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Name Chloroquine EINECS 200-191-2
CAS No. 54-05-7 Density 1.111 g/cm3/sup>
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 319.92 Flash Point 232.3 °C
Transport Information 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
Molecular Structure Molecular Structure of 54-05-7 (1,4-Pentanediamine,N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-) Hazard Symbols
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);

 

Chemistry

Molecule structure of Chloroquine (CAS NO.54-05-7) :

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

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.

 

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.

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

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.
 

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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