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50-63-5

Basic Information
CAS No.: 50-63-5
Name: Chloroquine diphosphate
Molecular Structure:
Molecular Structure of 50-63-5 (Chloroquine diphosphate)
Formula: C18H26ClN3.2(H3PO4)
Molecular Weight: 515.92
Synonyms: Nivaquine B;Chloroquin diphosphate;Sanoquin;Arolen;Tanakene;Aralen;Chingamin phosphate;Gontochin phosphate;Khingamin;Chingamin;1,4-Pentanediamine,N4-(7-chloro-4- quinolinyl)-N1,N1-diethyl-,phosphate (1:2);Aralen phosphate;Arechin;Aralen (TN);Chloroquine phosphate;Resochin;Aralen diphosphate;7-Chloro-4-[(4-diethylamino-1-methylbutyl)amino]quinoline diphosphate;Resoquine;Resochin diphosphate;Quinoline, 7-chloro-4-[[4- (diethylamino)-1-methylbutyl]amino]-, phosphate (1:2);Quinoline, 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]-, phosphate;Delagil;Prestwick_867;Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-, diphosphate;Quingamine;
EINECS: 200-055-2
Density: ==
Melting Point: 200 °C (dec.)(lit.)
Boiling Point: 460.6 °C at 760 mmHg
Flash Point: 232.3 °C
Solubility: H2O: 50 mg/mL, clear
Appearance: White Solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-40-20/21/22
Safety: 22-24/25-36
Transport Information: UN 1544
PSA: 203.30000
LogP: 3.02640
Synthetic route
54-05-7

Chloroquine

50-63-5

chloroquine phosphate

Conditions
ConditionsYield
With phosphoric acid In ethanol80.32%
With phosphoric acid In ethanol at 60 - 65℃;66.11%
50-63-5

chloroquine phosphate

54-05-7

Chloroquine

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate at 0℃; for 1h;94%
With sodium hydroxide In water at 0℃; for 0.5h;94%
With sodium hydroxide In water
With sodium hydroxide In dichloromethane; water
10025-99-7

potassium tetrachloroplatinate(II)

50-63-5

chloroquine phosphate

trans-Pt(chloroquine diphosphate)2(Cl)2

Conditions
ConditionsYield
In water at 20℃; for 18h;87.8%
14104-20-2

silver tetrafluoroborate

52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

50-63-5

chloroquine phosphate

[Ru(II)(η6-p-cymene)(η6-chloroquineH2)](BF4)2(H2PO4)2*2H2O

Conditions
ConditionsYield
In water under N2; Ru complex dissolved in water at 55°C, addn. of silver salt and chloroquine diphosphate, mixt. stirred at 55°C for 20 h; filtration throught Celite, filtrate evapd., residue dried under vac. for 20 h; elem. anal.;78%

potassium pentacyanonitrosylchromate(III) monohydrate

50-63-5

chloroquine phosphate

{Cr(NO)(CN)2(chloroquine)(H2O)}

Conditions
ConditionsYield
In acetic acid byproducts: CH3COOK, HCN, H2O; aq. acetic acid; heated at 80°C for 20-30 min.; added with shaking; CO2 passed for 2 h; filtered by suction; washed (diluted acetic acid, water); dried over silica gel in a vac. at room temp.; elem. anal.; TGA;46%
50-63-5

chloroquine phosphate

7585-39-9

β‐cyclodextrin

C42H70O35*C18H26ClN3

Conditions
ConditionsYield
In water at 40 - 45℃; for 96h; Thermodynamic data;
50-63-5

chloroquine phosphate

10016-20-3

alpha cyclodextrin

C36H60O30*C18H26ClN3

Conditions
ConditionsYield
In water at 40 - 45℃; for 96h; Thermodynamic data;
50-63-5

chloroquine phosphate

(+)-Chloroquine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
View Scheme
50-63-5

chloroquine phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
View Scheme
50-63-5

chloroquine phosphate

7-chloro-4-[4-diethylamino-L-methylbutylamino]quinoline diphosphate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
50-63-5

chloroquine phosphate

(R)-(-)-chloroquine diphosphate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; ethyl acetate / 1 h / 0 °C
2: diethylamine / hexane; isopropyl alcohol / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 0.5 h / 0 °C
2: diethylamine / isopropyl alcohol; hexane / 35 °C / Resolution of racemate
3: phosphoric acid / ethanol / 2 h / Reflux
View Scheme
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54-05-7
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Specification

The CAS register number of Chloroquine diphosphate is 50-63-5. It also can be called as N-(7-Chloro-4-quinolinyl)-N,N-dimethyl-1,4-pentanediamine diphosphate salt and the IUPAC name about this chemical is 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine; phosphoric acid. The molecular formula about this chemical is C18H26ClN3.2(H3PO4);C18H32ClN3O8P2 and the molecular weight is 515.87. It belongs to the following product categories, such as Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Miscellaneous Enzyme and so on. The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. This chemical can be used as standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ.

Physical properties about Chloroquine diphosphate are: (1)ACD/LogP: 3.71; (2)ACD/LogD (pH 5.5): -0.05; (3)ACD/LogD (pH 7.4): 0.89; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 3.73; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 19.37Å2; (12)Flash Point: 232.3 °C; (13)Enthalpy of Vaporization: 72.13 kJ/mol; (14)Boiling Point: 460.6 °C at 760 mmHg; (15)Vapour Pressure: 1.15E-08 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed and it is limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing and avoid contact with skin and eyes, you also do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(O)(O)O.O=P(O)(O)O.Clc1cc2nccc(c2cc1)NC(C)CCCN(CC)CC
(2)InChI: InChI=1/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)
(3)InChIKey: QKICWELGRMTQCR-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)
(5)Std. InChIKey: QKICWELGRMTQCR-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 intravenous 64500ug/kg (64.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
child LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: COMA Archiv fuer Toxikologie. Vol. 23, Pg. 204, 1968.
dog LDLo intravenous 8mg/kg (8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) "A Survey of Antimalarial Drugs, 1941-1945," Wiselogle, F.Y., 2 vols., Ann Arbor, MI, J.W. Edwards, 1946Vol. 1, Pg. 390, 1946.
man LDLo oral 179mg/kg (179mg/kg)   Archiv fuer Toxikologie. Vol. 23, Pg. 204, 1968.
man TDLo oral 8571ug/kg (8.571mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES
Human Toxicology. Vol. 8, Pg. 387, 1989.
man TDLo oral 8571ug/kg (8.571mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES
Human Toxicology. Vol. 8, Pg. 387, 1989.
mouse LD50 intraperitoneal 68mg/kg (68mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD "A Survey of Antimalarial Drugs, 1941-1945," Wiselogle, F.Y., 2 vols., Ann Arbor, MI, J.W. Edwards, 1946Vol. 1, Pg. 389, 1946.
mouse LD50 oral 500mg/kg (500mg/kg)   Tropenmedizin und Parasitologie. Vol. 30, Pg. 308, 1979.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Annals of Tropical Medicine and Parasitology. Vol. 74, Pg. 393, 1980.
rat LD50 oral 623mg/kg (623mg/kg)   EHP, Environmental Health Perspectives. Vol. 106(Suppl,
women LDLo oral 298mg/kg (298mg/kg) BEHAVIORAL: COMA

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Forensic Sciences. Vol. 41, Pg. 1077, 1996.
women TDLo oral 138mg/kg (138mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Japanese Journal of Toxicology. Vol. 12, Pg. 159, 1999.
women TDLo oral 167mg/kg (167mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 1067, 1982/1983.
women TDLo oral 600mg/kg/17W- (600mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Postgraduate Medical Journal. Vol. 55, Pg. 569, 1979.

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