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