- Chloroquine
- Chloroquine dihydrochloride
- Chloroquine diphosphate
- Chloroquine mustard
- Chloroquine sulfate
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Cas Database |
| Name |
Chloroquine |
EINECS | 200-191-2 |
| CAS No. | 54-05-7 | Density | 1.111 g/cm3/sup> |
| PSA | 28.16000 | LogP | 4.88360 |
| Solubility | Water Solubility: Soluble ,Soluble in chloroform, ether and dilute acids. | Melting Point |
87 C |
| Formula | C18H26 Cl N3 | Boiling Point | 460.6 °C at 760 mmHg |
| Molecular Weight | 319.878 | Flash Point | 232.3 °C |
| Transport Information | N/A | Appearance | White powder |
| Safety | Poison by ingestion, intraperitoneal, intravenous, intramuscular, and subcutaneous routes. Human systemic effects by ingestion: heart rate changes, nausea or vomiting. Human teratogenic effects by an unspecified route include developmental abnormalities of the urogenital system, eyes and ears, other unspecified areas, and postnatal effects. Human reproductive effects by an unspecified route: terminates pregnancy. Human mutation data reported. Questionable carcinogen. An antimalarial agent. When heated to decomposition it emits very toxic fumes of Cl− and NOx. | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Quinoline,7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]- (8CI);(?à)-Chloroquine;7-Chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline;Aralen;Artrichin;Bipiquin;Capquin;Chloraquine;Chlorochin;Chloroquine;NSC187208;RP 3377;Reumachlor;Ronaquine;ST 121;ST 121 (pharmaceutical); |
Article Data | 23 |
Chloroquine Synthetic route
| 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 |
| Conditions | Yield |
|---|---|
| With diethylamine; phenol at 90 - 100℃; under 1140.08 Torr; Temperature; Reagent/catalyst; Pressure; | 90.72% |
| With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction; | 73% |
| 1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h; | |
| at 135 - 140℃; for 24h; | |
| With N-ethyl-N,N-diisopropylamine; sodium sulfite In isopropyl alcohol at 133 - 138℃; for 10h; | 137.5 g |
| Conditions | Yield |
|---|---|
| With potassium phosphate; bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate In 1,4-dioxane at 85℃; for 18h; | 74% |
- 86-99-7
7-chloro-4-hydroxylquinoline
- 140-80-7
5-diethylamino-2-pentylamine
A
- 1915-92-0
4-(4-diethylamino-1-methylbutylamino)-quinoline
B
- 54-05-7
Chloroquine
| Conditions | Yield |
|---|---|
| With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 120℃; for 16h; Inert atmosphere; Schlenk technique; | A 12% B 56% |
| Conditions | Yield |
|---|---|
| In water at 22℃; Equilibrium constant; pH 6; porphyrin concn from 5E-5 to 5E-7; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 57 percent / PBr3 / dimethylformamide / 0.5 h / 20 °C 2: 74 percent / DPEphos; K3PO4 / Pd(OAc)2 / dioxane / 18 h / 85 °C View Scheme | |
| Multi-step reaction with 2 steps 1: POCl3 / 100 °C 2: 1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: HC(OEt)3 / 145 °C 1.2: 50 - 145 °C 1.3: diphenyl ether / 250 °C 2.1: 57 percent / PBr3 / dimethylformamide / 0.5 h / 20 °C 3.1: 74 percent / DPEphos; K3PO4 / Pd(OAc)2 / dioxane / 18 h / 85 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: diphenyl ether / 1 h / Heating 2: POCl3 / 100 °C 3: 1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h View Scheme |
- 16600-22-9
7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester
- 54-05-7
Chloroquine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 2 N aq. NaOH / 1 h / Heating 2: diphenyl ether / 1 h / Heating 3: POCl3 / 100 °C 4: 1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: diphenyl ether / 1 h / Heating 2: 2 N aq. NaOH / 1 h / Heating 3: diphenyl ether / 1 h / Heating 4: POCl3 / 100 °C 5: 1.) 100 deg C, 2 h, 2.) 150-160 deg C, 5 h View Scheme |
Chloroquine Chemical Properties
Molecule structure of Chloroquine (CAS NO.54-05-7) :
.gif)
Molecular Weight: 319.87214 g/mol
Molecular Formula: C18H26ClN3
IUPAC Name: 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
Density: 1.111 g/cm3
Melting Point: 289 °C
Boiling Point: 460.6 °C at 760 mmHg
Flash Point: 232.3 °C
Molar Volume: 287.8 cm3
Water Solubility 10.6 mg/L
Polarizability: 38.62*10-24 cm3
Surface Tension: 43.9 dyne/cm
Enthalpy of Vaporization: 72.13 kJ/mol
Vapour Pressure: 1.15E-08 mmHg at 25 °C
Henry's Law Constant: 1.07E-12 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 1.59E-10 cm3/molecule-sec at 25 °C
XLogP3: 4.6
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 8
Tautomer Count: 3
Exact Mass: 319.181526
MonoIsotopic Mass: 319.181526
Topological Polar Surface Area: 28.2
Heavy Atom Count: 22
Complexity: 309
Canonical SMILES: CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
InChI: InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChIKey: WHTVZRBIWZFKQO-UHFFFAOYSA-N
EINECS: 200-191-2
Chloroquine History
Chloroquine (CAS NO.54-05-7) (CQ), N'-(7-chloroquinolin-4-yl)-N,N-diethyl-pentane-1,4-diamine was discovered 1934 by Andersag and co-workers at the Bayer laboratories who named it "Resochin". It was ignored for a decade because it was considered too toxic for human use. During World War II United States government-sponsored clinical trials for anti-malarial drug development showed unequivocally that CQ has a significant therapeutic value as an anti-malarial drug. It was introduced into clinical practice in 1947 for the prophylactic treatment of malaria.
Chloroquine Uses
Chloroquine (CAS NO.54-05-7) has long been used in the treatment or prevention of malaria. After the malaria parasite Plasmodium falciparum started to develop widespread resistance to chloroquine, new potential utilisations of this cheap and widely available drug have been investigated. Chloroquine (CAS NO.54-05-7) has been extensively used in mass drug administrations which may have contributed to the emergence and spread of resistance. As it mildly suppresses the immune system, it is used in some autoimmune disorders, such as rheumatoid arthritis and lupus erythematosus. Chloroquine (CAS NO.54-05-7) is in clinical trials as an investigational antiretroviral in humans with HIV-1/AIDS and as a potential antiviral agent against chikungunya fever.The radiosensitizing and chemosensitizing properties of chloroquine are beginning to be exploited in anticancer strategies in humans.
Chloroquine Production
Chloroquine (CAS NO.54-05-7) is made from 4,7-dichloro-quinoline ([86-98-6]) and 2-amino-5-diethylamino-pentane condensation derived
Chloroquine Toxicity Data With Reference
| child | LDLo | oral | 37593ug/kg (37.593mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CHANGE IN RATE | Annals of Emergency Medicine. Vol. 19, Pg. 47, 1990. |
| human | LDLo | oral | 20mg/kg (20mg/kg) | SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE BEHAVIORAL: COMA VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. |
| man | LDLo | oral | 86mg/kg (86mg/kg) | CARDIAC: CHANGE IN RATE CARDIAC: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | New England Journal of Medicine. Vol. 318, Pg. 1, 1988. |
| mouse | LD50 | intramuscular | 71mg/kg (71mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983. | |
| mouse | LD50 | intraperitoneal | 66mg/kg (66mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 1219, 1982. | |
| mouse | LD50 | intravenous | 21600ug/kg (21.6mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983. | |
| mouse | LD50 | oral | 311mg/kg (311mg/kg) | BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 753, 1973. |
| mouse | LD50 | subcutaneous | 150mg/kg (150mg/kg) | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. | |
| rabbit | LD50 | intravenous | 8mg/kg (8mg/kg) | Therapie. Vol. 25, Pg. 823, 1970. | |
| rabbit | LD50 | subcutaneous | 75mg/kg (75mg/kg) | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. | |
| rabbit | LDLo | intramuscular | 20mg/kg (20mg/kg) | Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 15, Pg. 630, 1980. | |
| rat | LD50 | intraperitoneal | 102mg/kg (102mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 13, Pg. 401, 1975. |
| rat | LD50 | intravenous | 60mg/kg (60mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966. | |
| rat | LD50 | oral | 330mg/kg (330mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA | Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 271, 1983. |
| rat | LD50 | subcutaneous | 190mg/kg (190mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966. | |
| women | LDLo | oral | 110mg/kg (110mg/kg) | CARDIAC: CHANGE IN RATE CARDIAC: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | New England Journal of Medicine. Vol. 318, Pg. 1, 1988. |
| women | LDLo | oral | 180mg/kg (180mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Medical Journal of Australia. Vol. 160, Pg. 231, 1994. |
| women | TDLo | oral | 24mg/kg/12D-I (24mg/kg) | BRAIN AND COVERINGS: CHANGES IN SURFACE EEG BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Annals of Internal Medicine. Vol. 123, Pg. 76, 1995. |
| women | TDLo | oral | 3600mg/kg/3Y (3600mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE GASTROINTESTINAL: OTHER CHANGES | Tropical and Geographical Medicine. Vol. 32, Pg. 216, 1980. |
Chloroquine Specification
Chloroquine (CAS NO.54-05-7) is also called (7-Chloro-4-(4-diethylamino-1-methylbutylamino)-quinoline ; 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl- ; 1,4-Pentanediamine,n(sup4)-(7-chloro-4-quinolinyl)-n(sup1),n(sup1)-diethy ; 3377 RP ; 3377 RP opalate ; 4-(4-Diethylamino-1-methylbntyla-mino)-7-chloroquinoline ; 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-quinolin . Chloroquine (CAS NO.54-05-7) is stability stable, but light sensitive. It is incompatible with strong oxidizing agents. It is soluble in water, insoluble in alcohol, chloroform and ether .
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