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MedKoo Cat#: 591927 | Name: Chloroquine HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chloroquine is a medication used to prevent and to treat malaria in areas where malaria is known to be sensitive to its effects. Certain types of malaria, resistant strains, and complicated cases typically require different or additional medication. It is also occasionally used for amebiasis that is occurring outside the intestines, rheumatoid arthritis, and lupus erythematosus. Chloroquine enters the red blood cell, inhibiting the parasite cell and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup

Chemical Structure

Chloroquine HCl
Chloroquine HCl
CAS#3545-67-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 591927

Name: Chloroquine HCl

CAS#: 3545-67-3 (HCl)

Chemical Formula: C18H28Cl3N3

Exact Mass:

Molecular Weight: 392.79

Elemental Analysis: C, 55.04; H, 7.19; Cl, 27.08; N, 10.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
54-05-7 (free base) 132-73-0 (sulfate) 1446-17-9 (phosphate) 3545-67-3 (HCl) 50-63-5 (diphosphate) 151-69-9 (acetate)
Synonym
NSC 14050; NSC-14050; NSC14050; Chloroquine hydrochloride; Aralen hydrochloride; Aralen HCl;
IUPAC/Chemical Name
N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride
InChi Key
PCFGECQRSMVKCC-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H26ClN3.2ClH/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;;/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*1H
SMILES Code
CC(NC1=CC=NC2=CC(Cl)=CC=C12)CCCN(CC)CC.[H]Cl.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Chloroquine binds to heme (or FP) to form the FP-chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products. Parasites that do not form hemozoin are therefore resistant to chloroquine.

Preparing Stock Solutions

The following data is based on the product molecular weight 392.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Blignaut M, Espach Y, van Vuuren M, Dhanabalan K, Huisamen B. Revisiting the Cardiotoxic Effect of Chloroquine. Cardiovasc Drugs Ther. 2019 Feb;33(1):1-11. doi: 10.1007/s10557-018-06847-9. PMID: 30635818. 2: Goel P, Gerriets V. Chloroquine. 2019 Dec 5. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 31855356. 3: Nguyen AL, Tan AN, Lavrijsen APM. Retinopathie door chloroquine [Chloroquine retinopathy]. Ned Tijdschr Geneeskd. 2018 Dec 17;163:D2904. Dutch. PMID: 30570930. 4: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Chloroquine. 2018 Oct 31. PMID: 30000205. 5: Liu WD, Sun W, Hua YQ, Wang SG, Cai ZD. [Effect of rapamycin and chloroquine on osteosarcoma]. Zhonghua Yi Xue Za Zhi. 2017 May 23;97(19):1510-1514. Chinese. doi: 10.3760/cma.j.issn.0376-2491.2017.19.017. PMID: 28535645. 6: Stokkermans TJ, Trichonas G. Chloroquine And Hydroxychloroquine Toxicity. 2019 Jun 4. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 30725771. 7: Ganne P, Srinivasan R. Chloroquine retinopathy. JAMA Ophthalmol. 2015 May;133(5):603-4. doi: 10.1001/jamaophthalmol.2014.6127. PMID: 25974649. 8: Ippolito MM, Jacobson JM, Lederman MM, Winterberg M, Tarning J, Shapiro TA, Flexner C. Effect of Antiretroviral Therapy on Plasma Concentrations of Chloroquine and Desethyl-chloroquine. Clin Infect Dis. 2018 Oct 30;67(10):1617-1620. doi: 10.1093/cid/ciy405. PMID: 29771277; PMCID: PMC6206114. 9: Xue J, Moyer A, Peng B, Wu J, Hannafon BN, Ding WQ. Chloroquine is a zinc ionophore. PLoS One. 2014 Oct 1;9(10):e109180. doi: 10.1371/journal.pone.0109180. PMID: 25271834; PMCID: PMC4182877. 10: Bortoli R, Santiago M. Chloroquine ototoxicity. Clin Rheumatol. 2007 Nov;26(11):1809-10. doi: 10.1007/s10067-007-0662-6. Epub 2007 Jun 27. PMID: 17594118. 11: Nair PA, Patel T. Palmoplantar exfoliation due to chloroquine. Indian J Pharmacol. 2017 Mar-Apr;49(2):205-207. doi: 10.4103/ijp.IJP_659_16. PMID: 28706336; PMCID: PMC5497445. 12: Copeman PW. Chloroquine. Trans St Johns Hosp Dermatol Soc. 1967;53(1):24-45. PMID: 4865867. 13: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Chloroquine. 2017 Feb 2. PMID: 31643549. 14: Chen X. Hydroxychloroquine and chloroquine. Clin Infect Dis. 2020 Mar 26:ciaa338. doi: 10.1093/cid/ciaa338. Epub ahead of print. PMID: 32215614. 15: Ferner RE, Aronson JK. Chloroquine and hydroxychloroquine in covid-19. BMJ. 2020 Apr 8;369:m1432. doi: 10.1136/bmj.m1432. PMID: 32269046. 16: Touret F, de Lamballerie X. Of chloroquine and COVID-19. Antiviral Res. 2020 May;177:104762. doi: 10.1016/j.antiviral.2020.104762. Epub 2020 Mar 5. PMID: 32147496; PMCID: PMC7132364. 17: Hong W. Combating COVID-19 with Chloroquine. J Mol Cell Biol. 2020 Apr 1:mjaa015. doi: 10.1093/jmcb/mjaa015. Epub ahead of print. PMID: 32236561. 18: Mohr K. Chloroquin [Chloroquine]. Dtsch Med Wochenschr. 1994 Feb 25;119(8):273-4. German. doi: 10.1055/s-0029-1235021. PMID: 8112211. 19: Willkens RF. Chloroquine. Arthritis Rheum. 1972 Mar-Apr;15(2):228-9. PMID: 5027609. 20: Manic G, Obrist F, Kroemer G, Vitale I, Galluzzi L. Chloroquine and hydroxychloroquine for cancer therapy. Mol Cell Oncol. 2014 Jul 15;1(1):e29911. doi: 10.4161/mco.29911. PMID: 27308318; PMCID: PMC4905171.