QUINACRINE DIHYDROCHLORIDE

ChemicalBook > CAS DataBase List > QUINACRINE DIHYDROCHLORIDE

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℃)
Water Solubility: Water: 33.33 mg/mL (70.48 mM)
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: $146
Updated: 2024/03/01

Sigma-Aldrich

Product number: Q3251
Product name: Quinacrine dihydrochloride
Purity: ≥90%
Packaging: 100g
Price: $473
Updated: 2024/03/01

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: $71.1
Updated: 2024/03/01

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
C_max 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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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:

Everolimus Imatinib MK-2206 2HCl Panobinostat JNJ-26481585 BEZ235 (NVP-BEZ235, Dactolisib) Miboplatin MONODESETHYL QUINACRINE, DIHYDROCHLORIDE QUINACRINE DIHYDROCHLORIDE DIHYDRATE QUINACRINE DIHYDROCHLORIDE DIHYDRATE 97% QUINACRINE DIHYDROCHLORIDE DIHYDRATE

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