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22632

Sigma-Aldrich

Quinine hydrochloride dihydrate

tested according to Ph. Eur.

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C20H24N2O2 · HCl · 2H2O
Numéro CAS:
6119-47-7
Poids moléculaire :
396.91
Numéro Beilstein :
6112655
Numéro CE :
205-001-1
Numéro MDL:
MFCD00151248
Code UNSPSC :
12352210
ID de substance PubChem :
329752329
Nomenclature NACRES :
NA.25

Agence

USP/NF
tested according to Ph. Eur.

Niveau de qualité

100

Forme

solid

Solubilité

water: soluble 0.25 mg in 5 ml

Application(s)

pharmaceutical (small molecule)

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H317,H334

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
BCCL9059
BCCK4769
BCCG5754
BCCF7727
BCCB7934

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Sigma-Aldrich

145904

Quinine

Quinine sulfate United States Pharmacopeia (USP) Reference Standard

USP

1597005

Quinine sulfate

Chloroquine diphosphate salt powder or crystals, 98.5-101.0% (EP)

Sigma-Aldrich

C6628

Chloroquine diphosphate salt

Is alkylation the main mechanism of action of the antimalarial drug artemisinin?.
Robert A and Meunier B
Chemical Society Reviews, 273-274 (1998)
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
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
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
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