Introduction：Basic information about CAS 69-44-3|Amodiaquine dihydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Amodiaquine dihydrochloride |
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| CAS Number | 69-44-3 | Molecular Weight | 392.322 |
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| Density | / | Boiling Point | 478ºC at 760 mmHg |
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| Molecular Formula | C20H23Cl2N3O | Melting Point | / |
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| MSDS | / | Flash Point | / |
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Names
| Name | Acrichin dihydrochloride |
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| Synonym | More Synonyms |
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Amodiaquine dihydrochloride BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Epigenetics >>Histone MethyltransferaseResearch Areas >>Inflammation/ImmunologyResearch Areas >>Neurological Disease |
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| Target | EC50: ~20 μM (Nurr1-LBD (ligand binding domain))[1] Histamine N-methyltransferase[3] |
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| 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. |
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| 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. |
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| 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. |
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Chemical & Physical Properties
| Boiling Point | 478ºC at 760 mmHg |
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| Molecular Formula | C20H23Cl2N3O |
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| Molecular Weight | 392.322 |
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| Exact Mass | 391.121826 |
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| PSA | 48.39000 |
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| LogP | 6.05420 |
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| InChIKey | KBTNVJNLEFHBSO-UHFFFAOYSA-N |
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| SMILES | CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O.Cl |
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| Storage condition | -20℃ |
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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 DATAACUTE 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
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Safety Information
| Hazard Codes | N |
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| HS Code | 2933499090 |
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Customs
| HS Code | 2933499090 |
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| 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% |
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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 |
