Desethylchloroquine

Base Information

• Chemical Name: Desethylchloroquine
• CAS No.: 1476-52-4
• Molecular Formula: C₁₆H₂₂ClN₃
• Molecular Weight: 291.824
• Hs Code.: 2933497050
• NSC Number: 13254
• UNII: ZC9Z9XX2PD
• DSSTox Substance ID: DTXSID201033929
• Nikkaji Number: J413.950J
• Wikidata: Q90546665
• Metabolomics Workbench ID: 49590
• ChEMBL ID: CHEMBL1236
• Mol file: 1476-52-4.mol

Synonyms:7-chloro-4-((4-(ethylamino)-1-methylbutyl)amino)-quinoline;deethylchloroquine;desethylchloroquine;desethylchloroquine dihydrochloride;desethylchloroquine hydrochloride;desethylchloroquine oxalate (1:2);monodesethylchloroquine;monoethyl chloroquine;N-deethylchloroquine;N4-(7-chloro-4-quinolinyl)-n1-ethyl-1,4-pentanediamine

Chemical Property of Desethylchloroquine

Chemical Property:

• Vapor Pressure: 2.38E-08mmHg at 25°C
• Melting Point: 94-97?C
• Boiling Point: 451.7°Cat760mmHg
• PKA: 10.62±0.19(Predicted)
• Flash Point: 227°C
• PSA: 36.95000
• Density: 1.138g/cm³
• LogP: 4.54220
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Met
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 291.1502254
• Heavy Atom Count: 20
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

Desethyl Chloroquine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNCCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
• Uses: Desethyl Chloroquine is the major product of the stereoselective human metabolism of Chloroquine, used for the therapy and prevention of malaria. It is a COVID19-related research product. The major product of the stereoselective human metabolism of Chloroquine, used for the therapy and prevention of malaria

Technology Process of Desethylchloroquine

There total 8 articles about Desethylchloroquine 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: 90.0%

7-chloro-4-(4'-N-ethyl-N-2,2,2-trichloroethoxycarbonylamino-1'-methylbutylamino)quinoline → desethylchloroquine (1476-52-4)

Guidance literature:

With acetic acid; zinc; for 4.5h; Ambient temperature;

DOI:10.1055/s-1995-3886

Reference yield:

ethylamine (75-04-7,85404-22-4) → desethylchloroquine (1476-52-4)

Guidance literature:

With diethyl ether; at 140 ℃;

Reference yield:

Chloroquine (54-05-7) → N,N-Dideethylchloroquine (4298-14-0) + desethylchloroquine (1476-52-4)

Guidance literature:

With NADPH; In aq. buffer; at 30 ℃; pH=7.3; Enzymatic reaction;

DOI:10.1021/acs.joc.1c01407

upstream raw materials:

Chloroquine

4,7-dichloroquinoline

ethylamine

Downstream raw materials:

rac-N-acetyldesethylchloroquine

(R)-(-)-N-acetyldesethylchloroquine

(S)-(+)-N-acetyldesethylchloroquine

2-(3-{[4-(7-Chloro-quinolin-4-ylamino)-pentyl]-ethyl-amino}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester