Amodiaquine dihydrochloride

Modify Date: 2024-01-03 23:54:47

Amodiaquine dihydrochloride Structure
Amodiaquine dihydrochloride structure
Common Name Amodiaquine dihydrochloride
CAS Number 69-44-3 Molecular Weight 392.322
Density N/A Boiling Point 478ºC at 760 mmHg
Molecular Formula C20H23Cl2N3O Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Amodiaquine dihydrochloride


Amodiaquine dihydrochloride (Amodiaquin dihydrochloride), a 4-aminoquinoline class of antimalarial agent, is a potent and orally active histamine N-methyltransferase inhibitor. Amodiaquine dihydrochloride is also a Nurr1 agonist and specifically binds to Nurr1-LBD (ligand binding domain) with an EC50 of ~20 μM. Anti-inflammatory effect[1][2][3][4].

 Names

Name Acrichin dihydrochloride
Synonym More Synonyms

 Amodiaquine dihydrochloride Biological Activity

Description Amodiaquine dihydrochloride (Amodiaquin dihydrochloride), a 4-aminoquinoline class of antimalarial agent, is a potent and orally active histamine N-methyltransferase inhibitor. Amodiaquine dihydrochloride is also a Nurr1 agonist and specifically binds to Nurr1-LBD (ligand binding domain) with an EC50 of ~20 μM. Anti-inflammatory effect[1][2][3][4].
Related Catalog
Target

EC50: ~20 μM (Nurr1-LBD (ligand binding domain))[1] Histamine N-methyltransferase[3]

In Vitro Amodiaquine (10-20 μM; 4 hours) treatment suppresses LPS-induced expression of proinflammatory cytokines (IL-1β, interleukin-6, TNF-α and iNOS) in a dose-dependent manner[1]. Amodiaquine (5 μM; 24 hours) significantly inhibits neurotoxin (6-OHDA-induced cell death in primary dopamine cells as examined by the number of TH+ neurons and dopamine uptake. The neuroprotective effect of Amodiaquine is also observed in rat PC12 cells[1]. RT-PCR[1] Cell Line: Primary microglia Concentration: 10 µM, 15 µM, 20 µM Incubation Time: 4 hours Result: Suppressed LPS-induced expression of proinflammatory cytokines (IL-1β, interleukin-6, TNF-α and iNOS) in a dose-dependent manner.
In Vivo Amodiaquine (40 mg/kg; intraperitoneal injection; daily; for 3 days; male ICR mice) treatment diminishes perihematomal activation of microglia/macrophages and astrocytes. Amodiaquine also suppresses ICH-induced mRNA expression of IL-1β, CCL2 and CXCL2, and ameliorated motor dysfunction of mice[2]. Animal Model: Male ICR mice (8-10 weeks of age) induced ntracerebral hemorrhage (ICH)[2] Dosage: 40 mg/kg Administration: Intraperitoneal injection; daily; for 3 days Result: Diminished perihematomal activation of microglia/macrophages and astrocytes.
References

[1]. Chun-Hyung Kim, et al. Nuclear receptor Nurr1 agonists enhance its dual functions and improve behavioral deficits in an animal model of Parkinson's disease. Proc Natl Acad Sci U S A. 2015 Jul 14;112(28):8756-61.

[2]. Keita Kinoshita, et al. A Nurr1 agonist amodiaquine attenuates inflammatory events and neurological deficits in a mouse model of intracerebral hemorrhage. J Neuroimmunol. 2019 May 15;330:48-54.

[3]. Akira Yokoyama, et al. Effect of amodiaquine, a histamine N-methyltransferase inhibitor, on, Propionibacterium acnes and lipopolysaccharide-induced hepatitis in mice. Eur J Pharmacol. 2007 Mar 8;558(1-3):179-84.

[4]. M T HOEKENGA. The treatment of acute malaria with single oral doses of amodiaquin, chloroquine, hydroxychloroquine and pyrimethamine. Am J Trop Med Hyg. 1954 Sep;3(5):833-8.

 Chemical & Physical Properties

Boiling Point 478ºC at 760 mmHg
Molecular Formula C20H23Cl2N3O
Molecular Weight 392.322
Exact Mass 391.121826
PSA 48.39000
LogP 6.05420
Storage condition -20℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GO7300100
CHEMICAL NAME :
o-Cresol, 4-((7-chloro-4-quinolyl)amino)-alpha-(diethylamino)-, dihydrochloride
CAS REGISTRY NUMBER :
69-44-3
LAST UPDATED :
199707
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C20-H22-Cl-N3-O.2Cl-H
MOLECULAR WEIGHT :
428.82
WISWESSER LINE NOTATION :
T66 BNJ IG EMR DQ C1N2&2 &GH 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
52 mg/kg/13W-I
TOXIC EFFECTS :
Blood - agranulocytosis
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 292,717,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
137 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,1471,1981

 Safety Information

Hazard Codes N
HS Code 2933499090

 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%

 Synonyms

Phenol, 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-, hydrochloride (1:1)
TCMDC-123932
camoquinhydrochloride
EINECS 200-706-0
4-[(7-Chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]phenol hydrochloride (1:1)
Camoquin Hcl
AMODIAQUIN DIHYDROCHLORIDE
AMODIAQUINE HCL
AMODIAQUIN HYDROCHLORIDE
AMODIAQUINE DIHYDROCHLORIDE
4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol hydrochloride (1:1)
AMODIAQUINE HYDROCHLORIDE
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Price: ¥550/10 mM * 1 mL in DMSO

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