Desethyl Chloroquine

Names

[ Name ]:
Desethyl Chloroquine

[Synonym ]:
Chloroquine Related Compound D
4-N-(7-chloroquinolin-4-yl)-1-N-ethylpentane-1,4-diamine
7-Chloro-4-{[4-(ethylamino)-1-methylbutyl]amino}quinoline,Monodesethylchloroquine

Biological Activity

[Description]:

Desethyl chloroquine is a major desethyl metabolite of Chloroquine. Chloroquine diphosphate is an inhibitor of autophagy and toll-like receptors (TLRs). Desethyl chloroquine possesses antiplasmodic activity[1][2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Research Areas >> Infection

Signaling Pathways >> Autophagy >> Autophagy

[In Vitro]

P. falciparum[1]

[In Vivo]

Intraperitoneal injections of Chloroquine are administered to wild-type and Huntington's disease (Q175/Q175) mice. LC-MS/MS is used to compare the levels Chloroquine and its metabolites in blood, brain and muscle tissue. Concentrations of Chloroquine are lower (5-15M), but more stable in brain tissue compared to blood or muscle between 4 and 24 hours after the last dose. Levels of the active Chloroquine metabolite Desethyl chloroquine decreased in muscle and blood over the 24 hour post-injection period, while brain Desethyl chloroquine levels are lower and rose slightly over the same time frame[3].

[References]

[1]. Ajayi FO, et al. Comparison of the partitioning in vitro of chloroquine and its desethyl metabolites between the erythrocytes and plasma of healthy subjects and those with falciparum malaria. Afr J Med Med Sci. 1989 Jun;18(2):95-100.

[2]. Said A, et al. Chloroquine promotes IL-17 production by CD4+ T cells via p38-dependent IL-23 release by monocyte-derived Langerhans-like cells. J Immunol. 2014 Dec 15;193(12):6135-43.

[3]. Vodicka P, et al. Assessment of chloroquine treatment for modulating autophagy flux in brain of WT and HD mice. J Huntingtons Dis. 2014;3(2):159-74.

Chemical & Physical Properties

[ Density]:
1.138g/cm3

[ Boiling Point ]:
451.7ºC at 760mmHg

[ Melting Point ]:
94-97?C

[ Molecular Formula ]:
C₁₆H₂₂ClN₃

[ Molecular Weight ]:
291.81900

[ Flash Point ]:
227ºC

[ Exact Mass ]:
291.15000

[ PSA ]:
36.95000

[ LogP ]:
4.54220

[ Vapour Pressure ]:
2.38E-08mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
-20°C Freezer

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%