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Cinchonidine - 98%, high purity , CAS No.485-71-2

1 Citations

≥98%

CAS#: 485-71-2
Formula: C₁₉H₂₂N₂O
Molecular Weight: 294.39
Beilstein Registry Number: 89690
EC Number: 207-622-3
MDL number: MFCD00006783
PubChem CID: 101744
PubChem SID: 488187274

Item Number

C109632

Grouped product items
SKU	Size	Availability	Price
C109632-1g	1g	In stock	$9.90
C109632-5g	5g	In stock	$14.90
C109632-25g	25g	In stock	$56.90
C109632-100g	100g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$203.90

Quinine analog. Lysosomotropic agent.

View related series

Pyridines Six-Membered Heterocyclic Compounds

Basic Description

Synonyms	CINCHONIDINE \| 485-71-2 \| (-)-Cinchonidine \| (8S,9R)-Cinchonidine \| Cinchovatine \| alpha-Quinidine \| L-Cinchonidine \| Cinchovatine- \| MFCD00006783 \| a-quinidine \| TCMDC-123934 \| cinchonine \| (8S,9R)-cinchonan-9-ol \| (8alpha,9R)-Cinchonan-9-ol \| 1U622LRA8Z \| CHEBI:3703 \| 485-71-2 (free b
Specifications & Purity	≥98%
Biochemical and Physiological Mechanisms	Quinine analog. Lysosomotropic agent. Inhibits Plasmodium falciparum. Interferes with ferriprotoporphyrin formation. Weak SERT inhibitor. Shows antimalarial effects in vivo. Orally active.
Storage Temp	Protected from light
Shipped In	Normal
Note	Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description	application： It finds its uses as an antimalarial compound. It is a lysosomotropic agent, inhibits Plasmodium falciparum, interferes with ferriprotoporphyrin formation and is a weak SERT inhibitor.

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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WI-38 (2654 Activities)

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HepG2 (196354 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Plasmodium falciparum (966862 Activities)

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ht1 Hexose transporter 1 (14071 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Leishmania mexicana mexicana (27 Activities)

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SARS-CoV-2 (38078 Activities)

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Names and Identifiers

Pubchem Sid	488187274
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/488187274
IUPAC Name	(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
INCHI	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
InChi Key	KMPWYEUPVWOPIM-KODHJQJWSA-N
Canonical SMILES	C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
Isomeric SMILES	C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O
WGK Germany	3
RTECS	GD2975000
PubChem CID	101744
Molecular Weight	294.39
Beilstein	89690
Reaxy-Rn	5286475

Certificates

Certificate of Analysis(COA)

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10 results found

Lot Number	Certificate Type	Date	Item
D2410264	Certificate of Analysis	Mar 20, 2024	C109632
C23211017	Certificate of Analysis	Jul 15, 2022	C109632
C2426022	Certificate of Analysis	Jul 15, 2022	C109632
D2423057	Certificate of Analysis	Jul 15, 2022	C109632
J2211779	Certificate of Analysis	Jul 15, 2022	C109632
J2211843	Certificate of Analysis	Jul 15, 2022	C109632
J2211859	Certificate of Analysis	Jul 15, 2022	C109632
J2211921	Certificate of Analysis	Jul 15, 2022	C109632
D1816118	Certificate of Analysis	Feb 22, 2022	C109632
D1816119	Certificate of Analysis	Feb 22, 2022	C109632

Chemical and Physical Properties

Solubility	Insoluble in water; Soluble in Alcohol,Ether,Chloroform
Sensitivity	Light Sensitive
Specific Rotation[α]	-107.5 ° (C=1, EtOH)
Melt Point(°C)	204-206°C

Safety and Hazards(GHS)

Pictogram(s)	GHS08, GHS07
Signal	Warning
Hazard Statements	H373:Causes damage to organs through prolonged or repeated exposure H302:Harmful if swallowed H317:May cause an allergic skin reaction H361:Suspected of damaging fertility or the unborn child
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P260:Do not breathe dust/fume/gas/mist/vapors/spray. P270:Do not eat, drink or smoke when using this product. P272:Contaminated work clothing should not be allowed out of the workplace. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention. P362+P364:Take off contaminated clothing and wash it before reuse. P330:Rinse mouth. P203:Obtain, read and follow all safety instructions before use. P301+P317:IF SWALLOWED: Get medical help. P318:if exposed or concerned, get medical advice. P319:Get medical help if you feel unwell.
WGK Germany	3
RTECS	GD2975000
Reaxy-Rn	5286475
Merck Index	2286

Citations of This Product

1. Huan Xue, Hao-Jie Xing, Bin Wang, Chao Fu, Yu-Shan Zhang, Xi Qiao, Chao Guo, Xiao-Li Zhang, Bin Hu, Xin Zhao, Li-Jiao Deng, Xiao-Chan Zhu, Yi Zhang, Yun-Feng Liu. (2023) Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis. Drug Design Development and Therapy, [PMID:37197367]

References

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3. György Szöllösi,Abhijit Chatterjee,Péter Forgó,Mihály Bartók,Fujio Mizukami. (2006-07-15) Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.. The journal of physical chemistry. A, 109 ((5)): (860-868). [PMID:16838957]
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7. Chun-Yin Zhu,Xian-Ming Deng,Xiu-Li Sun,Jun-Cheng Zheng,Yong Tang. (2008-05-16) Highly enantioselective synthesis of isoxazoline N-oxides.. Chemical communications (Cambridge, England), ((6)): (738-740). [PMID:18478708]
8. Atsushi Urakawa,Daniel M Meier,Heinz Rüegger,Alfons Baiker. (2008-07-19) Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.. The journal of physical chemistry. A, 112 ((31)): (7250-7255). [PMID:18636698]
9. Jian Zhang,Shumei Chen,Tao Wu,Pingyun Feng,Xianhui Bu. (2008-09-09) Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.. Journal of the American Chemical Society, 130 ((39)): (12882-12883). [PMID:18774816]
10. Erik Schmidt,Wolfgang Kleist,Frank Krumeich,Tamas Mallat,Alfons Baiker. (2009-12-30) Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine.. Chemistry (Weinheim an der Bergstrasse, Germany), 16 ((7)): (2181-2192). [PMID:20039346]
11. Yueqi Liu,Kaori Hoshina,Jun Haginaka. (2010-02-16) Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization.. Talanta, 80 ((5)): (1713-1718). [PMID:20152401]
12. Sarfraz A Nawaz,Muhammad Ayaz,Wolfgang Brandt,Ludger A Wessjohann,Bernhard Westermann. (2010-12-28) Cation-π and π-π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids.. Biochemical and biophysical research communications, 404 ((4)): (935-940). [PMID:21185266]
13. Roman Büttiker,Jürgen Ebert,Christian Hinderling,Christian Adlhart. (2011-05-03) Membranes for specific adsorption: immobilizing molecularly imprinted polymer microspheres using electrospun nanofibers.. Chimia, 65 ((3)): (182-186). [PMID:21528654]
14. Zbigniew Karczmarzyk,Teodozja M Lipińska,Waldemar Wysocki,Monika Denisiuk,Katarzyna Piechocka. (2011-09-02) Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases.. Acta crystallographica. Section C, Crystal structure communications, 67 ((Pt 9)): (o346-o349). [PMID:21881184]
15. Nobutaka Maeda,Konrad Hungerbühler,Alfons Baiker. (2011-11-17) Asymmetric hydrogenation on chirally modified Pt: origin of hydrogen in the N-H-O interaction between cinchonidine and ketone.. Journal of the American Chemical Society, 133 ((49)): (19567-19569). [PMID:22084835]
16. Pierrick Nun,Violaine Pérez,Monique Calmès,Jean Martinez,Frédéric Lamaty. (2012-02-11) Preparation of chiral amino esters by asymmetric phase-transfer catalyzed alkylations of Schiff bases in a ball mill.. Chemistry (Weinheim an der Bergstrasse, Germany), 18 ((12)): (3773-3779). [PMID:22322525]
17. Arkajyoti Sengupta,Raghavan B Sunoj. (2012-11-17) Mechanistic insights on organocatalytic enantioselective decarboxylative protonation by epicinchona-thiourea hybrid derivatives.. The Journal of organic chemistry, 77 ((23)): (10525-10536). [PMID:23153357]
18. Fumihiko Kitagawa,Hiroshi Sudaki,Kenji Sueyoshi,Koji Otsuka. (2013-01-11) Open-tubular electrochromatographic chiral separation of amino acids using an organic nanocrystals immobilized capillary.. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 29 ((1)): (107-112). [PMID:23303094]
19. Matthew L Beckman,Akula Bala Pramod,Danielle Perley,L Keith Henry. (2013-10-29) Stereoselective inhibition of serotonin transporters by antimalarial compounds.. Neurochemistry international, 73 (98-106). [PMID:24161619]
20. Oleg V Larionov,David Stephens,Adelphe Mfuh,Gabriel Chavez. (2014-01-15) Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.. Organic letters, 16 ((3)): (864-867). [PMID:24410049]
21. Angelo Vargas,Norberto Bonalumi,Davide Ferri,Alfons Baiker. (2006-01-20) Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.. The journal of physical chemistry. A, 110 ((3)): (1118-1127). [PMID:16420016]
22. Simon Diezi,Davide Ferri,Angelo Vargas,Tamas Mallat,Alfons Baiker. (2006-03-23) The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.. Journal of the American Chemical Society, 128 ((12)): (4048-4057). [PMID:16551114]
23. Erik Schmidt,Davide Ferri,Alfons Baiker. (2007-06-23) Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.. Langmuir : the ACS journal of surfaces and colloids, 23 ((15)): (8087-8093). [PMID:17583922]
24. Kensuke Fukiya,Kunio Itoh,Satoshi Yamaguchi,Akiko Kishiba,Mayuko Adachi,Nobuaki Watanabe,Yorihisa Tanaka. (2009-11-17) A single amino acid substitution confers high cinchonidine oxidation activity comparable with that of rabbit to monkey aldehyde oxidase 1.. Drug metabolism and disposition: the biological fate of chemicals, 38 ((2)): (302-307). [PMID:19910515]
25. Ping Liu,Sun Liang,Ben-Jie Wang,Rui-Chen Guo. (2010-02-20) Construction of expression system of rabbit aldehyde oxidase cDNA for the clarification of species differences.. European journal of drug metabolism and pharmacokinetics, 34 ((3-4)): (205-211). [PMID:20166440]
26. Sonia Keunchkarian,Jaiver Osorio Grisales,Juan M Padró,Susana Boeris,Cecilia B Castells. (2012-05-11) Development of a chiral stationary phase based on cinchonidine. Comparison with a quinine-based chiral column.. Chirality, 24 ((7)): (512-518). [PMID:22573362]
27. Naoki Haraguchi,Parbhej Ahamed,Md Masud Parvez,Shinichi Itsuno. (2012-06-21) Synthesis of main-chain chiral quaternary ammonium polymers for asymmetric catalysis using quaternization polymerization.. Molecules (Basel, Switzerland), 17 ((6)): (7569-7583). [PMID:22713348]
28. Nicholas G Spiropulos,Jennifer M Heemstra. (2013-02-02) Templating effect in DNA proximity ligation enables use of non-bioorthogonal chemistry in biological fluids.. Artificial DNA, PNA & XNA, 3 ((3)): (123-128). [PMID:23370267]
29. Neng-jun Zhong,Li Liu,Dong Wang,Yong-Jun Chen. (2013-03-28) Enantioselective tandem reaction of chromone-derived Morita-Baylis-Hillman carbonates with benzylamines catalyzed by a trifunctional organocatalyst: the synthesis of chiral 3-aminomethylene-flavanones.. Chemical communications (Cambridge, England), 49 ((35)): (3697-3699). [PMID:23532090]
30. Huan Xue, Hao-Jie Xing, Bin Wang, Chao Fu, Yu-Shan Zhang, Xi Qiao, Chao Guo, Xiao-Li Zhang, Bin Hu, Xin Zhao, Li-Jiao Deng, Xiao-Chan Zhu, Yi Zhang, Yun-Feng Liu. (2023) Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis. Drug Design Development and Therapy, [PMID:37197367]

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