CAS Number50-63-5
SynonymsMFCD00069852; acide phosphorique - N-(7-chloroquinoléin-4-yl)-N,N-diéthylpentane-1,4-diamine (2:1); Chloroquine phosphate; 7-Chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Diphosphate; EINECS 200-055-2; N-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine bis(phosphate); N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine phosphate (1:2); N-(7-Chloro-4-quinolinyl)-N,N-diethyl-1,4-pentanediamine phosphate (1:2); N4-(7-Chloro-4-quinolyl)-N1,N1-diethyl-1,4-pentanediamine Diphosphate; Chloroquine diphosphate salt; 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2); Aralen phosphate; 1,4-Pentanediamine, N-(7-chloro-4-quinolinyl)-N,N-diethyl-, phosphate (1:2); 1,4-pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2); N-(7-Chloro
Molecular FormulaC18H32ClN3O8P2
Molecular Weight515.86
Purity98.5-101.0 (EP)%
Boiling Point460.6ºC at 760 mmHg
Melting Point192-198 °C
Appearancepowder or crystals
EINECS200-055-2
Symbol
Signal WordWarning
Please Login or Create an Account to: See VlP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 50-63-5 |
| Catalog No. | 2A-9009748 |
| Chinese Name | 磷酸氯喹 |
| Synonyms | MFCD00069852; acide phosphorique - N-(7-chloroquinoléin-4-yl)-N,N-diéthylpentane-1,4-diamine (2:1); Chloroquine phosphate; 7-Chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Diphosphate; EINECS 200-055-2; N-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine bis(phosphate); N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine phosphate (1:2); N-(7-Chloro-4-quinolinyl)-N,N-diethyl-1,4-pentanediamine phosphate (1:2); N4-(7-Chloro-4-quinolyl)-N1,N1-diethyl-1,4-pentanediamine Diphosphate; Chloroquine diphosphate salt; 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2); Aralen phosphate; 1,4-Pentanediamine, N-(7-chloro-4-quinolinyl)-N,N-diethyl-, phosphate (1:2); 1,4-pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2); N-(7-Chloro |
| Molecular Formula | C18H32ClN3O8P2 |
| Molecular Weight | 515.86 |
| Purity | 98.5-101.0 (EP) |
| Boiling Point | 460.6ºC at 760 mmHg |
| Melting Point | 192-198 °C |
| Appearance | powder or crystals |
| Water Solubility | H2O: 50 mg/mL, clear |
| Storage Condition | This product is sealed and stored in a dry place a |
| Packaging | III |
| Application | Chloroquine diphosphate is an antimalarial and anti-inflammatory drug widely used to treat malaria and rheumatoid arthritis. Chloroquine is an inhibitor of autophagy and toll-like receptors (TLRs). |
| EINECS | 200-055-2 |
| HTC | 2933499090 |
| PubChem ID | 24278090 |
| MDL Number | MFCD00069852 |
| SMILES | OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12 |
| InChI | 1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4) |
| InChI Key | QKICWELGRMTQCR-UHFFFAOYSA-N |
| Beilstein/REAXYS | 4223142 |
| NACRES Code | NA.77 |
| UNSPSC | 12352107 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/9748_1_50_63_5.pdf |
| Bioactivity | Chloroquine (diphosphate) is an antimalarial and anti-inflammatory drug widely used to treat malaria and rheumatoid arthritis. Chloroquine is an inhibitor of autophagy and toll-like receptors (TLRs). Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR) Research Areas >> Inflammation/Immunology Target Autophagy, TLRs[1][2][3] In Vitro Chloroquine (CHQ, 20 μM) inhibits IL-12p70 release and reduces Th1-priming capacity of activated human monocyte-derived Langerhans-like cells (MoLC). Chloroquine (CHQ, 20 μM) enhances IL-1-induced IL-23 secretion in MoLC and subsequently increases IL-17A release by primed CD4+ T cells[1]. Chloroquine (25 μM) suppresses MMP-9 mRNA expression in normoxia and hypoxia in parental MDA-MB-231 cells. Chloroquine has cell-, dose- and hypoxia-dependent effects on MMP-2, MMP-9 and MMP-13 mRNA expression[2]. TLR7 and TLR9 inhibition using IRS-954 or chloroquine significantly reduces HuH7 cell proliferation in vitro[3]. In Vivo Chloroquine (80 mg/kg, i.p.) does not prevent the growth of the triple-negative MDA-MB-231 cells with high or low TLR9 expression levels in the orthotopic mouse model[2]. TLR7 and TLR9 inhibition using IRS-954 or chloroquine significantly inhibits tumour growth in the mouse xenograft model. HCC development in the DEN/NMOR rat model is also significantly inhibited by chloroquine[3]. Cell Assay The cells are cultured in 6-well plates with normal culture medium in the presence of vehicle or 25 or 50 μM chloroquine, until near confluency, after which they are rinsed with sterile phosphate-buffered saline (PBS) and cultured further for the indicated times in serum-free culture medium. At the desired time-points, the culture medium is discarded and the cells are quickly harvested in lysis buffer and clarified by centrifugation. Subsequent to boiling the supernatants in reducing sodium dodecyl sulphate (SDS) sample buffer, equal amounts of protein (100 μg) are loaded per lane and the samples are electrophoresed into 10 or 4-20% gradient polyacrylamide SDS gels, then transferred to a nitrocellulose membrane. To detect TLR9, the blots are incubated overnight at 4°C with anti-TLR9 antibodies, diluted 1:500 in Tris-buffered saline with 0.1% (v/v) Tween-20 (TBST). Equal loading is confirmed with polyclonal rabbit anti-actin. Secondary detection is performed with horseradish peroxidase-linked secondary antibodies. The protein bands are visualized by chemiluminescence using an ECL kit. Animal Admin Control and TLR9 siRNA MDA-MB-231 cells (5×105 cells in 100 μL) are inoculated into the mammary fat pads of four-week-old, immune-deficient mice (athymic nude/nu Foxn1). Treatments are started seven days after tumor cell inoculation. The mice are treated daily either with intraperitoneal (i.p.) chloroquine (80 mg/kg) or vehicle (PBS). The animals are monitored daily for clinical signs. Tumor measurements are performed twice a week and tumor volume is calculated according to the formula V=(π/6) (d1×d2)3/2, where d1 and d2 are perpendicular tumor diameters. The tumors are allowed to grow for 22 days, at which point the mice are sacrificed and the tumors are dissected for a final measurement. Throughout the experiments, the animals are maintained under controlled pathogen-free environmental conditions (20-21°C, 30-60% relative humidity and a 12-h lighting cycle). The mice are fed with small-animal food pellets and supplied with sterile water ad libitum. References [1]. 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. [2]. Tuomela J, et al. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672. [3]. Mohamed FE, et al. Effect of toll-like receptor 7 and 9 targeted therapy to prevent the development of hepatocellular carcinoma. Liver Int. 2014 Jul 2. doi: 10.1111/liv.12626. Chemical & Physical Properties Boiling Point 460.6ºC at 760 mmHg Melting Point 200 °C (dec.)(lit.) Molecular Formula C18H32ClN3O8P2 Molecular Weight 515.862 Flash Point 232.3ºC Exact Mass 515.135315 PSA 203.30000 LogP 3.02640 InChIKey QKICWELGRMTQCR-UHFFFAOYSA-N SMILES CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=P(O)(O)O.O=P(O)(O)O Storage condition Desiccate at RT Water Solubility H2O: 50 mg/mL, clear |
| Use of | Chloroquine (diphosphate) is an antimalarial and anti-inflammatory drug widely used to treat malaria and rheumatoid arthritis. Chloroquine is an inhibitor of autophagy and toll-like receptors (TLRs). Properties Articles108 Name Chloroquine Diphosphate Synonym More Synonyms Chloroquine diphosphate Biological Activity Description Chloroquine (diphosphate) is an antimalarial and anti-inflammatory drug widely used to treat malaria and rheumatoid arthritis. Chloroquine is an inhibitor of autophagy and toll-like receptors (TLRs). Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR) Research Areas >> Inflammation/Immunology Autophagy, TLRs[1][2][3] References [1]. 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. [2]. Tuomela J, et al. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672. Chemical & Physical Properties Exact Mass 515.135315 PSA 203.30000 LogP 3.02640 InChIKey QKICWELGRMTQCR-UHFFFAOYSA-N Storage condition Desiccate at RT |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
| Related Products in API & Advanced Intermediates | ||
|---|---|---|
| Cephalexin | 15686-71-2 | 2A-9009695 |
| Cephalexin monhydrochloride | 23325-78-2 | 2A-9009696 |
| Cerivastatin | 145599-86-6 | 2A-9009700 |
| Chlorimipramine Hydrochlorideï¼3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride | 17321-77-6 | 2A-9009734 |
| Chloroquine | 54-05-7 | 2A-9009747 |
| Chlorotetracycline | 57-62-5 | 2A-9009749 |
| Chlortetracycline hydrochloride | 64-72-2 | 2A-9009761 |
| Cimetidine | 51481-61-9 | 2A-9009795 |
| Cimetidine hydrochloride | 70059-30-2 | 2A-9009796 |
| Ciprofloxacin | 85721-33-1 | 2A-9009818 |
| Browse all API & Advanced Intermediates products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS