Lasmiditan

Base Information

• Chemical Name: Lasmiditan
• CAS No.: 439239-90-4
• Molecular Formula: C19H18F3N3O2
• Molecular Weight: 377.366
• Hs Code.: 2933990090
• UNII: 760I9WM792
• ChEMBL ID: CHEMBL3039520
• DSSTox Substance ID: DTXSID40469435
• Metabolomics Workbench ID: 152839
• NCI Thesaurus Code: C166996
• Nikkaji Number: J2.994.454G
• Pharos Ligand ID: 9KXL97MJ25JM
• RXCUI: 2256930
• Wikidata: Q6493750
• Wikipedia: Lasmiditan
• Mol file: 439239-90-4.mol

Synonyms:2,4,6-trifluoro-N-(6-((1-methylpiperidin-4-yl)carbonyl)pyridin-2yl)benzamide;COL-144;lasmiditan;lasmiditan hydrochloride;LY573144;Reyvow

Chemical Property of Lasmiditan

Chemical Property:

• Melting Point: 255℃
• Boiling Point: 433.3±45.0 °C(Predicted)
• PKA: 9.91±0.70(Predicted)
• PSA: 62.30000
• Density: 1.351
• LogP: 3.28660
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 377.13511131
• Heavy Atom Count: 27
• Complexity: 530

Purity/Quality:

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

Lasmiditan(COL-144;LY573144) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Migraine Headache Agents
• Canonical SMILES: CN1CCC(CC1)C(=O)C2=NC(=CC=C2)NC(=O)C3=C(C=C(C=C3F)F)F
• Recent ClinicalTrials: A Study of Lasmiditan (LY573144) Treatment in Children Aged 6 to 17 With Migraine
• Recent EU Clinical Trials: Randomized Controlled Trial of Lasmiditan Over Four Migraine Attacks
• Recent NIPH Clinical Trials: Lasmiditan Addition for the Patients with POor Results of Triptan (LAPPORT)
• Description: Lasmiditan (Item No. 28369) is an analytical reference standard categorized as an agonist of the serotonin (5-HT) receptor subtype 5-HT1F. Formulations containing lasmiditan have been used in the treatment of migraine headache. Lasmiditan has low abuse potential. Lasmiditan is regulated as a Schedule V compound in the United States. This product is intended for research and forensic applications.
• Uses: Lasmiditan is used in diagnosing, treating and/or preventing periodontal disease and/or tooth loss.

Technology Process of Lasmiditan

There total 35 articles about Lasmiditan 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: 100.0%

(6-aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone (613678-03-8) + 2,4,6-trifluorobenzoyl chloride (79538-29-7) → Lasmiditan (439239-90-4)

Guidance literature:

In 1,4-dioxane; for 3h; Product distribution / selectivity; Heating / reflux;

Reference yield: 92.3%

2,4,6-trifluorobenzoyl chloride (79538-29-7) + 2-dimethylmethyleneamino-6-(1-methylpiperidin-4-yl)formylpyridine → Lasmiditan (439239-90-4)

Guidance literature:

2-dimethylmethyleneamino-6-(1-methylpiperidin-4-yl)formylpyridine; With hydrogenchloride; In dichloromethane; water; at 20 - 25 ℃; for 3h;

2,4,6-trifluorobenzoyl chloride; With triethylamine; at 20 - 25 ℃; for 4h;

Reference yield: 91.9%

2,4,6-trifluorobenzoyl chloride (79538-29-7) + C16H23N3O → Lasmiditan (439239-90-4)

Guidance literature:

C₁₆H₂₃N₃O; With hydrogenchloride; In chloroform; water; at 30 - 35 ℃; for 2h;

2,4,6-trifluorobenzoyl chloride; With triethylamine; at 30 - 35 ℃; for 3h;

upstream raw materials:

(6-aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

2,4,6-trifluorobenzoyl chloride

2,4,6-trifluoro-N-(6-(1-methylpiperidine-4-carbonyl)pyridine-2-yl)benzamide hydrochloride

2-amino-6-ethanoylpyridine

Downstream raw materials:

2,4,6-trifluoro-N- [6-(1-methylpiperidine-4-carbonyl)-2-pyridyl]benzamide hemisuccinate

2,4,6-trifluoro-N-[6-(1-methylpiperidin-4-ylcarbonyl)-pyridin-2-yl]benzamide hydrochloride

2,4,6-trifluoro-N-[6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl]benzamide hemisuccinate

Refernces

• 1、 -. "Preparation method of lasmiditan". . . Retrieved 2021/07/01.
• 2、 -. "CRYSTALLINE FORM OF RECEPTOR AGONIST, AND MANUFACTURING METHOD AND PHARMACEUTICAL COMPOSITION THEREOF". Paragraph 0252-0253. . Retrieved 2019/08/22.