Quinine (free base)
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MedKoo CAT#: 318603

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

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


Chemical Structure

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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: 324.18
Molecular Weight: 324.420
Elemental Analysis: C, 74.04; H, 7.46; N, 8.64; O, 9.86

Price and Availability

Size Price Availability Quantity
2g USD 250 2 weeks
5g USD 390 2 weeks
10g USD 520 2 weeks
20g USD 750 2 weeks
50g USD 950 2 weeks
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Related CAS #: 60-93-5 (2HCl)   6119-70-6 (sulfate dihydrate)   804-63-7 (sulfate)   130-95-0 (free base)   60-93-5 (2HCl)   6119-70-6 (sulfate dihydrate)   804-63-7 (sulfate)   130-95-0 (free base)   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)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

InChi Key: LOUPRKONTZGTKE-UHFFFAOYSA-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

SMILES Code: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

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:
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/

Solubility Data

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

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.

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
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: 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.
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.

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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.