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Naratriptan hydrochloride
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Name

Naratriptan hydrochloride

 EINECS N/A
CAS No. 143388-64-1 Density N/A
PSA 73.58000 LogP 4.28040
Solubility N/A Melting Point 234-236 °C
Formula C17H26ClN3O2S Boiling Point 541.3 °C at760mmHg
Molecular Weight 371.931 Flash Point 281.2 °C
Transport Information N/A Appearance Beige solid
Safety 26 Risk Codes 36
Molecular Structure Molecular Structure of 143388-64-1 (NARATRIPTAN HYDROCHLORIDE (125 MG)F0C3600.998MG/MG(AI)) Hazard Symbols Xi
Synonyms

1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochloride (9CI);Amerge;GR85548A;N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamidehydrochloride;Naramig;UNII-10X8X4P12Z;

Article Data 8

Naratriptan hydrochloride Synthetic route

121679-13-8

naratriptan

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 30℃; for 1h; pH=1.0 - 1.5; Product distribution / selectivity;93.4%
With hydrogenchloride In methanol; water at 0 - 10℃;84%
With hydrogenchloride In methanol; ethanol at 5 - 25℃; pH=1.0;71.7%
With hydrogenchloride In isopropyl alcohol; acetone at 5 - 10℃; pH=1;
palladium oxide on charcoal

palladium oxide on charcoal

166306-28-1

N-methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulphonamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
In hydrogenchloride; methanesulfonic acid; water88%
With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide
With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide
121679-20-7

N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
Stage #1: N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; platinum(IV) oxide In methanol at 50 - 60℃; under 3677.86 Torr;
Stage #2: With hydrogenchloride In ethanol; isopropyl alcohol for 1h; Product distribution / selectivity; Reflux;		85%
Multi-step reaction with 2 steps
1.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
1.2: 10 °C / pH 7.5 - 8.5
2.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
palladium oxide on charcoal

palladium oxide on charcoal

166306-29-2

(E)-N-Methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethene sulphonamide, hydrochloride

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
In methanol; water; ethyl acetate; N,N-dimethyl-formamide71.2%

C18H24N3O4S(1-)*Na(1+)

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 12h; pH=2; Product distribution / selectivity; Heating / reflux;
palladium oxide on charcoal

palladium oxide on charcoal

166306-28-1

N-methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulphonamide

7440-44-0

pyrographite

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate; N,N-dimethyl-formamide
With hydrogenchloride In ethyl acetate; N,N-dimethyl-formamide
98623-16-6

2-(4-amino-phenyl)ethanesulfonic acid methylamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C
2.1: dichloromethane / 1.5 h / 25 °C
3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
3.2: 25 °C
4.1: potassium hydroxide; ethanol / 15 - 25 °C
5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
5.2: 0.5 h / 25 °C
6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
6.2: 10 - 15 °C / pH 8
7.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
7.2: 10 °C / pH 7.5 - 8.5
8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C
2.1: dichloromethane / 1.5 h / 25 °C
3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
3.2: 25 °C
4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere
4.2: 0.5 h / 25 °C
5.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
5.2: 10 - 15 °C / pH 8
6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
6.2: 10 °C / pH 7.5 - 8.5
7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C
2.1: methanol / 25 - 30 °C
2.2: 4 h / 25 - 30 °C
3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
3.2: 25 °C
4.1: potassium hydroxide; ethanol / 15 - 25 °C
5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
7.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
Multi-step reaction with 9 steps
1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C
2.1: methanol / 25 - 30 °C
2.2: 4 h / 25 - 30 °C
3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
3.2: 25 °C
4.1: potassium hydroxide; ethanol / 15 - 25 °C
5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
7.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C
7.2: 25 - 30 °C
7.3: 10 - 15 °C
8.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr
8.2: 10 °C / pH 7.5 - 8.5
9.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
98623-50-8

N-Methyl-1H-indole-5-ethanesulphonamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
1.2: 10 - 15 °C / pH 8
2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
2.2: 10 °C / pH 7.5 - 8.5
3.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
1268265-90-2

N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
3.2: 0.5 h / 25 °C
4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
4.2: 10 - 15 °C / pH 8
5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
5.2: 10 °C / pH 7.5 - 8.5
6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere
2.2: 0.5 h / 25 °C
3.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
3.2: 10 - 15 °C / pH 8
4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
4.2: 10 °C / pH 7.5 - 8.5
5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
1268265-93-5

2-(4-benzylamino-3-iodophenyl)ethanesulfonic acid methylamide

143388-64-1

naratriptan hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
5.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C
5.2: 25 - 30 °C
5.3: 10 - 15 °C
6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr
6.2: 10 °C / pH 7.5 - 8.5
7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme
Multi-step reaction with 6 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
5.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

Naratriptan hydrochloride Chemical Properties

IUPAC Name: N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamidehydrochloride 
Following is the structure of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1):
                             
Empirical Formula: C17H26ClN3O2S
Molecular Weight: 371.9252
Flash Point: 281.2 °C
Melting point: 234-236 °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
Appearance of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1): Beige Solid
Product Categories of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1): Intermediates & Fine Chemicals; Pharmaceuticals
Canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C.Cl
InChI: InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
InChIKey: AWEZYKMQFAUBTD-UHFFFAOYSA-N

Naratriptan hydrochloride Uses

 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1) is a triptan drug and is used for the treatment of migraine headaches.

Naratriptan hydrochloride Specification

 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) , its cas register number 143388-64-1. It also can be called  Naratriptan hydrochloride ; Amerge ; GR 85548A ; Monohydrochloride ; Naratriptan HCl ; Naratriptan hydrochloride ; UNII-10X8X4P12Z ; and N-Methyl-3-(1-methylpiperidin-4-yl)-1H-indole-5-ethanesulfonamide hydrochloride . Its classification code is Antimigraine.

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