QUINACRINE DIHYDROCHLORIDE

Iupac Name：4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride

CAS No.: 69-05-6

Molecular Weight：399.9568

Modify Date.: 2022-11-09 02:09

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: QUINACRINE DIHYDROCHLORIDE
1.2 Synonyms: 1,4-Pentanediamine, N-(6-chloro-2-methoxy-9-acridinyl)-N,N-diethyl-, hydrochloride, hydrate (1:2:2) 1,4-Pentanediamine,N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, hydrochloride (1:2) 69-05-6 {Anhydrous} 6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-BUTYLAMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE 6-CHLORO-9-(4-DIETHYLAMINO-1-METHYL-N-BUTYL)AMINO-2-METHOXYACRIDINE DIHYDROCHLORIDE 866 R.P. Acrichine Acriquine Akrichin ARICHIN HYDROCHLORIDE ATABRINE Atebrin hydrochloride Chemiochin CHEMIOCHIN HYDROCHLORIDE CHINACRIN HYDROCHLORIDE Crinodora DL-QUINACRINE HYDROCHLORIDE EINECS 200-700-8 Erion ERION HYDROCHLORIDE Italchin Malaricida Mecryl Mepacrine dihydrochloride Metochin Metoquine MFCD00012659 N-(6-Chloro-2-methoxy-9-acridinyl)-N,N-diethyl-1,4-pentanediamine dihydrochloride dihydrate Palacrin Palusan Pentilen Quinacrine (dihydrochloride)

1.3 CAS No.: 69-05-6

1.4 CID: 6239

1.5 EINECS(EC#): 200-700-8

1.6 Molecular Formula: C23H32Cl3N3O (isomer)

1.7 Inchi: InChI=1S/C23H30ClN3O.2ClH/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H

1.8 InChkey: UDKVBVICMUEIKS-UHFFFAOYSA-N

1.9 Canonical Smiles: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC.Cl.Cl

1.10 Isomers Smiles: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC.Cl.Cl

2. Properties

2.1 Density: 1.2962 (rough estimate)

2.1 Melting point: ca. 248 - 250 C (decomposes)

2.1 Refractive index: 1.6300 (estimate)

2.1 PSA: 37.39000

2.1 logP: 6.84740

2.1 Appearance: yellow crystals or powder

2.2 Chemical Properties: yellow crystals or powder

2.3 Color/Form: Bright yellow crystals

2.4 PH: 3.0～5.0 (20g/l, 25℃)

2.5 pKa: pKa -6.3(H2O t undefined I not reported but low) (Uncertain)

2.6 Water Solubility: slight

2.7 Spectral Properties: MASS: 3099 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

2.8 Stability: Stable. Incompatible with strong oxidizing agents.

2.9 StorageTemp: +15C to +30C

3. Use and Manufacturing

3.1 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.

3.2 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 DIHYDROCHLORIDESupplier

3.3 Usage: A non-specific PLA2 inhibitor. and acetylcholine receptor antagonist

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: 22-36/37/38

4.1 Safety Statements: Poison by ingestion, subcutaneous, intrauterine, intravenous, and intraperitoneal routes. Human reproductive effects by intrauterine and intracervical routes: changes in fertility and unspecified effects on the uterus, cervix and vagina. Experimental reproductive effects. Mutation data reported. Used as a treatment for parasitic worms. When heated to decomposition it emits very toxic fumes of Cl− and NOx.

4.1 Octanol/Water Partition Coefficient: log Kow = 5.75 at 25 deg C (est)

4.2 Fire Hazard: Flash point data for QUINACRINE DIHYDROCHLORIDE are not available, but QUINACRINE DIHYDROCHLORIDE is probably combustible.

4.3 Hazard Declaration: H302-H315-H319-H335

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: NONH for all modes of transport

4.4 Caution Statement: P261-P305 + P351 + P338

4.4 Formulations/Preparations: Quinacrine is available as hydrochloride, designated quinacrine hydrochloride, USP (mepacrine hydrochloride; Atabrine). It contains approx 80% quinacrine base and is supplied as tablets, containing 100 mg of dihydrochloride. It is available also as methanesulfonate for im admin. /Quinacrine hydrochloride/

4.5 WGK Germany: 3

4.5 RTECS: AR7875000

4.5 Report: EPA Genetic Toxicology Program.

4.6 Safety: Poison by ingestion, subcutaneous, intrauterine, intravenous, and intraperitoneal routes. Human reproductive effects by intrauterine and intracervical routes: changes in fertility and unspecified effects on the uterus, cervix and vagina. Experimental reproductive effects. Mutation data reported. Used as a treatment for parasitic worms. When heated to decomposition it emits very toxic fumes of Cl⁻ and NO_x.
Safety Information of 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine dihydrochloride (CAS NO.69-05-6):
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22: Harmful if swallowed
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 36/37/39
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection

4.7 Specification: 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine dihydrochloride ,its CAS NO. is 69-05-6,the synonyms is Quinacrine dihydrochloride ; 6-Chloro-9-(4-diethylamino-1-methyl-butylamino)-2-methoxyacridine dihydrochloride ; 6-Chloro-9-(4-diethylamino-1-methyl-n-butyl)amino-2-methoxyacridine dihydrochloride ; Metochin hydrochloride ; Mepacrine ; Mepacrine dihydrochloride ; Erion hydrochloride ; Dl-quinacrine hydrochloride ; Chinacrin hydrochloride .

4.8 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intravenous	10mg/kg (10mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
cat	LDLo	oral	200mg/kg (200mg/kg)	BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: OTHER CHANGES	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
cat	LDLo	subcutaneous	100mg/kg (100mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: OTHER CHANGES LIVER: OTHER CHANGES	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
dog	LDLo	intravenous	20mg/kg (20mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) VASCULAR: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 34, Pg. 20, 1945.
gerbil	LDLo	intraperitoneal	70mg/kg (70mg/kg)		Contraception. Vol. 17, Pg. 231, 1978.
guinea pig	LD50	intravenous	14mg/kg (14mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
hamster	LDLo	intraperitoneal	80mg/kg (80mg/kg)		Contraception. Vol. 17, Pg. 231, 1978.
man	TDLo	oral	34mg/kg/8D-I (34mg/kg)	BEHAVIORAL: TOXIC PSYCHOSIS	Southern Medical Journal. Vol. 75, Pg. 359, 1982.
monkey	LDLo	intravenous	15mg/kg (15mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Contraception. Vol. 24, Pg. 269, 1981.
mouse	LD50	intraperitoneal	189mg/kg (189mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 133, 1947.
mouse	LD50	intravenous	38mg/kg (38mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse	LD50	oral	557mg/kg (557mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse	LD50	subcutaneous	212mg/kg (212mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Annals of Biochemistry and Experimental Medicine. Vol. 1, Pg. 317, 1941.
rabbit	LD50	intravenous	9mg/kg (9mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rabbit	LD50	oral	433mg/kg (433mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat	LD50	intrauterine	100mg/kg (100mg/kg)		Indian Journal of Experimental Biology. Vol. 16, Pg. 1074, 1978.
rat	LD50	intravenous	29mg/kg (29mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat	LD50	oral	660mg/kg (660mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
women	TDLo	oral	18mg/kg/3D-I (18mg/kg)	BEHAVIORAL: TOXIC PSYCHOSIS	Southern Medical Journal. Vol. 75, Pg. 359, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Other Information

6.0 Merck: 14,8044

6.1 BRN: 4834013

6.2 Target: Value

6.3 Cell Line:: SGC-7901 cells

6.4 Concentration:: 0, 5, 10, 15, and 20 μM

6.5 Incubation Time:: 24 hours

6.6 Result:: Cell viability was inhibited in a dose-dependent manner, and the mean IC ₅₀ value is 16.18 μM.

6.7 Concentration:: 7.5 and 15 μM

6.8 Result:: The percentage of apoptotic cells, including the early phase and late phase apoptosis, increased to 26.30%, compared with control group of 3.37%.

6.9 Concentration:: 15 μM

6.10 Result:: The relative quantity of cytochrome c protein was upregulated, increased from 0.10 to 0.24.
The relative quantity of p53 protein was dramatically increased, from 0.06 to 0.19.
The Bax/Bcl-2 ratio was dramatically elevated from 1.21 to 2.59.

6.11 Animal Model:: Female SCID mice with acute myeloid leukemia (AML)-PS model

6.12 Dosage:: 100 mg/kg

6.13 Administration:: Administered by oral gavage (po); three times a week for two consecutive weeks

6.14 Result:: In the first AML mouse in vivo study, evaluation of circulating leukemic cells detected in blood samples (in percent of white blood cells (WBC)) at day 30/31 showed 72% human tumor cells in the control mice, whereas in mice treated with Quinacrine, this was only 2.2%.
The MST of control mice was 34 days whereas it was 46 days in Quinacrine-treated mice.

6.15 Chemical Properties: yellow crystals or powder

6.16 Uses: A non-specific PLA2 inhibitor. and acetylcholine receptor antagonist

6.17 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).

6.18 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

7. Computational chemical data

Molecular Weight: 399.9568g/mol
Molecular Formula: C₂₃H₃₂Cl₃N₃O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 471.161096
Monoisotopic Mass: 471.161096
Complexity: 461
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 37.4
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 3
CACTVS Substructure Key Fingerprint: AAADcfB7IAAGAAAAAAAAAAAAAAAAAAAAAAA8YIAAAAAAAACx/AAAHgIQAAAADC7BniYyxvPIFACgAyRiRACCiCAhJyAImKA+bpgMJuLF89uENChk0BHI6AewwPAOBEABAAICAAAIgAIABAQAAAAAAAAAAA==

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