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:

99%, ^*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

• 1、 Csuk, Rene,Barthel, Alexander,Raschke, Christian,Kluge, Ralph,Stroehl, Dieter,Trieschmann, Lothar,Boehm, Gerald. "Synthesis of monomeric and dimeric acridine compounds as potential therapeutics in Alzheimer and prion diseases". experimental part. p. 699 - 709. Retrieved 2010/06/19.
• 2、 Bonse, Susanne,Santelli-Rouvier, Christiane,Barbe, Jacques,Krauth-Siegel, R. Luise. "Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: Kinetic studies and structure-activity relationships". . p. 5448 - 5454. Retrieved 2007/10/03.