2.99

44 (ddt) 1.64

1.97

43 (td) 2.63

1.94

10 (td) 3.13

1.97

6.08 2.01

72,75 (s) 3.71

1.99

3,6 (t) 6.80

3.05

12 (s) 8.10

1.5

1.0

0.5

Page 22 of 105

Ana l yte P4 i n DMF: 2C-P H+ Acqui s i on Da te 2013-05-07T20:17:09 Sol vent dmf Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10000.0 Nucl eus 1H Acqui red Si ze 65536

1H

NMR (500 MHz, DMF-d7) δ 8.64 (s , 3H), 6.99 (s , 1H), 6.87 (s , 1H), 3.82 (s , 3H), 3.80 (s , 3H), 3.26 – 3.19 (m, 2H), 3.10 – 3.03 (m, 2H), 2.59 – 2.52 (m, 2H), 1.63 – 1.52 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H).

75 O 65 44

6 5

1

4

45

43

+

10 11

NH3 12

2 3

O 62 72

MeO (s) 3.80 MeO (s) 3.82

11 (m) 3.23

8.7

8.6

7.0

6.9

3.8

1.60

3.3

43 (m) 2.56

1.59

1.58

2.02

1.61

1.91

3.13

2.93

0.88

0.96

2.91

1.62

10 (m) 3.07

3.2

3.1

1.57

44 (m) 1.57

1.56

1.55

1.54

2.6

45 (t) 0.92

1.53

2.5

1.6

3.12

ArH (s) 6.87

2.10

ArH (s) 6.99

2.04

12 (s) 8.64

1.5

0.9

Page 23 of 105 1H

O 65 44 45

6 5

1

4 43

+

10 11

NH3 12

2 3

O 62 72

8.5

8.0

7.5

7.0

10 (m) 3.07

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

44 (m) 1.57

2.5

2.0

1.5

45 (t) 0.92

3.12

43 (m) 2.56

2.10

11 (m) 3.23

2.93 3.13

MeO (s) 3.82

0.96 0.88

ArH (s) 6.99

2.91 9.0

MeO (s) 3.80

2.04

ArH (s) 6.87 12 (s) 8.64

NMR (500 MHz, DMF-d7) δ 8.64 (s , 3H), 6.99 (s , 1H), 6.87 (s , 1H), 3.82 (s , 3H), 3.80 (s , 3H), 3.26 – 3.19 (m, 2H), 3.10 – 3.03 (m, 2H), 2.59 – 2.52 (m, 2H), 1.63 – 1.52 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H).

75

1.91 2.02

Ana l yte P4 i n DMF: 2C-P H+ Acqui s i on Da te 2013-05-07T20:17:09 Sol vent dmf Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10000.0 Nucl eus 1H Acqui red Si ze 65536

1.0

0.5

0.0

Page 24 of 105

blank

Page 25 of 105

Ana l yte P5: 2C-IP H+ Acqui s i on Da te 2012-11-24T13:26:15 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

6

O 65

5

NMR (500 MHz, DMSO-d6) δ 8.00 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.76 (s , 3H), 3.74 (s , 3H), 3.21 (hept, J = 6.9 Hz, 1H), 2.99 – 2.92 (m, 2H), 2.85 – 2.78 (m, 2H), 1.15 (d, J = 6.9 Hz, 6H).

+

10 1

4

47

11

NH3 12

2 3

46 48

ArH (s) 6.79 12 (s) 8.00

1H

75

O 62 72

MeO (s) 3.74

ArH (s) 6.81

MeO (s) 3.76

46 (hept) 3.21

11 (m) 2.95

10 (m) 2.82

47,48 (d) 1.15

8.05

8.00

7.95

6.85

6.80

6.75

3.80

3.75

3.70

3.25

3.20

3.15

3.10

3.05

3.00

2.95

2.90

2.85

2.80

6.00

2.01

2.02

1.05

3.08

3.06

1.06

1.02

2.70

3.26 3.25 3.24 3.23 3.22 3.21 3.20 3.19 3.18 3.17 3.16

2.75

1.20

1.15

1.10

Page 26 of 105

Ana l yte P5: 2C-IP H+ Acqui s i on Da te 2012-11-24T13:26:15 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

12 (s) 8.00

1H

NMR (500 MHz, DMSO-d6) δ 8.00 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.76 (s , 3H), 3.74 (s , 3H), 3.21 (hept, J = 6.9 Hz, 1H), 2.99 – 2.92 (m, 2H), 2.85 – 2.78 (m, 2H), 1.15 (d, J = 6.9 Hz, 6H).

75 O 65

6 5

1

4

47 46

+

10 11

NH3 12

2 3

O 62

48

72

ArH (s) 6.79

MeO (s) 3.74

ArH (s) 6.81

MeO (s) 3.76

11 (m) 2.95 46 (hept) 3.21

47,48 (d) 1.15

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

6.00

2.02 2.01

1.05

3.06 3.08

1.02 1.06

2.70

10 (m) 2.82

2.5

2.0

1.5

1.0

0.5

Page 27 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-IP H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.97 (d, J = 1.0 Hz, 1H), 6.80 (d, J = 1.1 Hz, 1H), 3.74 (s , 3H), 3.71 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 3.05 (pd, J = 6.4, 1.0 Hz, 1H), 1.14 (d, J = 6.4 Hz, 6H).

75 O 65 47

6 5

1

4 46

+

10 11

NH3 12

2 O 62

3

48

72

6 (d) 6.80 12 (s) 8.10

72 (s) 3.71

3 (d) 6.97

75 (s) 3.74

46 (pd) 3.05 10 (td) 3.13

47,48 (d) 1.14

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

5.94

1.97 0.94

3.04 3.05 1.97

1.00

1.00

3.08

11 (t) 3.66

2.5

2.0

1.5

1.0

0.5

Page 28 of 105

Ana l yte P6a : 2C-E H+ Acqui s i on Da te 2012-11-24T13:50:28 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

42

6 5

2 3

O 62 72

MeO (s) 3.74 MeO (s) 3.74

11 (m) 2.95

8.00

6.85

6.80

3.75

2.56

10 (m) 2.82

2.55

2.54

2.03

2.96

3.12

1.01

1.05

2.66

2.57

8.05

NH3 12

11

1

4 41

+

10

3.70

3.00

2.95

41 (q) 2.54

2.53

2.52

2.51

2.50

2.90

2.85

42 (t) 1.11

2.49

2.80

2.75

2.70

2.65

2.60

2.55

3.04

ArH (s) 6.81

O 65

2.13

12 (s) 8.03

NMR (500 MHz, DMSO-d6) δ 8.03 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.74 (s , 3H), 3.74 (s , 3H), 2.98 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.54 (q, J = 7.5 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

2.01

ArH (s) 6.79

1H

75

2.50

1.15

1.10

1.05

Page 29 of 105

Ana l yte P6a : 2C-E H+ Acqui s i on Da te 2012-11-24T13:50:28 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768 ArH (s) 6.79

9.0

8.5

8.0

NMR (500 MHz, DMSO-d6) δ 8.03 (s , 3H), 6.81 (s , 1H), 6.79 (s , 1H), 3.74 (s , 3H), 3.74 (s , 3H), 2.98 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.54 (q, J = 7.5 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

O 65 42

6 5

11

1

4 41

+

10

NH3 12

2 3

O 62 72

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

42 (t) 1.11

2.5

3.04

11 (m) 41 (q) 2.95 2.54

2.03 2.01

3.12 2.96

1.05 1.01

MeO (s) 3.74

10 (m) 2.82

2.13

MeO (s) 3.74

ArH (s) 6.81

2.66

12 (s) 8.03

1H

75

2.0

1.5

1.0

0.5

Page 30 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-E H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.80 (d, J = 1.2 Hz, 2H), 3.71 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.50 (qd, J = 6.6, 1.0 Hz, 2H), 1.12 (t, J = 6.6 Hz, 3H).

75 O 65 42

6 5

1

4 41

+

10 11

NH3 12

2 3

O 62 72

11 (t) 3.66

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

42 (t) 1.12

3.0

2.5

2.95

41 (qd) 2.50

1.93

10 (td) 3.13

1.98

6.09 1.99

72,75 (s) 3.71

1.99

3,6 (d) 6.80

3.06

12 (s) 8.10

2.0

1.5

1.0

0.5

Page 31 of 105 1H

NMR (500 MHz, DMSO-d6) δ 8.18 (s , 3H), 7.07 (s , 1H), 7.05 (s , 1H), 3.80 (s , 3H), 3.76 (s , 3H), 3.00 – 2.93 (m, 2H), 2.90 – 2.83 (m, 2H).

75 O 65

6

+

10

5

1

4

11

NH3 12

2

Cl 14

O 62

3

72

8.25

8.20

8.15

8.10

7.10

7.05

7.00

3.85

3.80

11 (m) 2.96

3.75

10 (m) 2.87

1.99

3.05

MeO (s) 3.80

1.03

1.00

ArH (s) 7.07

2.91

12 (s) 8.18

MeO (s) 3.76

3.70

3.00

2.95

1.98

ArH (s) 7.05

3.04

Ana l yte P6b: 2C-C H+ Acqui s i on Da te 2013-03-26T19:35:22 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

2.90

2.85

2.80

Page 32 of 105

Ana l yte P6b: 2C-C H+ Acqui s i on Da te 2013-03-26T19:35:22 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

1H

NMR (500 MHz, DMSO-d6) δ 8.18 (s , 3H), 7.07 (s , 1H), 7.05 (s , 1H), 3.80 (s , 3H), 3.76 (s , 3H), 3.00 – 2.93 (m, 2H), 2.90 – 2.83 (m, 2H).

75 O 65

6 5

1

4 Cl 14

+

10 11

NH3 12

2 O 62

3

72

ArH (s) 7.05

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

10 (m) 2.87

1.99 1.98

11 (m) 2.96

3.05 3.04

MeO (s) 3.80

1.00 1.03

ArH (s) 7.07

2.91

12 (s) 8.18

MeO (s) 3.76

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 33 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-C H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

75 O 65

6 5 4

Cl 14

+

10 1

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 7.24 (s , 1H), 6.79 (t, J = 1.0 Hz, 1H), 3.96 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H).

11

NH3 12

2 O 62

3

72

72 (s) 3.74 12 (s) 8.10

3 (s) 7.24

6 (t) 6.79

75 (s) 3.96

10 (td) 3.13

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

2.02

2.99 2.04

2.98

1.00

0.99

2.98

11 (t) 3.66

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 34 of 105

Ana l yte P7: 2C-I H+ Acqui s i on Da te 2012-11-24T13:42:12 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 7.99 (s , 3H), 7.33 (s , 1H), 6.90 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 3.00 – 2.93 (m, 2H), 2.87 – 2.80 (m, 2H).

75 O 65

6 5

1

4 I 64

+

10 11

NH3 12

2 3

O 62 72

MeO (s) 3.76

8.05

8.00

7.95

7.35

7.30

7.25

7.20

7.15

7.10

7.05

7.00

6.95

6.90

6.85

3.80

3.75

3.70

3.00

2.95

2.02

10 (m) 2.83

2.04

11 (m) 2.97

3.03

3.06

MeO (s) 3.77

1.03

ArH (s) 6.90

1.04

ArH (s) 7.33

2.77

12 (s) 7.99

2.90

2.85

2.80

Page 35 of 105

Ana l yte P7: 2C-I H+ Acqui s i on Da te 2012-11-24T13:42:12 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 7.99 (s , 3H), 7.33 (s , 1H), 6.90 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 3.00 – 2.93 (m, 2H), 2.87 – 2.80 (m, 2H).

75 O 65

6 5

1

4 I 64

+

10 11

NH3 12

2 3

O 62 72

MeO (s) 3.76

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 2.97

2.04 2.02

3.06 3.03

MeO (s) 3.77

1.03

1.04

ArH (s) ArH (s) 7.33 6.90

2.77

12 (s) 7.99

10 (m) 2.83

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 36 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-C H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 7.34 (s , 1H), 6.62 (t, J = 1.0 Hz, 1H), 3.93 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H).

75 O 65

6 5

1

4 I 64

+

10 11

NH3 12

2 3

O 62 72

72 (s) 3.74 12 (s) 8.10 12

3 (s) 7.34

6 (t) 6.62

75 (s) 11 3.93 75 72

10 (td) 3.13

11 (t) 3.66

3

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.95

3.04 3.04 1.95

10

0.98

0.99

3.04

6

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 37 of 105

Ana l yte P8: 2C-T H+ Acqui s i on Da te 2012-11-24T14:06:55 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 7.97 (s , 3H), 6.83 (s , 1H), 6.76 (s , 1H), 3.80 (s , 3H), 3.76 (s , 3H), 2.98 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.41 (s , 3H).

75 O 65

5

NH3 12

2 3

S 64

11

1

4

80

+

10

6

O 62 72

MeO (s) 3.76

8.00

7.95

6.85

6.80

6.75

3.85

3.80

3.75

2.95

2.90

2.85

80 (s) 2.41

3.00

1.99

10 (m) 2.82

2.02

11 (m) 2.95

3.08

3.09

MeO (s) 3.80

1.03

ArH (s) 6.76

1.04

ArH (s) 6.83

2.74

12 (s) 7.97

2.80

2.40

Page 38 of 105

Ana l yte P8: 2C-T H+ Acqui s i on Da te 2012-11-24T14:06:55 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 7.97 (s , 3H), 6.83 (s , 1H), 6.76 (s , 1H), 3.80 (s , 3H), 3.76 (s , 3H), 2.98 – 2.91 (m, 2H), 2.86 – 2.79 (m, 2H), 2.41 (s , 3H).

75 O 65

5

NH3 12

2 3

S 64

11

1

4

80

+

10

6

O 62 72

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 2.82 10 (m) 2.95

2.02 1.99

3.09 3.08

MeO (s) 3.80

1.04 1.03

ArH (s) 6.83

2.74

12 (s) 7.97

MeO (s) 3.76

3.5

3.0

80 (s) 2.41

3.00

ArH (s) 6.76

2.5

2.0

1.5

1.0

0.5

0.0

Page 39 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-T H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.75 (t, J = 0.9 Hz, 1H), 6.67 (s , 1H), 3.79 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.47 (s , 3H).

75 O 65 80

5

11

1

4 S 64

+

10

6

NH3 12

2 3

O 62 72

3 (s) 6.67 12 (s) 8.10

72 (s) 3.74

6 (t) 6.75

75 (s) 3.79

10 (td) 3.13

80 (s) 2.47

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.00

1.98

3.01 2.99 2.00

1.03 0.99

3.00

11 (t) 3.66

3.0

2.5

2.0

1.5

1.0

0.5

Page 40 of 105

Ana l yte P9: 2C-T-2 H+ Acqui s i on Da te 2012-11-24T13:18:04 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

O 65 81 82

6 5 4

S 64

+

10 1

11

NH3 12

2 3

O 62 72

MeO (s) 3.76 11 (m) 2.96

8.00

7.95

6.90

6.85

6.80

3.80

3.75

2.97

2.96

2.02

3.05

3.09

1.01

1.03

2.63

2.98

3.00

81 (q) 2.92

2.95

10 (m) 2.83

2.94

2.93

2.92

2.95

2.90

2.91

82 (t) 1.23

2.90

2.89

2.85

3.02

MeO (s) 3.78

2.00

ArH (s) 6.85

2.15

ArH (s) 6.83 12 (s) 7.98

NMR (500 MHz, DMSO-d6) δ 7.98 (s , 3H), 6.85 (s , 1H), 6.83 (s , 1H), 3.78 (s , 3H), 3.76 (s , 3H), 3.01 – 2.92 (m, 2H), 2.92 (q, J = 7.3 Hz, 2H), 2.86 – 2.79 (m, 2H), 1.23 (t, J = 7.3 Hz, 3H).

75

2.80

1.25

1.20

Page 41 of 105

Ana l yte P9: 2C-T-2 H+ Acqui s i on Da te 2012-11-24T13:18:04 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

12 (s) 7.98

1H

NMR (500 MHz, DMSO-d6) δ 7.98 (s , 3H), 6.85 (s , 1H), 6.83 (s , 1H), 3.78 (s , 3H), 3.76 (s , 3H), 3.01 – 2.92 (m, 2H), 2.92 (q, J = 7.3 Hz, 2H), 2.86 – 2.79 (m, 2H), 1.23 (t, J = 7.3 Hz, 3H).

75 O 65 81 82

6 5

1

4 S 64

+

10 11

NH3 12

2 3

O 62 72

ArH (s) 6.83

MeO (s) 3.76

81 (q) 2.92

ArH (s) 6.85

MeO (s) 3.78

11 (m) 2.96

82 (t) 1.23

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

3.02

2.02 2.15 2.00

3.09 3.05

1.03 1.01

2.63

10 (m) 2.83

2.5

2.0

1.5

1.0

0.5

Page 42 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-T-2 H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.75 (t, J = 0.9 Hz, 1H), 6.67 (s , 1H), 3.79 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.86 (q, J = 6.6 Hz, 2H), 1.31 (t, J = 6.6 Hz, 3H).

75 O 65 81 82

6 5

11

1

4 S 64

+

10

NH3 12

2 3

O 62 72

3 (s) 6.67 12 (s) 8.10

72 (s) 3.74

6 (t) 6.75

75 (s) 3.79

81 (q) 2.86 10 (td) 3.13

82 (t) 1.31

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

3.01

2.01

1.95

3.03 3.05 1.95

0.98 0.98

3.04

11 (t) 3.66

2.5

2.0

1.5

1.0

0.5

Page 43 of 105

8.00

7.95

6.90

88

O 65

86 87

6 5

1

4 S 64

3.80

NH3 12

11

2 3

O 62 72

MeO (s) 3.76

3.57

3.75

3.65

3.60

3.55

3.56

3.55

3.50

3.45

3.54

3.70

3.53

10 (m) 2.84

3.52

3.00

3.51

3.50

87,88 (d) 1.21

3.49

2.95

2.90

2.85

6.05

3.58

1.10

3.59

11 (m) 2.96

2.05

86 (hept) 3.54

3.24

2.88 6.85

NMR (500 MHz, DMSO-d6) δ 7.98 (s , 3H), 6.91 (s , 1H), 6.87 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 3.54 (hept, J = 6.6 Hz, 1H), 3.01 – 2.93 (m, 2H), 2.87 – 2.80 (m, 2H), 1.21 (d, J = 6.6 Hz, 6H).

+

10

MeO (s) 3.77

1.01

ArH (s) 6.91

0.97

2.72

12 (s) 7.98

1H

75

2.06

Ana l yte P10: 2C-T-4 H+ Acqui s i on Da te 2012-11-24T13:09:47 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768 ArH (s) 6.87

2.80

1.25

1.20

1.15

Page 44 of 105

Ana l yte P10: 2C-T-4 H+ Acqui s i on Da te 2012-11-24T13:09:47 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

NMR (500 MHz, DMSO-d6) δ 7.98 (s , 3H), 6.91 (s , 1H), 6.87 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 3.54 (hept, J = 6.6 Hz, 1H), 3.01 – 2.93 (m, 2H), 2.87 – 2.80 (m, 2H), 1.21 (d, J = 6.6 Hz, 6H).

75

88

O 65

86 87

6 5

1

4 S 64

+

10 11

NH3 12

2 3

O 62 72

ArH (s) 6.87 12 (s) 7.98

MeO (s) 3.76

ArH (s) 6.91

MeO (s) 3.77

10 (m) 2.84 11 (m) 2.96

87,88 (d) 1.21

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

6.05

2.06 2.05

2.88 3.24 1.10

0.97 1.01

2.72

86 (hept) 3.54

2.5

2.0

1.5

1.0

0.5

Page 45 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-T-4 H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.75 (t, J = 0.9 Hz, 1H), 6.67 (s , 1H), 3.79 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.17 – 3.10 (m, 2H), 3.13 – 3.03 (m, 1H), 1.32 (d, J = 6.4 Hz, 6H).

75

88

O 65

86 87

6 5

1

4 S 64

+

10 11

NH3 12

2 3

O 62 72

3 (s) 6.67 12 (s) 8.10

72 (s) 3.74

6 (t) 6.75

75 (s) 3.79

86 (m) 3.09 10 (m) 3.13

87,88 (d) 1.32

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

6.01

1.82 1.13

3.01 3.00 2.01

1.03 0.99

3.01

11 (t) 3.66

2.5

2.0

1.5

1.0

0.5

Page 46 of 105

O 65 85

83

5

S 64

11

1

NH3 12

2 3

O 62 72

MeO (s) 3.76 83 (t) 2.88

3.80

2.05

3.03 6.80

2.99

6.85

1.03

1.08

2.76 8.00

3.75

2.95

1.62

10 (m) 2.83

1.61

2.90

1.60

84 (h) 1.58

1.59

1.58

1.57

2.85

1.56

85 (t) 0.98

1.55

1.54

2.80

1.65

1.60

2.97

11 (m) 2.95

1.99

MeO (s) 3.77

2.01

ArH (s) 6.85

1.63

8.05

NMR (500 MHz, DMSO-d6) δ 8.02 (s , 3H), 6.85 (s , 1H), 6.82 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 2.99 – 2.92 (m, 2H), 2.88 (t, J = 7.1 Hz, 2H), 2.86 – 2.79 (m, 2H), 1.58 (h, J = 7.3 Hz, 2H), 0.98 (t, J = 7.3 Hz, 3H).

+

10

6

4

84

ArH (s) 6.82 12 (s) 8.02

1H

75

2.09

Ana l yte P11: 2C-T-7 H+ Acqui s i on Da te 2012-11-24T14:15:22 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1.55

1.00

0.95

Page 47 of 105

Ana l yte P11: 2C-T-7 H+ Acqui s i on Da te 2012-11-24T14:15:22 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

12 (s) 8.02

1H

NMR (500 MHz, DMSO-d6) δ 8.02 (s , 3H), 6.85 (s , 1H), 6.82 (s , 1H), 3.77 (s , 3H), 3.76 (s , 3H), 2.99 – 2.92 (m, 2H), 2.88 (t, J = 7.1 Hz, 2H), 2.86 – 2.79 (m, 2H), 1.58 (h, J = 7.3 Hz, 2H), 0.98 (t, J = 7.3 Hz, 3H).

75 O 65 85

83 84

5

11

1

4 S 64

+

10

6

NH3 12

2 3

O 62 72

ArH (s) 6.82

MeO (s) 3.76

ArH (s) 6.85

MeO (s) 3.77

83 (t) 2.88 11 (m) 2.95

84 (h) 1.58

85 (t) 0.98

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

1.5

2.97

1.99

2.05 2.09 2.01

3.03 2.99

1.08 1.03

2.76

10 (m) 2.83

1.0

0.5

Page 48 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

2C-T-7 H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.75 (t, J = 0.9 Hz, 1H), 6.67 (s , 1H), 3.79 (s , 3H), 3.74 (s , 3H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 (td, J = 7.6, 1.0 Hz, 2H), 2.86 (t, J = 7.9 Hz, 2H), 1.54 (tq, J = 7.9, 6.6 Hz, 2H), 0.95 (t, J = 6.6 Hz, 3H).

75 O 65 85

83 84

6 5

1

4 S 64

+

10 11

NH3 12

2 3

O 62 72

3 (s) 6.67 12 (s) 8.10

72 (s) 3.74

6 (t) 6.75

75 (s) 3.79

83 (t) 2.86 10 (td) 3.13

84 (tq) 1.54

85 (t) 0.95

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

1.5

2.98

1.95

2.02

1.96

3.05 3.06 1.96

0.98 0.98

3.06

11 (t) 3.66

1.0

0.5

Page 49 of 105

8.25

8.15

6.55

5

51

10 1

4

12

2 3 O 63

73,75 (s) 3.75

2.12

51 (q) 3.85

3.85

11 (m) 3.02

3.80

3.75

10 (m) 2.84

3.70

3.05

52 (t) 1.20

3.00

2.95

2.90

2.85

3.04

73

3.90

11

1.96

O 64

NMR (500 MHz, DMSO-d6) δ 8.22 (s , 3H), 6.56 (s , 2H), 3.85 (q, J = 7.0 Hz, 2H), 3.75 (s , 6H), 3.06 – 2.99 (m, 2H), 2.89 – 2.81 (m, 2H), 1.20 (t, J = 7.0 Hz, 3H).

+ NH3

1.94

52

1.98 8.20

6

O 65

2,6 (s) 6.56

2.91

12 (s) 8.22

1H

75

6.05

Ana l yte P12: Es ca l i ne H+ Acqui s i on Da te 2013-01-17T01:53:27 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.80

1.25

1.20

1.15

Page 50 of 105 1H

75

51 52

6 5

10 1

4

11

12

2 3

O 64 73

O 63

73,75 (s) 3.75

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.94

11 (m) 3.02

2.12 6.05

51 (q) 3.85

1.98

2,6 (s) 6.56

2.91

12 (s) 8.22

10 (m) 2.84

3.5

3.0

52 (t) 1.20

3.04

O 65

NMR (500 MHz, DMSO-d6) δ 8.22 (s , 3H), 6.56 (s , 2H), 3.85 (q, J = 7.0 Hz, 2H), 3.75 (s , 6H), 3.06 – 2.99 (m, 2H), 2.89 – 2.81 (m, 2H), 1.20 (t, J = 7.0 Hz, 3H).

+ NH3

1.96

Ana l yte P12: Es ca l i ne H+ Acqui s i on Da te 2013-01-17T01:53:27 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.5

2.0

1.5

1.0

0.5

0.0

Page 51 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

Es ca l i ne H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

75 O 65 51 52

6 5

10 1

4

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.54 (t, J = 1.0 Hz, 2H), 4.08 (q, J = 5.9 Hz, 2H), 3.70 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 ( , J = 7.5, 1.1 Hz, 2H), 1.34 (t, J = 5.8 Hz, 3H).

+ NH3

11

12

2 3

O 64 73

O 63

73,75 (s) 3.70

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

52 (t) 1.34

3.5

1.64

10 (tt) 3.13

1.08

11 (t) 3.66

3.33 1.09

1.09

51 (q) 4.08

1.09

2,6 (t) 6.54

1.68

12 (s) 8.10

3.0

2.5

2.0

1.5

1.0

0.5

Page 52 of 105 75

8.3

8.2

8.1

O 63

53,73,75 (m) 3.76

3.74

8.0

6.6

11 (m) 3.03

1.65

1.64

8.21

3.75

2

2.04

3.76

2.88

3.77

2,6 (s) 6.56

12

3

73

12 (s) 8.05

3.78

4 O 64

11

6.5

3.8

1.63

10 (m) 2.82

1.62

1.61

3.7

3.1

1.60

1.59

3.0

2.9

2.8

54 (h) 1.61

1.58

1.57

55 (t) 0.94

1.56

1.6

3.00

53 54

10 1

1.97

55

6 5

NMR (500 MHz, DMSO-d6) δ 8.05 (s , 3H), 6.56 (s , 2H), 3.79 – 3.72 (m, 8H), 3.07 – 3.00 (m, 2H), 2.85 – 2.78 (m, 2H), 1.61 (h, J = 7.1 Hz, 2H), 0.94 (t, J = 7.4 Hz, 3H).

+ NH3

1.97

O 65

1H

1.92

Ana l yte P13a : Pros ca l i ne H+ Acqui s i on Da te 2012-11-24T12:58:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1.0

0.9

Page 53 of 105

Ana l yte P13a : Pros ca l i ne H+ Acqui s i on Da te 2012-11-24T12:58:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

75 O 65 55

53 54

1H

6 5 4

O 64

10 1

NMR (500 MHz, DMSO-d6) δ 8.05 (s , 3H), 6.56 (s , 2H), 3.79 – 3.72 (m, 8H), 3.07 – 3.00 (m, 2H), 2.85 – 2.78 (m, 2H), 1.61 (h, J = 7.1 Hz, 2H), 0.94 (t, J = 7.4 Hz, 3H).

+ NH3

11

12

2 3

73

O 63

10 (m) 2.82

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

1.5

55 (t) 0.94

3.00

1.97

54 (h) 1.61

1.97

11 (m) 3.03

1.92

8.21

53,73,75 (m) 3.76

2.04

2,6 (s) 6.56

2.88

12 (s) 8.05

1.0

0.5

Page 54 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

Pros ca l i ne H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11880 500.00 1H

75 O 65 55

53 54

1H

6 5 4

O 64

10 1

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.54 (t, J = 1.0 Hz, 2H), 4.02 (t, J = 7.5 Hz, 2H), 3.70 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 ( , J = 7.5, 1.1 Hz, 2H), 1.80 – 1.69 (m, 2H), 0.98 (t, J = 6.7 Hz, 3H).

+ NH3

11

12

2 3

73

O 63

73,75 (s) 3.70

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

55 (t) 0.98

3.03

54 (m) 1.74

1.85

10 (tt) 3.13

1.97

6.09 2.00

2.01

53 (t) 11 (t) 4.02 3.66

2.00

2,6 (t) 6.54

3.06

12 (s) 8.10

1.5

1.0

0.5

Page 55 of 105 75

8.3

8.2

O 63

53,73,75 (m) 3.75

3.74

8.1

8.0

6.6

11 (m) 3.02

1.65

1.64

8.28

3.75

2

1.99

3.76

3.04

3.77

12

6.5

3.8

1.63

10 (m) 2.84

1.62

1.61

3.7

3.1

3.0

1.60

1.59

2.9

54 (m) 1.60

1.58

1.57

55 (t) 0.93

1.56

2.8

1.6

2.93

2,6 (s) 6.56

11

3

O 64 73

12 (s) 8.20

3.78

4

53 54

10 1

1.84

55

6 5

NMR (500 MHz, DMSO-d6) δ 8.20 (s , 3H), 6.56 (s , 2H), 3.80 – 3.71 (m, 8H), 3.06 – 2.98 (m, 2H), 2.89 – 2.80 (m, 2H), 1.66 – 1.55 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H).

+ NH3

1.99

O 65

1H

1.92

Ana l yte P13b: Pros ca l i ne H+ Acqui s i on Da te 2013-03-26T19:44:08 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

1.0

0.9

Page 56 of 105

Ana l yte P13b: Pros ca l i ne H+ Acqui s i on Da te 2013-03-26T19:44:08 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

75 O 65 55

6 5

NMR (500 MHz, DMSO-d6) δ 8.20 (s , 3H), 6.56 (s , 2H), 3.80 – 3.71 (m, 8H), 3.06 – 2.98 (m, 2H), 2.89 – 2.80 (m, 2H), 1.66 – 1.55 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H).

+ NH3

10 1

4

53 54

1H

11

12

2 3

O 64 73

O 63

10 (m) 2.84

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

1.5

55 (t) 0.93

2.93

1.84

54 (m) 1.60

1.99

11 (m) 3.02

1.92

8.28

53,73,75 (m) 3.75

1.99

2,6 (s) 6.56

3.04

12 (s) 8.20

1.0

0.5

0.0

Page 57 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

Pros ca l i ne H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

75 O 65 55

53 54

6 5 4

O 64

10 1

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.54 (t, J = 1.0 Hz, 2H), 4.02 (t, J = 7.5 Hz, 2H), 3.70 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 ( , J = 7.5, 1.1 Hz, 2H), 1.80 – 1.69 (m, 2H), 0.98 (t, J = 6.7 Hz, 3H).

+ NH3

11

12

2 3

73

O 63

73,75 (s) 3.70

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

55 (t) 0.98

3.03

54 (m) 1.74

1.85

10 (tt) 3.13

1.97

6.09 2.00

2.01

53 (t) 11 (t) 4.02 3.66

2.00

2,6 (t) 6.54

3.06

12 (s) 8.10

1.5

1.0

0.5

Page 58 of 105

5.96

5.94

5.92

5.34

5.32

5.30

5.28

5.26

5.24

5.22

0.93

5.98

2.10

6.00

2.81

6.02

6.6

6.5

3 O 63

6.0

92' (dq) 5.28

92'' (m) 5.14

90 (dt) 4.35

4.37

4.36

4.35

4.34

4.33

5.18

5.16

5.14

5.12

5.10

5.20

5.3

5.2

73,75 (s) 3.76

5.1

4.4

11 (m) 3.03

10 (m) 2.83

4.32

4.3

3.8

3.1

1.97

91 (ddt) 5.98

12

2

O 64 73

6.04

8.1

4

11

1.98

90 91

10 1

6.19

92

6 5

2.05

2,6 (s) 6.57

O 65

NMR (500 MHz, DMSO-d6) δ 8.13 (s , 3H), 6.57 (s , 2H), 5.98 (ddt, J = 17.3, 10.4, 5.6 Hz, 1H), 5.28 (dq, J = 17.3, 1.8 Hz, 1H), 5.17 – 5.10 (m, 1H), 4.35 (dt, J = 5.6, 1.6 Hz, 2H), 3.76 (s , 6H), 3.06 – 2.99 (m, 2H), 2.87 – 2.80 (m, 2H).

+ NH3

0.99

12 (s) 8.13

1H

75

0.99

Ana l yte P14: AL H+ Acqui s i on Da te 2012-11-24T14:23:49 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

3.0

2.9

2.8

Page 59 of 105 1H

75 O 65 92

90

6 5 4

91

O 64

10 1

NMR (500 MHz, DMSO-d6) δ 8.13 (s , 3H), 6.57 (s , 2H), 5.98 (ddt, J = 17.3, 10.4, 5.6 Hz, 1H), 5.28 (dq, J = 17.3, 1.8 Hz, 1H), 5.17 – 5.10 (m, 1H), 4.35 (dt, J = 5.6, 1.6 Hz, 2H), 3.76 (s , 6H), 3.06 – 2.99 (m, 2H), 2.87 – 2.80 (m, 2H).

+ NH3

11

12

2 3

73

O 63

92'' (m) 5.14

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 3.03

0.92

73,75 (s) 3.76

2.87

90 (dt) 4.35

0.95

92' (dq) 5.28

0.46 0.46

91 (ddt) 5.98

0.43

0.98

2,6 (s) 6.57

1.30

12 (s) 8.13

10 (m) 2.83

3.5

3.0

0.91

Ana l yte P14: AL H+ Acqui s i on Da te 2012-11-24T14:23:49 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.5

2.0

1.5

1.0

0.5

Page 60 of 105

AL H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 500.00 1H

1H

75 O 65 92

90 91

6 5

10 1

4

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.41 (t, J = 1.0 Hz, 2H), 6.06 (ddt, J = 16.3, 10.0, 6.1 Hz, 1H), 5.47 – 5.36 (m, 2H), 4.66 (dt, J = 6.2, 1.1 Hz, 2H), 3.70 (s , 6H), 3.66 (t, J = 7.6 Hz, 2H), 3.13 ( , J = 7.6, 1.2 Hz, 2H).

+ NH3

11

12

2

O 64

3

73

O 63

91 (ddt) 6.06

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

6.01 2.02

73,75 (s) 3.70

1.99

90 (dt) 4.66

1.98

92 (m) 5.41

1.02

2.00

2,6 (t) 6.41

3.01

12 (s) 8.10

11 (t) 3.66

4.5

4.0

10 (tt) 3.13

1.97

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 61 of 105

8.05

8.00

O 65 93

4 O 64

6.55

5.00

2

O 63

95'' (m) 4.86

4.870

4.865

4.860

4.95

4.90

4.85

93 (m) 4.25

4.855

4.850

4.25

73,75 (s) 3.76

4.845

11 (m) 3.03

4.255

4.250

4.245

10 (m) 2.82

4.240

4.235

3.75

3.05

1.790

96 (m) 1.78

1.785

1.780

3.00

2.85

1.775

3.05

73

1.96

96

4.985

12

3

95' (m) 5.00

4.990

11

1.91

94

10 1

NMR (500 MHz, DMSO-d6) δ 8.03 (s , 3H), 6.56 (s , 2H), 5.02 – 4.97 (m, 1H), 4.89 – 4.83 (m, 1H), 4.27 – 4.22 (m, 2H), 3.76 (s , 6H), 3.06 – 3.00 (m, 2H), 2.86 – 2.78 (m, 2H), 1.81 – 1.76 (m, 3H).

+ NH3

5.93

95

6 5

1.03

4.995

1.92

5.000

3.22

5.005

2.6 (s) 6.56

1H

0.97

12 (s) 8.03

75

2.01

Ana l yte P15: MAL H+ Acqui s i on Da te 2012-11-24T12:41:39 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.80

1.80

Page 62 of 105 75

95

93 94

6 5 4

O 64

10 1

NMR (500 MHz, DMSO-d6) δ 8.03 (s , 3H), 6.56 (s , 2H), 5.02 – 4.97 (m, 1H), 4.89 – 4.83 (m, 1H), 4.27 – 4.22 (m, 2H), 3.76 (s , 6H), 3.06 – 3.00 (m, 2H), 2.86 – 2.78 (m, 2H), 1.81 – 1.76 (m, 3H).

+ NH3

11

12

2 3

96 73

O 63

95'' (m) 4.86

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 3.03

1.91

5.93

2.01

93 (m) 73,75 (s) 4.25 3.76

0.97 1.03

95' (m) 5.00

1.92

2,6 (s) 6.56

3.22

12 (s) 8.03

10 (m) 2.82

3.5

3.0

96 (m) 1.78

3.05

O 65

1H

1.96

Ana l yte P15: MAL H+ Acqui s i on Da te 2012-11-24T12:41:39 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.5

2.0

1.5

1.0

0.5

Page 63 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

MAL H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 500.00 1H

75 O 65 95

93 94

1H

10

6 5 4

12

11

1

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.41 (t, J = 1.0 Hz, 2H), 5.29 (dq, J = 2.2, 1.1 Hz, 1H), 5.17 (dq, J = 2.2, 1.1 Hz, 1H), 4.61 (t, J = 1.0 Hz, 2H), 3.68 (d, J = 19.9 Hz, 8H), 3.13 ( , J = 7.6, 1.2 Hz, 2H), 1.77 (t, J = 1.0 Hz, 3H).

+ NH3

2

O 64

3

96 73

O 63

95'' (dq) 5.17

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

96 (t) 1.77

3.5

2.98

10 (tt) 3.13

1.98

8.05

73,11,75 (d) 3.68

2.01

93 (t) 4.61

0.98 0.97

95' (dq) 5.29

2.01

2,6 (t) 6.41

3.02

12 (s) 8.10

3.0

2.5

2.0

1.5

1.0

0.5

Page 64 of 105

Ana lyte P16: BOD H+ Acquis i on Da te 2012-11-24T12:49:33 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

17

1H

NMR (500 MHz, DMSO-d6) δ 8.14 (s , 3H), 6.91 (d, J = 0.9 Hz, 1H), 6.82 (s , 1H), 4.78 (dd, J = 8.9, 3.9 Hz, 1H), 3.75 (s , 3H), 3.75 (s , 3H), 3.21 (s , 3H), 2.96 – 2.82 (m, 2H), 2.16 (d, J = 0.9 Hz, 3H).

O 16

75 O 65

5

11

1

NH3 12

2

4 40

+

10

6

3

O 62 72

MeO (s) 3.75

8.20

8.15

8.10

6.95

6.90

6.85

6.80

4.80

17 (s) 3.21

11 (m) 2.91

40 (d) 2.16

4.75

3.75

3.20

2.95

2.90

2.89

4.76

2.07

4.77

MeO (s) 3.75

2.84

4.78

10 (dd) 4.78

3.04 2.86

4.79

1.07

3.12

4.80

ArH (s) 6.82

1.04

ArH (d) 6.91

1.06

12 (s) 8.14

2.85

2.20

2.15

Page 65 of 105

Ana lyte P16: BOD H+ Acquis i on Da te 2012-11-24T12:49:33 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 8012.8 Nucleus 1H Acquired Size 32768

17

O 65

1H

NMR (500 MHz, DMSO-d6) δ 8.14 (s , 3H), 6.91 (d, J = 0.9 Hz, 1H), 6.82 (s , 1H), 4.78 (dd, J = 8.9, 3.9 Hz, 1H), 3.75 (s , 3H), 3.75 (s , 3H), 3.21 (s , 3H), 2.96 – 2.82 (m, 2H), 2.16 (d, J = 0.9 Hz, 3H).

O 16

75

5

11

1

4 40

+

10

6

NH3 12

2 O 62

3

72

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

11 (m) 2.91

3.5

40 (d) 2.16

3.0

2.89

17 (s) 3.21

2.84

3.04 2.86

MeO (s) 3.75

1.04

10 (dd) 4.78

1.07 1.06

ArH (d) 6.91

3.12

12 (s) 8.14

MeO (s) 3.75

2.07

ArH (s) 6.82

2.5

2.0

1.5

1.0

0.5

Page 66 of 105

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

BOD H+ Modgra ph NMRPredict Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

17

O 65

1H

NMR (500 MHz, DMSO-d6) δ 8.10 (s , 3H), 6.88 (d, J = 1.0 Hz, 1H), 6.78 (q, J = 1.1 Hz, 1H), 5.20 (td, J = 6.0, 1.0 Hz, 1H), 3.92 (dd, J = 12.4, 5.8 Hz, 1H), 3.74 (s , 3H), 3.71 (s , 3H), 3.67 (dd, J = 12.4, 5.9 Hz, 1H), 3.17 (s , 3H), 2.12 (d, J = 1.1 Hz, 3H).

O 16

75 6 5

1

4 40

+

10 11

NH3 12

2 3

O 62 72

11' (dd) 3.67 3 (q) 6.78 12 (s) 8.10

72 (s) 3.74

6 (d) 6.88

10 (td) 5.20

11'' (dd) 3.92

17 (s) 3.17

40 (d) 2.12

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

2.95

3.05

1.01 3.00 3.01 1.01

0.97

0.98 0.98

3.05

75 (s) 3.71

3.0

2.5

2.0

1.5

1.0

0.5

Page 67 of 105

Ana l yte P17: bk-2C-B H+ Acqui s i on Da te 2013-11-29T14:34:40 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 699.82 Spectra l Wi dth 11160.7 Nucl eus 1H Acqui red Si ze 50223

75 O 65

8.30

5

11

1

4

+

NH3 12

2 3

O 62 72

4.325

8.25

7.60

4.320

4.315

4.310

7.55

7.50

7.45

4.305

7.40

4.35

4.30

4.300

MeO (s) 3.86

4.295

3.95

3.00

8.26

MeO (s) 3.94

3.15

8.27

11 (q) 4.31

0.98

8.28

1.02

8.29

ArH (s) 7.43

1.98

ArH (s) 7.59

2.87 8.35

NMR (700 MHz, DMSO-d6) δ 8.28 (s , 3H), 7.59 (s , 1H), 7.43 (s , 1H), 4.31 (q, J = 5.2 Hz, 2H), 3.94 (s , 3H), 3.86 (s , 3H).

10

6

Br 64

12 (s) 8.28

8.30

1H

O 16

3.90

3.85

Page 68 of 105

Ana l yte P17: bk-2C-B H+ Acqui s i on Da te 2013-11-29T14:34:40 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 699.82 Spectra l Wi dth 11160.7 Nucl eus 1H Acqui red Si ze 50223

75 O 65

1H

NMR (700 MHz, DMSO-d6) δ 8.28 (s , 3H), 7.59 (s , 1H), 7.43 (s , 1H), 4.31 (q, J = 5.2 Hz, 2H), 3.94 (s , 3H), 3.86 (s , 3H).

O 16 5

11

1

4 Br 64

+

10

6

NH3 12

2 O 62

3

72

9.0

8.5

8.0

7.5

1.98

11 (q) 4.31

0.98

1.02

ArH (s) 7.59

2.87

12 (s) 8.28

MeO (s) 3.94

7.0

6.5

6.0

5.5

5.0

4.5

MeO (s) 3.86

3.15 3.00

ArH (s) 7.43

4.0

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 69 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

bk-2C-B H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 700.00 1H

O 65

1H

NMR (700 MHz, DMSO-d6) δ 7.40 (s , 1H), 7.29 (s , 1H), 7.20 (s , 3H), 4.59 (s , 2H), 3.93 (s , 3H), 3.88 (s , 3H).

O 16

75 6 5

1

4 Br 64

+

10 11

NH3 12

2 3

O 62 72

6 (s) 7.29

72 (s) 3.88

3 (s) 7.40

11 (s) 4.59

75 (s) 3.93

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

3.00 3.00

2.00

1.00 1.00 2.99

12 (s) 7.20

4.0

3.5

3.0

2.5

2.0

1.5

1.0

0.5

Page 70 of 105

Ana l yte B1: 25B-NBOMe H+ Acqui s i on Da te 2013-01-17T02:31:12 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

25 26

75 O 65

6 5

1

4 Br 40

+

10

NH2 12 20

11

21

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 9.18 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.19 (s , 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 7.02 (s , 1H), 7.00 (td, J = 7.4, 1.1 Hz, 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.79 (s , 3H), 3.75 (s , 3H), 3.10 – 3.03 (m, 2H), 3.00 – 2.93 (m, 2H).

24

28

O 27

72

ArH (s) 7.02 12 (s) 9.18

26 (dd) 24 (ddd) 7.49 7.41

ArH (s) 7.19

23 (dd) 7.08

25 (td) 7.00

MeO (s) 3.79 20 (s) 4.11

MeO (s) 3.83

11 (m) 3.06

10 (m) 2.97

9.2

9.1

7.5

7.4

7.3

7.2

7.1

7.0

4.1

4.0

3.9

3.8

3.7

3.1

1.91

1.91

3.05

3.02

3.07

1.92

1.12

1.01

1.04

1.03

1.05

1.03

1.86

MeO (s) 3.75

3.0

Page 71 of 105

Ana l yte B1: 25B-NBOMe H+ Acqui s i on Da te 2013-01-17T02:31:12 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

25 75

26

O 65

6 5

1

4 Br 40

+

10 11

NH2 12 20

21

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 9.18 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.19 (s , 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 7.02 (s , 1H), 7.00 (td, J = 7.4, 1.1 Hz, 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.79 (s , 3H), 3.75 (s , 3H), 3.10 – 3.03 (m, 2H), 3.00 – 2.93 (m, 2H).

24

28

O 27

72

23 (dd) 7.08

MeO (s) 3.75

24 (ddd) 7.41 12 (s) 9.18

MeO (s) 3.83

26 (dd) ArH (s) 7.49 7.02

20 (s) 4.11

ArH (s) 7.19

10 (m) 2.97 11 (m) 3.06

MeO (s) 3.79

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.91 1.91

3.07 3.02 3.05

1.92

1.03 1.05 1.03 1.04 1.01 1.12

1.86

25 (td) 7.00

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 72 of 105 1H

25 75

26

O 65

6 5

1

4

+

10 11

NH2 12 20

21

3

O 62

23 22

2

Br 40

NMR (500 MHz, DMSO-d6) δ 7.29 (s , 1H), 7.22 – 7.13 (m, 3H), 6.95 – 6.82 (m, 3H), 6.74 (t, J = 1.0 Hz, 1H), 3.93 (s , 3H), 3.74 (s , 6H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 5.2 Hz, 2H), 3.13 (td, J = 5.3, 1.0 Hz, 2H).

24

28

O 27

72

12,23 (m) 7.18 3 (s) 7.29

28,72 (s) 3.74 6 (t) 6.74

75 (s) 3.93

10.0

9.5

9.0

8.5

8.0

7.5

7.0

11 (t) 3.33

3.09 5.98 1.99

20 (d) 3.60

2.96 0.99

1.00 3.08

26,25,24 (m) 6.89

6.5

10 (td) 3.13

6.0

5.5

5.0

4.5

4.0

3.5

1.95

25B-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1.96

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.0

2.5

2.0

1.5

1.0

0.5

Page 73 of 105 1H

25 26

75 6 5

1

4

+

10 11

NH2 12 20

21

O 27

2 3

Cl 40

O 62

23 22

28

72

ArH (s) 7.08 26 (dd) 24 (ddd) 7.50 7.41

23 (m) 7.09

25 (td) 7.00

20 (s) 4.11

MeO (s) 3.83

9.3

9.2

7.5

7.4

7.3

7.2

7.1

7.0

4.1

4.0

3.9

2.99

3.10

1.94

MeO (s) 3.74

1.00

1.16 0.97 1.01

1.04

1.06

1.96

ArH (s) 7.04

11 (m) 10 (m) 3.06 2.98

3.8

3.7

3.1

1.90

12 (s) 9.23

MeO (s) 3.80

1.93

O 65

NMR (500 MHz, DMSO-d6) δ 9.23 (s , 2H), 7.50 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.2, 7.4, 1.7 Hz, 1H), 7.14 – 7.05 (m, 1H), 7.08 (s , 1H), 7.04 (s , 1H), 7.00 (td, J = 7.5, 1.1 Hz, 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.80 (s , 3H), 3.74 (s , 3H), 3.10 – 3.01 (m, 2H), 3.03 – 2.94 (m, 2H).

24

2.95

Ana l yte B2: 25C-NBOMe H+ Acqui s i on Da te 2013-01-17T02:39:37 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

3.0

2.9

Page 74 of 105

Ana l yte B2: 25C-NBOMe H+ Acqui s i on Da te 2013-01-17T02:39:37 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

25 26

75 6

O 65

5

1

4

11

NH2 12 20

21

O 62

23 22

2 3

Cl 40

+

10

NMR (500 MHz, DMSO-d6) δ 9.23 (s , 2H), 7.50 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.2, 7.4, 1.7 Hz, 1H), 7.14 – 7.05 (m, 1H), 7.08 (s , 1H), 7.04 (s , 1H), 7.00 (td, J = 7.5, 1.1 Hz, 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.80 (s , 3H), 3.74 (s , 3H), 3.10 – 3.01 (m, 2H), 3.03 – 2.94 (m, 2H).

24

28

O 27

72

ArH (s) 7.08

MeO (s) 3.74

24 (ddd) 7.41 12 (s) 9.23

26 (dd) 7.50

MeO (s) 3.83 25 (td) 7.00

20 (s) 4.11

23 (m) 7.09

10 (m) 2.98 11 (m) 3.06

MeO (s) 3.80

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.93 1.90

3.10 2.99 2.95

1.94

1.06 1.04 1.16 0.97 1.01 1.00

1.96

ArH (s) 7.04

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 75 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

25C-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

25 26

75 6

O 65

5

1

4

11

NH2 12 20

21

O 62

23 22

2 3

Cl 40

+

10

NMR (500 MHz, DMSO-d6) δ 7.24 (s , 1H), 7.20 (s , 2H), 7.17 (ddt, J = 7.7, 2.1, 1.1 Hz, 1H), 6.95 – 6.82 (m, 3H), 6.79 (t, J = 1.0 Hz, 1H), 3.96 (s , 3H), 3.74 (s , 6H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 5.1 Hz, 2H), 3.13 (td, J = 5.1, 1.0 Hz, 2H).

24

28

O 27

72

25,24,23 (m) 6.89 12 (s) 7.20 6 (t) 6.79

75 (s) 3.96

10.0

9.5

9.0

8.5

8.0

7.5

7.0

11 (t) 3.33

6.5

6.0

5.5

5.0

4.5

4.0

3.5

1.96

3.05 6.09 2.01

20 (d) 3.60

1.01 2.00 0.97 2.91 1.00

26 (ddt) 7.17

10 (td) 3.13

2.01

3 (s) 7.24

28,72 (s) 3.74

3.0

2.5

2.0

1.5

1.0

0.5

Page 76 of 105

Ana l yte B3: 25I-NBOMe H+ Acqui s i on Da te 2013-01-17T02:47:03 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

25 26

75 O 65

5

11

1

4

+

10

6

NH2 12 20

21

3

28

O 62

NMR (500 MHz, DMSO-d6) δ 9.15 (s , 2H), 7.48 (dd, J = 7.5, 1.8 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.32 (s , 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 6.99 (td, J = 7.4, 1.1 Hz, 1H), 6.90 (s , 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.77 (s , 3H), 3.73 (s , 2H), 3.09 – 3.00 (m, 2H), 2.99 – 2.92 (m, 2H).

23 22

2

I 40

1H

24

O 27

72

24 (ddd) 7.41 12 (s) 9.15

26 (dd) 7.48

MeO (s) 3.77 ArH (s) 7.32

23 (dd) 25 (td) ArH (s) 7.08 6.99 6.90

20 (s) 4.11

MeO (s) 3.83

11 (m) 3.06

10 (m) 2.96

9.2

9.1

7.5

7.4

7.3

7.2

7.1

7.0

6.9

4.1

4.0

3.9

3.8

3.7

3.1

1.91

1.97

2.71

2.93

3.18

1.99

1.03

1.12

1.13

0.99

1.10

1.04

1.90

MeO (s) 3.73

3.0

2.9

0.0

Page 77 of 105

Ana l yte B3: 25I-NBOMe H+ Acqui s i on Da te 2013-01-17T02:47:03 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

25 26

75

5

11

1

4 I 40

+

10

6

O 65

NH2 12 20

21

28

O 62

NMR (500 MHz, DMSO-d6) δ 9.15 (s , 2H), 7.48 (dd, J = 7.5, 1.8 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.32 (s , 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 6.99 (td, J = 7.4, 1.1 Hz, 1H), 6.90 (s , 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.77 (s , 3H), 3.73 (s , 2H), 3.09 – 3.00 (m, 2H), 2.99 – 2.92 (m, 2H).

23 22

2 3

1H

24

O 27

72

23 (dd) 7.08

MeO (s) 3.73

24 (ddd) 7.41 12 (s) 9.15

MeO (s) 3.83

26 (dd) 25 (td) 7.48 6.99

20 (s) 4.11

ArH (s) 7.32

10 (m) 2.96 11 (m) 3.06

MeO (s) 3.77

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

1.97 1.91

3.18 2.93 2.71

1.99

1.04 1.10 0.99 1.13 1.12 1.03

1.90

ArH (s) 6.90

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 78 of 105 25 26

75

5

11

1

4

+

10

6

O 65

NH2 12 20

21

3

28

O 62

NMR (500 MHz, DMSO-d6) δ 7.34 (s , 1H), 7.22 – 7.13 (m, 3H), 6.95 – 6.82 (m, 3H), 6.62 (t, J = 0.9 Hz, 1H), 3.93 (s , 3H), 3.74 (s , 6H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 5.1 Hz, 2H), 3.13 (td, J = 5.1, 1.0 Hz, 2H).

23 22

2

I 40

1H

24

O 27

72

12,23 (m) 7.18 3 (s) 7.34

28,72 (s) 3.74 6 (t) 6.62

75 (s) 3.93

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

11 (t) 3.33

3.04 6.08 2.00

20 (d) 3.60

1.02

2.91

1.01 2.97

26,25,24 (m) 6.89

10 (td) 3.13

6.0

5.5

5.0

4.5

4.0

3.5

1.96

25I-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 500.00 1H

2.01

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.0

2.5

2.0

1.5

1.0

0.5

Page 79 of 105 25

6

O 65

5

1

4 I 40

+

10 11

NH2 12 20

2 3

9.2

OH 27

O 62

9.0

7.4

7.3

7.2

7.1

7.0

6.9

6.8

4.1

4.0

3.9

3.8

2.03

11 (m) 3.05

2.90

MeO (s) 3.77

2.96

20 (s) 4.09

1.96

25 (td) 6.84

1.07

1.02

1.06

23 (dd) 6.97

MeO (s) 3.74

3.7

3.1

10 (m) 2.94

2.06

ArH (s) 6.89 24 (ddd) 7.23

0.94

1.03 9.1

23 22

72

26 (dd) 7.39

3.01 9.3

NMR (500 MHz, DMSO-d6) δ 9.22 (s , 3H), 7.39 (dd, J = 7.6, 1.7 Hz, 1H), 7.32 (s , 1H), 7.23 (ddd, J = 8.1, 7.3, 1.7 Hz, 1H), 6.97 (dd, J = 8.2, 1.1 Hz, 1H), 6.89 (s , 1H), 6.84 (td, J = 7.4, 1.1 Hz, 1H), 4.09 (s , 2H), 3.77 (s , 3H), 3.74 (s , 3H), 3.09 – 3.02 (m, 2H), 3.00 – 2.91 (m, 2H).

24

21

ArH (s) 7.32 12,27 (s) 9.22

1H

26

75

0.96

Ana l yte B4: 25I-NBOH H+ Acqui s i on Da te 2013-01-17T03:09:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

3.0

2.9

Page 80 of 105

Ana l yte B4: 25I-NBOH H+ Acqui s i on Da te 2013-01-17T03:09:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

25 26

75 O 65

5

1

4 I 40

+

10

6

11

NH2 12 20

2 3

1H

NMR (500 MHz, DMSO-d6) δ 9.22 (s , 3H), 7.39 (dd, J = 7.6, 1.7 Hz, 1H), 7.32 (s , 1H), 7.23 (ddd, J = 8.1, 7.3, 1.7 Hz, 1H), 6.97 (dd, J = 8.2, 1.1 Hz, 1H), 6.89 (s , 1H), 6.84 (td, J = 7.4, 1.1 Hz, 1H), 4.09 (s , 2H), 3.77 (s , 3H), 3.74 (s , 3H), 3.09 – 3.02 (m, 2H), 3.00 – 2.91 (m, 2H).

24 23

21 22 OH 27

O 62 72

23 (dd) 6.97 ArH (s) 25 (td) 7.32 6.84 26 (dd) ArH (s) 7.39 6.89

20 (s) 4.09

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

2.03 2.06

1.96

MeO (s) 3.74

1.03 0.94 1.06 1.02 0.96 1.07

3.01

24 (ddd) 7.23

10 (m) 2.94 11 (m) 3.05

2.96 2.90

12,27 (s) 9.22

MeO (s) 3.77

3.5

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 81 of 105 25 75 O 65

5

11

1

4 I 40

+

10

6

NH2 12 20

NMR (500 MHz, DMSO-d6) δ 9.68 (s , 1H), 7.34 (s , 1H), 7.20 (s , 2H), 7.01 (dd, J = 8.2, 6.4 Hz, 2H), 6.79 (td, J = 7.4, 2.0 Hz, 1H), 6.75 (dd, J = 7.2, 2.0 Hz, 1H), 6.62 (t, J = 0.9 Hz, 1H), 3.93 (s , 3H), 3.74 (s , 3H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 5.0 Hz, 2H), 3.13 (td, J = 5.0, 1.1 Hz, 2H).

21

23 22 OH 27

2 3

1H

24

26

O 62 72

12 (s) 23 (dd) 7.20 6.75 27 (s) 9.68

3 (s) 7.34

72 (s) 3.74

25 (td) 6.79

75 (s) 3.93

10.0

9.5

9.0

8.5

8.0

7.5

7.0

11 (t) 3.33

3.06 3.06 1.99

20 (d) 3.60

1.00 2.04 1.96 0.98 0.97 0.99

1.00

26,24 (dd) 7.01

10 (td) 3.13

6.5

6.0

5.5

5.0

4.5

4.0

3.5

1.97

25I-NBOH H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1.99

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.0

2.5

2.0

1.5

1.0

0.5

Page 82 of 105

Ana lyte B5: 25I-NBMD Acquis i on Da te 2013-05-07T19:21:56 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 10000.0 Nucleus 1H Acquired Size 65536

1H

25 75 O 65

10

6 5

11

1

4

NH 12 20

3

21

23 22

O 30

O 27

2

I 40

O 62

NMR (500 MHz, DMSO-d6) δ 7.25 (s , 1H), 6.84 (s , 1H), 6.86 – 6.78 (m, 1H), 6.81 – 6.72 (m, 2H), 5.96 (s , 2H), 3.73 (s , 3H), 3.71 (d, J = 0.3 Hz, 3H), 3.66 (d, J = 0.6 Hz, 2H), 2.69 – 2.65 (m, 4H), 1.98 (s , 1H).

24

26

29

72

6.80

6.75

5.95

3.75

3.70

3.65

12 (s) 1.98

2.70

0.78

10,11 (m) 2.67

4.03

20 (d) 3.66

3.03

MeO (s) 3.73

2.93

29 (s) 5.96

2.07

6.85

2.08

7.25

MDO-ArH (m) 6.77

1.00

1.03

ArH (s) 6.84

0.97

ArH (s) 7.25

MeO (d) 3.71

2.10

MDO-ArH (m) 6.83

2.65

2.00

1.95

Page 83 of 105

Ana lyte B5: 25I-NBMD Acquis i on Da te 2013-05-07T19:21:56 Solvent dms o Tempera ture 25 Number of Sca ns 16 Rela xa on Dela y 5 Spectrometer Frequency 499.67 Spectra l Width 10000.0 Nucleus 1H Acquired Size 65536

1H

25 75 O 65

11

1

4

NH 12 20

10

6 5

O 62

3

21

23 22 O 27

2

I 40

NMR (500 MHz, DMSO-d6) δ 7.25 (s , 1H), 6.84 (s , 1H), 6.86 – 6.78 (m, 1H), 6.81 – 6.72 (m, 2H), 5.96 (s , 2H), 3.73 (s , 3H), 3.71 (d, J = 0.3 Hz, 3H), 3.66 (d, J = 0.6 Hz, 2H), 2.69 – 2.65 (m, 4H), 1.98 (s , 1H).

24

26

O 30 29

72

MDO-ArH (m) 6.77 ArH (s) 6.84

MeO (d) 3.71 29 (s) 5.96

MeO (s) 3.73

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

12 (s) 1.98

6.0

5.5

5.0

4.5

4.0

3.5

3.0

0.78

2.93 3.03 2.10

20 (d) 3.66

2.07

1.03 1.00 2.08

0.97

MDO-ArH (m) 6.83

10,11 (m) 2.67

4.03

ArH (s) 7.25

2.5

2.0

1.5

1.0

0.5

Page 84 of 105 1H

25 75 O 65

26 6

10

5

1

4

NH 12 20

11

3

21

23 22 O 27

2

I 40

O 62

NMR (500 MHz, DMSO-d6) δ 9.70 (s , 1H), 7.13 (s , 1H), 6.93 (ddt, J = 7.5, 2.1, 1.0 Hz, 1H), 6.86 (t, J = 7.5 Hz, 1H), 6.80 (dd, J = 7.5, 2.2 Hz, 1H), 6.61 (t, J = 1.0 Hz, 1H), 5.83 (s , 2H), 4.03 (d, J = 0.9 Hz, 1H), 3.93 (s , 3H), 3.92 (d, J = 1.1 Hz, 1H), 3.74 (s , 3H), 3.27 (t, J = 7.6 Hz, 1H), 3.11 (t, J = 7.6 Hz, 1H), 2.68 (td, J = 7.6, 1.0 Hz, 2H).

24

O 30 29

72

24 (dd) 6.80

72 (s) 3.74

26 (ddt) 6.93 12 (s) 9.70

3 (s) 7.13

75 (s) 3.93

6 (t) 6.61

29 (s) 5.83

20'' (d) 4.03

9.5

9.0

8.5

8.0

7.5

7.0

11'' (t) 3.27

10 (td) 2.68

6.5

6.0

0.98 3.05 0.96 3.05

2.03

20' (d) 3.92

0.98 0.97 1.01 1.00 0.99

1.00

25 (t) 6.86

10.0

11' (t) 3.11

5.5

5.0

4.5

4.0

3.5

3.0

1.97

25I-NBMD Modgra ph NMRPredict Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1.00 1.00

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

2.5

2.0

1.5

1.0

0.5

Page 85 of 105

NH2 12 20

7.3

23 22

28

O 62

O 27

72

7.2

MeO (s) 3.73

6.9

6.8

6.7

4.1

4.0

3.9

3.8

3.7

3.1

40 (d) 2.13

3.0

2.98

11 (m) 3.03

2.01

MeO (s) MeO (s) 3.83 3.71

3.24 2.81

7.0

20 (s) 4.11

1.85

7.1

1.07

ArH (m) 6.82

10 (m) 2.94

1.94

ArH (s) 6.77

2.92

25 (td) 7.00 23 (dd) 7.08

7.4

NMR (500 MHz, DMSO-d6) δ 9.18 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 1.1 Hz, 1H), 6.88 – 6.79 (m, 1H), 6.77 (s , 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.71 (s , 3H), 3.10 – 2.96 (m, 2H), 3.00 – 2.88 (m, 2H), 2.13 (d, J = 0.7 Hz, 3H).

24

21

2 3

1.03

7.5

11

1

4 40

1.04

1.02 9.1

5

+

10

6

1.01

9.2

O 65

26 (dd) 7.49

1.98

12 (s) 9.18

1H

25 26

75

1.09

Ana l yte B6: 25D-NBOMe H+ Acqui s i on Da te 2013-01-17T02:54:51 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768 24 (ddd) 7.41

2.9

2.2

2.1

0.0

Page 86 of 105

Ana l yte B6: 25D-NBOMe H+ Acqui s i on Da te 2013-01-17T02:54:51 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

1H

25 26

75

5

11

1

4

+

10

6

O 65

NH2 12 20

21

3

28

O 62

23 22

2

40

NMR (500 MHz, DMSO-d6) δ 9.18 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 1.1 Hz, 1H), 6.88 – 6.79 (m, 1H), 6.77 (s , 1H), 4.11 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.71 (s , 3H), 3.10 – 2.96 (m, 2H), 3.00 – 2.88 (m, 2H), 2.13 (d, J = 0.7 Hz, 3H).

24

O 27

72

ArH (s) 6.77

26 (dd) 7.49

MeO (s) 3.83

25 (td) 7.00

20 (s) 4.11

10.0

9.5

9.0

8.5

8.0

7.5

7.0

11 (m) 3.03

40 (d) 2.13

6.5

6.0

5.5

5.0

4.5

2.92 3.24 2.81

1.85

MeO (s) 3.73

1.01 1.03 1.07 1.09

1.02 1.04

1.98

23 (dd) 7.08

10 (m) 2.94

4.0

3.5

3.0

2.98

12 (s) 9.18

ArH (m) 6.82

2.01 1.94

24 (ddd) 7.41

MeO (s) 3.71

2.5

2.0

1.5

1.0

0.5

0.0

Page 87 of 105 1H

25 26

75 O 65

6 5

11

1

4

+

10

NH2 12 20

21

O 62

3

23 22

2

40

NMR (500 MHz, DMSO-d6) δ 7.20 (s , 2H), 7.17 (ddt, J = 7.6, 2.1, 1.0 Hz, 1H), 6.95 – 6.82 (m, 3H), 6.75 (s , 2H), 3.74 (s , 3H), 3.71 (s , 6H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 7.5 Hz, 2H), 3.17 – 3.09 (m, 2H), 2.12 (d, J = 1.1 Hz, 3H).

24

28

O 27

72

26 (ddt) 7.17

72,75 (s) 3.71

12 (s) 3,6 (s) 7.20 6.75

28 (s) 11 (t) 3.74 3.33

9.5

9.0

8.5

8.0

7.5

7.0

6.0

5.5

5.0

4.5

4.0

3.5

3.09

3.06 6.20 2.05 6.5

40 (d) 2.12

20 (d) 3.60

2.98 1.82

2.05 0.99

25,24,23 (m) 6.89

10.0

10 (m) 3.13

1.96

25D-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1.81

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.0

2.5

2.0

1.5

1.0

0.5

Page 88 of 105

Ana l yte B7: 25E-NBOMe H+ 75 Acqui s i on Da te 2013-01-17T03:02:12 Sol vent dms o O 65 Tempera ture 25 Number of Sca ns 16 42 Rel a xa on Del a y 5 41 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

25 26

5

1

4

11

O 62

NMR (500 MHz, DMSO-d6) δ 9.20 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.09 (dd, J = 8.3, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 1.0 Hz, 1H), 6.80 (s , 1H), 6.78 (s , 1H), 4.12 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.72 (s , 3H), 3.07 – 2.99 (m, 2H), 2.98 – 2.91 (m, 2H), 2.53 (q, J = 7.4 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

21

23 22

28

O 27

72

24 (td) 7.00

26 (dd) 7.49

NH2 12 20

2 3

23 (ddd) 7.41 12 (s) 9.20

+

10

6

1H

24

ArH (s) 6.78

25 (dd) 7.09

MeO (s) 3.73

ArH (s) 6.80

20 (s) 4.12

10 (m) 2.95

MeO (s) 3.83

11 (m) 3.03

41 (q) 2.53

42 (t) 1.11

9.2

9.1

7.3

7.2

7.1

7.0

6.9

6.8

6.7

4.2

4.1

4.0

3.9

3.8

3.7

3.1

3.0

2.9

2.6

2.96

2.14

1.90

1.90

3.13 2.91

2.99

1.91

1.05 1.01

7.4

1.03

7.5

1.03

1.05

9.3

1.04

1.96

MeO (s) 3.72

2.5

1.1

0.0

Page 89 of 105 25 26 6

+

10

5

1

4

11

NH2 12 20

21

O 62

NMR (500 MHz, DMSO-d6) δ 9.20 (s , 2H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.09 (dd, J = 8.3, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 1.0 Hz, 1H), 6.80 (s , 1H), 6.78 (s , 1H), 4.12 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.72 (s , 3H), 3.07 – 2.99 (m, 2H), 2.98 – 2.91 (m, 2H), 2.53 (q, J = 7.4 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H).

23 22

2 3

1H

24

28

O 27

72

ArH (s) 6.78

26 (dd) 7.49

MeO (s) 3.83

25 (td) 7.00

20 (s) 4.12

10.0

9.5

9.0

8.5

8.0

7.5

7.0

11 (m) 3.03

41 (q) 2.53

42 (t) 1.11

6.5

6.0

5.5

5.0

4.5

2.99 3.13 2.91

1.91

MeO (s) 3.73

1.03 1.03 1.05 1.01

1.04 1.05

1.96

23 (dd) 7.09

10 (m) 2.95

4.0

3.5

3.0

2.5

2.96

12 (s) 9.20

ArH (s) 6.80

2.14

24 (ddd) 7.41

MeO (s) 3.72

1.90 1.90

Ana l yte B7: 25E-NBOMe H+ 75 Acqui s i on Da te 2013-01-17T03:02:12 Sol vent dms o O 65 Tempera ture 25 Number of Sca ns 16 42 Rel a xa on Del a y 5 41 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 32768

2.0

1.5

1.0

0.5

0.0

Page 90 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

25E-NBOMe H+ Modgra ph NMRPredi ct Des ktop 75 DMSO-d6 O Bes t 65 50 11591 42 41 500.00 1H

25

+

10

6 5

11

1

4

NH2 12 20

21

O 62

NMR (500 MHz, DMSO-d6) δ 7.20 (s , 2H), 7.17 (ddt, J = 7.6, 2.1, 1.1 Hz, 1H), 6.95 – 6.82 (m, 3H), 6.80 (d, J = 1.2 Hz, 2H), 3.74 (s , 3H), 3.71 (s , 6H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 5.1 Hz, 2H), 3.13 (td, J = 5.1, 1.1 Hz, 2H), 2.50 (qd, J = 6.6, 1.0 Hz, 2H), 1.12 (t, J = 6.6 Hz, 3H).

23 22

2 3

1H

24

26

28

O 27

72

25,23 (d) 6.80 26 (ddt) 7.17

72,75 (s) 3.71

12 (s) 7.20

28 (s) 11 (t) 3.74 3.33

9.5

9.0

8.5

8.0

7.5

7.0

41 (qd) 2.50

42 (t) 1.12

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

2.5

3.01

1.98

2.00

1.98

3.04 6.00 2.01

20 (d) 3.60

3.06 1.94

2.01 0.97

3,6,24 (m) 6.90

10.0

10 (td) 3.13

2.0

1.5

1.0

0.5

Page 91 of 105

Ana l yte B8: 25IP-NBOMe H+ Acqui s i on Da te 2013-03-26T19:52:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 47 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

O 65

6 5

11

NH2 12 20

48

O 62

NMR (500 MHz, DMSO-d6) δ 9.22 (s , 2H), 7.50 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.4, 1.7 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.99 (td, J = 7.4, 1.0 Hz, 1H), 6.80 (s , 1H), 6.79 (s , 1H), 4.12 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.73 (s , 3H), 3.21 (hept, J = 6.9 Hz, 1H), 3.07 – 2.99 (m, 2H), 2.98 – 2.91 (m, 2H), 1.15 (d, J = 6.9 Hz, 6H).

24

21

23 22

2 3

28

O 27

72

25 (td) 6.99

26 (dd) 7.50

+

10 1

4 46

24 (ddd) 7.41 12 (s) 9.22

1H

25 26

75

ArH (s) 6.79

23 (dd) 7.08

ArH (s) 6.80

MeO (s) 3.73 20 (s) 4.12

10 (m) 2.94

MeO (s) 3.83

46 (hept) 3.21

11 (m) 3.03

47,48 (d) 1.15

7.2

6.9

4.0

3.9

3.8

3.7

3.6

3.5

3.4

3.3

3.2

3.1

3.0

5.99

1.88

1.91

4.1

0.82

6.8

3.10 3.07

7.0

3.08

7.1

1.96

7.3

1.07 1.01

7.4

1.01

7.5

1.04

9.2

1.03

9.3

1.06

1.97

MeO (s) 3.73

2.9

1.2

1.1

Page 92 of 105 1H

25 26

75 +

10

6 5

11

1

4

NH2 12 20

21

2

46

O 62

3

48

23 22

28

O 27

72

ArH (s) 6.79 24 (ddd) 7.41 12 (s) 9.22

26 (dd) 7.50

MeO (s) 3.73

ArH (s) 6.80

MeO (s) 3.83

25 (td) 6.99

20 (s) 4.12

9.5

9.0

8.5

8.0

7.5

7.0

46 (hept) 3.21

6.5

6.0

5.5

5.0

4.5

3.08 3.10 3.07

1.96

MeO (s) 3.73

1.04 1.01 1.07 1.01

1.06 1.03

1.97

23 (dd) 7.08

4.0

11 (m) 3.03 47,48 (d) 1.15

10 (m) 2.94

3.5

3.0

5.99

O 65

NMR (500 MHz, DMSO-d6) δ 9.22 (s , 2H), 7.50 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.4, 1.7 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.99 (td, J = 7.4, 1.0 Hz, 1H), 6.80 (s , 1H), 6.79 (s , 1H), 4.12 (s , 2H), 3.83 (s , 3H), 3.73 (s , 3H), 3.73 (s , 3H), 3.21 (hept, J = 6.9 Hz, 1H), 3.07 – 2.99 (m, 2H), 2.98 – 2.91 (m, 2H), 1.15 (d, J = 6.9 Hz, 6H).

24

0.82 1.91 1.88

Ana l yte B8: 25IP-NBOMe H+ Acqui s i on Da te 2013-03-26T19:52:57 Sol vent dms o Tempera ture 25 Number of Sca ns 16 47 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10964.9 Nucl eus 1H Acqui red Si ze 65536

2.5

2.0

1.5

1.0

0.5

0.0

Page 93 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

25IP-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 47 11591 500.00 1H

1H

25 75 O 65

26 6

+

10

5

1

4

11

NH2 12 20

21

O 62

3

48

23 22

2

46

NMR (500 MHz, DMSO-d6) δ 7.22 – 7.14 (m, 3H), 6.97 (d, J = 1.0 Hz, 1H), 6.95 – 6.82 (m, 3H), 6.80 (d, J = 1.0 Hz, 1H), 3.73 (d, J = 15.0 Hz, 9H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 7.5 Hz, 2H), 3.17 – 3.09 (m, 2H), 3.05 (heptd, J = 6.4, 1.0 Hz, 1H), 1.14 (d, J = 6.4 Hz, 6H).

24

28

O 27

72

6 (d) 6.80 3 (d) 6.97

20 (d) 46 (heptd) 3.60 3.05

12,23 (m) 7.18

28,72,75 (d) 10 (m) 3.73 3.13

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

6.03

1.80 1.94 0.97

9.20 2.03

11 (t) 3.33

3.03 1.02 2.98 1.01

26,24,25 (m) 6.89

47,48 (d) 1.14

2.5

2.0

1.5

1.0

0.5

Page 94 of 105

72

O 27

MeO (s) 3.73

7.2

6.9

6.8

6.7

6.6

4.2

4.1

4.0

3.9

MeO (s) 3.58

3.04

3.04

7.0

MeO (s) 3.84

2.00

7.1

20 (s) 4.14

1.01

0.99

1.01

7.3

6 (s) 6.66

3.8

10 (m) 2.99

3.7

3.6

11 (m) 3.08

3.1

Me (s) 2.04 Me (s) 2.12

3.0

2.1

2.98

63

28

3.11

O 62

23 22

2 3

23 (dd) 7.09

7.4

21

2.03

4 40

1.00

7.5

11

1

NH2 12 20

25 (td) 7.00

26 (dd) 7.52

0.97

1.74 9.3

5

+

10

6

NMR (500 MHz, DMSO-d6) δ 9.29 (s , 2H), 7.52 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.09 (dd, J = 8.4, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 7.4, 1.0 Hz, 1H), 6.66 (s , 1H), 4.14 (s , 2H), 3.84 (s , 3H), 3.73 (s , 3H), 3.58 (s , 3H), 3.11 – 3.02 (m, 2H), 3.05 – 2.95 (m, 2H), 2.12 (s , 3H), 2.04 (s , 3H).

24

26

2.05

O 65

24 (ddd) 7.41 12 (s) 9.29

1H

25 75

3.04

Ana l yte B9: 25G-NBOMe H+ Acqui s i on Da te 2013-05-07T19:40:05 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10000.0 Nucl eus 1H Acqui red Si ze 65536

2.0

Page 95 of 105

5

26 (dd) 7.52

11

1

4 40

+

10

6

NH2 12 20

21

2 3

O 62

63

72

23 22

28

O 27

6 (s) 6.66

MeO (s) 3.84

25 (td) 7.00

20 (s) 4.14

10.0

9.5

9.0

8.5

8.0

7.5

7.0

Me (s) 2.04

MeO (s) 11 (m) 3.58 3.08

Me (s) 2.12

6.5

6.0

5.5

5.0

4.5

3.04 3.04 3.04

2.00

MeO (s) 3.73

1.01

1.00 0.99

0.97 1.01

1.74

23 (dd) 7.09

10 (m) 2.99

4.0

3.5

3.0

3.11 2.98

O 65

NMR (500 MHz, DMSO-d6) δ 9.29 (s , 2H), 7.52 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.3, 7.5, 1.7 Hz, 1H), 7.09 (dd, J = 8.4, 1.0 Hz, 1H), 7.00 (td, J = 7.5, 1.0 Hz, 1H), 6.66 (s , 1H), 4.14 (s , 2H), 3.84 (s , 3H), 3.73 (s , 3H), 3.58 (s , 3H), 3.11 – 3.02 (m, 2H), 3.05 – 2.95 (m, 2H), 2.12 (s , 3H), 2.04 (s , 3H).

24

26

24 (ddd) 7.41 12 (s) 9.29

1H

25 75

2.05 2.03

Ana l yte B9: 25G-NBOMe H+ Acqui s i on Da te 2013-05-07T19:40:05 Sol vent dms o Tempera ture 25 Number of Sca ns 16 Rel a xa on Del a y 5 Spectrometer Frequency 499.67 Spectra l Wi dth 10000.0 Nucl eus 1H Acqui red Si ze 65536

2.5

2.0

1.5

1.0

0.5

Page 96 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

25G-NBOMe H+ Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 11591 500.00 1H

1H

25 26

75 +

10

6

O 65

5

11

1

4

NH2 12 20

21

3

O 62

63

72

23 22

2

40

NMR (500 MHz, DMSO-d6) δ 7.22 – 7.13 (m, 3H), 6.95 – 6.82 (m, 3H), 6.65 (t, J = 1.0 Hz, 1H), 3.73 (d, J = 15.0 Hz, 9H), 3.60 (d, J = 0.9 Hz, 2H), 3.37 – 3.30 (m, 2H), 3.17 – 3.09 (m, 2H), 2.08 (s , 6H).

24

28

O 27

26,25,24 (m) 6.89 6,23 (m) 7.18

20 (d) 3.60

12 (t) 6.65

28,72,75 (d) 10 (m) 3.73 3.13

40,63 (s) 2.08

10.0

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

6.20

1.92

1.73

9.15 2.00

1.00

2.96

3.05

11 (m) 3.34

3.0

2.5

2.0

1.5

1.0

0.5

Page 97 of 105 25

9.4

9.3

7.6

7.5

23 22

2 28

O 27

75,73 (s) 3.76

7.4

7.3

7.2

7.1

7.0

6.9

6.8

6.7

6.6

6.5

4.1

4.0

3.9

3.8

11 (m) 3.12

3.7

3.6

10 (m) 2.96

3.2

3.1

1.97

74 (s) 3.62

1.99

28 (s) 3.83

3.01

20 (s) 4.11

1.98

2,6 (s) 6.55

2.00

1.02

23 (dd) 7.08

1.05

1.03 9.2

21

25 (td) 6.99

26 (dd) 7.53

1.59 9.5

NH2 12 20

NMR (500 MHz, DMSO-d6) δ 9.33 (s , 2H), 7.53 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.2, 7.4, 1.7 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.99 (td, J = 7.5, 1.0 Hz, 1H), 6.55 (s , 2H), 4.11 (s , 2H), 3.83 (s , 3H), 3.76 (s , 6H), 3.62 (s , 3H), 3.16 – 3.08 (m, 2H), 3.00 – 2.93 (m, 2H).

3.16

11

1

24 (ddd) 7.41 12 (s) 9.33

+

10

1H

24

26

6.16

B10: M-NBOMe H+ 75 2013-01-17T03:17:44 dms o O 6 65 5 25 16 74 4 5 O 3 499.67 64 8012.8 O 1H 73 63 32768

1.04

Ana lyte Acquis i on Da te Solvent Tempera ture Number of Sca ns Rela xa on Dela y Spectrometer Frequency Spectra l Width Nucleus Acquired Size

3.0

2.9

Page 98 of 105

B10: M-NBOMe H+ 75 2013-01-17T03:17:44 dms o O 6 65 5 25 16 74 4 5 O 3 499.67 64 8012.8 O 1H 73 63 32768

25

+

10 1

11

NH2 12 20

1H

NMR (500 MHz, DMSO-d6) δ 9.33 (s , 2H), 7.53 (dd, J = 7.5, 1.7 Hz, 1H), 7.41 (ddd, J = 8.2, 7.4, 1.7 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.99 (td, J = 7.5, 1.0 Hz, 1H), 6.55 (s , 2H), 4.11 (s , 2H), 3.83 (s , 3H), 3.76 (s , 6H), 3.62 (s , 3H), 3.16 – 3.08 (m, 2H), 3.00 – 2.93 (m, 2H).

24

26 21

23 22

2 28

O 27

24 (ddd) 7.41 26 (dd) 7.53

25 (td) 2,6 (s) 6.99 6.55

20 (s) 4.11

10.0

9.5

9.0

8.5

8.0

7.5

7.0

74 (s) 3.62

11 (m) 3.12

6.5

1.98

75,73 (s) 3.76

2.00

1.02 1.04

1.03 1.05

1.59

23 (dd) 7.08

10 (m) 2.96

6.0

5.5

5.0

4.5

4.0

3.5

1.99 1.97

12 (s) 9.33

28 (s) 3.83

3.01 6.16 3.16

Ana lyte Acquis i on Da te Solvent Tempera ture Number of Sca ns Rela xa on Dela y Spectrometer Frequency Spectra l Width Nucleus Acquired Size

3.0

2.5

2.0

1.5

1.0

0.5

0.0

Page 99 of 105

M-NBOMe H+ 75 Modgra ph NMRPredict Des ktop DMSO-d6 O 65 Bes t 50 74 11880 O 500.00 64 1H

25 26 6

+

10

5

1

4

11

NH2 12 20

21

73

NMR (500 MHz, DMSO-d6) δ 7.22 – 7.13 (m, 3H), 6.95 – 6.82 (m, 3H), 6.54 (d, J = 1.2 Hz, 2H), 3.74 (s , 3H), 3.70 (s , 9H), 3.60 (d, J = 0.9 Hz, 2H), 3.33 (t, J = 7.5 Hz, 2H), 3.17 – 3.09 (m, 2H).

23 22

2 28

3

1H

24

O 27

O 63

26,25,24 (m) 6.89 2,6,23 (m) 7.18

12,28,73 (s) 3.70

20 (d) 6.54

75 (s) 11 (t) 3.74 3.33

10.0

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

10 (m) 3.13

1.93

3.01 9.26 2.06

2.00

2.97

3.02

74 (d) 3.60

1.75

Predic on Origin Solvent Algorithm GMMX Cycles Vers ion Frequency Nucleus

3.0

2.5

2.0

1.5

1.0

0.5

Page 100 of 105

Ana l yte IM1: 25H-NBOMe i mi ne 75 Acqui s i on Da te 2013-11-08T17:11:08 Sol vent dms o O Tempera ture 25 65 Number of Sca ns 16 Rel a xa on Del a y 1 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058

1H

25 26 6 5

10 1

4

11

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 8.56 (s , 1H), 7.82 (dd, J = 7.7, 1.8 Hz, 1H), 7.42 (ddd, J = 8.3, 7.3, 1.8 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.98 ( , J = 7.5, 0.8 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H), 6.78 (d, J = 3.1 Hz, 1H), 6.72 (dd, J = 8.8, 3.1 Hz, 1H), 3.82 (s , 3H), 3.74 (s , 3H), 3.75 – 3.68 (m, 2H), 3.65 (s , 3H), 2.84 (t, J = 7.5 Hz, 2H).

24

28

O 27

72

4 (dd) 6.72 20 (s) 8.56

26 (dd) 7.82

24 (ddd) 7.42

23 (dd) 7.08

25 (tt) 6.98

3 (d) 6.87

6 (d) 6.78

MeO (s) 3.74 MeO (s) 11 (m) 3.82 3.72

10 (t) 2.84

MeO (s) 3.65

8.6

8.5

7.9

7.8

7.7

7.4

7.3

7.2

7.1

7.0

6.9

6.8

6.7

3.8

3.7

1.97

2.99

2.07

3.18

2.95

1.02

3.69

0.98

3.70

1.01

7.5

3.71

1.00

7.6

3.72

0.98

3.73

0.96

3.74

0.93

0.96

3.75

2.9

2.8

Page 101 of 105

Ana l yte IM1: 25H-NBOMe i mi ne 75 Acqui s i on Da te 2013-11-08T17:11:08 Sol vent dms o O Tempera ture 25 65 Number of Sca ns 16 Rel a xa on Del a y 1 Spectrometer Frequency 499.67 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058

1H

25 26 6 5

10 1

4

11

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 8.56 (s , 1H), 7.82 (dd, J = 7.7, 1.8 Hz, 1H), 7.42 (ddd, J = 8.3, 7.3, 1.8 Hz, 1H), 7.08 (dd, J = 8.4, 1.0 Hz, 1H), 6.98 ( , J = 7.5, 0.8 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H), 6.78 (d, J = 3.1 Hz, 1H), 6.72 (dd, J = 8.8, 3.1 Hz, 1H), 3.82 (s , 3H), 3.74 (s , 3H), 3.75 – 3.68 (m, 2H), 3.65 (s , 3H), 2.84 (t, J = 7.5 Hz, 2H).

24

28

O 27

72

6 (d) 6.78 24 (ddd) 7.42 20 (s) 8.56

26 (dd) 7.82

MeO (s) 3.65

3 (d) 6.87

MeO (s) 3.74

23 (dd) 7.08

MeO (s) 3.82

25 (tt) 6.98

10 (t) 2.84

11 (m) 3.72

10.0

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

1.97

2.95 3.18 2.07 2.99

0.98 1.00 1.01 0.98 1.02

0.96

0.93

0.96

4 (dd) 6.72

3.0

2.5

2.0

1.5

1.0

0.5

Page 102 of 105

25H-NBOMe i mi ne Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 500.00 1H

1H

25 26

75 O 65

6 5

10 11

1

4

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 8.06 (d, J = 1.0 Hz, 1H), 7.60 (ddd, J = 7.4, 2.0, 1.0 Hz, 1H), 7.49 (td, J = 7.5, 2.0 Hz, 1H), 7.28 (td, J = 7.5, 2.0 Hz, 1H), 7.14 (dd, J = 7.5, 2.1 Hz, 1H), 6.85 (d, J = 8.0 Hz, 1H), 6.81 – 6.75 (m, 2H), 3.82 (s , 3H), 3.80 (s , 3H), 3.78 (d, J = 5.0 Hz, 2H), 3.72 (s , 3H), 2.89 (td, J = 5.0, 1.0 Hz, 2H).

24

28

O 27

72

23 (dd) 7.14 26 (ddd) 7.60 20 (d) 8.06

24 (td) 7.49

75 (s) 3.72

4,6 (m) 6.78

72 (s) 3.80

3 (d) 6.85

28 (s) 3.82

9.5

9.0

8.5

7.5

7.0

3.03 3.03 1.97 2.97

8.0

11 (d) 3.78

1.00 2.00

1.00 1.00 1.00 1.00

10.0

0.99

25 (td) 7.28

10 (td) 2.89

6.5

6.0

5.5

5.0

4.5

4.0

3.5

1.99

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

3.0

2.5

2.0

1.5

1.0

0.5

Page 103 of 105

Ana l yte IM2: 25I-NBOMe i mi ne Acqui s i on Da te 2013-11-08T17:17:35 75 Sol vent dms o O Tempera ture 25 65 Number of Sca ns 16 Rel a xa on Del a y 1 I Spectrometer Frequency 499.67 19 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058

1H

25 26 6

10

5

1

4

11

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 8.54 (s , 1H), 7.82 (dd, J = 7.7, 1.8 Hz, 1H), 7.42 (ddd, J = 8.3, 7.3, 1.8 Hz, 1H), 7.28 (s , 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 6.97 ( , J = 7.5, 0.8 Hz, 1H), 6.87 (s , 1H), 3.82 (s , 3H), 3.75 (s , 3H), 3.76 – 3.69 (m, 2H), 3.69 (s , 3H), 2.85 (t, J = 7.3 Hz, 2H).

24

28

O 27

72

MeO (s) 3.75 20 (s) 8.54

26 (dd) 7.82

24 (ddd) 7.42

ArH (s) 7.28

23 (dd) 7.08

25 (tt) 6.97

ArH (s) 6.87

MeO (s) 3.82

MeO (s) 3.69

10 (t) 2.85

8.6

8.5

7.9

7.8

7.7

7.6

7.5

7.4

7.3

7.2

7.1

7.0

6.9

6.8

6.7

3.8

3.7

1.86

3.69

3.03 2.35 2.72

3.70

3.04

3.71

0.93

3.72

1.03

3.73

0.98

3.74

1.04

3.75

0.99

0.98

3.76

1.05

11 (m) 3.72

2.9

2.8

Page 104 of 105

Ana l yte IM2: 25I-NBOMe i mi ne Acqui s i on Da te 2013-11-08T17:17:35 75 Sol vent dms o O Tempera ture 25 65 Number of Sca ns 16 Rel a xa on Del a y 1 I Spectrometer Frequency 499.67 19 Spectra l Wi dth 8012.8 Nucl eus 1H Acqui red Si ze 36058

1H

25 26 6 5

10 1

4

11

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 8.54 (s , 1H), 7.82 (dd, J = 7.7, 1.8 Hz, 1H), 7.42 (ddd, J = 8.3, 7.3, 1.8 Hz, 1H), 7.28 (s , 1H), 7.08 (dd, J = 8.3, 1.0 Hz, 1H), 6.97 ( , J = 7.5, 0.8 Hz, 1H), 6.87 (s , 1H), 3.82 (s , 3H), 3.75 (s , 3H), 3.76 – 3.69 (m, 2H), 3.69 (s , 3H), 2.85 (t, J = 7.3 Hz, 2H).

24

28

O 27

72

25 (tt) 6.97

20 (s) 8.54

26 (dd) 7.82

ArH (s) 6.87

MeO (s) 3.75

ArH (s) 7.28

MeO (s) 3.82

10.0

9.5

9.0

8.5

8.0

7.5

7.0

3.04 3.03 2.35 2.72

11 (m) 3.72

1.04 0.98 1.03 1.05 0.93

0.99

0.98

23 (dd) 7.08

10 (t) 2.85

6.5

6.0

5.5

5.0

4.5

4.0

3.5

1.86

24 (ddd) 7.42

MeO (s) 3.69

3.0

2.5

2.0

1.5

1.0

0.5

Page 105 of 105

Predi c on Ori gi n Sol vent Al gori thm GMMX Cycl es Vers i on Frequency Nucl eus

25I-NBOMe i mi ne Modgra ph NMRPredi ct Des ktop DMSO-d6 Bes t 50 12489 500.00 1H

1H

25 26

75 O 65

6 5 4

I 19

10 1

11

N 12

21 20

O 62

23 22

2 3

NMR (500 MHz, DMSO-d6) δ 7.99 (d, J = 1.2 Hz, 1H), 7.58 (ddd, J = 7.5, 2.0, 0.9 Hz, 1H), 7.49 (td, J = 7.5, 2.0 Hz, 1H), 7.28 (td, J = 7.5, 2.0 Hz, 1H), 7.22 (s , 1H), 7.14 (dd, J = 7.5, 2.0 Hz, 1H), 6.72 (t, J = 1.0 Hz, 1H), 3.93 (s , 3H), 3.82 (s , 3H), 3.78 (t, J = 5.1 Hz, 2H), 3.74 (s , 3H), 2.87 (td, J = 5.1, 1.0 Hz, 2H).

24

28

O 27

72

3 (s) 7.22

72 (s) 3.74

26 (ddd) 7.58 20 (d) 7.99

28 (s) 3.82

24 (td) 7.49

6 (t) 6.72

75 (s) 3.93

25 (td) 7.28

10 (td) 2.87

11 (t) 3.78

10.0

9.5

9.0

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

2.00

2.96 2.98 2.08 2.98

0.99

1.00 1.01 1.02 0.99 1.00

0.99

23 (dd) 7.14

3.5

3.0

2.5

2.0

1.5

1.0

0.5