Amodiaquine

Modify Date: 2024-01-02 17:35:25

Amodiaquine Structure
Amodiaquine structure
 Common Name Amodiaquine
CAS Number 86-42-0 Molecular Weight 355.861
Density 1.3±0.1 g/cm3 Boiling Point 478.0±45.0 °C at 760 mmHg
Molecular Formula C20H22ClN3O Melting Point 208°C
MSDS N/A Flash Point 242.9±28.7 °C

 Use of Amodiaquine


Amodiaquine (Amodiaquin), a 4-aminoquinoline class of antimalarial agent, is a potent and orally active histamine N-methyltransferase inhibitor. Amodiaquine 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 amodiaquine
Synonym More Synonyms

 Amodiaquine Biological Activity

Description Amodiaquine (Amodiaquin), a 4-aminoquinoline class of antimalarial agent, is a potent and orally active histamine N-methyltransferase inhibitor. Amodiaquine 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

Density 1.3±0.1 g/cm3
Boiling Point 478.0±45.0 °C at 760 mmHg
Melting Point 208°C
Molecular Formula C20H22ClN3O
Molecular Weight 355.861
Flash Point 242.9±28.7 °C
Exact Mass 355.145142
PSA 48.39000
LogP 4.77
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.669
Storage condition -20°C Freezer

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GO7300000
CHEMICAL NAME :
o-Cresol, 4-((7-chloro-4-quinolyl)amino)-alpha-(diethylamino)-
CAS REGISTRY NUMBER :
86-42-0
BEILSTEIN REFERENCE NO. :
0300962
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C20-H22-Cl-N3-O
MOLECULAR WEIGHT :
355.90
WISWESSER LINE NOTATION :
T66 BNJ EMR DQ C1N2&2& IG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
72 mg/kg/7W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - pulmonary emboli Liver - other changes Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
20 mg/kg/25D-I
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
29 mg/kg/25D-I
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
550 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
225 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Phage inhibition capacity
TEST SYSTEM :
Bacteria - Escherichia coli
DOSE/DURATION :
5 mg/plate
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 222,311,1989

 Safety Information

Safety Phrases S22-S24/25-S8
WGK Germany 3
HS Code 2933499090

 Synthetic Route

4,7-Dichloroquinoline structure

4,7-Dichloroqui...

CAS#:86-98-6

4-Aminophenol structure

4-Aminophenol

CAS#:123-30-8

Diethylamine structure

Diethylamine

CAS#:109-89-7

~%

Amodiaquine Structure

Amodiaquine

CAS#:86-42-0

Literature: WO2013/138200 A1, ; Paragraph 0073; 0074 ;
Acetamide,N-[3-[(diethylamino)methyl]-4-hydroxyphenyl]- structure

Acetamide,N-[3-...

CAS#:121-78-8

~%

Amodiaquine Structure

Amodiaquine

CAS#:86-42-0

Literature: Zhurnal Obshchei Khimii, , vol. 25, p. 331,335; engl. Ausg. S. 313, 316 Journal of the American Chemical Society, , vol. 70, p. 1363,1372 Journal of the American Chemical Society, , vol. 72, p. 1024
4-Acetamidophenol structure

4-Acetamidophenol

CAS#:103-90-2

~%

Amodiaquine Structure

Amodiaquine

CAS#:86-42-0

Literature: Journal of Medicinal Chemistry, , vol. 37, # 9 p. 1362 - 1370
4-Nitrophenol structure

4-Nitrophenol

CAS#:100-02-7

~%

Amodiaquine Structure

Amodiaquine

CAS#:86-42-0

Literature: Journal of the American Chemical Society, , vol. 70, p. 1363,1372 Journal of the American Chemical Society, , vol. 72, p. 1024
4,7-Dichloroquinoline structure

4,7-Dichloroqui...

CAS#:86-98-6

4-AMINO-ALPHA-DIETHYLAMINO-O-CRESOL structure

4-AMINO-ALPHA-D...

CAS#:51387-92-9

~%

Amodiaquine Structure

Amodiaquine

CAS#:86-42-0

Literature: Journal of Medicinal Chemistry, , vol. 37, # 9 p. 1362 - 1370

 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

4-[(7-Chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]phenol
SN 10,751
CAM-AQI
Camoquinal
4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
Camoquine
EINECS 201-669-3
4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino) methyl]phenol
MFCD00552927
Camoquin
Flavoquine
Miaquin
Phenol, 4-((7-chloro-4-quinolinyl)amino)-2-((diethylamino)methyl)-
aminodiaquine
Amodiaquine
Phenol, 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-
CAM-AQ1
Camochin
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