Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
(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 -
13
- 2 -
UV Spectrum of Mirodenafil
IR spectrum of Mirodenafil
- 3 -
[M-2HCl+H]+
INT.
100.0000
32.3047
10.4836
2.2288
0.3699
0.0500
0.0057
0.0006
**********************************************************
*******************
******
*
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
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
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
HPLC RT (min) : 14.5
UV max (nm) : 214.4, 295.9
-1
- 6 -
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 -
[M]+
INT.
100.0000
28.0650
9.0275
1.7625
0.2685
0.0330
0.0034
0.0003
**********************************************************
****************
*****
*
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
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
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
HPLC RT (min) : 19.0
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)
+
- 11 -
13
- 12 -
UV Spectrum of Tadalafil
IR spectrum of Tadalafil
- 13 -
INT.
100.0000 **********************************************************
26.0086 ***************
4.0460 **
0.4666
0.0431
0.0033
0.0002
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
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
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
HPLC RT (min) : 18.4
UV max (nm) : 213.5, 296.7
-1
13
- 17 -
UV Spectrum of Udenafil
IR spectrum of Udenafil
- 18 -
[M]+
INT.
100.0000
31.4917
10.0293
2.0833
0.3326
0.0430
0.0046
0.0004
**********************************************************
******************
******
*
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
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
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
13
120.9(C-16),
- 22 -
UV Spectrum of Vardenafil
IR spectrum of Vardenafil
- 23 -
[M]+
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
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
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
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
HPLC RT (min) : 15.3
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)
+
13
- 27 -
UV Spectrum of Aminotadalafil
IR Spectrum of Aminotadalafil
- 28 -
INT.
100.0000 **********************************************************
25.2487 ***************
3.8568 **
0.4379
0.0399
0.0030
0.0002
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
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
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
HPLC RT (min) : 15.5
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)
+
13
- 32 -
UV Spectrum of epi-Aminotadalafil
IR Spectrum of epi-Aminotadalafil
- 33 -
INT.
100.0000 **********************************************************
25.2487 ***************
3.8568 **
0.4379
0.0399
0.0030
0.0002
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
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
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
13
- 37 -
- 38 -
[M]+
- 39 -
- 40 -
1H-NMR
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
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
HPLC RT (min) : 22.3
UV max (nm) : 276.28
-1
- 42 -
H NMR
13
C NMR
- 43 -
UV Spectrum of Demethylhongdenafil
RT
IR Spectrum of Demethylhongdenafil
- 44 -
[M]+
- 45 -
INT.
100.0000 **********************************************************
29.4920 *****************
4.7978 ***
0.5608
0.0517
0.0039
0.0003
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
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
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
HPLC RT (min) : 29.73
UV max (nm) : 292.13
-1
- 48 -
13
- 49 -
UV Spectrum of Dimethylsildenafil
RT
IR Spectrum of Dimethylsildenafil
- 50 -
[M]+
- 51 -
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
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
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
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
HPLC RT (min) : 15.20
UV max (nm) : 214.4, 295.9
-1
13
- 55 -
UV Spectrum of Homosildenafil
IR spectrum of Homosildenafil
- 56 -
[M]+
INT.
100.0000
29.2072
9.3484
1.8657
0.2887
0.0361
0.0038
0.0003
**********************************************************
*****************
*****
*
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
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
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
- 59 -
13
- 60 -
UV Spectrum of Hongdenafil
IR spectrum of Hongdenafil
- 61 -
[M]+
INT.
100.0000 **********************************************************
30.6343 ******************
5.1350 ***
0.6157
0.0581
0.0045
0.0003
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
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
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
HPLC RT (min) : 13.6
UV max (nm) : 214.4, 295.9
-1
- 64 -
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
- 65 -
UV Spectrum of Hydroxyhomosildenafil
IR spectrum of Hydroxyhomosildenafil
- 66 -
INT.
100.0000
29.2603
9.5644
1.9292
0.3084
0.0400
0.0044
0.0004
**********************************************************
*****************
******
*
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
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
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
HPLC RT (min) : 22.03
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)
+
- 69 -
13
- 70 -
UV Spectrum of Hydroxyhongdenafil
IR Spectrum of Hydroxyhongdenafil
- 71 -
- 72 -
INT.
100.0000 **********************************************************
30.6724 ******************
5.3471 ***
0.6791
0.0686
0.0058
0.0004
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
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
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
HPLC RT (min) : 20.9
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 -
13
- 76 -
UV Spectrum of Hydroxyvardenafil
IR Spectrum of Hydroxyvardenafil
- 77 -
- 78 -
INT.
100.0000
29.2453
9.5600
1.9278
0.3081
0.0400
0.0044
0.0004
**********************************************************
*****************
******
*
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
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
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
HPLC RT (min) : 42.12
UV max (nm) : 291.48
-1
- 81 -
13
- 82 -
UV Spectrum of Norneosildenafil
IR Spectrum of Norneosildenafil
- 83 -
- 84 -
INT.
100.0000
27.6826
8.9216
1.7283
0.2619
0.0320
0.0033
0.0003
**********************************************************
****************
*****
*
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
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
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
HPLC RT (min) : 26.08
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)
+
- 87 -
13
- 88 -
UV Spectrum of Piperidinohongdenafil
IR Spectrum of Piperidinohongdenafil
- 89 -
[M]+
- 90 -
INT.
100.0000 **********************************************************
29.1097 *****************
4.6864 ***
0.5429
0.0496
0.0037
0.0002
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
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
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
HPLC RT (min) : 21.6
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 -
13
- 94 -
UV Spectrum of Pseudovardenafil
IR spectrum of Pseudovardenafil
- 95 -
[M+H]+
INT.
100.0000
27.6976
8.9257
1.7297
0.2622
0.0321
0.0033
0.0003
**********************************************************
****************
*****
*
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
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
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
HPLC RT (min) : 37.14
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 -
13
- 99 -
UV Spectrum of Thiosildenafil
IR Spectrum of Thiosildenafil
- 100 -
[M]+
- 101 -
INT.
100.0000
28.8162
13.4682
3.0143
0.6753
0.1129
0.0161
0.0019
0.0002
**********************************************************
*****************
********
**
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
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
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
HPLC RT (min) : 37.30
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)
+
- 104 -
13
- 105 -
UV Spectrum of Xanthoanthrafil
IR Spectrum of Xanthoanthrafil
- 106 -
[M]+
INT.
100.0000 **********************************************************
22.8081 *************
3.6843 **
0.4452
0.0442
0.0037
0.0003
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
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
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
HPLC RT (min) : 34.61
UV max (nm) : 222.71
-1
- 109 -
13
- 110 -
UV Spectrum of Desmethylsibutramine
RT
IR Spectrum of Desmethylsibutramine
- 111 -
INT.
100.0000
18.5382
33.5970
6.0166
0.5210
0.0284
0.0011
**********************************************************
***********
*******************
***
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
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
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
HPLC RT (min) : 41.22
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 -
4.84(1H, m, H-2)
m, H-7, 9)
13
- 115 -
UV Spectrum of N-nitrosofenfluramine
IR Spectrum of N-nitrosofenfluramine
- 116 -
INT.
100.0000 **********************************************************
14.3596 ********
1.1559 *
0.0678
0.0030
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
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