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Naratriptan Hydrochloride

Product Name
Naratriptan Hydrochloride
CAS No.
143388-64-1
Chemical Name
Naratriptan Hydrochloride
Synonyms
Naramig;Amerge.;GR-85548A;Nariptan Hydrochloride;GR-85548A hydrochloride;Naratriptan Nitrate USP;Naratriptan Hydrochloride;Naratryptan hydrochloride;Naratriptan monohydrochloride;Naratriptan HCl (GR-85548A HCl)
CBNumber
CB4500391
Molecular Formula
C17H25N3O2S.ClH
Formula Weight
371.93
MOL File
143388-64-1.mol
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Naratriptan Hydrochloride Property

Melting point:
234-236°C
storage temp. 
-20°C Freezer
solubility 
H2O: ≥10mg/mL
form 
powder
color 
white to off-white
Water Solubility 
H2O: ≥10mg/mL
InChIKey
AWEZYKMQFAUBTD-UHFFFAOYSA-N
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
HS Code 
2935904000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N1415
Product name
Naratriptan hydrochloride
Purity
≥98% (HPLC)
Packaging
10mg
Price
$88.4
Updated
2025/07/31
Sigma-Aldrich
Product number
1457469
Product name
Naratriptan hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$550
Updated
2025/07/31
TCI Chemical
Product number
N1153
Product name
Naratriptan Hydrochloride
Packaging
50MG
Price
$157
Updated
2025/07/31
TCI Chemical
Product number
N1153
Product name
Naratriptan Hydrochloride
Packaging
250MG
Price
$468
Updated
2025/07/31
Cayman Chemical
Product number
23754
Product name
Naratriptan (hydrochloride)
Purity
≥95%
Packaging
5mg
Price
$34
Updated
2024/03/01
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Naratriptan Hydrochloride Chemical Properties,Usage,Production

Description

Naramig was launched in Germany, Sweden and the UK for use in migraine. It is chemically available via a number of related synthetic routes all having about three steps starting from 5-bromoindole. It is a new serotonin 5-HT1B/1D receptor antagonist with modest affinity for 5-HT1a, and very weak affinity for 5-HT3 receptors. It has little or no affinity for a wide range of non-serotonin receptors including a- and padrenoceptors, dopamine, neurokinin NK1, and opiate receptors. It mediates vasoconstriction in cerebral vasculature (extra cerebral intracranial vessels), reduces neurogenic inflammation, and inhibits responses mediated by the trigeminal nerves. It has a 6- and 3-fold greater affinity for 5-HT1B, and 5-HT1D, receptors, respectively, than sumatriptan which translates to a 2-3 fold increase in potency. The reoccurance of headache was less compared to sumatriptan, zolmitriptan and rizatriptan. Naramig had no clinical effects on blood pressure or heart rate, had a long duration of action with very good tolerability, and has high oral bioavailability.

Chemical Properties

Beige Solid

Originator

Glaxo Wellcome (UK)

Uses

Naratriptan Hydrochloride is a triptan drug that is used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist

Uses

Naratriptan Hydrochloride is a triptan drug and is used for the treatment of migraine headaches

Uses

laxative

brand name

Amerge (GlaxoSmithKline).

Synthesis

121679-20-7

143388-64-1

General procedure for the synthesis of N-methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide hydrochloride from N-methyl-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indole-5-ethane sulfonamide: 1. Compound VIII (50 g, 1501 mmol) was dissolved in a mixed solvent of methanol and acetic acid (0.2L:0.2L) and 2.5 g of platinum oxide catalyst was added. The hydrogenation reaction was carried out at 50 to 60°C for 6 to 8 hours under 5 kg/cm2 hydrogen pressure. After completion of the reaction, the reaction mixture was filtered and distilled to remove the solvent to obtain an oily product. 2. The above oily product was vaporized with isopropanol, followed by addition of 125 ml of ethanolic hydrochloric acid solution and refluxing the reaction mixture for 1 hour. The solid was stirred at 5 to 20°C for 1 hr to precipitate, filtered and washed with cold ethanol to give N-methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide hydrochloride (I). [Yield 50 g, 89.76%]. 3. Compound I (50 g, 1347 mmol) was dissolved in a mixed solvent of 400 ml of ethanol and 100 ml of water and 2 g of activated carbon was added. It was refluxed at 78-80°C for half an hour. After completion of the reaction, it was filtered through hyflow and washed with 100 ml of ethanol. The filtrate was stirred at 5 to 20°C for half an hour to precipitate a solid, filtered, washed with cold ethanol and dried. [Yield 42.5 g, 85%]. Purity: 99.8%.

References

[1] Patent: WO2009/118753, 2009, A2. Location in patent: Page/Page column 28
[2] Patent: WO2011/21000, 2011, A2

Naratriptan Hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Naratriptan Hydrochloride Suppliers

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MedChemexpress LLC
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View Lastest Price from Naratriptan Hydrochloride manufacturers

Career Henan Chemical Co
Product
NARATRIPTAN HYDROCHLORIDE (125 MG)F0C3600.998MG/MG(AI) 143388-64-1
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

143388-64-1, Naratriptan HydrochlorideRelated Search:

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  • NARATRIPTAN HYDROCHLORIDE (125 MG)F0C3600.998MG/MG(AI)
  • Amerge.
  • Naramig
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  • Nariptan Hydrochloride
  • Naratriptan Nitrate USP
  • 1H-Indole-5-ethanesulfonaMide,N-Methyl-3-(1-Methyl-4-piperidinyl)-, hydrochloride (1:1)
  • GR-85548A
  • N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride
  • 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-,hydrochloride
  • NARATRIPTAN HYDROCHLORIDE (125 MG)F0C36099%8MG/MG(AI)
  • Naratriptan Hydrochloride USP/EP/BP
  • Naratryptan hydrochloride
  • Naratriptan HCl (GR-85548A HCl)
  • Naratriptan HydrochlorideQ: What is Naratriptan Hydrochloride Q: What is the CAS Number of Naratriptan Hydrochloride Q: What is the storage condition of Naratriptan Hydrochloride
  • Naratriptan Hydrochloride (1457469)
  • N-Methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide hydrochloride
  • 2-[3-(1-Methyl- piperidin-4-yl) -1H-indol-5-yl]- ethanesulfonic acid methylamide. Hydrochloride, USP
  • Naratriptan hydrochloride, 10 mM in DMSO
  • 143388-64-1
  • C17H25N3O2SHCl
  • C17H25N3O2SClH
  • C17H26ClN3O2S
  • Amerge, Naramig
  • Pharmaceuticals
  • Inhibitors
  • APIs
  • Intermediates & Fine Chemicals