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MedKoo Cat#: 318602 | Name: Quinidine (free base)
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Description:

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

Quinidine (free base) is a dextrorotatory stereoisomer of quinine with antimalarial and antiarrhythmic properties.

Chemical Structure

Quinidine (free base)
Quinidine (free base)
CAS#56-54-2 (free base)

Theoretical Analysis

MedKoo Cat#: 318602

Name: Quinidine (free base)

CAS#: 56-54-2 (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 Quantity
2g USD 250.00
5g USD 350.00
10g USD 450.00
20g USD 750.00
50g USD 1,050.00
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Related CAS #
747-45-5 (bisulfate) 27555-34-6 (polygalacturonate) 56-54-2 (free base) 1668-99-1 (HCl) 7054-25-3 (gluconate)
Synonym
Quinidine (free base); Chinidin; Pitayine; (+)-Quinidine; Quinidex; Chinidin; Fawns and McAllan Brand of Quinidine Sulfate; Nelson Brand of Quinidine Sulfate; Quincardine; Quinidex; Quinidine; Quinidine Sulfate; Quinora; Robins Brand of Quinidine Sulfate; Sulfate, Quinidine;
IUPAC/Chemical Name
(S)-[(2R,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 DMSO, not in water
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:
Quinidine is a potent, orally active, selective cytochrome P450db inhibitor. Quinidine is also a K+ channel blocker with an IC50 of 19.9 μM, and can induce apoptosis.
In vitro activity:
Before advancing to clinical trials, new drugs are screened for their pro-arrhythmic potential. Significant AP prolongation (a pro-arrhythmia marker) was seen in response to quinidine. This study developed an in silico-in vitro pipeline that identifies pro-arrhythmia risk and mechanism of ion channel-blocking drugs. It offers a new tool for evaluating cardiotoxicity during preclinical drug screening. Reference: Br J Pharmacol. 2022 Oct;179(20):4829-4843. https://pubmed.ncbi.nlm.nih.gov/35781252/
In vivo activity:
Zolmitriptan (ZOL), a member of triptans, has been used for the treatment of migraine with definite therapeutic effects. However, there have been several reported cases of ZOL-associated liver injury, and its underlying mechanisms remain unclear. Pre-treatment of ZOL-treated rat primary hepatocytes with quinidine was able to reverse ZOL-induced cytotoxicity. Reference: Xenobiotica. 2021 Nov;51(11):1292-1302. https://pubmed.ncbi.nlm.nih.gov/34096834/
Solvent mg/mL mM
Solubility
DMSO 32.4 100.00
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.

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. Clark AP, Wei S, Kalola D, Krogh-Madsen T, Christini DJ. An in silico-in vitro pipeline for drug cardiotoxicity screening identifies ionic pro-arrhythmia mechanisms. Br J Pharmacol. 2022 Oct;179(20):4829-4843. doi: 10.1111/bph.15915. Epub 2022 Jul 24. Erratum in: Br J Pharmacol. 2023 Mar;180(6):786-788. PMID: 35781252; PMCID: PMC9489646. 2. Turnheim K, Plass H, Wyskovsky W. Basolateral potassium channels of rabbit colon epithelium: role in sodium absorption and chloride secretion. Biochim Biophys Acta. 2002 Feb 18;1560(1-2):51-66. doi: 10.1016/s0005-2736(01)00456-4. PMID: 11958775. 3. Xu D, Chen S, Yang J, Wang X, Fang Z, Li M. Precision therapy with quinidine of KCNT1-related epileptic disorders: A systematic review. Br J Clin Pharmacol. 2022 Dec;88(12):5096-5112. doi: 10.1111/bcp.15479. Epub 2022 Sep 20. PMID: 35940594. 4. Han L, Jia Y, Zhao Y, Sun C, Zhao M, Peng Y, Zheng J. Metabolic activation of zolmitriptan mediated by CYP2D6. Xenobiotica. 2021 Nov;51(11):1292-1302. doi: 10.1080/00498254.2021.1938290. Epub 2021 Nov 3. PMID: 34096834.
In vitro protocol:
1. Clark AP, Wei S, Kalola D, Krogh-Madsen T, Christini DJ. An in silico-in vitro pipeline for drug cardiotoxicity screening identifies ionic pro-arrhythmia mechanisms. Br J Pharmacol. 2022 Oct;179(20):4829-4843. doi: 10.1111/bph.15915. Epub 2022 Jul 24. Erratum in: Br J Pharmacol. 2023 Mar;180(6):786-788. PMID: 35781252; PMCID: PMC9489646. 2. Turnheim K, Plass H, Wyskovsky W. Basolateral potassium channels of rabbit colon epithelium: role in sodium absorption and chloride secretion. Biochim Biophys Acta. 2002 Feb 18;1560(1-2):51-66. doi: 10.1016/s0005-2736(01)00456-4. PMID: 11958775.
In vivo protocol:
1. Xu D, Chen S, Yang J, Wang X, Fang Z, Li M. Precision therapy with quinidine of KCNT1-related epileptic disorders: A systematic review. Br J Clin Pharmacol. 2022 Dec;88(12):5096-5112. doi: 10.1111/bcp.15479. Epub 2022 Sep 20. PMID: 35940594. 2. Han L, Jia Y, Zhao Y, Sun C, Zhao M, Peng Y, Zheng J. Metabolic activation of zolmitriptan mediated by CYP2D6. Xenobiotica. 2021 Nov;51(11):1292-1302. doi: 10.1080/00498254.2021.1938290. Epub 2021 Nov 3. PMID: 34096834.
1: Wang Q, Zhu P, Ruan M, Wu H, Peng K, Han H, Somsen GW, Crommen J, Jiang Z. Chiral separation of acidic compounds using an O-9-(tert-butylcarbamoyl)quinidine functionalized monolith in micro-liquid chromatography. J Chromatogr A. 2016 Apr 29;1444:64-73. doi: 10.1016/j.chroma.2016.03.047. Epub 2016 Mar 19. PubMed PMID: 27038701. 2: Ruan X. The Effect of Quinidine, a Strong P-Glycoprotein Inhibitor, on the Pharmacokinetics and Central Nervous System Distribution of Naloxegol. J Clin Pharmacol. 2016 Apr;56(4):506-7. doi: 10.1002/jcph.651. PubMed PMID: 26954552. 3: Al-Huniti N. Reply to: Letter to the Editor "Effect of Quinidine, a Strong P-Glycoprotein Inhibitor, on the Pharmacokinetics and Central Nervous System Distribution of Naloxegol". J Clin Pharmacol. 2016 Apr;56(4):508. doi: 10.1002/jcph.674. PubMed PMID: 26954553. 4: Bui K, She F, Zhou D, Butler K, Al-Huniti N, Sostek M. The effect of quinidine, a strong P-glycoprotein inhibitor, on the pharmacokinetics and central nervous system distribution of naloxegol. J Clin Pharmacol. 2016 Apr;56(4):497-505. doi: 10.1002/jcph.613. Epub 2015 Nov 9. PubMed PMID: 26248047. 5: Garcia-Baran D, Johnson TM, Wagner J, Shen J, Geers M. Therapeutic Approach of a High Functioning Individual With Traumatic Brain Injury and Subsequent Emotional Volatility With Features of Pathological Laughter and Crying With Dextromethorphan/Quinidine. Medicine (Baltimore). 2016 Mar;95(12):e2886. doi: 10.1097/MD.0000000000002886. PubMed PMID: 27015166. 6: Cummings JL, Siffert J. Dextromethorphan-Quinidine for Agitation in Alzheimer Disease--Reply. JAMA. 2016 Mar 15;315(11):1166-7. doi: 10.1001/jama.2015.18289. PubMed PMID: 26978215. 7: Chong PF, Nakamura R, Saitsu H, Matsumoto N, Kira R. Ineffective quinidine therapy in early onset epileptic encephalopathy with KCNT1 mutation. Ann Neurol. 2016 Mar;79(3):502-3. doi: 10.1002/ana.24598. Epub 2016 Feb 12. PubMed PMID: 26748457. 8: Newman JC, Steinman MA. Dextromethorphan-Quinidine for Agitation in Alzheimer Disease. JAMA. 2016 Mar 15;315(11):1166. doi: 10.1001/jama.2015.18286. PubMed PMID: 26978214. 9: Wu H, Wang Q, Ruan M, Peng K, Zhu P, Crommen J, Han H, Jiang Z. Enantioseparation of N-derivatized amino acids by micro-liquid chromatography/laser induced fluorescence detection using quinidine-based monolithic columns. J Pharm Biomed Anal. 2016 Mar 20;121:244-52. doi: 10.1016/j.jpba.2015.12.011. Epub 2015 Dec 15. PubMed PMID: 26732881. 10: Turner J, Mitchell JL, Carroll BT, Denysenko L. Dextromethorphan/quinidine withdrawal-emergent catatonia. Ann Clin Psychiatry. 2016 Feb 1;28(1):e8-e9. [Epub ahead of print] PubMed PMID: 26855991. 11: Corbett A, Ballard C. Dextromethorphan and quinidine are suitable for off-label short-term treatment of agitation in people with Alzheimer's disease following first-line non-drug approaches. Evid Based Med. 2016 Feb;21(1):25. doi: 10.1136/ebmed-2015-110324. Epub 2015 Dec 23. PubMed PMID: 26701197. 12: Wang Q, Sánchez-López E, Han H, Wu H, Zhu P, Crommen J, Marina ML, Jiang Z. Separation of N-derivatized di- and tri-peptide stereoisomers by micro-liquid chromatography using a quinidine-based monolithic column - Analysis of l-carnosine in dietary supplements. J Chromatogr A. 2016 Jan 8;1428:176-84. doi: 10.1016/j.chroma.2015.09.016. Epub 2015 Sep 8. PubMed PMID: 26410182. 13: Fukao M, Kondo E, Nishino H, Hattori R, Horie A, Hashimoto Y. Presence of an H(+)/Quinidine Antiport System in Madin-Darby Canine Kidney Cells. Eur J Drug Metab Pharmacokinet. 2015 Dec 1. [Epub ahead of print] PubMed PMID: 26628429. 14: Higgins AY, Waks JW, Josephson ME. Influence of Gender on the Tolerability, Safety, and Efficacy of Quinidine Used for Treatment of Supraventricular and Ventricular Arrhythmias. Am J Cardiol. 2015 Dec 15;116(12):1845-51. doi: 10.1016/j.amjcard.2015.09.042. Epub 2015 Oct 9. PubMed PMID: 26514302. 15: Probst V, Gourraud JB. Quinidine in Brugada Syndrome: Still a Long Way to Go…. Circ Arrhythm Electrophysiol. 2015 Dec;8(6):1309-10. doi: 10.1161/CIRCEP.115.003576. PubMed PMID: 26671933. 16: Mikati MA, Jiang YH, Carboni M, Shashi V, Petrovski S, Spillmann R, Milligan CJ, Li M, Grefe A, McConkie A, Berkovic S, Scheffer I, Mullen S, Bonner M, Petrou S, Goldstein D. Quinidine in the treatment of KCNT1-positive epilepsies. Ann Neurol. 2015 Dec;78(6):995-9. doi: 10.1002/ana.24520. Epub 2015 Nov 18. PubMed PMID: 26369628; PubMed Central PMCID: PMC4811613. 17: Liu L, Collier AC, Link JM, Domino KB, Mankoff DA, Eary JF, Spiekerman CF, Hsiao P, Deo AK, Unadkat JD. Modulation of P-glycoprotein at the Human Blood-Brain Barrier by Quinidine or Rifampin Treatment: A Positron Emission Tomography Imaging Study. Drug Metab Dispos. 2015 Nov;43(11):1795-804. doi: 10.1124/dmd.114.058685. Epub 2015 Sep 9. PubMed PMID: 26354948; PubMed Central PMCID: PMC4613948. 18: Doody RS, D'Amico S, Cutler AJ, Davis CS, Shin P, Ledon F, Yonan C, Siffert J. An open-label study to assess safety, tolerability, and effectiveness of dextromethorphan/quinidine for pseudobulbar affect in dementia: PRISM II results. CNS Spectr. 2015 Oct 16:1-10. [Epub ahead of print] PubMed PMID: 26471212. 19: Wrighton DC, Muench SP, Lippiat JD. Mechanism of inhibition of mouse Slo3 (KCa 5.1) potassium channels by quinine, quinidine and barium. Br J Pharmacol. 2015 Sep;172(17):4355-63. doi: 10.1111/bph.13214. Epub 2015 Jul 14. PubMed PMID: 26045093; PubMed Central PMCID: PMC4556473. 20: Sokolov AY, Lyubashina OA, Berkovich RR, Panteleev SS. Intravenous dextromethorphan/quinidine inhibits activity of dura-sensitive spinal trigeminal neurons in rats. Eur J Pain. 2015 Sep;19(8):1086-94. doi: 10.1002/ejp.631. Epub 2014 Nov 20. PubMed PMID: 25410439.