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171596-29-5

Basic Information
CAS No.: 171596-29-5
Name: Tadalafil
Article Data: 48
Molecular Structure:
Molecular Structure of 171596-29-5 (Tadalafil)
Formula: C22H19N3O4
Molecular Weight: 389.411
Synonyms: 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;
EINECS: 200-835-2
Density: 1.51 g/cm3
Melting Point: 298-300 °C
Boiling Point: 679.1 °C at 760 mmHg
Flash Point: 364.5 °C
Appearance: white to off-white cyrstalline solid
Hazard Symbols: F,Xn
Risk Codes: 11-20/21/22-36
Safety: 16-36/37
PSA: 74.87000
LogP: 2.08710
Synthetic route

C22H19ClN2O5*(x)ClH

74-89-5

methylamine

171596-29-5

(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
ConditionsYield
In dichloromethane at 0 - 5℃; for 3h; Temperature; Solvent;99.3%
74-89-5

methylamine

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

171596-29-5

(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
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃;95%
In N,N-dimethyl-formamide at 20℃; for 10h;95%
In methanol for 3h; Reflux; Large scale;95.3%

(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

74-95-3

1,2-dibromomethane

171596-29-5

(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
ConditionsYield
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%
1224724-00-8

(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

171596-29-5

(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
ConditionsYield
With hydrogen; Raney Ni In ISOPROPYLAMIDE at 80℃; under 2280.15 Torr; for 22h; Product distribution / selectivity;94%
171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

171596-29-5

(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
ConditionsYield
With methylamine In dichloromethane for 2h;93.5%
With methylamine In water for 20h; Ionic liquid;355 mg
52605-49-9

sarcosine ethyl ester hydrochloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

171596-29-5

(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
ConditionsYield
With potassium carbonate In ethylene glycol at 110℃; Solvent; Reagent/catalyst; Temperature; Green chemistry;92.7%
749864-18-4

1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

171596-29-5

(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
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 20℃; for 1h;92%

C22H20N4O3

171596-29-5

(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
ConditionsYield
Stage #1: C22H20N4O3 With sulfuric acid In isopropyl alcohol for 12h; Reflux;
Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h; Temperature;
91.2%

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

74-89-5

methylamine

171596-29-5

(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
ConditionsYield
In tetrahydrofuran; water at 50℃; Solvent; Temperature;91%
107-97-1

sarcosine

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

171596-29-5

(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
ConditionsYield
Stage #1: sarcosine; (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride With triethylamine In tetrahydrofuran at 30℃; for 0.333333h;
Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Solvent; Reagent/catalyst; Temperature; Further stages;
90.54%
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    Tadalafil Citrate Alias: Tadalafei;Cialis CAS No: 171596-29-5 MF: C22H19N3O4 MW: 389.41 Purity: 99.5% Appearance: white powder, odorless, tasteless, insoluble in water and alcohol. Appearance:white Storage:cool and dryer Package:durm Ap

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Chemistry

The Molecular Structure of Tadalafil (CAS NO.171596-29-5):

Empirical Formula: C22H19N3O4
Molecular Weight: 389.404 
Appearance:  Off-White Cyrstalline Solid
Nominal Mass: 389 Da
Average Mass: 389.404 Da
Monoisotopic Mass: 389.137556 Da 
Index of Refraction: 1.758
Molar Refractivity: 105.27 cm3
Molar Volume: 256.2 cm3
Surface Tension: 81.5 dyne/cm
Density: 1.51 g/cm3
Flash Point: 364.5 °C
Enthalpy of Vaporization: 99.67 kJ/mol
Boiling Point: 679.1 °C at 760 mmHg
Vapour Pressure: 2.67E-18 mmHg at 25°C 
Melting Point: 298-300°C
Product Categories: Active Pharmaceutical Ingredients;Cnbio;Erectile Dysfunction;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's
InChI: InChI=1/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
Smiles: C1N(C([C@H]2Cc3c([C@H](N2C1=O)c1ccc2c(c1)OCO2)[nH]c1ccccc31)=O)C

History

 Tadalafil (CAS NO.171596-29-5) was discovered by Glaxo Wellcome (now GlaxoSmithKline) under a partnership between Glaxo and ICOS to develop new drugs that began in August 1991. In December 2003, after sildenafil (Viagra) and vardenafil (Levitra),the Food and Drug Administration approved tadalafil (as Cialis) for sale in the United States as the third ED prescription drug pill. Then in May 2009,Tadalafil  was approved  in the United States for the treatment of pulmonary arterial hypertension and is currently under regulatory review in other regions for this condition.

Uses

 Tadalafil (CAS NO.171596-29-5) can be used for the treatment of erectile dysfunction under the name Cialis. Recently Tadalafil  (CAS NO.171596-29-5) has been approved for the treatment of pulmonary arterial hypertension and other onditions.

Safety Profile

The most common side effects of tadalafil are: are headache, indigestion, flushing,back pain, muscle aches and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen), these usually go away after a few hours. Back pain and muscle aches maybe occur 12 to 24 hours after taking the drug,and the symptom usually disappears after 48 hours.

Specification

 Tadalafil  (CAS NO.171596-29-5) is the main raw materials of Cialis,compare with Sildenafil,Tadalafil have less side effects, after taking two days,30% of people have muscles ache feeling (mainly waist and legs). It is also called as Tadalafil [USAN] ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (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 ; Cialis ; Tadalafil ; Tadalafil Lilly ;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,12aR)- ; 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)- .