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SMB00963

Sigma-Aldrich

Desethylchloroquine

≥95% (HPLC)

Synonym(s):

7-Chloro-4-{[4-(ethylamino)-1-methylbutyl]amino}quinoline, 4-[[1-Methyl-4-((ethylamino)butyl]amino)]-7-chloroquinoline, 7-Chloro-4-(4-N-ethylamino-1-methylbutylamino)quinoline, N-Desethyl chloroquine, N-Desethylchloroquine, N4-(7-Chloro-4-quinolinyl)-N1-ethyl-1,4-pentanediamine, Monodeethylchloroquine, Monodesethylchloroqu​ine

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About This Item

Empirical Formula (Hill Notation):
C16H22ClN3
CAS Number:
1476-52-4
Molecular Weight:
291.82
MDL number:
MFCD00871808
UNSPSC Code:
41116107
NACRES:
NA.77

biological source

synthetic

Quality Level

200

grade

research grade

Assay

≥95% (HPLC)

form

powder or crystals

technique(s)

HPLC: suitable

color

white to off-white

shipped in

wet ice

storage temp.

2-8°C

SMILES string

ClC(C=C1)=CC2=C1C(NC(CCCNCC)C)=CC=N2

InChI

1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)

InChI key

MCYUUUTUAAGOOT-UHFFFAOYSA-N

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General description

Desethylchloroquine is a metabolite of hydroxychloroquine and chloroquine. Hydroxychloroquine and chloroquine have antimalarial properties and are used as a therapeutic for rheumatoid arthritis (RA), systemic lupus erythematosus (SLE) and other inflammatory rheumatic diseases. They have also been in the spotlight due to their activity on patients with COVID-19, the disease caused by the SARS-CoV-2 virus. Hydroxychloroquine and chloroquine interfere with lysosomal activity and autophagy, interact with membrane stability and alter signalling pathways and transcriptional activity, which can result in modulation of cytokine production. Their mode of action is still emerging and their metabolism is of great interest.

Application

Application: Metabolomics research

Other Notes

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000257597
SLCJ0926

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Karnrawee Kaewkhao et al.
Bioanalysis, 11(5), 333-347 (2019-03-16)
Chloroquine is an antimalarial drug used in the treatment of Plasmodium vivax malaria. Three methods to quantify chloroquine and its metabolite in blood matrices were developed and validated. Methodology & results: Different high-throughput extraction techniques were used to recover the
Gaëlle Noé et al.
Therapeutic drug monitoring, 41(4), 476-482 (2019-02-27)
Hydroxychloroquine (HCQ) is approved for the treatment of systemic lupus erythematosus (SLE). Therapeutic drug monitoring of HCQ is necessary to detect nonadherence and to improve treatment efficacy in patients with SLE. Liquid chromatographic-tandem mass spectroscopy and high performance liquid chromatography
Yingshan Han et al.
Journal of medical virology, 91(7), 1182-1190 (2019-02-26)
Studies aimed at repurposing existing drugs revealed that some antimalarial compounds possess anti-Zika virus (anti-ZIKV) activity. Here, we further tested 14 additional antimalarial drugs and their metabolites or analogs for anti-ZIKV activity using a phenotypic screening approach. We identified four

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