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QUINACRINE DIHYDROCHLORIDE

Product Name
QUINACRINE DIHYDROCHLORIDE
CAS No.
69-05-6
Chemical Name
QUINACRINE DIHYDROCHLORIDE
Synonyms
QUINACRINE;MEPACRINE;ATABRINE;sn390;erion;mecryl;866r.p.;palusan;erionHCl;italchin
CBNumber
CB8320579
Molecular Formula
C23H32Cl3N3O
Formula Weight
472.88
MOL File
69-05-6.mol
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QUINACRINE DIHYDROCHLORIDE Property

Melting point:
249-251℃ (Decomposition)
Density 
1.2962 (rough estimate)
refractive index 
1.6300 (estimate)
storage temp. 
+15C to +30C
solubility 
DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
form 
Yellow solid
pka
pKa -6.3(H2O t undefined I not reported but low) (Uncertain)
color 
Light Yellow to Yellow
PH
3.0~5.0 (20g/l, 25℃)
Merck 
14,8044
BRN 
4834013
Stability:
Stable. Incompatible with strong oxidizing agents.
EPA Substance Registry System
Quinacrine hydrochloride (69-05-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
36/37/39
WGK Germany 
3
RTECS 
AR7875000
Toxicity
LD50 oral in rabbit: 433mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Q3251
Product name
Quinacrine dihydrochloride
Purity
≥90%
Packaging
25g
Price
$142
Updated
2023/01/07
Sigma-Aldrich
Product number
Q3251
Product name
Quinacrine dihydrochloride
Purity
≥90%
Packaging
100g
Price
$461
Updated
2023/01/07
Sigma-Aldrich
Product number
551850
Product name
Quinacrine, Dihydrochloride - CAS 69-05-6 - Calbiochem
Purity
A non-specific phospholipase A2 (PLA2) inhibitor.
Packaging
100mg
Price
$68.9
Updated
2023/01/07
TCI Chemical
Product number
Q0056
Product name
Quinacrine Dihydrochloride Hydrate
Packaging
25g
Price
$106
Updated
2021/12/16
TRC
Product number
Q550610
Product name
Quinacrine dihydrochloride
Packaging
25g
Price
$275
Updated
2021/12/16
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QUINACRINE DIHYDROCHLORIDE Chemical Properties,Usage,Production

Chemical Properties

yellow crystals or powder

Uses

A non-specific PLA2 inhibitor. and acetylcholine receptor antagonist

Uses

Quinacrine is a derivative of acridine that is chemically and clinically very similar to 4-aminoquinolines. It was the primary drug for prevention and therapy of malaria during World War II. Today it is rarely used for treating malaria, although it is used to treat amebiasis. Synonyms of this drug are mepacrine, atabrine, acrisuxin, and others. In treating resistant forms of malaria, tetracycline is also used in combination with pyrimethamine, sulfonamides, sulfones, and dapsone, which is widely used for treating leprosy (as a rule, in combination with pyrimethamine).

Uses

Quinacrine dihydrochloride has been used:

  • in its uptake and accumulation studies in mouse lung slices using fluorescence microscope
  • in the staining of ATP vesicles in mesenchymal stem cells (MSCs)
  • in uptake-release assay for characterization of dense granule functionality of platelets

Indications

Quinacrine is no longer used extensively as an antimalarial drug and has been largely replaced by the 4- aminoquinolines.

brand name

Dormison (Schering).

Antimicrobial activity

Mepacrine is active against the asexual erythrocytic stage of all four Plasmodium spp. that infect humans and the gametocytes of P. vivax and P. malariae. The enantiomers have equal antimalarial activity. It exhibits broad activity in experimental models against T. cruzi, Leishmania spp., E. histolytica, Trichomonas vaginalis, G. lamblia and Blastocystis hominis. It is also active against tapeworms.

Acquired resistance

The structural resemblance to chloroquine suggests the likelihood of cross-resistance with that drug, but evidence for this is equivocal.

General Description

Bright yellowish needles or bright yellow powder. Odorless. pH of a 1% aqueous solution is about 4.5.. Used as an anti-malarial drug. Moderately toxic.

Air & Water Reactions

Water soluble.

Reactivity Profile

QUINACRINE DIHYDROCHLORIDE is an acidic salt of an amine. React as a weak acid to neutralize bases.

Fire Hazard

Flash point data for QUINACRINE DIHYDROCHLORIDE are not available, but QUINACRINE DIHYDROCHLORIDE is probably combustible.

Pharmaceutical Applications

A synthetic acridine derivative, formulated as the hydrochloride for oral use.

Biochem/physiol Actions

Target IC50: 4.4 μM in suppressing glibenclamide-sensitive K+-currents

Pharmacokinetics

Oral absorption: Good
Cmax 100 mg oral: 50 μg/L after 1–3 h
Plasma half-life: 5 days
Plasma protein binding: 85%
There is extensive tissue binding and a six-fold concentration into leukocytes from plasma. About 10% of the daily dose is excreted in the urine. It is widely distributed throughout the body.

Clinical Use

Giardiasis
Prophylaxis of malaria
Tapeworm infections

Side effects

Dizziness, headache and gastric problems are common. Toxic psychoses, bone marrow depression, yellow skin and exfoliative dermatitis are described. Poor toleration is noted, especially in children. It should not be used in combination with 8-aminoquinolines.

Synthesis

Quinacrine, 6-chloro-9-(4-diethylamino-1-methylbutylamino)-2-methoxyacridine (37.1.4.3), is synthesized from 6,9-dichloro-2-methoxyacridine (37.1.4.2) and aforementioned 4-diethylamino-1-methylbutylamine (37.1.1.2). The 6,9-dichloro- 2-methoxyacridine (37.1.4.2) necessary for the synthesis is made in two stages. The initial reaction of 2,4-dichlorobenzoic acid and p-anizidine in the presence of copper dust and potassium carbonate gives 2-(4-methoxyanilino)-4-chlorobenzoic acid (37.1.4.1), which upon reaction with phosphorus oxychloride turns into the necessary 6,9-dichloro- 2-methoxyacridine (37.1.4.2).

Purification Methods

It crystallises from H2O (solubility is 2.8% at room temperature) as yellow crystals. It is slightly soluble in MeOH and EtOH. The free base crystallises from Me2CO or pet ether with m 86-88o, or aqueous EtOH with 85-87.5o. The bismethiodide has m 224o (from MeOH/EtOAc/Et3N), and the picrate has m 207-208o(dec) when crystallised from Me2CO/EtOH. It is an antimalarial, antiprotozoal and intercalates DNA. [Wolfe Antibiot 3 (Springer-Verlag) 203 1975, Beilstein 22 III/IV 6247, 22/12 V 235.]

QUINACRINE DIHYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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QUINACRINE DIHYDROCHLORIDE Suppliers

J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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18621169121
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86-21-61259102
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market03@meryer.com
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TCI (Shanghai) Development Co., Ltd.
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021-67121386
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021-67121385
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Sales-CN@TCIchemicals.com
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China
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BeiJing Hwrk Chemicals Limted
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0757-86329057 18516978288
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Energy Chemical
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sale@xiyashiji.com
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BEST-REAGENT
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Aemon Chemical
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0086-755-86198205
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China
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Maya High Purity Chemicals
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+86 (573) 82222445 (0)18006601000 QQ:452520369
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+86 (573) 82222643
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Spectrum Chemical Manufacturing Corp.
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021-67601398-809 15221380277
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021-57711696
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View Lastest Price from QUINACRINE DIHYDROCHLORIDE manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Quinacrine Dihydrochloride Hydrate 69-05-6
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
500 tons
Release date
2020-04-27
Career Henan Chemical Co
Product
Quinacrine (dihydrochloride) 69-05-6
Price
US $1.00/kg
Min. Order
1kg
Purity
95%-99%
Supply Ability
1000kg
Release date
2018-12-25

69-05-6, QUINACRINE DIHYDROCHLORIDERelated Search:


  • 6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-BUTYLAMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE
  • 6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-N-BUTYL)AMINO-2-METHOXYACRIDINE DIHYDROCHLORIDE
  • ERION HYDROCHLORIDE
  • DL-QUINACRINE HYDROCHLORIDE
  • CHINACRIN HYDROCHLORIDE
  • CHEMIOCHIN HYDROCHLORIDE
  • ARICHIN HYDROCHLORIDE
  • ATABRINE
  • ATABRINE HYDROCHLORIDE
  • ATEBRIN DIHYDROCHLORIDE
  • ATEBRIN HYDROCHLORIDE
  • QUINACRINE
  • QUINACRINE DIHYDROCHLORIDE
  • METOCHIN HYDROCHLORIDE
  • sn390
  • Quinacrine, DiHCl
  • Quinacine dihydrochloride
  • QUINACRINE DIHYDROCHLORIDE, FOR FLUORESC ENCE
  • QUINACRINE DIHYDROCHLORIDE MAO INHIBITOR
  • DL-QUINACRINE HYDROCHLORIDE USP
  • QUINACRINE DIHYDROCHLORIDE CRYSTALLINE
  • MEPACRINE HYDROCHLORIDE USP
  • erionHCl
  • MEPACRINE
  • MEPACRINE DIHYDROCHLORIDE
  • quinacrine2HCl
  • Quinacrine Dihydrochloride Hydrate
  • Atebrin dihydrochloride, Mepacrine dihydrochloride, 6-Chloro-9-(4-diethylamino-1-methylbutylamino)-2-methoxyacridine dihydrochloride
  • 1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, dihydrochloride
  • 2-Chloro-5-[[.omega.-(diethylamino)-.alpha.-methylbutyl)amino]-7-methoxyacridine dihydrochloride
  • 2-Methoxy-6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]acridine dihydrochloride
  • 3-Chloro-7-methoxy-9-[1-methyl-4-(diethylamino)butylamino]acridine dihydrochloride
  • 3-Chloro-9-[4'-(diethylamino)-1'-methylbutyl]amino]-7-methoxyacridine dihydrochloride
  • Acridine, 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxy-, dihydrochloride
  • Quinacrine Dihydrochloride&nbsp
  • 1,4-Pentanediamine,N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, hydrochloride (1:2)
  • NSC 14229
  • Atebrine hydrochloride
  • 2-chloro-5-(omega-diethylamino-alpha-methylbutylamino)-7-methoxyacridinedihy
  • 2-methoxy-6-chloro-9-(4-diethylamino-1-methylbutylamino)acridinedihydrochlor
  • 3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridinedihydrochlor
  • 3-chloro-9-(4’-diethylamino-1’-methylbutylamino)-7-methoxyacridinedihydrochl
  • 866r.p.
  • atabrinedihydrochloride
  • chemiochin
  • chinacrin
  • crinodora
  • erion
  • italchin
  • malaricida
  • mecryl
  • methoquine
  • metochin
  • metoquin
  • metoquine
  • palacrin
  • palusan
  • pentilen