Quinine free base | CAS#130-95-0 (free base)| MedKoo

MedKoo Cat#: 318603 | Name: Quinine free base

Description:

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

Quinine (free base) is an optical isomer of Quinidine and an anti-malarial, skeletal, muscle relaxant.

Chemical Structure

Quinine free base

CAS#130-95-0 (free base)

Theoretical Analysis

MedKoo Cat#: 318603

Name: Quinine free base

CAS#: 130-95-0 (free base)

Chemical Formula: C20H24N2O2

Exact Mass: 324.1838

Molecular Weight: 324.42

Elemental Analysis: C, 74.04; H, 7.46; N, 8.64; O, 9.86

Price and Availability

Size	Price	Availability
1g	USD 150.00	Ready to ship
2g	USD 200.00	Ready to ship
5g	USD 390.00	Ready to ship
10g	USD 520.00	Ready to ship
20g	USD 750.00	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 free base; Chinin; Chininum; 6'-Methoxycinchonidine; (8S,9R)-Quinine; Qualaquin; Odan Brand of Quinine Sulfate; Plough Brand of Quinine Sulfate; Prosana Brand of Quinine Bisulfate; Quinamm; Quinbisan; Quinbisul; Quindan;

IUPAC/Chemical Name

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

InChi Key

LOUPRKONTZGTKE-WZBLMQSHSA-N

InChi Code

InChI=1S/C20H24N2O2/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/t13-,14-,19-,20+/m0/s1

SMILES Code

COC1=CC=C2C(C([C@@H](O)[C@]3([H])C[C@H]4[C@@H](C=C)C[N@@]3CC4)=CC=N2)=C1

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 Ethanol, DMSO, and DMF

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

Certificate of Analysis

View CoA: current batch, Lot#C24B09B18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Quinine interferes with Plasmodium falciparum’s ability to dissolve and metabolize hemoglobin. The precise mechanism of action of quinine is not fully understood. Quinine may target the malaria purine nucleoside phosphorylase enzyme.

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 an anti-malarial agent belongs to the quinoline alkaloid that can inhibit angiogenesis. Vitamin C is also an important antioxidant and has been shown to reduce angiogenesis in tumor. 12 to 14 week old male albino rats were used for the study. The findings suggest that the activity of quinine with vitamin C synergism can greatly lower blood vessels growth in rat aorta rings and CAM assays. Quinine has an inhibitory effect on tumor growth and can be used alone or in combination with vitamin C. References: Asian Pac J Cancer Prev. 2022 Dec 1;23(12):4185-4192. https://pubmed.ncbi.nlm.nih.gov/36580001/

	Solvent	mg/mL	mM
Solubility
	Ethanol	1.0	3.08
	DMSO	25.0	77.06
	DMF	30.0	92.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 324.42 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. Jalil ZH, Sahib HB. Antiangiogenic Activity of Quinine Alone and in Combination with vitamin C in both ex vivo and in vivo Assays. Asian Pac J Cancer Prev. 2022 Dec 1;23(12):4185-4192. doi: 10.31557/APJCP.2022.23.12.4185. PMID: 36580001; PMCID: PMC9971453 4. Khanmohammadi A, Sadighian S, Ramazani A. Anti-plasmodial effects of quinine-loaded magnetic nanocomposite coated with heparin. Int J Pharm. 2022 Nov 25;628:122260. doi: 10.1016/j.ijpharm.2022.122260. Epub 2022 Oct 12. PMID: 36241033.

In vitro protocol:

In vivo protocol:

1. Jalil ZH, Sahib HB. Antiangiogenic Activity of Quinine Alone and in Combination with vitamin C in both ex vivo and in vivo Assays. Asian Pac J Cancer Prev. 2022 Dec 1;23(12):4185-4192. doi: 10.31557/APJCP.2022.23.12.4185. PMID: 36580001; PMCID: PMC9971453 2. Khanmohammadi A, Sadighian S, Ramazani A. Anti-plasmodial effects of quinine-loaded magnetic nanocomposite coated with heparin. Int J Pharm. 2022 Nov 25;628:122260. doi: 10.1016/j.ijpharm.2022.122260. Epub 2022 Oct 12. PMID: 36241033.

1: Roersch Van Der Hoogte A, Pieters T. Quinine, Malaria, and the Cinchona Bureau: Marketing Practices and Knowledge Circulation in a Dutch Transoceanic Cinchona-Quinine Enterprise (1920s-30s). J Hist Med Allied Sci. 2016 Apr;71(2):197-225. doi: 10.1093/jhmas/jrv009. Epub 2015 Jun 7. PubMed PMID: 26054829. 2: Rotella FM, Vig V, Olsson K, Pagirsky J, Aminov A, Kohen I, Bodnar RJ. Baclofen differentially mediates fructose-conditioned flavor preference and quinine-conditioned flavor avoidance in rats. Eur J Pharmacol. 2016 Mar 15;775:15-21. doi: 10.1016/j.ejphar.2016.02.015. Epub 2016 Feb 4. PubMed PMID: 26852956. 3: Mirijello A, Pacilli M, Pennacchia I, Manfrini A, Pacilli G. Giant "turtle-egg tumors": a forgotten complication of quinine injections. Intern Emerg Med. 2016 Mar;11(2):269-71. doi: 10.1007/s11739-015-1275-8. Epub 2015 Jun 23. PubMed PMID: 26099280. 4: Saguil A, Lauters R. Quinine for Leg Cramps. Am Fam Physician. 2016 Feb 1;93(3):177-8. PubMed PMID: 26926610. 5: Falade OB, Falusi AG, Olaniyi AA, Ezeasor C, Kwasi DA, Babalola CP. Significant Pharmacokinetic Interactions Between Quinine and Ampicillin-Cloxacillin Combination. Drugs R D. 2016 Mar 28. [Epub ahead of print] PubMed PMID: 27020278. 6: de Pablos-Martinez C, Porte L, Fraissinet F, Berry A, Séraissol P, Lavit M, Chatelut E, Concordet D, Gandia P. Quinine unbound concentration is the best marker for therapeutic drug monitoring. Ther Drug Monit. 2016 Mar 25. [Epub ahead of print] PubMed PMID: 27019100. 7: Song T, Chen J, Huang L, Gan W, Yin H, Jiang J, He T, Huang H, Hu X. Should we abandon quinine plus antibiotic for treating uncomplicated falciparum malaria? A systematic review and meta-analysis of randomized controlled trials. Parasitol Res. 2016 Mar;115(3):903-12. doi: 10.1007/s00436-015-4842-z. Epub 2015 Dec 14. PubMed PMID: 26661109. 8: Adegbola AJ, Soyinka JO, Adeagbo BA, Igbinoba SI, Nathaniel TI. Alteration of the Disposition of Quinine in Healthy Volunteers After Concurrent Ciprofloxacin Administration. Am J Ther. 2016 Mar-Apr;23(2):e398-404. doi: 10.1097/MJT.0000000000000087. PubMed PMID: 25406952. 9: Burger RJ, van Eijk AM, Bussink M, Hill J, Ter Kuile FO. Artemisinin-Based Combination Therapy Versus Quinine or Other Combinations for Treatment of Uncomplicated Plasmodium falciparum Malaria in the Second and Third Trimester of Pregnancy: A Systematic Review and Meta-Analysis. Open Forum Infect Dis. 2015 Nov 12;3(1):ofv170. doi: 10.1093/ofid/ofv170. eCollection 2016 Jan. Review. PubMed PMID: 26788543; PubMed Central PMCID: PMC4716351. 10: Ianni F, Sardella R, Carotti A, Natalini B, Lindner W, Lämmerhofer M. Quinine-Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio- and Stereoselectivity of Underivatized Oligopeptides. Chirality. 2016 Jan;28(1):5-16. doi: 10.1002/chir.22541. Epub 2015 Oct 20. PubMed PMID: 26483276. 11: Zhang Y, Zhu Y, Zhao N, Wu J, Hu Y. Application of isothermal titration calorimeter for screening bitterness-suppressing molecules of quinine. Food Chem. 2016 Jan 1;190:1007-12. doi: 10.1016/j.foodchem.2015.06.070. Epub 2015 Jun 22. PubMed PMID: 26213068. 12: Kluska M, Marciniuk-Kluska A, Prukała D, Prukała W. Analytics of Quinine and its Derivatives. Crit Rev Anal Chem. 2016;46(2):139-45. doi: 10.1080/10408347.2014.996700. PubMed PMID: 25831406. 13: Roszak K, Piasecka M, Katrusiak A, Kacprzak K. Double helix quinine-based supergelator. Soft Matter. 2016 Feb 7;12(5):1368-73. doi: 10.1039/c5sm02723c. Epub 2015 Dec 24. PubMed PMID: 26701368. 14: González Reyes AB, Hardisson de la Torre A, Gutiérrez Fernández AJ, Rubio Armendáriz C, Frías Tejera I, Revert Gironés C. [CAFFEINE AND QUININE IN SOFT DRINKS; CONTRIBUTION TO THE DIETARY INTAKE]. Nutr Hosp. 2015 Dec 1;32(6):2880-6. doi: 10.3305/nh.2015.32.6.9714. Spanish. PubMed PMID: 26667747. 15: Babalonis S, Hampson AJ, Lofwall MR, Nuzzo PA, Walsh SL. Quinine as a potential tracer for medication adherence: A pharmacokinetic and pharmacodynamic assessment of quinine alone and in combination with oxycodone in humans. J Clin Pharmacol. 2015 Dec;55(12):1332-43. doi: 10.1002/jcph.557. Epub 2015 Jul 29. PubMed PMID: 26032168; PubMed Central PMCID: PMC4666817. 16: Liles NW, Page EE, Liles AL, Vesely SK, Raskob GE, George JN. Diversity and severity of adverse reactions to quinine: A systematic review. Am J Hematol. 2016 Jan 28. doi: 10.1002/ajh.24314. [Epub ahead of print] PubMed PMID: 26822544. 17: Yang S, Shen LL, Kim YJ, Jeong JH. Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine. Org Biomol Chem. 2016 Jan 14;14(2):623-30. doi: 10.1039/c5ob01656h. PubMed PMID: 26540619. 18: Wang SW, Yang SG, Liu W, Zhang YX, Xu PX, Wang T, Ling TJ, Liu RT. Alpha-tocopherol quinine ameliorates spatial memory deficits by reducing beta-amyloid oligomers, neuroinflammation and oxidative stress in transgenic mice with Alzheimer's disease. Behav Brain Res. 2016 Jan 1;296:109-17. doi: 10.1016/j.bbr.2015.09.003. Epub 2015 Sep 7. PubMed PMID: 26358659. 19: Zhou D, Huang Z, Yu X, Wang Y, Li J, Wang W, Xie H. A Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction of Cyclic Trifluoromethyl Ketimines with Naphthols and Electron-Rich Phenols. Org Lett. 2015 Nov 20;17(22):5554-7. doi: 10.1021/acs.orglett.5b02668. Epub 2015 Nov 2. PubMed PMID: 26524623. 20: Rattanapunya S, Cressey TR, Rueangweerayut R, Tawon Y, Kongjam P, Na-Bangchang K. Pharmacokinetic Interactions Between Quinine and Lopinavir/Ritonavir in Healthy Thai Adults. Am J Trop Med Hyg. 2015 Dec;93(6):1383-90. doi: 10.4269/ajtmh.15-0453. Epub 2015 Sep 28. PubMed PMID: 26416104; PubMed Central PMCID: PMC4674263.