CAS No.54-05-7,CHLOROQUINE Suppliers

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Basic Information

Molecular Structure:
CAS No.:	54-05-7
Name:	CHLOROQUINE
Article Data:	23

Formula:	C18H26 Cl N3
Molecular Weight:	319.878
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);
EINECS:	200-191-2
Density:	1.111 g/cm^3/sup>
Melting Point:	87 C
Boiling Point:	460.6 °C at 760 mmHg
Flash Point:	232.3 °C
Solubility:	Water Solubility: Soluble ,Soluble in chloroform, ether and dilute acids.
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 NO_x.
PSA:	28.16000
LogP:	4.88360

Synthetic route

: 50-63-5
chloroquine phosphate

: 54-05-7
Chloroquine

Conditions

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

: 86-98-6
4,7-dichloroquinoline

: 140-80-7
5-diethylamino-2-pentylamine

: 54-05-7
Chloroquine

Conditions

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

: 98519-65-4
7-chloro-4-bromo-quinoline

: 140-80-7
5-diethylamino-2-pentylamine

: 54-05-7
Chloroquine

Conditions

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

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%

...Expand

: 114422-77-4
uroporphyrin I - chloroquine complex

A: 54-05-7
Chloroquine

B: 607-14-7
uroporphyrin I

Conditions

Conditions	Yield
In water at 22℃; Equilibrium constant; pH 6; porphyrin concn from 5E-5 to 5E-7;

: 86-99-7
7-chloro-4-hydroxylquinoline

: 54-05-7
Chloroquine

Conditions

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

: 108-42-9
3-chloro-aniline

: 54-05-7
Chloroquine

Conditions

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

: 86-47-5
4-hydroxy-7-chloro-3-quinoline-carboxylic acid

: 54-05-7
Chloroquine

Conditions

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

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

: 3412-99-5
2-(3-chlorophenylamino)methylenemalonic acid diethyl ester

: 54-05-7
Chloroquine

Conditions

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

Raw Materials

86-98-6

108-42-9

86-99-7

140-80-7

16600-22-9

50-63-5

98519-65-4

86-47-5

Downstream Products

1476-52-4

Total:77 Page 1 of 3 1 2 3 Next>>

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Chemistry

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

Molecular Weight: 319.87214 g/mol
Molecular Formula: C₁₈H₂₆ClN₃IUPAC 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 .