CAS No.130-95-0,Quinine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	130-95-0
Name:	Quinine
Article Data:	83
Cas Database

Formula:	C₂₀H₂₄N₂O₂
Molecular Weight:	324.423
Synonyms:	Quinine(8CI);(-)-Quinine;(8S,9R)-Quinine;(R)-(-)-Quinine;6'-Methoxycinchonidine;Chinine;NSC 192949;(8α,9R)-6'-methoxycinchonan-9-ol;(3α,8α,9R)-6'-methoxycinchonan-9-ol;(R)-(6-Methoxy-4-chinolinyl)[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol;
EINECS:	205-003-2
Density:	1.21 g/cm³
Melting Point:	176-177 °C
Boiling Point:	495.9 °C at 760 mmHg
Flash Point:	253.7 °C
Solubility:	slightly soluble in water
Appearance:	white to light yellow crystal powder
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38
Safety:	36-37/39
PSA:	45.59000
LogP:	3.11110

Synthetic route

: 865853-18-5
(3R,4S)-4-[(2R,3R)-3-(6-Methoxy-quinolin-4-yl)-oxiranylmethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 130-95-0
Quinine

Conditions

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide; tert-butyl alcohol at 110℃; for 12h;	98%

: 1207974-85-3
2-(trimethylsilyl)ethyl 6-methoxy-4-((2S,3S)-3-(((3R,4S)-1-((2-(trimethylsilyl)ethoxy)carbonyl)-3-vinylpiperidin-4-yl)methyl)oxiran-2-yl)quinoline-1(2H)-carboxylate

: 130-95-0
Quinine

Conditions

Conditions	Yield
Stage #1: 2-(trimethylsilyl)ethyl 6-methoxy-4-((2S,3S)-3-(((3R,4S)-1-((2-(trimethylsilyl)ethoxy)carbonyl)-3-vinylpiperidin-4-yl)methyl)oxiran-2-yl)quinoline-1(2H)-carboxylate With cesium fluoride In N,N-dimethyl-formamide at 180℃; for 0.25h; Microwave irradiation; Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; for 24h;	73%

: C21H26N4O4S

: 130-95-0
Quinine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; methanol at 0 - 20℃; for 0.166667h; Schlenk technique; Inert atmosphere;	53%

: 5263-87-6
6-methoxy quinoline

: 130-95-0
Quinine

Conditions

Conditions	Yield
In s-BuOH	140 mg (26%)

6'-methoxy-cinchonan-9-one: 6'-methoxy-cinchonan-9-one

A: 56-54-2
quinidine

B: 130-95-0
Quinine

Conditions

Conditions	Yield
With sodium isopropylate; toluene
With 2-pentanol; sodium

: 56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2
9-epiquinine

: 130-95-0
Quinine

Conditions

Conditions	Yield
With acetic acid at 70 - 80℃; for 168h;

: C26H36N2O3Si

: 130-95-0
Quinine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 17 h / 20 °C 2.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.2: 6 h / 0 - 20 °C / Inert atmosphere 2.3: 0.5 h / 20 °C / Inert atmosphere 3.1: cesium fluoride / N,N-dimethyl-formamide; tert-butyl alcohol / 12 h / 110 °C View Scheme

: 865853-24-3
(3R,4S)-4-[(2R,3R)-2,3-Dihydroxy-3-(6-methoxy-quinolin-4-yl)-propyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 130-95-0
Quinine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere 1.2: 6 h / 0 - 20 °C / Inert atmosphere 1.3: 0.5 h / 20 °C / Inert atmosphere 2.1: cesium fluoride / N,N-dimethyl-formamide; tert-butyl alcohol / 12 h / 110 °C View Scheme

: 524-63-0, 70877-75-7
Cuprein

: 124-41-4
sodium methylate

: 130-95-0
Quinine

Conditions

Conditions	Yield
With methyl nitrate at 100℃; im Rohr;

: C13H17N3O

: 130-95-0
Quinine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: palladium diacetate; silver carbonate; Trimethylacetic acid / N,N-dimethyl-formamide / 16 h / 100 °C 2.1: ruthenium trichloride; sodium periodate / water; ethyl acetate; acetonitrile / 18 h / 20 °C / Sealed tube 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 5.2: 0.75 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 6.1: zinc trifluoromethanesulfonate; hydrogenchloride / water / 0.08 h / 20 °C 6.2: 1.5 h 7.1: toluene-4-sulfonic acid / acetonitrile / 0.17 h / 20 °C 7.2: 2 h / 70 °C 8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 8.2: 1 h / -78 °C / Inert atmosphere 9.1: triisopropoxytitanium(IV) chloride / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere 9.2: 3 h / 0 - 20 °C / Inert atmosphere 10.1: lithium aluminium tetrahydride / tetrahydrofuran; methanol / 0.17 h / 0 - 20 °C / Schlenk technique; Inert atmosphere View Scheme

Yield

Multi-step reaction with 10 steps
1.1: palladium diacetate; silver carbonate; Trimethylacetic acid / N,N-dimethyl-formamide / 16 h / 100 °C
2.1: ruthenium trichloride; sodium periodate / water; ethyl acetate; acetonitrile / 18 h / 20 °C / Sealed tube
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C
4.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
5.2: 0.75 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
6.1: zinc trifluoromethanesulfonate; hydrogenchloride / water / 0.08 h / 20 °C
6.2: 1.5 h
7.1: toluene-4-sulfonic acid / acetonitrile / 0.17 h / 20 °C
7.2: 2 h / 70 °C
8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.2: 1 h / -78 °C / Inert atmosphere
9.1: triisopropoxytitanium(IV) chloride / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere
9.2: 3 h / 0 - 20 °C / Inert atmosphere
10.1: lithium aluminium tetrahydride / tetrahydrofuran; methanol / 0.17 h / 0 - 20 °C / Schlenk technique; Inert atmosphere
View Scheme

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490-11-9

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612-11-3

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Quinine, with the CAS registry number 130-95-0 and EINECS registry number 205-003-2, has the systematic name of (8α,9R)-6'-methoxycinchonan-9-ol. And the molecular formula of this chemical is C₂₀H₂₄N₂O₂. It is a kind of white to light yellow crystal powder. In addition, it is very sensitive to ultraviolet light (UV) and will fluoresce in direct sunlight, due to its highly conjugated resonance structure.

The physical properties of Quinine are as following: (1)ACD/LogP: 3.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.35; (4)ACD/LogD (pH 7.4): 1.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 3.48; (7)ACD/KOC (pH 5.5): 1.45; (8)ACD/KOC (pH 7.4): 25.45; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 34.59 Å²; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 95.78 cm³; (15)Molar Volume: 266.3 cm³; (16)Polarizability: 37.97×10^-24cm³; (17)Surface Tension: 56 dyne/cm; (18)Density: 1.21 g/cm³; (19)Flash Point: 253.7 °C; (20)Enthalpy of Vaporization: 80.41 kJ/mol; (21)Boiling Point: 495.9 °C at 760 mmHg; (22)Vapour Pressure: 1.19E-10 mmHg at 25°C.

Preparation and uses of Quinine: The bark of the cinchona tree is the only known natural source of quinine. It is a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](/C=C)C3)cc4)C
(2)InChI: InChI=1/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
(3)InChIKey: LOUPRKONTZGTKE-WZBLMQSHBR

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intravenous	100mg/kg (100mg/kg)		Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
cat	LDLo	subcutaneous	100mg/kg (100mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
dog	LDLo	subcutaneous	180mg/kg (180mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog	LDLo	intramuscular	400mg/kg (400mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog	LDLo	oral	1500mg/kg (1500mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog	LDLo	subcutaneous	200mg/kg (200mg/kg)	BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
guinea pig	LD50	oral	1800mg/kg (1800mg/kg)		Schweizerische Medizinische Wochenschrift. Vol. 84, Pg. 351, 1954.
man	LDLo	unreported	294mg/kg (294mg/kg)		"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse	LD50	intraperitoneal	115mg/kg (115mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 1760, 1985.
mouse	LD50	intravenous	68mg/kg (68mg/kg)		Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
mouse	LDLo	subcutaneous	200mg/kg (200mg/kg)	CARDIAC: OTHER CHANGES BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA BLOOD: OTHER CHANGES	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
pigeon	LDLo	intramuscular	500mg/kg (500mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rabbit	LDLo	intravenous	70mg/kg (70mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rabbit	LDLo	oral	500mg/kg (500mg/kg)		Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
rabbit	LDLo	subcutaneous	231mg/kg (231mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rat	LD	intraperitoneal	> 100mg/kg (100mg/kg)		Cancer Research. Vol. 52, Pg. 2797, 1992.
rat	LDLo	oral	800mg/kg (800mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 100, Pg. 408, 1950.
rat	LDLo	subcutaneous	200mg/kg (200mg/kg)	CARDIAC: OTHER CHANGES BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA BLOOD: OTHER CHANGES	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
women	TDLo	oral	74mg/kg (74mg/kg)	SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR GASTROINTESTINAL: NAUSEA OR VOMITING	American Journal of Ophthalmology. Vol. 90, Pg. 403, 1980.

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