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CAS No.: | 121679-13-8 |
---|---|
Name: | Naratriptan |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C17H25N3O2S |
Molecular Weight: | 335.47 |
Synonyms: | N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide;Naratriptan(Amerge); |
Density: | 1.227 g/cm3 |
Melting Point: | 170-171° |
Boiling Point: | 541.3 °C at 760 mmHg |
Flash Point: | 281.2 °C |
PSA: | 73.58000 |
LogP: | 3.47840 |
N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
naratriptan
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran for 0.166667h; | 84% |
Stage #1: N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; palladium 10% on activated carbon at 25℃; under 724.026 Torr; Stage #2: With ammonia In water at 10℃; pH=7.5 - 8.5; |
2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide
naratriptan
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran; ammonia at -78℃; for 0.75h; | 80% |
N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide
naratriptan
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 35℃; Product distribution / selectivity; | 73.3% |
With hydrogen; palladium 10% on activated carbon In ethanol; N,N-dimethyl-formamide at 25 - 35℃; under 2206.72 Torr; for 2h; Product distribution / selectivity; | 72.7% |
With 5% Pd(II)/C(eggshell); hydrogen; acetic acid In methanol; water at 25 - 35℃; under 6840.46 - 7600.51 Torr; Reactivity; Reagent/catalyst; Solvent; Time; | 64% |
A
naratriptan
B
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
With lithium triamylborohydride In tetrahydrofuran for 26h; dequaternisation; Heating; | A n/a B 44% |
A
naratriptan
B
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran at 60℃; for 22h; dequaternisation; Title compound not separated from byproducts; |
2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 2: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 3: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 2.2: 25 - 30 °C 2.3: 10 - 15 °C 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 3.2: 10 °C / pH 7.5 - 8.5 View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme |
2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 2: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 3: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 4: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 2: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme | |
With triethylsilane; ethanol; hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃; | |
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 1.2: 25 - 30 °C 1.3: 10 - 15 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme |
N-benzylindoline-5-carboxaldehyde
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C 2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.2: 73 percent / tetrahydrofuran / -78 - 0 °C 3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
1-benzyl-1H-indole-5-carbaldehyde
naratriptan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 73 percent / tetrahydrofuran / -78 - 0 °C 2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme |
IUPAC name: N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Molecular Formula: C17H25N3O2S
Molecular Weight: 335.464300 g/mol
Index of Refraction: 1.605
Surface Tension: 51.3 dyne/cm
Density: 1.227 g/cm3
Flash Point: 281.2 °C
Enthalpy of Vaporization: 81.91 kJ/mol
Boiling Point: 541.3 °C at 760 mmHg
Vapour Pressure: 8.81E-12 mmHg at 25 °C
Product Categories: Indoline & Oxindole
Following is the structure of Naratriptan (CAS NO.121679-13-8):
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
women | TDLo | oral | 3750ug/kg/22W (3.75mg/kg) | BEHAVIORAL: HEADACHE | Lancet. Vol. 353, Pg. 378, 1999. |
Naratriptan , its cas register number is 121679-13-8. It also can be called N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide ; 1H-indole-5-ethanesulfonamide, N-Methyl-3-(1-methyl-4-piperidinyl)- naratriptan .
Naratriptan (trade names include Amerge and Naramig) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. Naratriptan is available in 2.5 mg tablets. It is a selective 5-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-( 1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide.