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Quinine dihydrochloride

CAS：60-93-5
MW:397.3
MF：C20H26Cl2N2O2

Quinine dihydrochloride, with the chemical formula C20H26Cl2N2O2 and CAS registry number 60-93-5, is a compound known for its medicinal properties. This white crystalline powder is derived from the bark of the cinchona tree and is commonly used as an antimalarial drug. Quinine dihydrochloride works by interfering with the growth and reproduction of the malaria parasite in the body. It is often administered in combination with other antimalarial drugs to increase effectiveness and reduce the risk of drug resistance. Quinine dihydrochloride has also been used to treat other conditions such as leg cramps and nocturnal leg muscle spasms. However, it is important to note that the use of quinine dihydrochloride for these purposes is off-label and should only be done under the guidance of a healthcare professional. Overall, quinine dihydrochloride plays a crucial role in the treatment and prevention of malaria, making it an essential compound in the field of medicine.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Quinine dihydrochloride

1.2 Synonyms: (-)-Quinine dihydrochloride; (6-Methoxy-4-quinolyl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol dihydrochloride; Acid quinine hydrochloride; Cinchonan-9-ol, 6′-methoxy-, dihydrochloride, (8α,9R)-; Cinchonan-9-ol, 6′-methoxy-, hydrochloride (1:2), (8α,9R)-; Quinine bimuriate; QUININE DI HCL; Quinine dichloride; Quinine dihydrochloride powder; Quinine, dihydrochloride; quininebimuriate; QuinineDihydrochlorideInjection;

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1.3 CAS No.: 60-93-5

1.4 CID: 91429

1.5 EINECS: 200-493-4

1.6 Molecular Formula: C20H26Cl2N2O2

1.7 Inchi: InChI=1S/C20H24N2O2.2ClH/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;2*1H/t13-,14-,19-,20+;;/m0../s1

1.8 InChkey: NNKXWRRDHYTHFP-HZQSTTLBSA-N

1.9 Canonical Smiles: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.Cl.Cl

1.10 Isomers Smiles: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.Cl.Cl

2. Properties

2.1 Appearance: white solid

2.2 Chemical Properties: White Solid

2.3 Stability: Stable, but may be light sensitive. Efflorescent. Incompatible with strong oxidizing agents.

3. Use and Manufacturing

3.1 Description

Quinine dihydrochloride, with the chemical formula C20H24N2O2·2HCl, has the CAS number 60-93-5. It appears as a white crystalline powder with a bitter taste. Quinine dihydrochloride is a natural alkaloid derived from the bark of the cinchona tree. Its basic structure consists of a quinoline ring system with various functional groups attached. This compound is soluble in water and slightly soluble in alcohol. Quinine dihydrochloride is commonly used as an antimalarial drug and also has analgesic and antipyretic properties. It is important to note that quinine dihydrochloride should be used under medical supervision and its use may be associated with certain side effects. It is recommended to consult a healthcare professional before using this compound.

Applicable Fields

Antimalarial: Quinine dihydrochloride is primarily used as an antimalarial drug. Its mechanism of action involves inhibiting the growth and reproduction of the malaria parasite within the red blood cells. Quinine dihydrochloride is effective against various species of Plasmodium, the causative agent of malaria. It is often used in combination with other antimalarial drugs to enhance efficacy and reduce the risk of drug resistance.

Muscle Relaxant: Quinine dihydrochloride also has muscle relaxant properties. It can be used to treat muscle cramps and spasms, particularly those associated with conditions such as nocturnal leg cramps. The exact mechanism of action for its muscle relaxant effects is not fully understood, but it is believed to involve modulation of calcium channels and inhibition of muscle contractions.

Storage

Conditions: Store in a cool and dry place, away from direct sunlight.

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3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H317 (33.33%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501

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3.3 Usage: Primary alkaloid of various species of Cinchona (Rubiaceae). Optical isomer of Quinidine. Antimalarial; muscle relaxant (skeletal)

4. Safety and Handling

4.1 Safety Profile: Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and HCl. See also QUININE . Quinine dihydrochlorideSupplier

4.2 Safety: Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and HCl. Safety Information of Quinine dihydrochloride (CAS NO.60-93-5) is:
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 36: Wear suitable protective clothing
RIDADR: 1544
HazardClass: 6.1(b)
PackingGroup: III

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4.3 Specification: Quinine dihydrochloride , its cas register number is 60-93-5. It also can be called (-)-Quinine dihydrochloride ; Acid quinine hydrochloride ; Chinindihydrochlorid ; Quinine HCl ; Cinchonan-9-ol, 6'-methoxy-, dihydrochloride, (8-alpha,9R) (9CI) ; (6-Methoxy-4-quinolyl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol dihydrochloride .It is a white solid.

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4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	intravenous	630mg/kg/1W-I (630mg/kg)	SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE GASTROINTESTINAL: NAUSEA OR VOMITING	Japanese Journal of Ophthalmology. Vol. 28, Pg. 409, 1984.
guinea pig	LD50	intravenous	57mg/kg (57mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
guinea pig	LDLo	subcutaneous	199mg/kg (199mg/kg)		Proceedings of the Society for Experimental Biology and Medicine. Vol. 32, Pg. 595, 1935.
mouse	LD50	intravenous	86mg/kg (86mg/kg)		Biochemical Journal. Vol. 28, Pg. 426, 1934.
mouse	LD50	oral	660mg/kg (660mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rabbit	LD50	intravenous	35mg/kg (35mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rabbit	LD50	oral	641mg/kg (641mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat	LD50	intravenous	78mg/kg (78mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat	LD50	oral	1392mg/kg (1392mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1A

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

60-93-5Total: 2 Synthesis Route

76-60-8 213 Suppliers

121-54-0 193 Suppliers

56-54-2 133 Suppliers

135754-90-4

60-93-5 101 Suppliers

121-54-0 193 Suppliers

56-54-2 133 Suppliers

115-39-9 206 Suppliers

135754-88-0

60-93-5 101 Suppliers

7. Precursor and Product

precursor:

56-54-2

115-39-9

76-60-8

121-54-0

product:

522-66-7

8. Computed Properties

Molecular Weight：397.3g/mol
Molecular Formula：C₂₀H₂₆Cl₂N₂O₂
Compound Is Canonicalized：True
XLogP3-AA：396.1371335
Monoisotopic Mass：396.1371335
Complexity：457
Rotatable Bond Count：4
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：45.6
Heavy Atom Count：：26
Defined Atom Stereocenter Count：4
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：3
CACTVS Substructure Key Fingerprint：AAADceB7MAAGAAAAAAAAAAAAAAAAAAAAAAA8WLFiAAAAAACx8AAAHgAACAAADTzhngY+xvMIFgCgAzRnRACCiCAxIiAI2CA+bJgONuLEsZuEcChkwBHY+Aew4PwOgEABAAACAAAAgAIAAAQAAAAAAAAAAA==