Introduction：Basic information about CAS 86-42-0|Amodiaquine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / | Flash Point | 242.9±28.7 °C |
|---|
Names
| Name | amodiaquine |
|---|
| Synonym | More Synonyms |
|---|
Amodiaquine BiologicalActivity
| 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 | Research Areas >>InfectionSignaling Pathways >>Epigenetics >>Histone MethyltransferaseResearch Areas >>Inflammation/ImmunologyResearch Areas >>Neurological Disease |
|---|
| 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 |
|---|
| InChIKey | OVCDSSHSILBFBN-UHFFFAOYSA-N |
|---|
| SMILES | CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O |
|---|
| 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 DATAACUTE 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 |
|---|
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 |
