CasNo： 171596-29-5
Molecular Formula： C22H19N3O4
Appearance： white to off-white cyrstalline solid
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Tadalafil is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.
![(6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione](/upload/2023/8/b2906a5a-02a3-4d95-a53d-ae59186a15d8.png)
(6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione
1,1-dibromomethane
![(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione](/upload/2023/8/74ff697e-4f0a-4268-a09d-b0ec9e4e620f.png)
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
| Conditions | Yield |
|---|---|
|
With
sodium hydroxide;
In
N,N-dimethyl-formamide;
at 60 ℃;
for 6h;
|
95% |
|
With
caesium carbonate;
In
N,N-dimethyl-formamide;
at 80 ℃;
for 8h;
|
93% |
|
With
caesium carbonate;
In
N,N-dimethyl-formamide;
at 80 ℃;
for 8h;
|
93% |
|
With
caesium carbonate;
In
N,N-dimethyl-formamide;
at 80 ℃;
for 8h;
|
93% |
![(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate](/upload/2023/8/298ae24b-bb17-4d41-a272-7d02da781a18.png)
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
| Conditions | Yield |
|---|---|
|
With
hydrogen;
Raney Ni;
In
ISOPROPYLAMIDE;
at 80 ℃;
for 22h;
under 2280.15 Torr;
Product distribution / selectivity;
|
94% |
The CAS number of Tadalafil is 171596-29-5.
More information of Tadalafil 171596-29-5 are:
|
CAS Number |
171596-29-5 |
|
Density |
1.51 g/cm3 |
|
Melting Point |
298-300 °C |
|
Boiling Point |
679.1 °C at 760 mmHg |
|
Flash Point |
364.5 °C |
|
Vapor Pressure |
5.29E-13mmHg at 25°C |
|
Refractive Index |
1.705 |
|
HS CODE |
2934990002 |
|
PSA |
74.87000 |
|
LogP |
2.08710 |
|
Pka |
16.68±0.40(Predicted) |
Synonyms for Tadalafil 171596-29-5:Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-;(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;GF 196960;Tadalafil [USAN];Tildenafil;Calais;(6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;Adcirca;
The chemical formula of Tadalafil is C22H19N3O4 which containing 22 Carbon atoms,19 Hydrogen atoms,3 Nitrogen atoms and 4 Oxygen atoms,and the molecular weight of Tadalafil is 389.411.
Tadalafil (market name “Cialis” or “Adcirca”) is a kind of PDE5 inhibitor used for the treatment of erectile dysfunction, benign prostatic hypertrophy and pulmonary arterial hypertension. The effect of Tadalafil is relaxing the blood vessels muscles and increasing the blood flow into the corpus cavernosum. The mechanism of action of tadalafil is through inhibiting the activity of the cGMP specific phosphodiesterase type 5 (PDE5). PDE5 degrades cGMP in the corpus cavernosum located around the penis. Therefore, tadalafi leads to the increased concentration of cGMP which further causes the smooth muscle relaxation and increased blood flow into the corpus cavernosum. Some clinical studies also implied that tadalafil could improve endothelia function in men with increased cardiovascular risk and lower the urinary tract symptoms secondary to benign prostatic hyperplasia.
InChI:InChI=1/C22H23N3O3/c1-24-8-9-25-17(22(24)26)11-15-14-4-2-3-5-16(14)23-20(15)21(25)13-6-7-18-19(10-13)28-12-27-18/h2-7,10,15,17,20-21,23H,8-9,11-12H2,1H3/t15?,17-,20?,21-/m1/s1
Relevant articles related to Tadalafil:
|
Article |
Source |
|
Preparation method of tadalafil |
- Paragraph 0015; 0041-0042, (2022/03/27) |
|
TADALAFIL SYNTHESIS METHOD |
- Page/Page column 11-22, (2020/11/03) |
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