Evodiamine

Base Information

• Chemical Name: Evodiamine
• CAS No.: 518-17-2
• Molecular Formula: C₁₉H₁₇N₃O
• Molecular Weight: 303.363
• Hs Code.: 29339900
• European Community (EC) Number: 637-111-4
• UNII: C01825BVNL
• DSSTox Substance ID: DTXSID10966123
• Nikkaji Number: J9.430G
• Wikipedia: Evodiamine
• Wikidata: Q27894193
• Metabolomics Workbench ID: 136216
• ChEMBL ID: CHEMBL463165
• Mol file: 518-17-2.mol

Synonyms:evodiamine;evodiamine, (S)-isomer;isoevodiamine

Chemical Property of Evodiamine

Chemical Property:

• Appearance/Colour: Fine Powder Color
• Vapor Pressure: 3.15E-13mmHg at 25°C
• Melting Point: 263 - 265oC
• Refractive Index: 1.764
• Boiling Point: 575.1 °C at 760 mmHg
• PKA: 17.27±0.20(Predicted)
• Flash Point: 301.6 °C
• PSA: 39.34000
• Density: 1.39 g/cm³
• LogP: 3.31770
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 5 mg/ml).
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 303.137162174
• Heavy Atom Count: 23
• Complexity: 495

Purity/Quality:

more than 98% ^*data from raw suppliers

Evodiamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• Isomeric SMILES: CN1[C@@H]2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• Description: Evodiamine (518-17-2) is a quinolone alkaloid isolated from Evodia rutaecarpa.1 Evodia Rutaecarpa is a very popular herb used in traditional chinese medicine to treat a variety of ailments. Evodiamine has been shown to elicit a variety of biological effects including induction of apoptosis, inhibiting cancer cell proliferation, promoting cell cycle arrest in G2/M, inhibiting invasion and metastasis of cancer cells, inhibiting angiogenesis, induction of oxidative stress and subsequent apoptosis and inhibition of NF-κB.2 It also functions as an activator of TRPV1 (EC50 = 1.03 μM)3 and acts as an anti-inflammatory agent4.
• Uses: An antiangiogenic and antiinflammatory agonist of TRPV1. A chemical extracted from Evodia plants, and has been shown to reduce fat uptake. A vanilloid receptor agonist that induces apoptosis in leukemia U937 cells

Technology Process of Evodiamine

There total 37 articles about Evodiamine 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: 95.0%

3,4-dihydro-β-carboline (4894-26-2) + N-Methylanthranilic acid (119-68-6) → evodiamine (518-17-2,518-18-3,5956-87-6)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In toluene; at 90 ℃; for 20h;

DOI:10.1016/j.tet.2014.04.066

Reference yield: 92.0%

N-(2-(1H-indol-3-yl)ethyl)-2-(methylamino)benzamide (72502-82-0) + orthoformic acid triethyl ester (122-51-0) → evodiamine (518-17-2,518-18-3,5956-87-6)

Guidance literature:

With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 100 ℃; for 5h; Inert atmosphere;

DOI:10.1039/c9cc00434c

Reference yield: 87.0%

N-[2-(1H-Indol-3-yl)-ethyl]-2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-benzamide (95274-61-6) → evodiamine (518-17-2,518-18-3,5956-87-6)

Guidance literature:

With acetic anhydride; for 1h; Heating;

DOI:10.1021/jo00208a018

upstream raw materials:

N-[2-(1H-Indol-3-yl)-ethyl]-2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-benzamide

orthoformic acid triethyl ester

ethanol

chloroform

Downstream raw materials:

N-(3-chlorobenzoyl)evodiamine

N-(2-chlorobenzoyl)evodiamine

N-(2,4-dichlorobenzyl)evodiamine

N-benzylevodiamine

Refernces

• 1、 -. "Production process of evodiamine and method for recycling solvent in production". . . Retrieved 2021/02/24.
• 2、 Zhang, Tianhua,Lai, Zengwei,Yuan, Suying,Huang, Yi-You,Dong, Guoqiang,Sheng, Chunquan,Ke, Hengming,Luo, Hai-Bin. "Discovery of Evodiamine Derivatives as Highly Selective PDE5 Inhibitors Targeting a Unique Allosteric Pocket". . p. 9828 - 9837. Retrieved 2020/10/19.