Quinine dihydrochloride | CAS# 60-93-5 (2HCl) | antimalarial, antipyretic, analgesic

MedKoo Cat#: 412825 | Name: Quinine dihydrochloride

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Description:

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

Quinine dihydrochloride is an alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.

Chemical Structure

Quinine dihydrochloride

CAS#60-93-5 (2HCl)

Theoretical Analysis

MedKoo Cat#: 412825

Name: Quinine dihydrochloride

CAS#: 60-93-5 (2HCl)

Chemical Formula: C20H26Cl2N2O2

Exact Mass: 0.0000

Molecular Weight: 397.34

Elemental Analysis: C, 60.46; H, 6.60; Cl, 17.84; N, 7.05; O, 8.05

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 450.00	2 Weeks

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Related CAS #

130-95-0 (free base) 60-93-5 (2HCl) 6119-70-6 (sulfate dihydrate) 804-63-7 (sulfate) 549-49-5 (HBr)

Synonym

Quinine dihydrochloride; Quinine 2HCl; CCRIS5754; CCRIS-5754; CCRIS 5754

IUPAC/Chemical Name

(1R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol dihydrochloride

InChi Key

NNKXWRRDHYTHFP-HZQSTTLBSA-N

InChi Code

InChI=1S/C20H24N2O2.2ClH/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*1H/t13-,14-,19-,20+;;/m0../s1

SMILES Code

O[C@H](C1=CC=NC2=CC=C(OC)C=C12)[C@H]3N4C[C@H](C=C)[C@](CC4)([H])C3.[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

To be determined

Shelf Life

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinine dihydrochloride is a salt form of quinine.

In vitro activity:

Quinine can act as an agonist to activate the family of bitter taste G protein-coupled receptor family of proteins. Using normal mammary epithelial (MCF-10A) and non-invasive mammary epithelial (MCF-7) cell lines, this study investigated the effect of quinine in regulating Ras p21 and RalA activity. Although RalGDS was detected in MCF-10A and MCF-7 cells, it did not result in RalA activation upon Ras p21 activation with quinine. This suggests that the Ras p21-RalGDS-RalA pathway is not active in the MCF-10A cells. Reference: Mol Cell Biochem. 2023 May 2. https://pubmed.ncbi.nlm.nih.gov/37131040/

In vivo activity:

Quinine is a commonly used drug for severe and chloroquine-resistant malaria. Cardiotoxicity associated with quinine has been largely reported. However, this was often more common with toxic doses. In this case study, a 5-year-old Nigerian girl was being treated for uncomplicated malaria with quinine dihydrochloride infusion. All the laboratory investigations done were within normal limits, except for positive blood films for malarial parasites. However, pre-treatment electrocardiographic evaluation of the patient was not carried out. She developed ventricular fibrillation and died less than 1.5 hours into the quinine dihydrochloride infusion. References: J Natl Med Assoc. 2008 Sep;100(9):1063-5. https://pubmed.ncbi.nlm.nih.gov/18807436/

Preparing Stock Solutions

The following data is based on the product molecular weight 397.34 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.

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

Formulation protocol:

1. Bhatia V, Esmati L, Bhullar RP. Regulation of Ras p21 and RalA GTPases activity by quinine in mammary epithelial cells. Mol Cell Biochem. 2023 May 2. doi: 10.1007/s11010-023-04725-z. Epub ahead of print. PMID: 37131040. 2. Gendrot M, Andreani J, Boxberger M, Jardot P, Fonta I, Le Bideau M, Duflot I, Mosnier J, Rolland C, Bogreau H, Hutter S, La Scola B, Pradines B. Antimalarial drugs inhibit the replication of SARS-CoV-2: An in vitro evaluation. Travel Med Infect Dis. 2020 Sep-Oct;37:101873. doi: 10.1016/j.tmaid.2020.101873. Epub 2020 Sep 8. PMID: 32916297; PMCID: PMC7477610. 3. Busari O, Busari O. Ventricular fibrillation in a 5-year-old child on therapeutic dose of quinine dihydrochloride infusion for acute malaria. J Natl Med Assoc. 2008 Sep;100(9):1063-5. doi: 10.1016/s0027-9684(15)31445-0. PMID: 18807436. 4. Gupta Y, Jain A, Jain SK. Transferrin-conjugated solid lipid nanoparticles for enhanced delivery of quinine dihydrochloride to the brain. J Pharm Pharmacol. 2007 Jul;59(7):935-40. doi: 10.1211/jpp.59.7.0004. PMID: 17637187.

In vitro protocol:

In vivo protocol:

1. Busari O, Busari O. Ventricular fibrillation in a 5-year-old child on therapeutic dose of quinine dihydrochloride infusion for acute malaria. J Natl Med Assoc. 2008 Sep;100(9):1063-5. doi: 10.1016/s0027-9684(15)31445-0. PMID: 18807436. 2. Gupta Y, Jain A, Jain SK. Transferrin-conjugated solid lipid nanoparticles for enhanced delivery of quinine dihydrochloride to the brain. J Pharm Pharmacol. 2007 Jul;59(7):935-40. doi: 10.1211/jpp.59.7.0004. PMID: 17637187.

1: Niu B, Liu L, Gao Q, Zhu MM, Chen L, Peng XH, Qin B, Zhou X, Li F. Genetic mutation of Tas2r104/Tas2r105/Tas2r114 cluster leads to a loss of taste perception to denatonium benzoate and cucurbitacin B. Animal Model Exp Med. 2024 Jun;7(3):324-336. doi: 10.1002/ame2.12357. Epub 2023 Dec 28. PMID: 38155461; PMCID: PMC11228091. 2: Coulibaly WH, Jean-Paul Bouatenin KM, Boli ZBIA, Kohi Alfred K, Tra Bi YC, Celaire N'sa KM, Cot M, Djameh C, Djè KM. Influence of yeasts on bioactive compounds content of traditional sorghum beer (tchapalo) produced in Côte d'Ivoire. Curr Res Food Sci. 2020 Jun 23;3:195-200. doi: 10.1016/j.crfs.2020.06.001. PMID: 32914135; PMCID: PMC7473363. 3: Al-Zaydani IA, Al-Hakami A, Kumar A, Abdalla SA, Otaif M, Thiqa R, Ahmed H, Alnahili K. Severe unresolving Plasmodium falciparum malaria following artemisinin combination therapy: Emergence of drug resistance in Saudi Arabia. Indian J Med Microbiol. 2016 Oct-Dec;34(4):553-557. doi: 10.4103/0255-0857.195352. PMID: 27934844. 4: Mbinze JK, Sacré PY, Yemoa A, Mavar Tayey Mbay J, Habyalimana V, Kalenda N, Hubert P, Marini RD, Ziemons E. Development, validation and comparison of NIR and Raman methods for the identification and assay of poor-quality oral quinine drops. J Pharm Biomed Anal. 2015;111:21-7. doi: 10.1016/j.jpba.2015.02.049. Epub 2015 Mar 12. PMID: 25828509. 5: Hendriksen IC, Maiga D, Lemnge MM, Mtove G, Gesase S, Reyburn H, Lindegardh N, Day NP, von Seidlein L, Dondorp AM, Tarning J, White NJ. Population pharmacokinetic and pharmacodynamic properties of intramuscular quinine in Tanzanian children with severe Falciparum malaria. Antimicrob Agents Chemother. 2013 Feb;57(2):775-83. doi: 10.1128/AAC.01349-12. Epub 2012 Nov 26. PMID: 23183442; PMCID: PMC3553700. 6: Sadeghipour F, Lorenzini KI, Ziewitz C, Dobrinas M, Fleury M, Bonnabry P. Chemical contamination during the preparation of cytotoxics: validation protocol for operators in hospital pharmacies. J Oncol Pharm Pract. 2013 Mar;19(1):57-64. doi: 10.1177/1078155212452764. Epub 2012 Jul 9. PMID: 22777996. 7: Kharal SA, Hussain Q, Ali S, Fakhuruddin. Quinine is bactericidal. J Pak Med Assoc. 2009 Apr;59(4):208-12. PMID: 19402279. 8: Busari O, Busari O. Ventricular fibrillation in a 5-year-old child on therapeutic dose of quinine dihydrochloride infusion for acute malaria. J Natl Med Assoc. 2008 Sep;100(9):1063-5. doi: 10.1016/s0027-9684(15)31445-0. PMID: 18807436. 9: Busari O, Busari O. Ventricular fibrillation in a 5-year-old child on therapeutic dose of quinine dihydrochloride infusion for acute malaria. J Natl Med Assoc. 2008 Aug;100(8):945-7. doi: 10.1016/s0027-9684(15)31409-7. PMID: 18717145. 10: Matsiegui PB, Missinou MA, Issifou S, Necek M, Mavoungou E. Ibuprofen does not affect levels of tumor necrosis factor alpha and soluble tumor necrosis factor receptor types I and II in Gabonese children with uncomplicated Plasmodium falciparum malaria. Eur Cytokine Netw. 2007 Dec;18(4):201-5. doi: 10.1684/ecn.2007.0105. Epub 2007 Oct 26. PMID: 17964975. 11: Gupta Y, Jain A, Jain SK. Transferrin-conjugated solid lipid nanoparticles for enhanced delivery of quinine dihydrochloride to the brain. J Pharm Pharmacol. 2007 Jul;59(7):935-40. doi: 10.1211/jpp.59.7.0004. PMID: 17637187. 12: Matsiegui PB, Missinou MA, Necek M, Issifou S, Kremsner PG. Short course of quinine plus a single dose of sulfadoxine/pyrimethamine for Plasmodium falciparum malaria. Wien Klin Wochenschr. 2006 Oct;118(19-20):610-4. doi: 10.1007/s00508-006-0657-3. PMID: 17136336. 13: Reichard U, Möller H, Eiffert H, Ramadori G, Schwörer H. Erfolgreiche Therapie einer Malaria tropica mit 50%-iger Parasitämie [Successful management of malaria tropica with 50% parasitaemia]. Dtsch Med Wochenschr. 2006 Sep 15;131(37):2010-2. German. doi: 10.1055/s-2006-951326. PMID: 16960767. 14: Das BK, Mishra S, Padhi PK, Manish R, Tripathy R, Sahoo PK, Ravindran B. Pentoxifylline adjunct improves prognosis of human cerebral malaria in adults. Trop Med Int Health. 2003 Aug;8(8):680-4. doi: 10.1046/j.1365-3156.2003.01087.x. PMID: 12869088. 15: Moyou-Somo R, Tietche F, Ondoa M, Kouemeni LE, Ekoe T, Mbonda E, Nsangou C, Jemea B, Guemkam G. Clinical trial of beta-arteether versus quinine for the treatment of cerebral malaria in children in Yaounde, Cameroon. Am J Trop Med Hyg. 2001 May-Jun;64(5-6):229-32. doi: 10.4269/ajtmh.2001.64.229. PMID: 11463108. 16: Krishna S, Nagaraja NV, Planche T, Agbenyega T, Bedo-Addo G, Ansong D, Owusu-Ofori A, Shroads AL, Henderson G, Hutson A, Derendorf H, Stacpoole PW. Population pharmacokinetics of intramuscular quinine in children with severe malaria. Antimicrob Agents Chemother. 2001 Jun;45(6):1803-9. doi: 10.1128/AAC.45.6.1803-1809.2001. PMID: 11353629; PMCID: PMC90549. 17: Sukontason K, Klaolaor P, Sukontason K, Piangjai S, Methanitikorn R, Morakote N. Lack of efficacy of quinine and artemether against advanced third- stage larvae of Gnathostoma spinigerum in vitro. Southeast Asian J Trop Med Public Health. 2000 Jun;31(2):412-4. PMID: 11127349. 18: Gulprasutdilog S, Chongkolwatana V, Buranakitjaroen P, Jaroonvesama N. Exchange transfusion in severe falciparum malaria. J Med Assoc Thai. 1999 Jan;82(1):1-8. PMID: 10087731. 19: Claessen FA, van Boxtel CJ, Perenboom RM, Tange RA, Wetsteijn JC, Kager PA. Quinine pharmacokinetics: ototoxic and cardiotoxic effects in healthy Caucasian subjects and in patients with falciparum malaria. Trop Med Int Health. 1998 Jun;3(6):482-9. doi: 10.1046/j.1365-3156.1998.00252.x. PMID: 9657511. 20: Seaton RA, Trevett AJ, Wembri JP, Nwokolo N, Naraqi S, Black J, Laurenson IF, Kevau I, Saweri A, Lalloo DG, Warrell DA. Randomized comparison of intramuscular artemether and intravenous quinine in adult, Melanesian patients with severe or complicated, Plasmodium falciparum malaria in Papua New Guinea. 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