Naratriptan hydrochloride

Base Information

• Chemical Name: Naratriptan hydrochloride
• CAS No.: 143388-64-1
• Molecular Formula: C17H26ClN3O2S
• Molecular Weight: 371.931
• Hs Code.: 2935904000
• European Community (EC) Number: 662-728-0
• UNII: 10X8X4P12Z
• DSSTox Substance ID: DTXSID6049064
• Wikidata: Q27107505
• NCI Thesaurus Code: C47633
• RXCUI: 236690
• Pharos Ligand ID: B9RF9VJ1M3NK
• ChEMBL ID: CHEMBL1200601
• Mol file: 143388-64-1.mol

Synonyms:1H-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochloride;Amerge;Colatan;GR 85548A;N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide;N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide monohydrochloride;Naramig;naratriptan;naratriptan hydrochloride

Chemical Property of Naratriptan hydrochloride

Chemical Property:

• Appearance/Colour: Beige solid
• Vapor Pressure: 8.81E-12mmHg at 25°C
• Melting Point: 234-236 °C
• Boiling Point: 541.3 °C at760mmHg
• Flash Point: 281.2 °C
• PSA: 73.58000
• LogP: 4.28040
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: ≥10mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 371.1434259
• Heavy Atom Count: 24
• Complexity: 483

Purity/Quality:

Naratriptan hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C.Cl
• Recent ClinicalTrials: Bioequivalency Study of Naratriptan Hydrochloride 2.5 mg Under Fasted Conditions
• 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.
• Uses: Naratriptan Hydrochloride is a triptan drug and is used for the treatment of migraine headaches Naratriptan Hydrochloride is a triptan drug that is used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist laxative

Technology Process of Naratriptan hydrochloride

There total 19 articles about Naratriptan hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.4%

naratriptan (121679-13-8) → naratriptan hydrochloride (143388-64-1)

Guidance literature:

With hydrogenchloride; In ethanol; at 0 - 30 ℃; for 1h; pH=1.0 - 1.5; Product distribution / selectivity;

Reference yield: 88.0%

palladium oxide on charcoal + N-methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulphonamide (166306-28-1) → naratriptan hydrochloride (143388-64-1)

Guidance literature:

In hydrogenchloride; methanesulfonic acid; water;

Reference yield: 85.0%

N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide (121679-20-7) → naratriptan hydrochloride (143388-64-1)

Guidance literature:

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;

With hydrogenchloride; In ethanol; isopropyl alcohol; for 1h; Product distribution / selectivity; Reflux;

upstream raw materials:

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

pyrographite

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

naratriptan

Downstream raw materials:

naratriptan

Refernces

• 1、 -. "PROCESS FOR PREPARING INDOLE DERIVATIVES". Page/Page column 20. . Retrieved 2010/04/03.
• 2、 -. "PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE". Page/Page column 28. . Retrieved 2009/10/22.