Naratriptan

Base Information

• Chemical Name: Naratriptan
• CAS No.: 121679-13-8
• Molecular Formula: C17H25N3O2S
• Molecular Weight: 335.47
• Hs Code.: 2935009090
• European Community (EC) Number: 601-800-8
• UNII: QX3KXL1ZA2
• DSSTox Substance ID: DTXSID7023354
• Nikkaji Number: J550.688C
• Wikipedia: Naratriptan
• Wikidata: Q421315
• NCI Thesaurus Code: C61857
• RXCUI: 141366
• Pharos Ligand ID: B9RF9VJ1M3NK
• Metabolomics Workbench ID: 43210
• ChEMBL ID: CHEMBL1278
• Mol file: 121679-13-8.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

Chemical Property:

• Vapor Pressure: 8.81E-12mmHg at 25°C
• Melting Point: 170-171°
• Refractive Index: 1.605
• Boiling Point: 541.3 °C at 760 mmHg
• Flash Point: 281.2 °C
• PSA: 73.58000
• Density: 1.227 g/cm³
• LogP: 3.47840
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 335.16674822
• Heavy Atom Count: 23
• Complexity: 483

Purity/Quality:

98%,99%, ^*data from raw suppliers

Naratriptan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
• Recent ClinicalTrials: Efficacy and Safety of a Fixed-dose Combination of Naratriptan and Naproxen in Acute Treatment of Migraine
• Recent NIPH Clinical Trials: MATRIX(Migrainer Assess TRiptane eXamination)
• Uses: Antimigraine. Naratriptan is a triptan drug that is used for the treatment of migraine headaches.
• Therapeutic Function: Serotonin antagonist, Migraine therapy
• Clinical Use: 5HT1 receptor agonist: Acute treatment of migraine
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: increased CNS toxicity with citalopram - avoid; possibly increased serotonergic effects with duloxetine, SSRIs and venlafaxine; increased serotonergic effects with St John’s wort - avoid. Dapoxetine: possible increased risk of serotonergic effects - avoid for 2 weeks after stopping 5HT1 agonists. Ergot alkaloids: increased risk of vasospasm - avoid.

Technology Process of Naratriptan

There total 41 articles about Naratriptan 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: 84.0%

N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide (894351-87-2) → naratriptan (121679-13-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; for 0.166667h;

DOI:10.3987/COM-06-10670

Reference yield: 80.0%

2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide (639008-15-4) → naratriptan (121679-13-8)

Guidance literature:

With sodium; In tetrahydrofuran; ammonia; at -78 ℃; for 0.75h;

DOI:10.3987/COM-03-9838

Reference yield: 76.0%

N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide (121679-20-7) → naratriptan (121679-13-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 6h; under 6840.46 - 7600.51 Torr;

DOI:10.1039/d1cc04225d

upstream raw materials:

2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide

N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide

2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide

2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide

Downstream raw materials:

naratriptan hydrochloride

2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide

Refernces

• 1、 Kumar, U. Sampath,Sankar, V. Ravi,Kumar, S. Bharani,Prabhu, M. Pandi,Rao, S. Mahender. "An investigation into the formation of impurity B during the optimization of naratriptan hydrochloride". . p. 468 - 470. Retrieved 2009.
• 2、 Chen, Miaomiao,Ding, Xin,Gao, Yongyue,He, Xingxing,Kang, Jin,Lu, Aidang,Wang, Qingmin,Wang, Ziwen,Zhang, Mingjun. "The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan". supporting information. p. 9140 - 9143. Retrieved 2021/09/14.
• 3、 -. "A PROCESS FOR THE SYNTHESIS OF NARATRIPTAN". Page/Page column 42. . Retrieved 2011/04/13.