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MedKoo Cat#: 592567 | Name: Cinchonine
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Description:

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

Cinchonine prevents High-Fat-Diet-Induced Obesity through downregulation of Adipogenesis and Adipose inflammation.

Chemical Structure

Cinchonine
Cinchonine
CAS#118-10-5

Theoretical Analysis

MedKoo Cat#: 592567

Name: Cinchonine

CAS#: 118-10-5

Chemical Formula: C19H22N2O

Exact Mass: 294.1732

Molecular Weight: 294.40

Elemental Analysis: \C, 77.52; H, 7.53; N, 9.52; O, 5.43

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Cinchonine; NSC 6176; NSC-6176; NSC6176; Cinchonan-9-ol; (9S)- Cinchonine; (9S)-Cinchonan-9-ol; d-Cinchonine; (+)-Cinchonine; (8R,9S)-Cinchonine
IUPAC/Chemical Name
(S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
InChi Key
KMPWYEUPVWOPIM-QAMTZSDWSA-N
InChi Code
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
SMILES Code
O[C@@H](C1=CC=NC2=C1C=CC=C2)[C@]3([H])[N@@]4C[C@@H]([C@](CC4)([H])C3)C=C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 294.40 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: Jung SA, Choi M, Kim S, Yu R, Park T. Cinchonine Prevents High-Fat-Diet-Induced Obesity through Downregulation of Adipogenesis and Adipose Inflammation. PPAR Res. 2012;2012:541204. doi: 10.1155/2012/541204. Epub 2012 May 16. PubMed PMID: 22675336; PubMed Central PMCID: PMC3362995. 2: Youn SW, Song HS, Park JH. Asymmetric domino multicatalysis for the synthesis of 3-substituted phthalides: cinchonine/NHC cooperative system. Org Lett. 2014 Feb 7;16(3):1028-31. doi: 10.1021/ol5000617. Epub 2014 Jan 24. PubMed PMID: 24460222. 3: Xi Y, Shi X. Cinchonine and thiourea. Chem Commun (Camb). 2013 Oct 7;49(77):8583-5. doi: 10.1039/c3cc40825f. PubMed PMID: 23948716. 4: Lee SY, Rhee YH, Jeong SJ, Lee HJ, Lee HJ, Jung MH, Kim SH, Lee EO, Ahn KS, Ahn KS, Kim SH. Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells. Environ Toxicol. 2011 Aug;26(4):424-31. doi: 10.1002/tox.20568. Epub 2010 Mar 1. PubMed PMID: 20196146. 5: Furusawa S, Nakano S, Wu J, Sakaguchi S, Takayanagi M, Sasaki KI, Satoh S. Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. J Pharm Pharmacol. 2001 Jul;53(7):1029-39. PubMed PMID: 11480538. 6: Genne P, Duchamp O, Solary E, Magnette J, Belon JP, Chauffert B. Cinchonine per os: efficient circumvention of P-glycoprotein-mediated multidrug resistance. Anticancer Drug Des. 1995 Mar;10(2):103-18. PubMed PMID: 7710633. 7: Genne P, Dimanche-Boitrel MT, Mauvernay RY, Gutierrez G, Duchamp O, Petit JM, Martin F, Chauffert B. Cinchonine, a potent efflux inhibitor to circumvent anthracycline resistance in vivo. Cancer Res. 1992 May 15;52(10):2797-801. PubMed PMID: 1581892. 8: Shah BH, Nawaz Z, Virani SS, Ali IQ, Saeed SA, Gilani AH. The inhibitory effect of cinchonine on human platelet aggregation due to blockade of calcium influx. Biochem Pharmacol. 1998 Oct 15;56(8):955-60. PubMed PMID: 9776305. 9: Kuhlmann O, Hofmann HS, Müller SP, Weiss M. Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin. Anticancer Drugs. 2003 Jul;14(6):411-6. PubMed PMID: 12853881. 10: Genne P, Duchamp O, Solary E, Pinard D, Belon JP, Dimanche-Boitrel MT, Chauffert B. Comparative effects of quinine and cinchonine in reversing multidrug resistance on human leukemic cell line K562/ADM. Leukemia. 1994 Jan;8(1):160-4. PubMed PMID: 8289482. 11: Solary E, Mannone L, Moreau D, Caillot D, Casasnovas RO, Guy H, Grandjean M, Wolf JE, André F, Fenaux P, Canal P, Chauffert B, Wotawa A, Bayssas M, Genne P. Phase I study of cinchonine, a multidrug resistance reversing agent, combined with the CHVP regimen in relapsed and refractory lymphoproliferative syndromes. Leukemia. 2000 Dec;14(12):2085-94. PubMed PMID: 11187897. 12: el Benna J, Labro MT. Effect of quinine and cinchonine on human neutrophils functions in vitro. J Antimicrob Chemother. 1990 Jun;25(6):949-57. PubMed PMID: 2164514. 13: ANDREWS JC, CORNATZER WE. The metabolism of cinchonine in dogs and in man. J Natl Malar Soc. 1948 Dec;6(4):246-50. PubMed PMID: 18895752. 14: Karczmarzyk Z, Lipińska TM, Wysocki W, Denisiuk M, Piechocka K. Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases. Acta Crystallogr C. 2011 Sep;67(Pt 9):o346-9. doi: 10.1107/S0108270111027272. Epub 2011 Aug 5. PubMed PMID: 21881184. 15: Gu Q, You SL. Desymmetrization of cyclohexadienones via asymmetric Michael reaction catalyzed by cinchonine-derived urea. Org Lett. 2011 Oct 7;13(19):5192-5. doi: 10.1021/ol202073p. Epub 2011 Sep 14. PubMed PMID: 21913734. 16: Karbwang J, Bunnag D, Harinasuta T, Chittamas S, Berth J, Druilhe P. Pharmacokinetics of quinine, quinidine and Cinchonine when given as combination. Southeast Asian J Trop Med Public Health. 1992 Dec;23(4):773-6. PubMed PMID: 1298088. 17: ROBINSON R. Constitution of strychnine and its relation to cinchonine. Nature. 1947 Feb 22;159(4034):263. PubMed PMID: 20287526. 18: SINHA GN. My experience with cinchonine. Antiseptic. 1946 Jan;43:54. PubMed PMID: 21016099. 19: Kaczorowski T, Justyniak I, Prochowicz D, Zelga K, Kornowicz A, Lewiński J. New insights into cinchonine-aluminium complexes and their application as chiral building blocks: unprecedented ligand-exchange processes in the presence of ZnR2 compounds. Chemistry. 2012 Oct 15;18(42):13460-5. doi: 10.1002/chem.201202295. Epub 2012 Sep 5. PubMed PMID: 22952022. 20: Király P, Soós T, Varga S, Vakulya B, Tárkányi G. Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchon ine. Magn Reson Chem. 2010 Jan;48(1):13-9. doi: 10.1002/mrc.2531. PubMed PMID: 19862796.