Rizatriptan

Base Information

• Chemical Name: Rizatriptan
• CAS No.: 144034-80-0
• Molecular Formula: C15H19N5
• Molecular Weight: 269.349
• Hs Code.: 2933990090
• European Community (EC) Number: 812-626-9
• UNII: 51086HBW8G
• DSSTox Substance ID: DTXSID2023565
• Nikkaji Number: J666.053C
• Wikipedia: Rizatriptan
• Wikidata: Q212171
• NCI Thesaurus Code: C61930
• RXCUI: 88014
• Pharos Ligand ID: DUKZ85G4J6MR
• Metabolomics Workbench ID: 43211
• ChEMBL ID: CHEMBL905
• Mol file: 144034-80-0.mol

Synonyms:L 705,126;L 705126;L-705,126;L-705126;Maxalt;MK 0462;MK 462;MK-0462;MK-462;N,N-dimethyl-2-(5-(1,2,4-triazol-1-ylmethyl)-1H-indole-3-yl)ethylamine;rizatriptan;rizatriptan benzoate

Chemical Property of Rizatriptan

Chemical Property:

• Vapor Pressure: 2.58E-10mmHg at 25°C
• Melting Point: 178-180 °C
• Boiling Point: 504.8 °C at 760 mmHg
• PKA: 16.98±0.30(Predicted)
• Flash Point: 259.1 °C
• PSA: 49.74000
• Density: 1.21 g/cm³
• LogP: 1.91180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: 42 mg/mL
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 269.16404563
• Heavy Atom Count: 20
• Complexity: 309

Purity/Quality:

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

2-(5-((1H-1,2,4-Triazol-1-yl)methyl)-1H-indol-3-yl)-N,N-dimethylethanamine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)CN3C=NC=N3
• Recent ClinicalTrials: Efficacy and Safety of Rizatriptan-Naproxen (10/550 mg) in the Acute Treatment of Migraine
• Recent EU Clinical Trials: A Double-Blind, Placebo Crontrolled, Prallel Group Study to Compare the Efficacy of Rizatriptan 10 mg Iyophilized wafer in the Acute Treatment of Migraine in Patients with Unilateral Trigeminal Autonomic Symptoms.
• Recent NIPH Clinical Trials: MATRIX(Migrainer Assess TRiptane eXamination)
• Uses: Rizatriptan is reported to be a very effective acute migraine drug. It is reported to display high agonist activity at mainly the serotonin 5-HT1B and 5-HT1D receptor subtypes. Ca channel blocker
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: increased risk of CNS excitation with citalopram - avoid; risk of CNS toxicity with MAOIs, moclobemide and linezolid - avoid for 2 weeks after discontinuation of MAOI and moclobemide; possibly increased serotonergic effects with duloxetine 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. Propranolol: rizatriptan levels increased, reduce dose of rizatriptan to 5 mg (max 10 mg in 24 hours).

Technology Process of Rizatriptan

There total 42 articles about Rizatriptan 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: 98.0%

5-((1H-1,2,4-triazol-1-yl)methyl)-3-(2-bromoethyl)-1H-indole (327173-96-6) + dimethyl amine (124-40-3) → rizatriptan (144034-80-0)

Guidance literature:

In tetrahydrofuran; methanol; at 50 ℃; for 48h; Inert atmosphere;

DOI:10.1002/anie.201505713

Reference yield: 93.0%

C20H27N5O2 → rizatriptan (144034-80-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 60 ℃; for 2h;

Reference yield: 86.0%

3-(2-dimethylaminoethyl)-5-[1,2,4]triazol-1-ylmethyl-1H-indol-2-carboxylic acid (658697-16-6) → rizatriptan (144034-80-0)

Guidance literature:

With copper(I) oxide; In quinoline; at 200 ℃; for 0.25 - 0.333333h;

upstream raw materials:

dimethyl amine

2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl mesylate

formaldehyd

2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine

Downstream raw materials:

rizatriptan benzoate

N,N-dimethyl-5-(1H-1,2,4-triazol-1-yl-methyl)-1H-indol-3-ethanamine N-oxide

Refernces

• 1、 Chen, Cheng-Yi,Lieberman, David R.,Larsen, Robert D.,Reamer, Robert A.,Verhoeven, Thomas R.,Reider, Paul J.,Cottrell, Ian F.,Houghton, Peter G.. "Synthesis of the 5-HT1D receptor agonist MK-0462 via a Pd-catalyzed coupling reaction". . p. 6981 - 6984. Retrieved 1994.
• 2、 -. "the advantage grips Qu Tan a method of preparing benzoic acid". . . Retrieved 2016/10/07.
• 3、 Tong, Shuo,Xu, Zhengren,Mamboury, Mathias,Wang, Qian,Zhu, Jieping. "Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine". . p. 11809 - 11812. Retrieved 2015/10/05.