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Name |
Chloroquine diphosphate |
EINECS | 200-055-2 |
CAS No. | 50-63-5 | Density | == |
PSA | 203.30000 | LogP | 3.02640 |
Solubility | H2O: 50 mg/mL, clear | Melting Point |
200 °C (dec.)(lit.) |
Formula | C18H26ClN3.2(H3PO4) | Boiling Point | 460.6 °C at 760 mmHg |
Molecular Weight | 515.868 | Flash Point | 232.3 °C |
Transport Information | UN 1544 | Appearance | White Solid |
Safety | 22-24/25-36 | Risk Codes | 22-40-20/21/22 |
Molecular Structure | Hazard Symbols | Xn | |
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; |
Article Data | 2 |
Conditions | Yield |
---|---|
With phosphoric acid In ethanol | 80.32% |
With phosphoric acid In ethanol at 60 - 65℃; | 66.11% |
Conditions | Yield |
---|---|
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 |
potassium tetrachloroplatinate(II)
chloroquine phosphate
Conditions | Yield |
---|---|
In water at 20℃; for 18h; | 87.8% |
silver tetrafluoroborate
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
water
chloroquine phosphate
Conditions | Yield |
---|---|
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% |
chloroquine phosphate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In water at 40 - 45℃; for 96h; Thermodynamic data; |
Conditions | Yield |
---|---|
In water at 40 - 45℃; for 96h; Thermodynamic data; |
chloroquine phosphate
Conditions | Yield |
---|---|
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 |
chloroquine phosphate
(R)-(-)-chloroquine
Conditions | Yield |
---|---|
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 |
chloroquine phosphate
Conditions | Yield |
---|---|
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 |
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. |