Instrumental Analysis Data of Illegal Disfuccion Erectil

11-1470550-000001-14
Instrumental Analysis Data of Illegal

Compounds in Food
(2008 Norneovardenafil )
1. Mirodenafil 1
2. Sildenafil 6
3. Tadalafil 11
4. Udenafil 16
5. Vardenafil 21

1. Aminotadalafil 26
2. epi-Aminotadalafil 31
3. Benzylsildenafil 36
4. Demethylhongdenafil 42
5. Dimethylsildenafil 48
6. Homosildenafil 54
7. Hongdenafil 59
8. Hydroxyhomosildenafil 64
9. Hydroxyhongdenafil 69
10. Hydroxyvardenafil 75
11. Norneosildenafil 81
- i -
12. Piperidinohongdenafil 87
13. Pseudovardenafil 93
14. Thiosildenafil 98
15. Xanthoanthrafil 104
1. Desmethylsibutramin 109
2. N-Nitrosofenfluramin 114
- ii -
Mirodenafil

// : Mirodenafil / SK3530 / Mvix
/ : C26H37N5O5S / 531.67
: 5-Ethyl-3,5-dihydro-2-[5-[[4-(2-hydroxyethyl)-1-piperazinyl]sulfonyl]-2-propoxyphenyl]-7-propyl-4H-pyrrolo[3,2-d]pyrimidin-4-one
O
HN
S
N
N
N
HO

HPLC RT (min) : 21.84
UV max (nm) : 210.9, 252.6
IR (cm-1) : (CHCl3). 3365(m), 2965(m), 1710(s), 1636(m),
1459(w), 1352(w), 1284(w), 1168(m), 1090(w), 940(w), 752(w)
- 1 -
Mass (m/z) : FAB+ (m-NBA). 532([M-2HCl+H]+, 17%), 500(1%),

431(3%), 404(2%)
1
H NMR (400 MHz, DMSO-d6) : 0.92(3H, t, J = 7.1 Hz, H-14),

0.93(3H, t, J = 7.1 Hz, H-23), 1.37(3H, t, J = 7.1 Hz, H-11), 1.61(2H,
m, H-13), 1.73(2H, m, H-22), 2.62(2H, t, J = 7.5 Hz, H-12), 2.94(2H,
t, J = 11.8 Hz, H-31), 3.18(4H, br m, H-27,29), 2.97(4H, br m,
H-26,30), 2.77(2H, t, J = 7.5 Hz, H-32), 4.15(2H, t, J = 6.3 Hz,
H-21), 4.39(2H, q, J = 7.1 Hz, H-10), 7.46(1H, d, J = 8.8 Hz, H-19),
7.47(1H, s, H-2), 7.93(1H, dd, J = 8.8, 1.9 Hz, H-18), 8.06(1H, d, J =
1.9 Hz, H-16), 11.00(1H, br s, NH)
13
C NMR (100 MHz, DMSO-d6) : 10.3(C-23), 13.8(C-14), 17.3(C-11),
21.7(C-22), 23.2(C-13), 25.3(C-12), 42.7(C-31), 43.0(C-10),

50.6(C-26,30), 55.1(C-27,29), 57.6(C-32), 70.7(C-21), 113.7(C-19),
114.8(C-9), 115.1(C-1), 126.5(C-15), 130.0(C-2), 130.8(C-16),
132.1(C-18), 147.9(C-6), 153.1(C-4), 160.4(C-20)
HPLC Chromatogram of Mirodenafil
- 2 -
UV Spectrum of Mirodenafil
IR spectrum of Mirodenafil
- 3 -
Mass spectrum of Mirodenafil (FAB+)
[M-2HCl+H]+
Theoretical Ion Distribution of Mirodenafil (FAB+)

Molecular Formula : C26 H38 N5 O5 S
(m/z 532.2594, MW 532.6842, U.S. 11.5)
Base Peak : 532.2594, Averaged MW : 532.6846 (a), 532.6856 (w)
m/z
532.2594
533.2623
534.2608
535.2617
536.2628
537.2643
538.2659
539.2676
INT.
100.0000
32.3047
10.4836
2.2288
0.3699
0.0500
0.0057
0.0006
**********************************************************
*******************
******
*
Elemental Composition of Mirodenafil (FAB+)

Observed m/z
532.2590
Int%
90.8
Err[ppm
-3.1
+4.4
-0.6
+6.9
+1.9
-9.1
+9.1
-4.4
+3.1
/
/
/
/
/
/
/
/
/
mmu]
-1.7
+2.3
-0.3
+3.7
+1.0
-4.9
+4.8
-2.4
+1.7
- 4 -
Unsaturation
11.0
7.0
11.5
7.5
12.0
3.0
12.0
8.0
4.0
Composition
C 28 H 40 O
C 23 H 40 O
C 26 H 38 O
C 21 H 38 O
C 24 H 36 O
C 17 H 40 O
C 27 H 40 O
C 21 H 40 O
C 16 H 40 O
6
8
5
7
4
9
3
4
6
N
N
N
N
N
N
N
N
N
2S
4S
5S
7S
8S
8S
4S2
8S2
10 S 2
1H-NMR
spectrum of Mirodenafil (400MHz, DMSO)
32
31
15
HO
16
27
18
30
HN
26
11
23 14
2
8
1
12
21
19
29
11
10
22
13
14
23
21
19
2
16
32
27
29
12
10
26
30
18
22
13
31
13C-NMR
spectrum of Mirodenafil (100MHz, DMSO)
4
26
32
HO
16
27
31
30
15
18
19
29
HN
11
10
O
N
2
8
1
12
21
22
23
13
14
14 23
13
20
1
15
4
6
31
9
19
21
16
18 2
- 5 -
32
27
29
26
30
10
12
11
22
Sildenafil

/ : Sildenafil / Viagra
/ : C22H30N6O4S / 474.59
:
1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo
[4,3-d]
pyrimidine-5-yl)-4-ethoxyphenyl]sulfonyl]-4-
methylpierazine
O
HN
S
N
N
N
O

UV max (nm) : 214.4, 295.9
-1
IR (cm ) : KBr. 3445(s), 1702(s), 1582(m), 1461(w), 1360(w),

1172(m), 940(w), 736(w)
+
Mass (m/z) : EI+ (70eV). 474([M] , 9%), 410(14%), 404(90%),

381(10%), 311(18%), 283(17%), 99(100%), 70(15%), 56(49%)
- 6 -
1.33(3H, t, J = 6.9 Hz, H-21), 1.73(2H, m, H-12), 2.29(3H, s, H-29),

2.59(4H, br m, H-25,27), 2.77(2H, t, J = 7.5 Hz, H-11), 2.97(4H, br
m, H-24,28), 4.16(3H, s, H-10), 4.21(2H, q, J = 6.9 Hz, H-20),
7.38(1H, d, J = 8.8 Hz, H-18), 7.84(1H, dd, J = 8.8, 2.4 Hz, H-17),
7.86(1H, d, J = 2.3 Hz, H-15), 12.23(1H, br s, NH)
13
27.2(C-11),
37.9(C-10),
64.9(C-20),
113.3(C-18),
130.0(C-15),
44.5(C-29),
131.6(C-17),
45.1(C-24,28),
123.8(C-16),
137.8(C-8),
124.4(C-9),
53.1(C-25,27),
126.1(C-14),
145.0(C-1),
153.8(C-4), 160.0(C-19)
Elemental Analysis (%) : 12.49(N), 49.79(C), 5.80(H), 4.82(S)
HPLC Chromatogram of Sildenafil
- 7 -
148.2(C-6),
UV Spectrum of Sildenafil
IR spectrum of Sildenafil
- 8 -
Mass spectrum of Sildenafil (EI+)
[M]+
Theoretical Ion Distribution of Sildenafil (EI+)

(m/z 474.2049, MW 474.5840, U.S. 12.0)
m/z
474.2049
475.2077
476.2056
477.2065
478.2075
479.2088
480.2104
481.2120
INT.
100.0000
28.0650
9.0275
1.7625
0.2685
0.0330
0.0034
0.0003
**********************************************************
****************
*****
*
Elemental Composition of Sildenafil (EI+)

Observed m/z
474.2050
Int%
100.0
Err[ppm
-2.6
-8.2
+0.3
-5.4
+8.7
/
/
/
/
/
/
mmu]
-1.2
-3.9
+0.1
-2.6
+4.1
- 9 -
Unsaturation
11.5
16.0
12.0
16.5
8.0
Composition
C 24 H 32 O
C 27 H 30 O
C 22 H 30 O
C 25 H 28 O
C 17 H 30 O
5N
2N
4N
N7
6N
3
4
6
S
8
S
S
S
S
1H-NMR
spectrum of Sildenafil (400MHz, DMSO)
10
10
4
24
N
29
15
25
14
17
28
18
27
HN
N
N2
20
29
1
11
21
12
21
13
15
25
11 27
24
28
20
18
17
13
12
13C-NMR
spectrum of Sildenafil (100MHz, DMSO)
10
4
24
N
29
15
25
HN
28
17
18
27
14
N
N2
20
1
11
21
12
13
13
12
25
27
14
19
4
15 9
8
17
16
20
18
- 10 -
21
29
24
28
10
11
Tadalafil

/ : Tadalafil / Cialis
/ : C22H19N3O4 / 389.40
: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
O
N
N
N
H
O
O

UV max (nm) : 285.0
IR (cm-1) : (CHCl3). 3305(w), 2908(w), 1661(s), 1490(w),
1428(w), 1323(w), 1239(w), 1037(w), 924(w), 747(w)
+
Mass (m/z) : EI+ (70eV). 389([M] , 100%), 317(12%), 289(22%),

268(30%), 262(73%), 233(30%), 204(54%), 169(31%), 115(8%)
- 11 -
H NMR (400 MHz, DMSO-d6) : 2.93(3H, s, H-18), 2.99(1H, dd, J

= 15.7, 11.9 Hz, H-16), 3.54(1H, dd, J = 15.8, 4.5 Hz, H-16'),
3.95(1H, d, J = 17.1 Hz, H-3), 4.18(1H, d, J = 17.1 Hz, H-3'),
4.40(1H, dd, J = 11.6, 4.2 Hz, H-17), 5.93(2H, s, H-25), 6.14(1H, s,
H-6), 6.79(2H, H-23,24), 6.88(1H, s, H-20), 7.00(1H, t, J = 7.3 Hz,
H-12), 7.06(1H, t, J = 7.5 Hz, H-11), 7.31(1H, d, J = 8.0 Hz, H-10),
7.55(1H, d, J = 7.7 Hz, H-13), 11.04(1H, br s, NH)
13
55.3(C-17), 55.5(C-6), 100.9(C-25), 104.7(C-15), 107.0(C-20),

108.0(C-23), 111.3(C-10), 118.1(C-13), 118.9(C-12), 119.3(C-24),
121.2(C-11), 125.7(C-14), 133.9(C-7), 136.2(C-19), 137.0(C-9),
146.1(C-22), 147.0(C-21), 166.6(C-4), 166.9(C-1)
Elemental Analysis (%) : 10.95(N), 68.09(C), 4.86(H), 0(S)
HPLC Chromatogram of Tadalafil
- 12 -
UV Spectrum of Tadalafil
IR spectrum of Tadalafil
- 13 -
Mass spectrum of Tadalafil (EI+)

[M]+
Theoretical Ion Distribution of Tadalafil (EI+)

Molecular Formula : C22 H19 N3 O4
(m/z 389.1376, MW 389.4106, U.S. 15.0)
m/z
389.1376
390.1407
391.1434
392.1460
393.1486
394.1511
395.1537
INT.
100.0000 **********************************************************
26.0086 ***************
4.0460 **
0.4666
0.0431
0.0033
0.0002
Elemental Composition of Tadalafil (EI+)

Observed m/z
389.1373
Int%
100.0
Err[ppm
+6.3
-0.6
-7.5
+9.8
+2.9
-12.2
/
/
/
/
/
/
/
mmu]
+2.5
-0.2
-2.9
+3.8
+1.1
-4.8
- 14 -
Unsaturation
10.5
15.0
19.5
11.0
15.5
6.5
Composition
C 19 H 21 O
C 22 H 19 O
C 25 H 17 O
C 17 H 19 O
C 20 H 17 O
C 13 H 21 O
7N
4N
N4
6N
3N
8N
2
3
5
6
6
1H-NMR
spectrum of Tadalafil (400MHz, DMSO)
12
13
14
11
10
8
N
H
16
15
17
N
24
20
25
18
19
23
24
18
N
21
23
22
20
25
3
10
8
13
12
11
16
17
13C-NMR
spectrum of Tadalafil (100MHz, DMSO)
12
13
14
11
10
15
N
H
16
17
N
19
24
20
22
O
O
18
N
21
23
18
25
21
24
22
9
19
12
11 13
23
20
25
15
10
6 17
3
16
14
- 15 -
Udenafil

/ : Udenafil / Zydena
/ : C25H36N6O4S / 516.67
: 3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidine-5-yl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-4propoxybenzenesulfonamide
O
HN
S
HN

UV max (nm) : 213.5, 296.7
-1
IR (cm ) : (CHCl3). 3305(w), 2962(w), 1695(s), 1595(w),

1463(w), 1328(w), 1273(w), 1157(m), 754(w)
Mass (m/z) : EI+ (70eV). 516([M]+, 7%), 473(9%), 441(6%), 405(4%),
326(7%), 283(3%), 136(5%), 127(5%), 97(5%), 84(100%), 57(10%)
- 16 -
1H NMR (400 MHz, DMSO-d6) : 0.93(3H, t, J = 7.2 Hz, H-13),

0.95(3H, t, J = 7.2 Hz, H-22), 1.29(2H, m, H-26,31), 1.54(2H, m,
H-30), 1.73(6H, m, H-12,21,26,31), 1.97(2H, m, H-27,29), 2.11(3H, s,
H-32), 2.77(4H, t, J = 7.5 Hz, H-11,25), 2.86(1H, m, H-29), 4.09(2H,
t, J = 6.3 Hz, H-20), 4.16(3H, s, H-10), 7.34(1H, d, J = 8.8 Hz,
H-18), 7.87(1H, dd, J = 8.7, 2.4 Hz, H-17), 7.96(1H, d, J = 2.4 Hz,
H-15), 12.13(1H, br s, NH)
13
21.7, 21.8(C-12,21), 27.1(C-11), 29.7(C-31), 32.5(C-26), 37.9(C-10),

56.5(C-29), 63.1(C-27), 70.2(C-20), 113.1(C-18), 123.4(C-16),
124.3(C-9), 128.9(C-15), 130.4(C-17), 132.0(C-14), 137.8(C-8),
144.9(C-1), 148.4(C-6), 153.6(C-4), 159.3(C-19)
HPLC Chromatogram of Udenafil
- 17 -
UV Spectrum of Udenafil
IR spectrum of Udenafil
- 18 -
Mass spectrum of Udenafil (EI+)
[M]+
Theoretical Ion Distribution of Udenafil (EI+)

(m/z 516.2519, MW 516.6646, U.S. 12.0)
m/z
516.2519
517.2547
518.2531
519.2539
520.2549
521.2563
522.2579
523.2596
INT.
100.0000
31.4917
10.0293
2.0833
0.3326
0.0430
0.0046
0.0004
**********************************************************
******************
******
*
Elemental Composition of Udenafil (EI+)

Observed m/z
516.2521
Int%
100.0
Err[ppm
-2.1
-7.3
+0.5
-4.7
+8.3
+7.9
-6.0
+1.8
/
/
/
/
/
/
/
/
/
mmu]
-1.1
-3.8
+0.3
-2.4
+4.3
+4.1
-3.1
+0.9
- 19 -
Unsaturation
11.5
16.0
12.0
16.5
8.0
12.0
8.0
4.0
Composition
C 27 H 38 O
C 30 H 36 O
C 25 H 36 O
C 28 H 34 O
C 20 H 36 O
C 28 H 40 O
C 22 H 40 O
C 17 H 40 O
5N
2N
4N
N7
6N
3N
4N
6N
3
4
6
S
8
2
6
8
S
S
S
S
S2
S2
S2
1H-NMR
spectrum of Udenafil (400MHz, DMSO)
10
4
HN
15
S
HN 24
26
27
32
12
13
23
30
29
22 13
11
22
31
32
21
18
10
N
N
14
17
25
20
15
12
21
26?
31
11
25
27
29
18
17
13C-NMR
30 26
31
29
24
spectrum of Udenafil (100MHz, DMSO)
10
4
15
S
HN 24
26
25
17
18
27
32
29
N
N
14
21
22
31
HN
1
11
25
32
12
13
23
12
21
30
30
27
29
31
10
26
19
1
4
15 9
16
17
8 14
20
18
- 20 -
11
22
13
Vardenafil

/ : Vardenafil / Levitra
/ : C23H32N6O4S / 488.62
: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethylpiperazine
O
HN
N
O

HPLC RT (min) : 6.1
UV max (nm) : 218.1
-1
IR (cm ) : (CHCl3). 3398(w), 2966(w), 1697(s), 1626(w),

1470(w), 1355(w), 1283(w), 1162(m), 942(w), 753(w)
Mass (m/z) : EI+ (70eV). 488([M]+, 58%), 473(14%), 311(15%),
283(13%), 113(100%), 98(24%), 84(18%), 70(57%), 56(52%)
- 21 -

1.23(3H, t, J = 7.2 Hz, H-30), 1.35(3H, t, J = 6.9 Hz, H-21), 1.76(2H,
m, H-12), 2.50(3H, s, H-10), 2.86(2H, t, J = 7.4 Hz, H-11), 2.90(2H,
br m, H-29), 3.10(4H, br m, H-25,27), 3.50(2H, br m, H-24,28),
3.81(2H, br m, H-24,28), 4.24(2H, q, J = 6.9 Hz, H-20), 7.45(1H,
H-18), 7.95(2H, m, H-15,17), 11.82(1H, br s, NH)
13
14.3(C-13), 20.2(C-12), 27.1(C-11), 43.0(C-24,28), 49.4(C-25,27),

50.6(C-29), 65.1(C-20), 113.6(C-18), 113.7(C-9),
120.9(C-16),
126.4(C-14), 130.3(C-15), 132.2(C-17), 137.6(C-3), 144.4(C-1),

146.1(C-6), 155.0(C-4), 160.7(C-19)
HPLC Chromatogram of Vardenafil
- 22 -
UV Spectrum of Vardenafil
IR spectrum of Vardenafil
- 23 -
Mass spectrum of Vardenafil (EI+)
[M]+
Theoretical Ion Distribution of Vardenafil (EI+)

(m/z 488.2206, MW 488.6109, U.S. 12.0)
m/z
488.2206
489.2234
490.2214
491.2223
492.2233
493.2247
494.2262
495.2279
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
Elemental Composition of Vardenafil (EI+)

Observed m/z
488.2200
Int%
100.0
Err[ppm
-3.9
-9.4
-1.1
-6.6
+7.1
/
/
/
/
/
/
mmu]
-1.9
-4.6
-0.5
-3.2
+3.5
- 24 -
Unsaturation
11.5
16.0
12.0
16.5
8.0
Composition
C 25 H 34 O
C 28 H 32 O
C 23 H 32 O
C 26 H 30 O
C 18 H 32 O
5N
2N
4N
N7
6N
3
4
6
S
8
S
S
S
S
1H-NMR
spectrum of Vardenafil (400MHz, DMSO)
10
25
30
15
S
N
29
HN
24
18
27
10
21
13
14
17
28
20
11
21
12
30
11,29
13
15 17
20
12
18
5
25,27
24,28
13C-NMR
spectrum of Vardenafil (100MHz, DMSO)
10
4
24
25
30
15
S
N
29
HN
28
14
17
18
27
20
11
21
12
21
13
10
12 13
11
18
9
19
1
4
20
15 14 16
29
25
27
24
28
17
30
- 25 -
Aminotadalafil

: Aminotadalafil
/ : C21H18N4O4 / 390.39
: 2-amino-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro(6R,12aR)-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
O
NH2
N
N
N
H
O
O

UV max (nm) : 285.0
IR (cm-1) : KBr. 3436(s), 2896(w), 1655(s), 1499(w), 1415(w),
1320(w), 1240(m), 1038(w), 925(w), 739(w)
+
Mass (m/z) : EI+ (70eV). 390([M] , 100%), 375(11%), 318(11%),

289(32%), 269(12%), 262(49%), 233(19%), 204(47%), 169(26%)
- 26 -
1H NMR (400 MHz, DMSO-d6) : 3.00(1H, dd, J = 15.4, 11.9 Hz,

H-16), 3.58(1H, dd, J = 15.7, 4.2 Hz, H-16), 3.97(1H, d, J = 17.1
Hz, H-3), 4.27(1H, d, J = 17.2 Hz, H-3), 4.44(1H, dd, J = 11.6, 3.5
Hz, H-17), 5.13(2H, s, H-18), 5.93(2H, s, H-25), 6.10(1H, s, H-6),
6.78(1H, d, J = 8.0 Hz, H-23), 6.82(1H, dd, J = 8.2, 1.4 Hz, H-24),
6.88(1H, d, J = 1.2 Hz, H-20), 7.02(1H, t, J = 8.4 Hz, H-12), 7.06
(1H, t, J = 7.1 Hz, H-11), 7.30(1H, d, J = 7.9 Hz, H-10), 7.56(1H, d,
J = 7.7 Hz, H-13), 11.02(1H, br s, NH)
13
55.6(C-6), 100.9(C-25), 104.8(C-15), 106.9(C-20), 108.3(C-23),

111.3(C-10), 118.1(C-13), 118.9(C-12), 119.3(C-24), 121.2(C-11),
125.7(C-14), 134.0(C-7), 136.2(C-19), 137.1(C-9), 146.0(C-22),
147.0(C-21), 164.6(C-4), 166.3(C-1)
HPLC Chromatogram of Aminotadalafil
- 27 -
UV Spectrum of Aminotadalafil
IR Spectrum of Aminotadalafil
- 28 -
Mass spectrum of Aminotadalafil (EI+)

[M]+
Theoretical Ion Distribution of Aminotadalafil (EI+)

(m/z 390.1328, MW 390.3983, U.S. 15.0)
m/z
390.1328
391.1358
392.1385
393.1410
394.1435
395.1460
396.1485
INT.
100.0000 **********************************************************
25.2487 ***************
3.8568 **
0.4379
0.0399
0.0030
0.0002
Elemental Composition of Aminotadalafil (EI+)

Observed m/z
390.1324
Int%
100.0
Err[ppm
-11.4
-1.1
-7.9
+9.2
+2.4
/
/
/
/
/
/
mmu]
-4.4
-0.4
-3.1
+3.6
+0.9
- 29 -
Unsaturation
19.0
15.0
19.5
11.0
15.5
Composition
C 26 H 18 O
C 21 H 18 O
C 24 H 16 O
C 16 H 18 O
C 19 H 16 O
2N
4N
N5
6N
3N
2
4
6
7
1H-NMR
spectrum of Aminotadalafil (400MHz, DMSO)
12
13
14
11
10
15
17
19
25
18
24
NH 2
N
H
18
16
24 23
20
21
23
22
O
O
20
25
10
12
11
13
16
17
13C-NMR
spectrum of Aminotadalafil (100MHz, DMSO)
12
13
14
11
10
8
N
H
15
16
18
17
N
NH 2
N
19
20
24
21
23
22
O
O
25
24
1
4
21
22
9
19
14
11
12
13 10
23
20 25
15
6 17
3
- 30 -
16
epi-Aminotadalafil

: epi-aminotadalafil
/ : C21H18N4O4 / 390.39
: 2-amino-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro(6S,12aR)-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
O
NH2
N
N
N
H
O
O

UV max (nm) : 283.7
IR (cm-1) : KBr. 3394(m), 1659(s), 1489(m), 1455(m), 1324(w),
1239(w), 1159(w), 1094(w), 1038(w), 932(w), 796(w), 745(w)
+
Mass (m/z) : EI+ (70eV). 390([M] , 100%), 374(23%), 318(23%),

289(70%), 269(20%), 263(72%), 233(27%), 204(43%), 169(23%)
- 31 -
1H NMR (100 MHz, DMSO-d6) : 2.95(1H, dd, J = 14.7, 12.3 Hz,

H-16), 3.29(1H, dd, J = 15.3, 4.3 Hz, H-16), 4.08(1H, d, J = 17.4
Hz, H-3), 4.14(1H, dd, J = 11.7, 4.1 Hz, H-17), 4.34(1H, d, J = 17.5
Hz, H-3), 5.76(2H, s, H-18), 6.00(1H, d, J = 0.7 Hz, H-25), 6.01(1H,
H-25), 6.62(1H, dd, J = 8.1, 1.5 Hz, H-24), 6.76(1H, d, J = 1.7 Hz,
H-20), 6.83(1H, s, H-6), 6.87(1H, d, J = 8.0 Hz, H-23), 7.02(1H, t, J
= 7.3 Hz, H-12), 7.11(1H, t, J = 7.6 Hz, H-11), 7.32(1H, d, J = 8.0
Hz, H-10), 7.50(1H, d, J = 7.8 Hz, H-13), 11.11(1H, br s, NH)
13
52.3(C-3), 101.3(C-25), 107.4(C-15), 108.2(C-20), 108.3(C-23),

111.4(C-10), 118.1(C-13), 118.9(C-12), 121.7(C-24), 121.7(C-11),
125.9(C-14), 130.3(C-7), 132.9(C-19), 136.3(C-9), 147.3(C-22),
147.6(C-21), 162.1(C-4), 162.8(C-1)
HPLC Chromatogram of epi-Aminotadalafil
- 32 -
UV Spectrum of epi-Aminotadalafil
IR Spectrum of epi-Aminotadalafil
- 33 -
Mass spectrum of epi-Aminotadalafil (EI+)

[M]+
Theoretical Ion Distribution of epi-Aminotadalafil (EI+)

(m/z 390.1328, MW 390.3983, U.S. 15.0)
m/z
390.1328
391.1358
392.1385
393.1410
394.1435
395.1460
396.1485
INT.
100.0000 **********************************************************
25.2487 ***************
3.8568 **
0.4379
0.0399
0.0030
0.0002
Elemental Composition of epi-Aminotadalafil (EI+)

Observed m/z
390.1324
Int%
100.0
Err[ppm
-11.4
-1.1
-7.9
+9.2
+2.4
/
/
/
/
/
/
mmu]
-4.4
-0.4
-3.1
+3.6
+0.9
- 34 -
Unsaturation
19.0
15.0
19.5
11.0
15.5
Composition
C 26 H 18 O
C 21 H 18 O
C 24 H 16 O
C 16 H 18 O
C 19 H 16 O
2N
4N
N5
6N
3N
2
4
6
7
1H-NMR
spectrum of epi -Aminotadalafil (400MHz, DMSO)
12
13
14
11
10
15
17
NH2
N
H
18
16
19
24
20
18
25
21
23
22
23
6
O
O
25
20
10
13
12
11
16
24
17
13C-NMR
spectrum of epi -Aminotadalafil (400MHz, DMSO)
12
13
14
11
10
15
N
H
16
18
17
N
19
24
20
22
O
O
NH2
N
21
23
21
25
22
9 19
14
11
20
23
25
24
12 13 10 15
17
3
- 35 -
6
16
Benzylsildenafil

: Benzylsildenafil
/ : C28H34N6O4S / 550.68
: 5-[5-(4-Benzyl-piperazine-1-sulfonyl)-2-ethoxy-phenyl]-1methyl-3-propyl-1,6-dihydro-pyrazolo [4,3-d]pyrimidin-7-one
HN
N
N
O

HPLC Rt (min) : 34.71
UV max (nm) : 291.25
-1
IR (cm ) : (CHCl3). 3319(w), 2957(w), 1698(s), 1598(w),

1490(w), 1455(w), 1351(m), 1167(m), 949(w), 814(w), 746(m), 700(w)
+
Mass (m/z) : EI+ (70eV). 550([M] , 19%), 459(16%), 404(84%),

395(18%), 311(26%), 283(18%), 282(5%), 254(15%), 175(100%),
132(36%), 91(100%), 72(18%)
- 36 -
H NMR (400MHz, DMSO-d6) : 0.91(3H, t, J = 7.4 Hz, H-13),

1.34(3H, t, J = 6.9 Hz, H-21), 1.72(2H, m, H-12), 2.43(4H, br m,
H-25, 27), 2.76(2H, t, J = 7.4 Hz, H-11), 2.91(4H, br m, H-24, 28),
3.45(2H, s, H-29), 4.16(3H, s, H-10), 4.21(2H, q, J = 6.9 Hz, H-20),
7.23(3H, m, H-31, 33, 35), 7.28(2H, m, H-32, 34), 7.37(1H, d, J = 8.7
Hz, H-18), 7.80(1H, m, H-17), 7.83(1H, m, H-15), 12.17(1H, br s, NH)
13
C NMR (100MHz, DMSO-d6) : 13.8(C-13), 14.2(C-21), 21.6(C-12),
27.1(C-11), 37.8(C-10), 45.9(C-24, 28), 51.4(C-25, 27), 61.3(C-29),

64.8(C-20), 113.2(C-18), 123.7(C-16), 124.4(C-9), 126.0(C-14),
127.0(C-33), 128.1(C-32, 34), 128.7(C-31, 35), 130.0(C-15),
131.4(C-17), 137.7(C-8, 30), 144.9(C-1), 148.1(C-6), 153.7(C-4),
159.9(C-19)
- 37 -
- 38 -
[M]+
- 39 -
- 40 -
1H-NMR
Spectrum of Benzylsildenafil (400MHz, DMSO)
10
O
4
O
32
33
24
31
30
34
25
16
29
35
28
HN
O
15
14
10
N
N
6
N
20
18
27
12
11
19
17
21
13
21
13
31,33,35
29
32,34
25,27
24,28
11
15
13C-NMR
20
17
Spectrum of Benzylsildenafil (100MHz, DMSO)
10
4
O
32
33
24
31
30
34
35
12
18
25
29
S
N
16
15
18
27
1
11
19
17
28
14
HN
20
21
31,35 32,34
12
13
9
14
19
4 61
33
8,30 15
17
18
16
- 41 -
20
25,27
24,28 10
29
11
12
21
13
Demethylhongdenafil

/ : Demethylhongdenafil / Nor-acetildenafil
/ : C24H32N6O3 / 452.55
: 5-{2-Ethoxy-5-[2-(4-methyl-piperazine-1-yl)acetyl]phenyl}1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidine7-one
O
HN
N
N
N

UV max (nm) : 276.28
-1
IR (cm ) : (CHCl3). 3316(w), 2936(w), 2801(w), 1695(s),

1603(m), 1494 (w), 1394 (w), 1246(m), 1147 (w), 1031 (w), 926 (w),
754(m)
+
Mass (m/z) : EI+ (70eV). 452([M] , 28%), 354(7%), 311(10%),

297(6%), 283(5%), 166(7%), 136(10%), 113(100%), 70(100%), 56(14%)
- 42 -
H NMR
(500MHz, DMSO-d6) : 0.94(3H, t, J = 7.4 Hz, H-13),
1.34(3H, t, J = 7.0 Hz, H-21), 1.75(2H, m, H-12), 2.12(3H, s, H-30),

2.37(4H, br m, H-26, 28), 2.50(4H, br m, H-25, 29), 2.79(2H, t, J =
7.4 Hz, H-11), 3.74(2H, s, H-23), 4.16(3H, s, H-10), 4.21(2H, q, J =
7.0 Hz, H-20), 7.23(1H, d, J = 8.8 Hz, H-18), 8.15(1H, dd, J = 8.8,
2.1 Hz, H-17), 8.27(1H, d, J = 2.1 Hz, H-15), 12.08(1H, br s, NH)
13
C NMR
(125MHz, DMSO-d6) : 13.8(C-13), 14.3(C-21),
21.7(C-12), 27.1(C-11), 37.8(C-10), 45.4(C-30), 52.6(C-25, 29),

54.4(C-26, 28), 64.0(C-23), 64.5(C-20), 112.3(C-18), 122.7(C-16),
124.3(C-9), 128.2(C-14), 131.1(C-15), 132.4(C-17), 137.9(C-8),
144.9(C-1), 148.8(C-6), 153.6(C-4), 160.1(C-19), 195.2(C-22)
HPLC Chromatogram of Demethylhongdenafil

Chrom Ttpe : Fixed WL Chromatogram, 291nm
- 43 -
UV Spectrum of Demethylhongdenafil
RT
22.55 m in (S) Current Spectrum
IR Spectrum of Demethylhongdenafil
- 44 -
Mass Spectrum of Demethylhongdenafil (EI+)
[M]+
- 45 -
Theoretical Ion Distribution of Demethylhongdenafil (EI+)

(m/z 452.2536, MW 452.5565, U.S. 12.0)
m/z
452.2536
453.2565
454.2592
455.2618
456.2644
457.2699
458.2694
INT.
100.0000 **********************************************************
29.4920 *****************
4.7978 ***
0.5608
0.0517
0.0039
0.0003
Elemental Composition of Demethylhongdenafil (EI+)

Observed m/z
452.2531
Int%
42.3
Err[ppm
+5.9
-7.1
+7.8
+1.8
-4.1
-10.0
+10.7
+4.8
-1.1
-7.0
+7.8
+1.8
-1.5
+7.4
-5.6
+10.3
-2.7
-8.6
+6.2
+0.3
-5.6
+9.2
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
+2.7
-3.2
+3.5
+0.8
-1.8
-4.5
+4.9
+2.2
-0.5
-3.2
+3.5
+0.8
-0.7
+3.3
-2.5
+4.7
-1.2
-3.9
+2.8
+0.1
-2.5
+4.2
- 46 -
Unsaturation
20.0
11.0
2.5
7.0
11.5
16.0
3.0
7.5
12.0
16.5
8.0
12.5
16.0
12.0
3.0
12.5
3.5
8.0
-0.5
4.0
8.5
0.0
Composition
C 35 H 32
C 28 H 36 O 5
C 20 H 38 O 10 N
C 23 H 36 O 7 N 2
C 26 H 34 O 4 N 3
C 29 H 32 O N 4
C 18 H 36 O 9 N 4
C 21 H 34 O 6 N 5
C 24 H 32 O 3 N 6
C 27 H 30 N 7
C 19 H 32 O 5 N 8
C 22 H 30 O 2 N 9
C 32 H 36 S
C 27 H 36 O 2 N 2 S
C 20 H 40 O 7 N 2 S
C 25 H 34 O N 5 S
C 18 H 38 O 6 N 5 S
C 21 H 36 O 3 N 6 S
C 13 H 38 O 8 N 7 S
C 16 H 36 O 5 N 8 S
C 19 H 34 O 2 N 9 S
C 11 H 36 O 7 N 10 S
1H-NMR
Spectrum of Demethylhongdenafil (500MHz, DMSO)
O
26
30
4
O
25
23
29
30
HN
15
28
10
10
14
22
12
11
19
17
25,29
20
18
21
21
26,28
23
13
13
11
15
20
17
12
18
13C-NMR
Spectrum of Demethylhongdenafil (125MHz, DMSO)
O
26
30
4
O
25
29
23
HN
15
28
22
10
N
14
18
1
11
19
17
20
21
15
22
19
1
4 6
12
13
26,28
25,29
17 14
9
18
16
- 47 -
20
23
30
10
11 12
21 13
Dimethylsildenafil

/ : Dimethylsildenafil / Methisosildenafil
/
: C23H32N6O4S / 488.60
: 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidine-5-yl)-4-ethoxyphenyl]sulfonyl]-3,5dimethylpiprazine
O
HN
N
HN
O

UV max (nm) : 292.13
-1
IR (cm ) : (CHCl3). 3316(w), 2963(w), 1698(s), 1599(w),

1489(w), 1347(w), 1247(w), 1167(m), 1014(w), 928(w), 754(w)
+
Mass (m/z) : EI+ (70eV). 488([M] , 11%), 487(8%), 377(5%),

312(63%), 311(45%), 283(33%) , 254(9%), 225(5%), 166(5%),
113(100%), 84(44%), 70(93%)
- 48 -
H NMR (400MHz, DMSO-d6) : 0.92(9H, m, H-13, 29, 30),

1.33(3H, t, J = 6.8 Hz, H-21), 1.77(4H, m, H-24, 28, 12), 2.77(4H, m,
H-25, 27, 11), 3.45(2H, m, H-24, 28), 4.16(3H, s, H-10), 4.21(2H, m,
H-20), 7.36(1H, d, J = 8.4 Hz, H-18), 7.81(1H, m, H-17), 7.86(1H, m,
H-15), 12.14(2H, br s, NH)
13
C NMR (100MHz, DMSO-d6) : 13.8(C-13), 14.2(C-21), 18.8(C-29,
30), 21.6(C-12), 27.2(C-11), 37.8(C-10), 49.6(C-25, 27), 51.7(C-24, 28),

64.8(C-20), 113.1(C-18), 123.5(C-16), 124.4(C-9), 126.5(C-14),
129.8(C-15), 131.3(C-17), 137.7(C-8), 144.9(C-1), 148.1(C-6),
153.6(C-4), 159.7(C-19)
HPLC Chromatogram of Dimethylsildenafil

Chrom Ttpe : Fixed WL Chromatogram, 291nm
- 49 -
UV Spectrum of Dimethylsildenafil
RT
29.73min (S) Current Spectrum
IR Spectrum of Dimethylsildenafil
- 50 -
Mass Spectrum of Dimethylsildenafil (EI+)
[M]+
- 51 -
Theoretical Ion Distribution of Dimethylsildenafil (EI+)

(m/z 488.2206, MW 488.6109, U.S. 12.0)
m/z
488.2206
489.2234
490.2214
491.2223
492.2233
493.2247
494.2262
495.2279
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
Elemental Composition of Dimethylsildenafil (EI+)

Observed m/z
488.2212
Int%
100.0
Err[ppm
+2.7
-2.8
+5.4
-6.6
-0.1
+8.2
-3.9
-9.4
-1.1
-6.6
+7.8
-4.2
-9.7
+4.0
-1.5
-7.0
+6.8
+1.3
-4.2
+9.5
+4.0
-8.0
-1.5
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
+1.3
-1.4
+2.6
-3.2
+0.0
+4.0
-1.9
-4.6
-0.5
-3.2
+3.8
-2.1
-4.7
+2.0
-0.7
-3.4
+3.3
+0.6
-2.1
+4.6
+2.0
-3.9
-0.7
- 52 -
Unsaturation
15.0
19.5
15.5
6.5
20.0
16.0
7.0
11.5
7.5
12.0
20.0
11.0
15.5
7.0
11.5
16.0
7.5
12.0
16.5
8.0
12.5
3.5
17.0
Composition
C 30 H 32 O 6
C 33 H 30 O 3 N
C 28 H 30 O 5 N 3
C 21 H 34 O 10 N 3
C 31 H 28 O 2 N 4
C 26 H 28 O 4 N 6
C 19 H 32 O 9 N 6
C 22 H 30 O 6 N 7
C 17 H 30 O 8 N 9
C 20 H 28 O 5 N 10
C 34 H 32 O S
C 27 H 36 O 6 S
C 30 H 34 O 3 N S
C 22 H 36 O 8 N 2 S
C 25 H 34 O 5 N 3 S
C 28 H 32 O 2 N 4 S
C 20 H 34 O 7 N 5 S
C 23 H 32 O 4 N 6 S
C 26 H 30 O N 7 S
C 18 H 32 O 6 N 8 S
C 21 H 30 O 3 N 9 S
C 14 H 34 O 8 N 9 S
C 24 H 28 N 10 S
1H-NMR
Spectrum of Dimethylsildenafil (400MHz, DMSO)
13,29,30
10
O
10
4
O
29
25
24
15
S
N
HN
27
N
14
11
20
18
24,28,12
19
17
28
HN
12
21
13
21
25,27,11
30
15
20
18
24,28
17
5,26
13C-NMR
Spectrum of Dimethylsildenafil (100MHz, DMSO)
10
4
O
29
25
24
15
N
14
HN
28
HN
1
11
19
17
27
18
20
21
12
13
30
25,27
14
24,28
19
15
1
8 17
4 6
18
16
- 53 -
20
29,30
12
10 11 21 13
Homosildenafil

: Homosildenafil
/ : C23H32N6O4S / 488.62
: 1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]-pyrimidine-5-yl)-4-ethoxyphenyl]-sulfonyl]-4-ethylPiperazine
O
HN
S
N
N
O

UV max (nm) : 214.4, 295.9
-1
IR (cm ) : (CHCl3). 3309(w), 2964(w), 1696(s), 1594(w),

1490(w), 1393(w), 1351(w), 1166(m), 1030(w), 954(w), 742(w)
+
Mass (m/z) : EI+ (70eV). 488([M] , 26%), 404(79%), 312(31%),

283(30%), 113(100%), 98(23%), 84(18%), 70(54%), 56(51%)
- 54 -

0.92(3H, t, J = 7.4 Hz, H-13), 1.33(3H, t, J = 6.9 Hz, H-21), 1.73(2H,
m, H-12), 2.28(2H, q, J = 7.1 Hz, H-29), 2.40(4H, br m, H-25,27),
2.76(2H, t, J = 7.5 Hz, H-11), 2.89(4H, br m, H-24,28), 4.16(3H, s,
H-10), 4.21(2H, q, J = 6.9 Hz, H-20), 7.37(1H, d, J = 8.7 Hz, H-18),
7.82(1H, dd, J = 8.6, 2.4 Hz, H-17), 7.84(1H, d, J = 2.4 Hz, H-15),
12.16(1H, br s, NH)
13
21.7(C-12), 27.1(C-11), 37.8(C-10), 45.9(C-24,28), 51.0(C-29),

51.2(C-25,27), 64.8(C-20), 113.2(C-18), 123.7(C-16), 124.4(C-9),
126.0(C-14), 130.0(C-15), 131.5(C-17), 137.8(C-8), 144.9(C-1),
148.1(C-6), 153.7(C-4), 159.9(C-19)
Elemental Analysis (%) : C(56.51), H(6.61), N(17.38), S(6.55)
HPLC Chromatogram of Homosildenafil
- 55 -
UV Spectrum of Homosildenafil
IR spectrum of Homosildenafil
- 56 -
Mass spectrum of Homosildenafil (EI+)
[M]+
Theoretical Ion Distribution of Homosildenafil (EI+)

(m/z 488.2206, MW 488.6109, U.S. 12.0)
m/z
488.2206
489.2234
490.2214
491.2223
492.2233
493.2247
494.2262
495.2279
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
Elemental Composition of Homosildenafil (EI+)

Observed m/z
488.2200
Int%
17.2
Err[ppm
-3.9
-9.4
-1.1
-6.6
+7.1
/
/
/
/
/
/
mmu]
-1.9
-4.6
-0.5
-3.2
+3.5
Unsaturation
11.5
16.0
12.0
16.5
8.0
- 57 -
Composition
C 25 H 34 O
C 28 H 32 O
C 23 H 32 O
C 26 H 30 O
C 18 H 32 O
5N
2N
4N
N7
6N
3
4
6
S
8
S
S
S
S
1H-NMR
spectrum of Homosildenafil (400MHz, DMSO)
10
4
O
24
25
30
15
14
29
HN
28
20
18
27
21
N2
17
13,30
10
9
1
11
12
21
13
15
24
28
20
18
17
25
11 27
12
29
13C-NMR
spectrum of Homosildenafil (100MHz, DMSO)
10
24
25
30
15
14
29
HN
28
20
18
27
N
N2
17
1
11
12
12
25
24
27
28
21
13
13
10
29
14
19
15
4
17
9
16
20
18
- 58 -
11
21 30
Hongdenafil

/ : Hongdenafil / Acetildenafil
/ : C25H34N6O3 / 466.58
: 5-[2-ethoxy-5-[(4-ethyl-1-piperazinyl)acetyl]phenyl]-1,4dihydro-1-methyl-3-propyl-7H-Pyrazolo[4,3-d]pyrimidine-7one
O
HN
N
N
N

HPLC RT (min) : 8.8
UV max (nm) : 234.6, 289.2
-1
IR (cm ) : (CHCl3). 3315(w), 2962(w), 2815(w), 1693(s),

1604(w), 1494(w), 1393(w), 1258(w), 1163(w), 1031(w), 752(w)
Mass (m/z) : EI+ (70eV). 466([M]+, 76%), 409(9%), 354(29%),
339(16%), 326(10%), 311(40%), 297(27%), 166(24%), 127(100%),
112(55%), 98(40%), 84(75%), 70(74%), 56(47%)
- 59 -

0.98(3H, t, J = 7.2 Hz, H-31), 1.34(3H, t, J = 6.9 Hz, H-21), 1.74(2H,
m, H-12), 2.29(2H, q, J = 7.1 Hz, H-30), 2.38(4H, br m, H-26,28),
2.50(4H, br m, H-25,29), 2.79(2H, t, J = 7.5 Hz, H-11), 3.74(2H, s,
H-23), 4.16(3H, s, H-10), 4.20(2H, q, J = 7.0 Hz, H-20), 7.24(1H, d, J
= 8.8Hz, H-18), 8.16(1H, dd, J = 8.8, 2.2 Hz, H-17), 8.27(1H, d, J =

2.2 Hz, H-15), 12.14(1H, br s, NH)
13
21.8(C-12), 27.2(C-11), 37.8(C-10), 51.6(C-26,28), 52.3(C-30),

52.8(C-25,29), 64.3(C-23), 64.6(C-20), 112.3(C-18), 122.8(C-16),
124.3(C-9), 128.2(C-14), 131.2(C-15), 132.5(C-17), 137.9(C-8),
144.9(C-1), 148.9(C-6), 153.8(C-4), 160.1(C-19), 195.3(C-22)
HPLC Chromatogram of Hongdenafil
- 60 -
UV Spectrum of Hongdenafil
IR spectrum of Hongdenafil
- 61 -
Mass spectrum of Hongdenafil (EI+)
[M]+
Theoretical Ion Distribution of Hongdenafil (EI+)

(m/z 466.2692, MW 466.5834, U.S. 12.0)
m/z
466.2692
467.2722
468.2749
469.2776
470.2801
471.2827
472.2852
INT.
100.0000 **********************************************************
30.6343 ******************
5.1350 ***
0.6157
0.0581
0.0045
0.0003
Elemental Composition of Hongdenafil (EI+)

Observed m/z
466.2713
Int%
100.0
Err[ppm
+1.5
-4.3
+10.1
+4.4
/
/
/
/
/
mmu]
+0.7
-2.0
+4.7
+2.0
- 62 -
Unsaturation
11.5
16.0
7.5
12.0
Composition
C 27 H 36 O
C 30 H 34 O
C 22 H 36 O
C 25 H 34 O
4N3
N4
6N5
3N6
1H-NMR
spectrum of Hongdenafil (400MHz, DMSO)
10
10
30
26
N
31
25
15
28
14
23
29
HN
17
18
N
N2
12
11
20
31 13
21
21
13
23
15
11
20
18
17
26
28
25
12
29 30
13C-NMR
spectrum of Hongdenafil (100MHz, DMSO)
10
30
31
26
N
25
28
29
HN
15
14
23
17
18
N
N2
20
1
11
12
13
21
13
30
25 26
29 28
14
22
19
15
8 17
23
16
- 63 -
10
21
11
31
20
18
12
Hydroxyhomosildenafil

: Hydroxyhomosildenafil
/ : C23H32N6O5S / 504.62
: 4-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo-(4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-1-Piperazineethanol
O
HN
S
N
N
HO

UV max (nm) : 214.4, 295.9
-1
IR (cm ) : (CHCl3). 3314(w), 2955(w), 1696(s), 1595(w),

1490(w), 1394(w), 1350(w), 1166(m), 952(w), 740(w)
Mass (m/z) : FAB+ (m-NBA). 527([M+Na]+, 10%), 505([M+H]+,
100%), 486(8%), 473(15%), 404(11%), 312(9%), 283(3%), 129(20%),
99(13%), 56(5%)
- 64 -

1.33(3H, t, J = 6.9 Hz, H-21), 1.74(2H, m, H-12), 2.36(2H, q, J = 5.8
Hz, H-29), 2.48(4H, br m, H-25,27), 2.77(2H, t, J = 7.5 Hz, H-11),
2.88(4H, br m, H-24,28), 3.42(2H, t, J = 5.8 Hz, H-30), 4.16(3H, s,
H-10), 4.21(2H, q, J = 6.9 Hz, H-20), 4.39(1H, br s, OH), 7.38(1H, d,
J = 8.6 Hz, H-18), 7.82(1H, dd, J = 8.6, 2.3 Hz, H-17), 7.85(1H, d, J
= 2.3 Hz, H-15), 12.23(1H, br s, NH)
13
27.2(C-11), 37.9(C-10), 45.9(C-24,28), 51.9(C-25,27), 58.4(C-29),

59.5(C-30), 64.9(C-20), 113.2(C-18), 123.7(C-16), 124.4(C-9),
125.8(C-14), 130.0(C-15), 131.6(C-17), 137.8(C-8), 145.0(C-1),
148.2(C-6), 153.8(C-4), 159.9(C-19)
HPLC Chromatogram of Hydroxyhomosildenafil
- 65 -
UV Spectrum of Hydroxyhomosildenafil
IR spectrum of Hydroxyhomosildenafil
- 66 -
Mass spectrum of Hydroxyhomosildenafil (FAB+)

[M+H]+
Theoretical Ion Distribution of Hydroxyhomosildenafil (FAB+)

(m/z 505.2233, MW 505.6182, U.S. 11.5)
m/z
505.2233
506.2261
507.2242
508.2252
509.2262
510.2276
511.2292
512.2308
INT.
100.0000
29.2603
9.5644
1.9292
0.3084
0.0400
0.0044
0.0004
**********************************************************
*****************
******
*
Elemental Composition of Hydroxyhomosildenafil (FAB+)

Observed m/z
505.2236
Int%
100.0
Err[ppm
+4.6
-9.6
-7.0
+3.3
-2.0
+5.9
+0.6
+3.3
+8.2
-8.7
-6.0
-8.7
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
+2.3
-4.9
-3.5
+1.7
-1.0
+3.0
+0.3
+1.7
+4.2
-4.4
-3.1
-4.4
- 67 -
Unsaturation
15.0
11.0
11.5
6.5
11.0
7.0
11.5
12.0
11.5
7.0
7.5
12.5
Composition
C 28 H 31 O
C 22 H 31 O
C 20 H 29 O
C 22 H 37 O
C 25 H 35 O
C 20 H 35 O
C 23 H 33 O
C 21 H 31 O
C 26 H 37 O
C 22 H 39 O
C 20 H 37 O
C 21 H 33 O
6N3
7N7
6 N 10
9N2S
6N3S
8N5S
5N6S
4N9S
4N2S2
6N3S2
5N6S2
N 10 S 2
1H-NMR
spectrum of Hydroxyhomosildenafil (400MHz, DMSO)
10
4
24
30
HO
15
25
29
14
17
28
HN
18
27
21
10
N
N2
1
11
20
21
12
13
15
20
30
24
28
25
11 27
29
18
17
12
OH
13C-NMR
spectrum of Hydroxyhomosildenafil (100MHz, DMSO)
10
4
24
30
HO
15
25
14
17
28
18
27
29
HN
N
N2
20
1
11
21
12
13
12
13
21
10
25
27
19
1
6
15 14
17
916
24
28
20
18
30
29
- 68 -
11
13
Hydroxyhongdenafil

/ : Hydroxyhongdenafil / Hydroxyacetildenafil
/ : C25H34N6O4 / 482.58
: 5-[2-Ethoxy-5-[2-(4-(2-hydroxyethylpiperazine-1-yl)acetyl]
phenyl]-1-methyl-3-propyl-1,6-dihydropyrazolo[4,3-d]pyrimidine-7-one
O
HO
N
HN
N
N

UV max (nm) : 276.33
IR (cm-1) : (CHCl3). 3314(w), 2937(w), 2818(w), 1694(s),
1504(w), 1495(w), 1394(w), 1245(w), 1155(w), 1030(w), 929(w), 752(w)
+
Mass (m/z) : EI+ (70eV). 482([M] , 32%), 464(11%), 395(5%),

354(9%), 311(12%), 297(9%), 283(6%), 212(10%), 143(100%),
141(17%), 100(65%), 70(67%), 56(21%)
- 69 -
1H NMR (400MHz, DMSO-d6) : 0.93(3H, t, J = 7.4 Hz, H-13),

1.33(3H, t, J = 6.9 Hz, H-21), 1.78(2H, m, H-12), 2.38(2H, m, H-30),
2.50(8H, m, H-25, 26, 28, 29), 2.79(2H, t, J = 7.5 Hz, H-11), 3.48(2H,
t, J = 6.2 Hz, H-31), 3.73(2H, s, H-23), 4.16(3H, s, H-10), 4.19(2H, q,
J = 7.0 Hz, H-20), 7.23(1H, d, J = 8.9 Hz, H-18), 8.14(1H, dd, J =

8.8, 2.2 Hz, H-17), 8.27(1H, d, J = 2.1 Hz, H-15), 12.08(1H, br s,
NH)
13
27.1(C-11), 37.8(C-10), 52.7(C-25, 29), 53.0(C-26, 28), 58.3(C-31),

60.1(C-30), 64.2(C-23), 64.6(C-20), 112.3(C-18), 122.8(C-16),
124.3(C-9), 128.2(C-14), 131.2(C-15), 132.5(C-17), 137.9(C-8),
144.9(C-1), 148.9(C-6), 153.7(C-4), 160.1(C-19), 195.3(C-22)
HPLC Chromatogram of Hydroxyhongdenafil

Chrom Ttpe : Fixed WL Chromatogram, 223 nm
- 70 -
UV Spectrum of Hydroxyhongdenafil
RT 22.03 min (S) Current Spectrum
IR Spectrum of Hydroxyhongdenafil
- 71 -
- 72 -
Theoretical Ion Distribution of Hydroxyhongdenafil (EI+)

(m/z 482.2642, MW 482.5828, U.S. 12.0)
m/z
482.2642
483.2671
484.2698
485.2724
486.2749
487.2774
488.2799
INT.
100.0000 **********************************************************
30.6724 ******************
5.3471 ***
0.6791
0.0686
0.0058
0.0004
Elemental Composition of Hydroxyhongdenafil (EI+)

Observed m/z
482.2653
Int%
100.0
Err[ppm
+8.9
-3.3
-8.8
+5.1
-0.5
-6.1
+7.8
+2.3
-9.9
-3.3
+5.1
-7.1
-0.5
+1.9
-10.3
+10.3
-1.9
+4.7
-7.5
+0.9
-4.7
-10.3
+9.2
+3.6
-1.9
-7.5
/ mmu]
/ +4.3
/ -1.6
/ -4.3
/ +2.4
/ -0.2
/ -2.9
/ +3.8
/ +1.1
/ -4.8
/ -1.6
/ +2.4
/ -3.4
/ -0.2
/ +0.9
/ -5.0
/ +4.9
/ -0.9
/ +2.3
/ -3.6
/ +0.4
/ -2.3
/ -4.9
/ +4.4
/ +1.8
/ -0.9
/ -3.6
- 73 -
Unsaturation
20.0
11.0
15.5
7.0
11.5
16.0
7.5
12.0
3.0
16.5
12.5
3.5
17.0
16.0
7.0
12.0
3.0
16.5
7.5
3.5
8.0
12.5
-0.5
4.0
8.5
13.0
Composition
C 36 H 34 O
C 29 H 38 O 6
C 32 H 36 O 3 N
C 24 H 38 O 8 N 2
C 27 H 36 O 5 N 3
C 30 H 34 O 2 N 4
C 22 H 36 O 7 N 5
C 25 H 34 O 4 N 6
C 18 H 38 O 9 N 6
C 28 H 32 O N 7
C 23 H 32 O 3 N 9
C 16 H 36 O 8 N 9
C 26 H 30 N 10
C 33 H 38 O S
C 26 H 42 O 6 S
C 28 H 38 O 3 N 2 S
C 22 H 42 O 8 N 2 S
C 31 H 36 N 3 S
C 24 H 40 O 5 N 3 S
C 19 H 40 O 7 N 5 S
C 22 H 38 O 4 N 6 S
C 25 H 36 O N 7 S
C 14 H 40 O 9 N 7 S
C 17 H 38 O 6 N 8 S
C 20 H 36 O 3 N 9 S
C 23 H 34 N 10 S
1H-NMR
Spectrum of Hydroxyhongdenafil (400MHz, DMSO)
10
O
HO
30
31
26
4
25
28
O
23
29
HN
13
10
N
21
15
14
22
25,26,28,29
1
12
11
17
O
18
20
23
21
13
31
20
15
11 30
12
18
17
5
13C-NMR
Spectrum of Hydroxyhongdenafil (100MHz, DMSO)
O
HO
31
30
26
4
25
28
O
23
29
10
9
HN
15
14
22
18
20
21
4 6
17
12
13
25,29
23
15
19
1
11
17
22
26,28
14 916
18
- 74 -
20 3031
10
11 12
21
13
Hydroxyvardenafil

: Hydroxyvardenafil
/ : C23H32N6O5S / 504.60
: 1-[[3-(1,4-Dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f]
[1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-1-piperazineethanol
O
HN
N
N
S
N
N
N
O
HO

UV max (nm) : 216
IR (cm-1) : (CHCl3). 3331(w), 2932(m), 1695(s), 1624(m),
1471(m), 1415(w), 1282(m), 1166(m), 1034(w), 951(w), 817(w), 754(m)
Mass (m/z) : EI+ (70eV). 504([M]+, 7%), 473(100%), 312(8%),
283(12%), 223(13%), 129(100%), 99(17%), 56(20%)
- 75 -
1H NMR (500MHz, DMSO-d6) : 0.94(3H, t, J = 7.4 Hz, H-13),

1.35(3H, t, J = 6.8 Hz, H-21), 1.72(2H, m, H-12), 2.36(2H, q, J = 4.8
Hz, H-29), 2.47(7H, m, H-10, 25, 27), 2.82(2H, m, H-11), 2.88(4H, br
m, H-24, 28), 3.42(2H, t, J = 4.8 Hz, H-30), 4.21(2H, q, J = 6.8 Hz,
H-20), 4.35(1H, br s, OH), 7.38(1H, d, J = 7.0 Hz, H-18), 7.84(1H, s,
H-15), 7.86(1H, d, J = 7.0 Hz, H-17), 11.65(1H, br s, NH)
13
C NMR (125MHz, DMSO-d6) : 13.6(C-21), 14.2(C-10, 13),
20.2(C-12), 27.1(C-11), 45.8(C-24, 28), 52.0(C-25, 27), 58.4(C-30),

59.5(C-29), 64.9(C-20), 113.1(C-18), 113.6(C-9), 120.8(C-16),
126.0(C-14), 130.1(C-15), 132.1(C-17), 137.6(C-3), 144.3(C-1),
146.1(C-6), 155.0(C-4), 160.2(C-19)
HPLC Chromatogram of Hydroxyvardenafil

- 76 -
UV Spectrum of Hydroxyvardenafil
IR Spectrum of Hydroxyvardenafil
- 77 -
- 78 -
Theoretical Ion Distribution of Hydroxyvardenafil (EI+)

(m/z 504.2155, MW 504.6103, U.S. 12.0)
m/z
504.2155
505.2183
506.2164
507.2174
508.2184
509.2198
510.2213
511.2230
INT.
100.0000
29.2453
9.5600
1.9278
0.3081
0.0400
0.0044
0.0004
**********************************************************
*****************
******
*
Elemental Composition of Hydroxyvardenafil (EI+)

Observed m/z
504.2147
Int%
100.0
Err[ppm
-0.3
-5.6
+7.7
+2.4
-2.9
+5.0
-6.6
+7.7
-3.9
-9.3
+4.7
-7.0
+1.0
-4.3
-9.6
+3.7
-1.6
-7.0
+6.3
+1.0
-4.3
/ mmu]
/ -0.1
/ -2.8
/ +3.9
/ +1.2
/ -1.5
/ +2.5
/ -3.3
/ +3.9
/ -2.0
/ -4.7
/ +2.4
/ -3.5
/ +0.5
/ -2.2
/ -4.9
/ +1.9
/ -0.8
/ -3.5
/ +3.2
/ +0.5
/ -2.2
- 79 -
Unsaturation
15.0
19.5
11.0
15.5
20.0
16.0
7.0
16.5
7.5
12.0
20.0
11.0
7.0
11.5
16.0
7.5
12.0
16.5
8.0
12.5
17.0
Composition
C 30 H 32 O
C 33 H 30 O
C 25 H 32 O
C 28 H 30 O
C 31 H 28 O
C 26 H 28 O
C 19 H 32 O
C 24 H 26 O
C 17 H 30 O
C 20 H 28 O
C 34 H 32 O
C 27 H 36 O
C 22 H 36 O
C 25 H 34 O
C 28 H 32 O
C 20 H 34 O
C 23 H 32 O
C 26 H 30 O
C 18 H 32 O
C 21 H 30 O
C 24 H 28 O
7
4N
9N2
6N3
3N4
3N4
10 N 6
4N9
9N9
6 N 10
2S
7S
9N2S
6N3S
3N4S
8N5S
5N6S
2N7S
7N8S
4N9S
N 10 S
1H-NMR
Spectrum of Hydroxyvardenafil (500MHz, DMSO)
10
4
O
24
25
30
29
HO
HN
O
15
S
N
18
27
20
13
12
11
19
17
28
14
10,25,27
13
21
21
24,28
15
11
20
5
13C-NMR
OH
spectrum of Hydroxyvardenafil (125MHz, DMSO)
10
4
O
24
25
30
HO
12
30
18
17
29
29
15
S
N
14
18
27
1
11
19
17
28
HN
20
21
12
13
24,28
25,27
19
4
1
6
1514
18
17
16 9
- 80 -
30
20 29
10,13
11
12
21
Norneosildenafil

: Norneosildenafil
C22H29N5O4S
M.W. = 459.56
: 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo
[4,3-d]pyrimidine-5-yl)-4-ethoxyphenyl]sulfonyl]piperizine
O
HN
S
N
N
O

UV max (nm) : 291.48
-1
IR (cm ) : (CHCl3). 3306(w), 2939(w), 1693(s), 1558(w),

1488(w), 1340(m), 1279(w), 1167(m), 1028(w), 930(w), 818(w), 755(w)
+
Mass (m/z) : EI+ (70eV). 459([M] , 100%), 431(77%), 387(8%),

312(27%), 283(23%), 282(14%) , 254(10%), 166(25%), 136(18%),
84(25%), 55(7%)
- 81 -
1H NMR (400MHz, DMSO-d6) :
0.92(3H, t, J = 7.4 Hz, H-13),
1.32(3H, t, J = 7.0 Hz, H-21), 1.37(2H, br m, H-26), 1.54(4H, br m,

H-25, 27), 1.75(2H, m, H-12), 2.77(2H, t, J = 7.5 Hz, H-11), 2.91(4H,
br m, H-24, 28), 4.16(3H, s, H-10), 4.21(2H, q, J = 7.0 Hz, H-20),
7.36(1H, d, J = 8.8 Hz, H-18), 7.82(1H, d, J = 8.8 Hz, H-17),
7.88(1H, s, H-15), 12.14(1H, br s, NH)
13
22.9(C-26), 24.6(C-25, 27), 27.1(C-11), 37.8(C-10), 46.5(C-24, 28),

64.8(C-20), 113.2(C-18), 123.4(C-16), 124.3(C-9), 127.2(C-14),
129.7(C-15), 131.2(C-17), 137.7(C-8), 144.9(C-1), 148.1(C-6),
153.6(C-4), 159.6(C-19)
HPLC Chromatogram of Norneosildenafil

- 82 -
UV Spectrum of Norneosildenafil
IR Spectrum of Norneosildenafil
- 83 -
- 84 -
Theoretical Ion Distribution of Norenosildenafil (EI+)

(m/z 459.1940, MW 459.5694, U.S. 12.0)
m/z
459.1940
460.1969
461.1947
462.1957
463.1967
464.1981
465.1996
466.2013
INT.
100.0000
27.6826
8.9216
1.7283
0.2619
0.0320
0.0033
0.0003
**********************************************************
****************
*****
*
Elemental Composition of Norneosildenafil (EI+)

Observed m/z
459.1934
Int%
33.8
Err[ppm
-5.7
+8.9
+3.1
-9.7
-2.7
+6.0
-6.8
+8.9
-3.8
-9.7
+4.9
+1.6
-4.2
-10.1
+10.4
+4.5
-1.3
-7.2
+7.4
+1.6
-4.2
+10.4
-2.4
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
-2.6
+4.1
+1.4
-4.5
-1.3
+2.8
-3.1
+4.1
-1.8
-4.4
+2.3
+0.7
-1.9
-4.6
+4.8
+2.1
-0.6
-3.3
+3.4
+0.7
-1.9
+4.8
-1.1
- 85 -
Unsaturation
19.5
11.0
15.5
6.5
20.0
16.0
7.0
16.5
7.5
12.0
3.5
7.0
11.5
16.0
3.0
7.5
12.0
16.5
8.0
12.5
17.0
8.5
-0.5
Composition
C 32 H 27 O 3
C 24 H 29 O 8 N
C 27 H 27 O 5 N 2
C 20 H 31 O 10 N 2
C 30 H 25 O 2 N 3
C 25 H 25 O 4 N 5
C 18 H 29 O 9 N 5
C 23 H 23 O 3 N 8
C 16 H 27 O 8 N 8
C 19 H 25 O 5 N 9
C 11 H 27 O 10 N 10
C 21 H 33 O 8 N S
C 24 H 31 O 5 N 2 S
C 27 H 29 O 2 N 3 S
C 16 H 33 O 10 N 3 S
C 19 H 31 O 7 N 4 S
C 22 H 29 O 4 N 5 S
C 25 H 27 O N 6 S
C 17 H 29 O 6 N 7 S
C 20 H 27 O 3 N 8 S
C 23 H 25 N 9 S
C 15 H 27 O 5 N 10 S
C 8 H 31 O 10 N 10 S
1H-NMR
Spectrum of Norneosildenafil (400MHz, DMSO)
10
O
10
4
O
24
O
15
25
N
14
13
21
12
11
20
18
27
19
17
28
26
HN
21
13
26
24,28 25,27
15
17
13C-NMR
11
20
18
12
Spectrum of Norneosildenafil (100MHz, DMSO)
O
4
O
24
25
15
S
N
28
26
27
HN
10
N
14
19
17
11
O
18
20
21
12
13
26
25,27
24,28
15
10
19
4 6
18
17 149
8
16
- 86 -
20
12
11
21 13
Piperidinohongdenafil

/ : Piperidinohongdenafil / Piperidinoacetildenafil
/ : C24H31N5O3 / 437.53
: 5-{2-Ethoxy-5-[2-piperidine-1-yl-acetyl]-phenyl}-1-methyl
-3-propyl-1,6-dihydro-pyrazolo[4,3-d]-pyrimidine-7-one
O
O
HN
N
N

UV max (nm) : 276.54
IR (cm-1) : (CHCl3). 3310(w), 2935(m), 1691(s), 1561(w), 1494(w),
1393(w), 1260(w), 1149(w), 1033(w), 753(w)
+
Mass (m/z) : EI+ (70eV). 437([M] , 7%), 354(14%), 339(7%),

311(16%), 283(8%), 282(4%) , 254(4%), 166(7%), 136(11%), 98(100%),
55(17%)
- 87 -
1H NMR (500MHz, DMSO-d6) :
0.93(3H, t, J = 7.4 Hz, H-13),
1.34(3H, t, J = 7.0 Hz, H-21), 1.37(2H, m, H-27), 1.48(4H, m, H-26,

28), 1.74(2H, m, H-12), 2.44(4H, br m, H-25, 29), 2.78(2H, t, J = 7.6
Hz, H-11), 3.69(2H, s, H-23), 4.16(3H, s, H-10), 4.20(2H, q, J = 7.0
Hz, H-20), 7.23(1H, d, J = 8.9 Hz, H-18), 8.16(1H, dd, J = 8.8, 2.2
Hz, H-17), 8.33(1H, d, J = 2.2 Hz, H-15), 12.03(1H, br s, NH)
13
23.8(C-27), 25.7(C-26, 28), 27.4(C-11), 38.1(C-10), 54.3(C-25, 29),

64.8(C-20), 65.5(C-23), 112.6(C-18), 122.9(C-16), 124.6(C-9),
128.6(C-14), 131.6(C-15), 132.8(C-17), 138.2(C-8), 145.2(C-1),
149.2(C-6), 153.9(C-4), 160.4(C-19), 195.8(C-22)
HPLC Chromatogram of Piperidinohongdenafil
- 88 -
UV Spectrum of Piperidinohongdenafil
IR Spectrum of Piperidinohongdenafil
- 89 -
Mass Spectrum of Piperidinohongdenafil (EI+)
[M]+
- 90 -
Theoretical Ion Distribution of Piperidinohongdenafil (EI+)

(m/z 437.2427, MW 437.5418, U.S. 12.0)
m/z
437.2427
438.2457
439.2485
440.2511
441.2537
442.2563
443.2588
INT.
100.0000 **********************************************************
29.1097 *****************
4.6864 ***
0.5429
0.0496
0.0037
0.0002
Elemental Composition of Piperidinohongdenafil (EI+)

Observed m/z
437.2441
Int%
98.1
Err[ppm
-9.0
+6.3
+0.2
-6.0
+9.4
+3.2
-10.2
-2.9
+6.3
-7.1
+2.1
-1.4
-7.5
+1.7
-4.5
-10.6
+10.9
+4.7
-1.4
+7.8
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
-3.9
+2.8
+0.1
-2.6
+4.1
+1.4
-4.5
-1.3
+2.8
-3.1
+0.9
-0.6
-3.3
+0.7
-2.0
-4.6
+4.8
+2.1
-0.6
+3.4
- 91 -
Unsaturation
15.5
7.0
11.5
16.0
7.5
12.0
3.0
16.5
12.5
3.5
-0.5
3.0
7.5
3.5
8.0
12.5
-0.5
4.0
8.5
4.5
Composition
C 31 H 33 O 2
C 23 H 35 O 7 N
C 26 H 33 O 4 N 2
C 29 H 31 O N 3
C 21 H 33 O 6 N 4
C 24 H 31 O 3 N 5
C 17 H 35 O 8 N 5
C 27 H 29 N 6
C 22 H 29 O 2 N 8
C 15 H 33 O 7 N 8
C 10 H 33 O 9 N 10
C 20 H 39 O 7 N S
C 23 H 37 O 4 N 2 S
C 18 H 37 O 6 N 4 S
C 21 H 35 O 3 N 5 S
C 24 H 33 N 6 S
C 13 H 37 O 8 N 6 S
C 16 H 35 O 5 N 7 S
C 19 H 33 O 2 N 8 S
C 14 H 33 O 4 N 10 S
1H-NMR
Spectrum of Piperidinohongdenafil(500MHz, DMSO)
O
26
27
25
28
29
23
22
HN
13
21
15
16
10
10
14
19
17
20
18
12
26,28
11
13
21
11
20
15
18
23
25,29 27
12
17
5
13C-NMR
Spectrum of Piperidinohongdenafil(125MHz, DMSO)
O
26
27
25
28
29
10
23
22
16
HN
15
14
19
17
18
12
11
20
21
13
25,29
19 4
1
6
15
17 14 9
18
16
22
- 92 -
20
23
26,28
12
13
10 11
21
27
Pseudovardenafil

/ : Pseudovardenafil / Piperidenafil
/ : C22H29N5O4S / 459.57
: 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]piperidine
O
HN
N

UV max (nm) : 218.1
IR (cm-1) : (CHCl3). 2938(m), 1697(s), 1624(m), 1472(m), 1339(w),
1281(w), 1167(m), 1111(w), 1034(w), 931(w), 755(w)
Mass (m/z) : FAB+ (m-NBA). 482([M+Na]+, 5%), 460([M+H]+, 100%),
431(7%), 312(8%), 283(4%), 151(8%), 84(8%)
- 93 -

1.32(3H, t, J = 7.0 Hz, H-21), 1.36(2H, br m, H-26), 1.53(4H, br m,
H-25,27), 1.73(2H, m, H-12), 2.48(3H, s, H-10), 2.82(2H, t, J = 7.5
Hz, H-11), 2.90(4H, br m, H-24,28), 4.20(2H, q, J = 7.0 Hz, H-20),
7.37(1H, d, J = 8.8 Hz, H-18), 7.86(2H, m, H-15,17), 11.69(1H, br s,
NH)
13
20.2(C-12), 22.9(C-26), 24.6(C-25,27), 27.2(C-11), 46.6(C-24,28),

64.9(C-20), 113.2(C-18), 113.7(C-9), 120.7(C-16), 127.0(C-14),
129.9(C-15), 131.9(C-17), 137.6(C-3), 144.4(C-1), 146.1(C-6),
155.1(C-4), 160.1(C-19)
Elemental Analysis (%) : 57.58(C), 6.34(H), 15.26(N), 7.02(S)
HPLC Chromatogram of Pseudovardenafil
- 94 -
UV Spectrum of Pseudovardenafil
IR spectrum of Pseudovardenafil
- 95 -
Mass spectrum of Pseudovardenafil(FAB+)
[M+H]+
Theoretical Ion Distribution of Pseudovardenafil (FAB+)

Molecular Formula : C22 H30 O4 N5 S
(m/z 460.2019, MW 460.5773, U.S. 11.5)
m/z
460.2019
461.2047
462.2025
463.2035
464.2045
465.2059
466.2075
467.2092
INT.
100.0000
27.6976
8.9257
1.7297
0.2622
0.0321
0.0033
0.0003
**********************************************************
****************
*****
*
Elemental Composition of Pseudovardenafil (FAB+)

Observed m/z
460.2019
Int%
100.0
Err[ppm
-1.4
-5.4
+1.6
-2.5
+0.0
+3.0
-2.9
-1.5
+1.5
-4.4
+4.4
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
-0.6
-2.5
+0.7
-1.1
+0.0
+1.4
-1.3
-0.7
+0.7
-2.0
+2.0
- 96 -
Unsaturation
19.5
6.5
20.0
7.0
11.5
12.0
16.5
3.0
3.5
8.0
4.0
Composition
C 30 H 26 O 2 N 3
C 18 H 26 O 4 N 5
C 28 H 24 O N 6
C 16 H 28 O 8 N 8
C 22 H 30 O 4 N 5 S
C 20 H 28 O 3 N 8 S
C 23 H 26 N 9 S
C 16 H 36 O 7 N 4 S 2
C 14 H 34 O 6 N 7 S 2
C 17 H 32 O 3 N 8 S 2
C 12 H 32 O 5 N 10 S 2
1H-NMR
spectrum of Pseudovardenafil (400MHz, DMSO)
10
24
25
HN
15
S
N
26
20
18
27
21
13
14
17
28
10
15,17
12
11
21
13
11
20
24
28
25
27
12
18
26
5
13C-NMR
spectrum of Pseudovardenafil (100MHz, DMSO)
10
24
25
HN
14
26
18
27
17
28
3
N
15
20
11
21
12
13
24,28
25,27
12
11
19
20
18
15 14
26
17
16
- 97 -
10
13
21
Thiosildenafil

: Thiosildenafil
/ : C20H30N6O3S2 / 490.64
: 5-[2-Ethoxy-5-(4-methylpiperazine-1-sulfonyl)phenyl]-1methyl-3-propyl-1,6-dihydropyrazolo [4,3-d]pyrimidin-7thione
S
HN
S
N
N
N
O

UV max (nm) : 353.30
IR (cm-1) : (CHCl3). 3278(w), 2938(w), 2800(w), 1546(m),
1502(m), 1457(m), 1349(m), 1255(m), 1160(s), 941(w), 740(w)
Mass (m/z) : EI+ (70eV). 490([M]+, 70%), 420(70%), 397(12%),
384(5%), 327(38%), 312(4%) , 299(34%), 298(12%), 269(9%), 228(5%),
99(100%), 56(79%)
- 98 -
1H NMR (500MHz, CDCl3) : 1.06(3H, t, J = 7.4 Hz, H-13), 1.72(3H,

t, J = 6.9 Hz, H-21), 1.85(2H, m, H-12), 2.27(3H, s, H-29), 2.50(4H,
br m, H-25, 27), 2.94(2H, t, J = 7.5 Hz, H-11), 3.11(4H, br m, H-24,
28), 4.39(2H, q, J = 6.9 Hz, H-20), 4.52(3H, s, H-10), 7.17(1H, d, J =
8.8 Hz, H-18), 7.85(1H, dd, J = 8.8, 2.3 Hz, H-17), 8.85(1H, d, J =
2.3 Hz, H-15), 12.39(1H, br s, NH)
13
C NMR (125MHz, CDCl3) : 14.0(C-13), 14.6(C-21), 22.1(C-12),
27.6(C-11), 39.4(C-10), 45.7(C-29), 45.9(C-24, 28), 54.0(C-25, 27),

66.4(C-20), 113.1(C-18), 119.8(C-16), 129.2(C-14), 130.8(C-15),
132.0(C-17), 132.3(C-9), 133.9(C-8), 146.0(C-6), 146.5(C-1),
159.4(C-19), 171.8(C-4)
HPLC Chromatogram of Thiosildenafil

- 99 -
UV Spectrum of Thiosildenafil
IR Spectrum of Thiosildenafil
- 100 -
Mass Spectrum of Thiosildenafil (EI+)
[M]+
- 101 -
Theoretical Ion Distribution of Thiosildenafil (EI+)

Molecular Formula : C22 H30 N6 O4 S2
(m/z 490.1821, MW 490.6506, U.S. 13.0)
m/z
490.1821
491.1848
492.1811
493.1823
494.1807
495.1811
496.1813
497.1820
498.1828
INT.
100.0000
28.8162
13.4682
3.0143
0.6753
0.1129
0.0161
0.0019
0.0002
**********************************************************
*****************
********
**
Elemental Composition of Thiosildenafil (EI+)

Observed m/z
490.1808
Int%
100.0
Err[ppm
+5.6
-6.4
-3.7
-9.1
-0.9
-6.4
+7.3
+1.8
-3.7
-1.3
+6.9
+1.4
+9.6
+4.2
-7.8
+0.4
+6.9
-5.1
-8.2
+5.5
+0.0
-5.4
+8.2
+2.8
-2.7
-8.2
+5.5
-6.5
+0.0
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
+2.7
-3.1
-1.8
-4.5
-0.5
-3.1
+3.6
+0.9
-1.8
-0.6
+3.4
+0.7
+4.7
+2.0
-3.8
+0.2
+3.4
-2.5
-4.0
+2.7
+0.0
-2.7
+4.0
+1.4
-1.3
-4.0
+2.7
-3.2
+0.0
- 102 -
Unsaturation
20.0
11.0
11.5
16.0
12.0
16.5
8.0
12.5
17.0
16.0
12.0
16.5
12.5
17.0
8.0
4.0
17.5
8.5
12.0
3.5
8.0
12.5
4.0
8.5
13.0
17.5
9.0
0.0
13.5
Composition
C 32 H 26 O 5
C 25 H 30 O 10
C 23 H 28 O 9 N 3
C 26 H 26 O 6 N 4
C 21 H 26 O 8 N 6
C 24 H 24 O 5 N 7
C 16 H 26 O 10 N 8
C 19 H 24 O 7 N 9
C 22 H 22 O 4 N 10
C 29 H 30 O 5 S
C 24 H 30 O 7 N 2 S
C 27 H 28 O 4 N 3 S
C 22 H 28 O 6 N 5 S
C 25 H 26 O 3 N 6 S
C 18 H 30 O 8 N 6 S
C 13 H 30 O 10 N 8 S
C 23 H 24 O 2 N 9 S
C 16 H 28 O 7 N 9 S
C 26 H 34 O 5 S 2
C 18 H 36 O 10 N S 2
C 21 H 34 O 7 N 2 S 2
C 24 H 32 O 4 N 3 S 2
C 16 H 34 O 9 N 4 S 2
C 19 H 32 O 6 N 5 S 2
C 22 H 30 O 3 N 6 S 2
C 25 H 28 N 7 S 2
C 17 H 30 O 5 N 8 S 2
C 10 H 34 O 10 N 8 S 2
C 20 H 28 O 2 N 9 S 2
1H-NMR
Spectrum of Thiosildenafil (500MHz, CDCl3)
10
4
O
24
14
25
N
29
15
28
1
12
11
20
18
27
N2
8
19
17
10
HN
13
13
21
25,27
15
5
13C-NMR
24,28
11
21
12
Spectrum of Thiosildenafil (125MHz, CDCl3)
10
4
O
24
15
28
HN
25
29
20
18
17
29
N2
14
19
17
18
27
11
20
12
13
21
25,27
9
4
19
15
17
14
16
18
- 103 -
20
24,28
29
10
11
12
21
13
Xanthoanthrafil

/ : Xanthoanthrafil / Benzamidenafil
/ : C19H23N3O6 / 389.40
: N-(3,4-dimethoxybenzyl)-2-{[(1R)-2-hydroxy-1-methylethyl]amino}-5-nitrobenzamide
OH
HN
O
N
H
OCH3
OCH3
NO2

UV max (nm) : 377.42
IR (cm-1) : (CHCl3). 3347(w), 2935(w), 1636(m), 1589(m), 1516(s),
1463(w), 1325(s), 1277(s), 1026(w), 818(w), 750(w)
+
Mass (m/z) : EI+ (70eV). 389([M] , 27%), 358(42%), 220(4%),

191(24%), 152(75%), 151(100%) , 107(20%), 106(15%), 90(11%), 65(6%)
- 104 -
1H NMR (500MHz, DMSO-d6) : 1.17(3H, d, J = 8.1 Hz, H-21),

3.46(2H, m, H-22), 3.73(1H, m, H-20), 3.75(3H, s, H-8), 3.78(3H, s,
H-7), 4.37(2H, m, H-9), 6.83(1H, m, H-10), 6.86(1H, d, J = 9.4 Hz,
H-16), 6.89(1H, d, J = 7.8 Hz, H-6), 6.92(1H, s, H-3), 6.96(1H, d, J =
7.8 Hz, H-5), 8.11(1H, dd, J = 9.4, 2.6 Hz, H-15), 8.58(1H, d, J =
2.6 Hz, H-13), 9.08(1H, d, J = 7.8 Hz, H-19)
13
55.5(C-7, 8), 64.1(C-22), 111.2(C-16), 111.6(C-3), 111.8(C-6),

113.1(C-12), 119.5(C-5), 125.7(C-13), 128.0(C-15), 131.7(C-4),
134.2(C-14), 147.9(C-1), 148.6(C-2), 153.5(C-17), 167.4(C-11)
HPLC Chromatogram of Xanthoanthrafil

- 105 -
UV Spectrum of Xanthoanthrafil
IR Spectrum of Xanthoanthrafil
- 106 -
Mass Spectrum of Xanthoanthrafil (EI+)
[M]+
Theoretical Ion Distribution of Xanthoanthrafil (EI+)

(m/z 389.1587, MW 389.4081, U.S. 10.0)
m/z
389.1587
390.1618
391.1642
392.1668
393.1692
394.1716
395.1741
INT.
100.0000 **********************************************************
22.8081 *************
3.6843 **
0.4452
0.0442
0.0037
0.0003
Elemental Composition of Xanthoanthrafil (EI+)

Observed m/z
389.1592
Int%
56.9
Err[ppm
-2.2
-9.1
+8.2
+1.3
-5.6
-12.5
+11.6
+4.7
-10.4
-2.2
+8.2
-6.9
+1.3
/
/
/
/
/
/
/
/
/
/
/
/
/
/
mmu]
-0.8
-3.5
+3.2
+0.5
-2.2
-4.9
+4.5
+1.8
-4.0
-0.8
+3.2
-2.7
+0.5
- 107 -
Unsaturation
9.5
14.0
5.5
10.0
14.5
19.0
6.0
10.5
1.5
15.0
11.0
2.0
15.5
Composition
C 21 H 25 O 7
C 24 H 23 O 4 N
C 16 H 25 O 9 N 2
C 19 H 23 O 6 N 3
C 22 H 21 O 3 N 4
C 25 H 19 N 5
C 14 H 23 O 8 N 5
C 17 H 21 O 5 N 6
C 10 H 25 O 10 N 6
C 20 H 19 O 2 N 7
C 15 H 19 O 4 N 9
C 8 H 23 O 9 N 9
C 18 H 17 O N 10
1H-NMR
Spectrum of Xanthoanthrafil (500MHz, DMSO)
21
20
HN 19
7,8,20
OH
22
O
5
17
12
16
11
N
H 10
OCH 3
7
3
13
13C-NMR
OCH 3
8
14
18
NO 2
15
19
13
15
6
9
16
22
10
Spectrum of Xanthoanthrafil (125MHz, DMSO)
21
20
HN 19
17
16
OH
22
O
11
N10
H
6
1
13
15
9
12
14
18
NO2
OCH3
8
OCH3
7
11
17 2
4 15 13
14
12
7,8
3
6
16
- 108 -
22
21
20 9
Desmethylsibutramine

: Desmethylsibutramine
/ : C16H24ClN / 265.84
: {1-[1-(4-Chloro-phenyl)-cyclobutyl]-3-methyl-butyl}methyl-amine
HN
Cl

UV max (nm) : 222.71
-1
IR (cm ) : (CHCl3). 3408(w), 2958(s), 2731(w), 1591(w),

1493(m), 1466(m), 1415(w), 1095(w), 1012(w), 753(w)
Mass (m/z) : FAB+ (m-NBA). 289([M+Na]+, 7%), 266([M+H]+, 100%),
176(9%), 165(5%)
- 109 -
H NMR (400MHz, DMSO-d6) : 0.85(6H, m, H-1, 2), 1.12(1H, m,

H-4), 1.25(1H, m, H-4), 1.58(1H, m, H-3), 1.71(1H, m, H-10), 1.94(1H,
m, H-10), 2.30-2.61(4H, m, H-9, 11), 2.55(3H, s, H-7), 3.44(1H, m,
H-5), 7.42(2H, d, J = 8.4 Hz, H-13, 17), 7.48(2H, d, J = 8.4 Hz,
H-14, 16), 8.38(1H, br s, H-6), 8.66(1H, br s, H-6)
13
C NMR (100MHz, DMSO-d6) : 15.1(C-10), 21.6, 22.7(C-1, 2),
25.2(C-3), 31.8, 32.2(C-9, 11), 33.0(C-7), 36.6(C-4), 49.0(C-8),

63.9(C-5), 128.0(C-14, 16), 129.8(C-13, 17), 131.4(C-12), 141.7(C-15)
HPLC Chromatogram of Desmethylsibutramine

- 110 -
UV Spectrum of Desmethylsibutramine
RT
34.61 min (S) Current Spectrum
IR Spectrum of Desmethylsibutramine
- 111 -
Theoretical Ion Distribution of Desmethylsibutramine (FAB+)

Molecular Formula : C16 H25 Cl N
(m/z 266.1676, MW 266.8342, U.S. 4.5)
m/z
266.1676
267.1708
268.1651
269.1680
270.1712
271.1745
272.1778
INT.
100.0000
18.5382
33.5970
6.0166
0.5210
0.0284
0.0011
**********************************************************
***********
*******************
***
Elemental Composition of Desmethylsibutramine (FAB+)

Observed m/z
266.1682
Int%
100.0
Err[ppm / mmu]
+9.5 / +2.5
+2.6 / +0.7
- 112 -
Unsaturation
9.5
4.5
Composition
C 17 H 20 N 3
C 16 H 25 N 35 Cl
1H-NMR
Spectrum of Desmethylsibutramine (400MHz, DMSO)
10
11
9
17
16
Cl
15
14
12
1,2
HN
13
1
3
14,16 13,17
5
6
13C-NMR
9,11
9,11
10 10 3 4
Spectrum of Desmethylsibutramine (100MHz, DMSO)
10
11
9
17
16
Cl
15
14
12
13
1
3
2
HN
7
9/11
13,17 14,16
5
15 12
- 113 -
47
1/2
10
N-nitrosofenfluramine

: N-nitrosofenfluramine
/ : C12H15F3N2O / 260.26
N
N

UV max (nm) : 233.22
IR (cm-1) : (CHCl3). 2981(w), 2940(w), 1448(w), 1330(s),
1164(m), 1124(s), 1074(m), 914(w), 803(w), 704(w)
Mass (m/z) : FAB+ (m-NBA). 283([M+Na]+, 10%), 261([M+H]+,
100%), 260(7%), 230(7%), 187(26%), 186(20%), 159(44%), 154(7%),
137(7%), 101(30%), 70(11%), 56(5%)
- 114 -
1H NMR (400MHz, DMSO-d6) : 0.87(3H, t, J = 7.2 Hz, H-5)

1.42(3H, d, J = 6.8 Hz, H-3) 3.17(2H, m, H-1), 3.41(1H, m, H-4)
3.51(1H, m, H-4')
4.84(1H, m, H-2)
7.52(2H, m, H-10, 11), 7.57(2H,
m, H-7, 9)
13
39.9(C-1), 59.9(C-2), 123.1(C-9), 125.6(C-7, 12), 129.2(C-8, 10),

133.3(C-11), 139.5(C-6)
HPLC Chromatogram of N-nitrosofenfluramine

- 115 -
UV Spectrum of N-nitrosofenfluramine
IR Spectrum of N-nitrosofenfluramine
- 116 -
Molecular Formula : C12 H16 F3 N2 O

(m/z 261.1215, MW 261.2670, U.S. 4.5)
m/z
261.1215
262.1246
263.1273
264.1299
265.1325
INT.
100.0000 **********************************************************
14.3596 ********
1.1559 *
0.0678
0.0030
Elemental Composition of N-nitrosofenfluramine (FAB+)

Observed m/z
261.1219
Int%
100.0
Err[ppm
-7.9
-12.3
+16.1
+5.8
-16.6
+11.7
+1.5
/
/
/
/
/
/
/
/
mmu]
-2.1
-3.2
+4.2
+1.5
-4.3
+3.1
+0.4
Unsaturation
7.5
3.5
4.0
8.5
-0.5
0.0
4.5
- 117 -
Composition
C 14 H 17 O 3 N 2
C 11 H 18 O 4 N 2 F
C 12 H 17 O 3 N F 2
C 15 H 15 N 2 F 2
C 8 H 19 O 5 N 2 F 2
C 9 H 18 O 4 N F 3
C 12 H 16 O N 2 F 3
1H-NMR
Spectrum of N-nitrosofenfluramine(400MHz, DMSO)
3
5
10,11
F
12
F
11
N
N
O
10
7,9
44
2
- 118 -

Instrumental Analysis Data of Illegal
Compounds in Food
2009 6
2009 6

, , , , ,
, , , ,
(), ()

122-704 194
02-380-1674~5, 02-355-6037
National Institute of Food and Drug Safety
Evaluation
194 Tongilro Eunpyeong-gu Seoul 122-704,
Korea
Tel 82-2-380-1674, Fax 82-2-355-6037
Web site : http//www.nifds.go.kr

Instrumental Analysis Data of Illegal Disfuccion Erectil

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Instrumental Analysis Data of Illegal Disfuccion Erectil

Uploaded by

Copyright:

Available Formats

11-1470550-000001-14

Instrumental Analysis Data of Illegal

Mass (m/z) : FAB+ (m-NBA). 532([M-2HCl+H]+, 17%), 500(1%),

H NMR (400 MHz, DMSO-d6) : 0.92(3H, t, J = 7.1 Hz, H-14),

C NMR (100 MHz, DMSO-d6) : 10.3(C-23), 13.8(C-14), 17.3(C-11),

21.7(C-22), 23.2(C-13), 25.3(C-12), 42.7(C-31), 43.0(C-10),

Mass spectrum of Mirodenafil (FAB+)

Theoretical Ion Distribution of Mirodenafil (FAB+)

Elemental Composition of Mirodenafil (FAB+)

spectrum of Mirodenafil (400MHz, DMSO)

spectrum of Mirodenafil (100MHz, DMSO)

IR (cm ) : KBr. 3445(s), 1702(s), 1582(m), 1461(w), 1360(w),

Mass (m/z) : EI+ (70eV). 474([M] , 9%), 410(14%), 404(90%),

H NMR (400 MHz, DMSO-d6) : 0.93(3H, t, J = 7.3 Hz, H-13),

1.33(3H, t, J = 6.9 Hz, H-21), 1.73(2H, m, H-12), 2.29(3H, s, H-29),

C NMR (100 MHz, DMSO-d6) : 13.9(C-13), 14.3(C-21), 21.7(C-12),

Mass spectrum of Sildenafil (EI+)

Theoretical Ion Distribution of Sildenafil (EI+)

Elemental Composition of Sildenafil (EI+)

spectrum of Sildenafil (400MHz, DMSO)

spectrum of Sildenafil (100MHz, DMSO)

Mass (m/z) : EI+ (70eV). 389([M] , 100%), 317(12%), 289(22%),

H NMR (400 MHz, DMSO-d6) : 2.93(3H, s, H-18), 2.99(1H, dd, J

C NMR (100 MHz, DMSO-d6) : 23.1(C-16), 32.9(C-18), 51.5(C-3),

55.3(C-17), 55.5(C-6), 100.9(C-25), 104.7(C-15), 107.0(C-20),

Mass spectrum of Tadalafil (EI+)

Theoretical Ion Distribution of Tadalafil (EI+)

Elemental Composition of Tadalafil (EI+)

spectrum of Tadalafil (400MHz, DMSO)

spectrum of Tadalafil (100MHz, DMSO)

IR (cm ) : (CHCl3). 3305(w), 2962(w), 1695(s), 1595(w),

1H NMR (400 MHz, DMSO-d6) : 0.93(3H, t, J = 7.2 Hz, H-13),

C NMR (100 MHz, DMSO-d6) : 10.4(C-22), 13.8(C-13), 21.6(C-30),

21.7, 21.8(C-12,21), 27.1(C-11), 29.7(C-31), 32.5(C-26), 37.9(C-10),

Mass spectrum of Udenafil (EI+)

Theoretical Ion Distribution of Udenafil (EI+)

Elemental Composition of Udenafil (EI+)

spectrum of Udenafil (400MHz, DMSO)

spectrum of Udenafil (100MHz, DMSO)

IR (cm ) : (CHCl3). 3398(w), 2966(w), 1697(s), 1626(w),

H NMR (400 MHz, DMSO-d6) : 0.94(3H, t, J = 7.4 Hz, H-13),

C NMR (100 MHz, DMSO-d6) : 8.7(C-30), 13.7(C-21), 14.1(C-10),

14.3(C-13), 20.2(C-12), 27.1(C-11), 43.0(C-24,28), 49.4(C-25,27),

126.4(C-14), 130.3(C-15), 132.2(C-17), 137.6(C-3), 144.4(C-1),

Mass spectrum of Vardenafil (EI+)

Theoretical Ion Distribution of Vardenafil (EI+)

Elemental Composition of Vardenafil (EI+)

spectrum of Vardenafil (400MHz, DMSO)

spectrum of Vardenafil (100MHz, DMSO)

Mass (m/z) : EI+ (70eV). 390([M] , 100%), 375(11%), 318(11%),

1H NMR (400 MHz, DMSO-d6) : 3.00(1H, dd, J = 15.4, 11.9 Hz,

J = 7.7 Hz, H-13), 11.02(1H, br s, NH)

C NMR (100 MHz, DMSO-d6) : 23.5(C-16), 53.3(C-3), 55.4(C-17),

55.6(C-6), 100.9(C-25), 104.8(C-15), 106.9(C-20), 108.3(C-23),

HPLC Chromatogram of Aminotadalafil

Mass spectrum of Aminotadalafil (EI+)

Theoretical Ion Distribution of Aminotadalafil (EI+)

Elemental Composition of Aminotadalafil (EI+)

spectrum of Aminotadalafil (400MHz, DMSO)

spectrum of Aminotadalafil (100MHz, DMSO)

Mass (m/z) : EI+ (70eV). 390([M] , 100%), 374(23%), 318(23%),

1H NMR (100 MHz, DMSO-d6) : 2.95(1H, dd, J = 14.7, 12.3 Hz,

C NMR (100 MHz, DMSO-d6) : 26.7(C-16), 50.9(C-6), 51.8(C-17),

52.3(C-3), 101.3(C-25), 107.4(C-15), 108.2(C-20), 108.3(C-23),