Determine the necessary mass, volume, or concentration for preparing a solution.
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SKU | Size | Availability | Price | Qty |
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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.
Synonyms | BRD-K17661460-001-04-0 | BRD-K39079086-001-05-0 | IDI1_000501 | AKOS016008633 | HY-N0173 | KBio2_006781 | KBioGR_001805 | PDSP2_000142 | (R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol | SDCCGMLS-0066969.P001 | Spectrum5_000964 | QUININE |
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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. |
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Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Pubchem Sid | 488187274 |
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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 |
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
Lot Number | Certificate Type | Date | Item |
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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 |
Solubility | Insoluble in water; Soluble in Alcohol,Ether,Chloroform |
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Sensitivity | Light Sensitive |
Specific Rotation[α] | -107.5 ° (C=1, EtOH) |
Melt Point(°C) | 204-206°C |
Pictogram(s) | GHS08, GHS07 |
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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 |
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] [10.2147/DDDT.S404055] |
2. Zhi-Yuan Zhang, Li-Li Rui, Ya-Li Lin, Hui-Dan Zhang, Ji-Ming Ou, Jian-Feng He, Quan-Zhou Wu. (2021) Preparation of ordered macroporous molecularly imprinted polymers and their applications in purifying cinchona alkaloids from cinchona extract. POLYMER INTERNATIONAL, 70 (9): (1344-1355). [PMID:] [10.1002/pi.6205] |
3. Yuan Tan, Lijing Jing, Yonghong Ding, Tianxin Wei. (2015) A novel double-layer molecularly imprinted polymer film based surface plasmon resonance for determination of testosterone in aqueous media. APPLIED SURFACE SCIENCE, 342 (84). [PMID:] [10.1016/j.apsusc.2015.03.031] |
4. Li Liu, Xuecai Tan, Xiaoxue Fang, Yuexin Sun, Fuhou Lei, Zaiyin Huang. (2012) Electrochemical Sensor Based on Molecularly Imprinted Polymer Film Prepared with Functional Abietic-Type Acids as Cross-Linker for the Determination of Quinine. ELECTROANALYSIS, 24 (7): (1647-1654). [PMID:] [10.1002/elan.201200085] |
1. K Itoh,M Yamamura,S Muramatsu,K Hoshino,A Masubuchi,T Sasaki,Y Tanaka. (2005-09-30) Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.. Xenobiotica; the fate of foreign compounds in biological systems, 35 ((6)): (561-573). [PMID:16192108] |
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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] |
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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] |
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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] |
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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] |
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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] |
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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] [10.2147/DDDT.S404055] |
31. Zhi-Yuan Zhang, Li-Li Rui, Ya-Li Lin, Hui-Dan Zhang, Ji-Ming Ou, Jian-Feng He, Quan-Zhou Wu. (2021) Preparation of ordered macroporous molecularly imprinted polymers and their applications in purifying cinchona alkaloids from cinchona extract. POLYMER INTERNATIONAL, 70 (9): (1344-1355). [PMID:] [10.1002/pi.6205] |
32. Yuan Tan, Lijing Jing, Yonghong Ding, Tianxin Wei. (2015) A novel double-layer molecularly imprinted polymer film based surface plasmon resonance for determination of testosterone in aqueous media. APPLIED SURFACE SCIENCE, 342 (84). [PMID:] [10.1016/j.apsusc.2015.03.031] |
33. Li Liu, Xuecai Tan, Xiaoxue Fang, Yuexin Sun, Fuhou Lei, Zaiyin Huang. (2012) Electrochemical Sensor Based on Molecularly Imprinted Polymer Film Prepared with Functional Abietic-Type Acids as Cross-Linker for the Determination of Quinine. ELECTROANALYSIS, 24 (7): (1647-1654). [PMID:] [10.1002/elan.201200085] |