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22632

Sigma-Aldrich

Quinine hydrochloride dihydrate

tested according to Ph. Eur.

Synonym(s):

Chinini hydrochloridum, (8α, 9R)-6′-Methoxycinchonan-9-ol monohydrochloride dihydrate

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O2 · HCl · 2H2O
CAS Number:
6119-47-7
Molecular Weight:
396.91
Beilstein/REAXYS Number:
6112655
EC Number:
205-001-1
MDL number:
MFCD00151248
UNSPSC Code:
12352210
PubChem Substance ID:
329752329
NACRES:
NA.25

agency

USP/NF
tested according to Ph. Eur.

Quality Level

100

form

solid

solubility

water: soluble 0.25 mg in 5 ml

application(s)

pharmaceutical (small molecule)

SMILES string

O.O.Cl.COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1

InChI

1S/C20H24N2O2.ClH.2H2O/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;1H;2*1H2/t13-,14-,19-,20+;;;/m0.../s1

InChI key

MPQKYZPYCSTMEI-FLZPLBAKSA-N

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Application

Quinine hydrochloride dehydrate has been used for fluorescent in situ detection of quinine in cinchona bark using UV resonance raman spectroscopy. It has also been used as a actinometric system to measure the light-induced changes in ruthenium anticancer agent, NAMI-A.

Biochem/physiol Actions

Quinine is a very effective anti-malarial treatment but is considered toxic for routine treatment due to the development of drug resistance in the malarial parasites. It acts as blood schizonticide.Quinine reportedly blocks the membrane conductance of potassium in enteric neurons.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK4769
BCCG5754
BCCF7727
BCCB7934
BCBX1210

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USP

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C6628

Chloroquine diphosphate salt

E Cherubini et al.
British journal of pharmacology, 83(1), 3-5 (1984-09-01)
Quinine (100 microM) abolished the slow calcium-dependent afterhyperpolarization which occurs after an action potential in some neurones of the guinea-pig myenteric and submucous plexus. This occurred without any effect on the amplitude or time course of the action potential itself
D A Warrell
Journal of the Royal Society of Medicine, 82 Suppl 17, 44-50 (1989-01-01)
In the treatment of severe Plasmodium falciparum infection antimalarial drugs should, ideally, be given by controlled rate intravenous infusion until the patient is able to swallow tablets. In cases where infection has been acquired in a chloroquine resistant area, and
Is alkylation the main mechanism of action of the antimalarial drug artemisinin?.
Robert A and Meunier B
Chemical Society Reviews, 273-274 (1998)
Torsten Frosch et al.
The journal of physical chemistry. B, 111(16), 4171-4177 (2007-03-31)
Deep UV resonance Raman micro-spectroscopy (lambda(exc) = 244 nm) was applied for a highly sensitive, selective, and gentle localization of the antimalarial quinine in situ in cinchona bark. The high potential of the method was demonstrated by the detection of
Marjan Bouma et al.
Journal of pharmaceutical and biomedical analysis, 30(4), 1287-1296 (2002-11-01)
NAMI-A is a novel ruthenium complex with selective activity against metastases currently in Phase I clinical trials in The Netherlands. The photostability of this new agent in solid state and in solution has been investigated utilizing a stability-indicating reversed-phase high
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