Desethylamodiaquine

Base Information

• Chemical Name: Desethylamodiaquine
• CAS No.: 79352-78-6
• Molecular Formula: C18H18 Cl N3 O
• Molecular Weight: 327.813
• Hs Code.: 28459000
• European Community (EC) Number: 632-821-0
• UNII: BY36SG7NP9
• DSSTox Substance ID: DTXSID20229630
• Nikkaji Number: J407.181F
• Wikidata: Q83109927
• Pharos Ligand ID: 8NAVJ8LMCFQK
• ChEMBL ID: CHEMBL1235
• Mol file: 79352-78-6.mol

Synonyms:4-((7-chloro-4-quinolinyl)amino)-2-((ethylamino)methyl)phenol;desethylamodiaquine;monodesethylamodiaquine;N-desethylamodiaquine

Chemical Property of Desethylamodiaquine

Chemical Property:

• Vapor Pressure: 9.44E-10mmHg at 25°C
• Melting Point: 168-174°C
• Boiling Point: 477.8°C at 760 mmHg
• PKA: 9.42±0.50(Predicted)
• Flash Point: 242.7°C
• PSA: 57.18000
• Density: 1.304g/cm³
• LogP: 4.91080
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 327.1138399
• Heavy Atom Count: 23
• Complexity: 370

Purity/Quality:

98% ^*data from raw suppliers

N-DesethylAmodiaquineDihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNCC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O

Technology Process of Desethylamodiaquine

There total 2 articles about Desethylamodiaquine 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:

amodiaquin (86-42-0) → N-desethylamodiaquine (79352-78-6)

Guidance literature:

With NADPH; recombinant human CYP₂C₈; In phosphate buffer; at 37 ℃; pH=7.4; Further Variations:; Catalysts; Enzyme kinetics;

DOI:10.1007/s00228-003-0636-9

Reference yield:

4,7-dichloroquinoline (86-98-6,1138471-54-1) + 4-Amino-2-ethylaminomethyl-phenol; hydrochloride (86177-06-2) → N-desethylamodiaquine (79352-78-6)

Guidance literature:

In water; at 100 ℃; for 2h; Yield given; pH 4.5-5.0;

DOI:10.1021/jm00144a020

Reference yield: 91.0%

N-desethylamodiaquine (79352-78-6) + 4-methylpiperazine-1-carbonyl chloride monohydrochloride (55112-42-0) → 7-chloro-4-<α-amino>-4-hydroxy-m-toluidino>quinoline (79352-86-6)

Guidance literature:

With triethylamine; In chloroform; 1.) 28 deg C, 1 h, 2.) reflux, 4 h;

DOI:10.1021/jm00144a020

upstream raw materials:

4,7-dichloroquinoline

4-Amino-2-ethylaminomethyl-phenol; hydrochloride

amodiaquin

Downstream raw materials:

7-chloro-4-<α-amino>-4-hydroxy-m-toluidino>quinoline

7-chloro-4-<α--4-hydroxy-m-toluidino>quinoline

Refernces

• 1、 Tsukada, Chiharu,Saito, Takahiro,Maekawa, Masamitsu,Mano, Nariyasu,Oda, Akifumi,Hirasawa, Noriyasu,Hiratsuka, Masahiro. "Functional characterization of 12 allelic variants of CYP2C8 by assessment of paclitaxel 6α-hydroxylation and amodiaquine N-deethylation". . p. 366 - 373. Retrieved 2015/10/19.
• 2、 Kaspera, Ruediger,Naraharisetti, Suresh B.,Evangelista, Eric A.,Marciante, Kristin D.,Psaty, Bruce M.,Totah, Rheem A.. "Drug metabolism by CYP2C8.3 is determined by substrate dependent interactions with cytochrome P450 reductase and cytochrome b5". body text. p. 681 - 691. Retrieved 2012/03/26.