Quinacrine

Base Information

• Chemical Name: Quinacrine
• CAS No.: 83-89-6
• Deprecated CAS: 66777-81-9
• Molecular Formula: C₂₃H₃₀ClN₃O
• Molecular Weight: 399.964
• European Community (EC) Number: 200-700-8,201-508-7
• UNII: H0C805XYDE
• DSSTox Substance ID: DTXSID7022627
• Nikkaji Number: J3.877F
• Wikipedia: Mepacrine
• Wikidata: Q417208
• NCI Thesaurus Code: C87656
• Pharos Ligand ID: YNBYCUC8A8TY
• Metabolomics Workbench ID: 145826
• ChEMBL ID: CHEMBL7568
• Mol file: 83-89-6.mol

Synonyms:Acrichine;Atabrine;Atebrin;Dihydrochloride, Quinacrine;Dimesylate, Quinacrine;Hydrochloride, Quinacrine;Mepacrine;Monoacetate, Quinacrine;Monohydrochloride, Quinacrine;Monomesylate, Quinacrine;Quinacrine;Quinacrine Dihydrochloride;Quinacrine Dihydrochloride, Dihydrate;Quinacrine Dihyrochloride, (R)-Isomer;Quinacrine Dihyrochloride, (S)-Isomer;Quinacrine Dimesylate;Quinacrine Hydrochloride;Quinacrine Monoacetate;Quinacrine Monohydrochloride;Quinacrine Monomesylate;Quinacrine, (+-)-Isomer;Quinacrine, (R)-Isomer;Quinacrine, (S)-Isomer

Chemical Property of Quinacrine

Chemical Property:

• Melting Point: 247-250 °C
• Refractive Index: 1.5790 (estimate)
• Boiling Point: 557.1 °C at 760 mmHg
• Flash Point: 290.7 °C
• PSA: 37.39000
• Density: 1.156 g/cm³
• LogP: 6.04540
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 399.2077403
• Heavy Atom Count: 28
• Complexity: 461

Purity/Quality:

97% ^*data from raw suppliers

Mepacrine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antimalarial Agents
• Canonical SMILES: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC
• Recent ClinicalTrials: Treatment of Advanced Renal Cell Carcinoma With Quinacrine
• Uses: anthelmintic, antimalarial, intercalating agent Quinacrine is an acridine that was used extensively from the mid-1920s to the end of World War II. It acts much like chloroquine and is reasonably effective. Because it causes the skin to turn yellow and, in high doses, causes yellow vision, the drug is no longer in use as an antimalarial.

Technology Process of Quinacrine

There total 16 articles about Quinacrine 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: 75.0%

6,9-dichloro-2-methoxyacridine (86-38-4) + 5-diethylamino-2-pentylamine (140-80-7) → quinacrine (83-89-6,66777-81-9,139345-02-1,139345-03-2)

Guidance literature:

With indium(III) chloride; In acetonitrile; at 120 ℃; for 2h; regioselective reaction; Microwave irradiation;

DOI:10.1002/adsc.201400674

Reference yield:

6,9-dichloro-2-methoxyacridine (86-38-4) + 1-aminooctadecane (124-30-1) + phenol (108-95-2,27073-41-2) → quinacrine (83-89-6,66777-81-9,139345-02-1,139345-03-2)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate;

Reference yield:

9-acetylmercapto-6-chloro-2-methoxy-acridine + 5-diethylamino-2-pentylamine (140-80-7) → quinacrine (83-89-6,66777-81-9,139345-02-1,139345-03-2)

Guidance literature:

With zinc diacetate; phenol; at 120 ℃;

upstream raw materials:

6,9-dichloro-2-methoxyacridine

5-diethylamino-2-pentylamine

N-(6-chloro-2-methoxy-acridin-9-yl)-acetamide

(6-chloro-2-methoxy-acridin-9-yl)-methyl-amine

Downstream raw materials:

(+)-N⁴,N⁴-diethyl-N¹-(6-chloro-2-methoxy-acridin-9-yl)-1-methyl-butanediyldiamine

(-)-N⁴,N⁴-diethyl-N¹-(6-chloro-2-methoxy-acridin-9-yl)-1-methyl-butanediyldiamine

Refernces

Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position

10.1016/j.ejmech.2011.04.016

The research focuses on the synthesis and evaluation of functionalized quinacrine analogs for their anti-prion activities and drug-like potential. The study involves the replacement of the basic alkyl side chain of quinacrine with various 4-(substituted phenyl)piperazinyl and 1-benzylpiperidin-4-yl moieties to derive new analogs. The anti-prion activity of these analogs was assessed using different prion-infected murine cell models, with potency, activity across models, and binding affinities to a human prion protein fragment (hPrP121e231) being key parameters. The experiments included cell-based assays to determine the effective concentration reducing PrPSc content (EC50), full anti-prion activity (FAA), and maximal tolerant concentration (TC). Additionally, the binding affinities were measured using surface plasmon resonance (SPR), and permeability across the blood-brain barrier was evaluated using the PAMPA-BBB assay. The analogs were also tested for their susceptibility to P-glycoprotein (Pgp) efflux activity, which can limit brain accumulation. The reactants used in the synthesis of these analogs included amines, acridine derivatives, and other chemical moieties, while analyses involved NMR, MS, HPLC, and combustion analysis to confirm the structures and purities of the synthesized compounds.