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Q1125

Sigma-Aldrich

Quinine hydrochloride dihydrate

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O2 · HCl · 2H2O
CAS Number:
6119-47-7
Molecular Weight:
396.91
EC Number:
205-001-1
MDL number:
MFCD00078498
UNSPSC Code:
12352210
PubChem Substance ID:
57654577
NACRES:
NA.77

Quality Level

200

solubility

H2O: 0.25/5 g/mL, clear, colorless

antibiotic activity spectrum

parasites

Mode of action

enzyme | inhibits

SMILES string

O.Cl.[H][C@]1(C[C@@H]2CC[N@H]1C[C@@H]2C=C)[C@H](O)c3ccnc4ccc(OC)cc34

InChI

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

InChI key

SGVZDMWHXVXUBY-HZQSTTLBSA-N

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General description

Quinine is derived from the stem of cinchona (quina-quina) tree. It is an alkaloid having various applications in the field of medicine. Quinine is a basic compound with aryl amino alcohol group.

Application

Quinine hydrochloride dihydrate has been used in Drosophila larval behavioral assay. It has also been used in taste preference analysis among rats.

Biochem/physiol Actions

Quinine is widely used in the treatment of malaria. It possesses erythrocytic and gametocytocidal action against Plasmodium sp. It also serves as an analgesic drug. Upon administration, quinine is present mostly bound to α-1 acid glycoprotein in the body fluids. Quinine has the ability to cross the placenta and the blood brain barrier. It has a half-life of 11-18 hours. Tinnitus, hearing defects, nausea and headache are some of its side effects.
Potassium channel blocker

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H317 - H334

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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High-NaCl perception in Drosophila melanogaster
Alves G, et al.
The Journal of Neuroscience, 34(33), 10884-10891 (2014)
The first stereoselective total synthesis of quinine
Stork G, et al.
Journal of the American Chemical Society, 123(14), 3239-3242 (2001)
Preferences of 14 rat strains for 17 taste compounds
Tordoff MG, et al.
Physiology & Behavior, 95(3), 308-332 (2008)
Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria
Achan J, et al
Malaria Journal, 10(1), 144-144 (2011)
Hu Chen et al.
Addiction biology, 25(6), e12821-e12821 (2019-08-23)
One of the most pernicious characteristics of alcohol use disorder is the compulsion to drink despite negative consequences. The insular cortex controls decision making under conditions of risk or conflict. Cortical activity is tightly controlled by inhibitory interneurons that are
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