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Quinine
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Name

Quinine

 EINECS 205-003-2
CAS No. 130-95-0 Density 1.21 g/cm3
PSA 45.59000 LogP 3.11110
Solubility slightly soluble in water Melting Point 176-177 °C
Formula C20H24N2O2 Boiling Point 495.9 °C at 760 mmHg
Molecular Weight 324.423 Flash Point 253.7 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 36-37/39 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 130-95-0 (Quinine) Hazard Symbols HarmfulXn
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;

Article Data 83

Quinine 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In s-BuOH140 mg (26%)
6'-methoxy-cinchonan-9-one

6'-methoxy-cinchonan-9-one

A

56-54-2

quinidine

B

130-95-0

Quinine

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

C26H36N2O3Si

130-95-0

Quinine

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

C13H17N3O

130-95-0

Quinine

Conditions
ConditionsYield
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

Quinine Consensus Reports

Reported in EPA TSCA Inventory.

Quinine 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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