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Cinchonidine - 98%, high purity , CAS No.485-71-2
Quinine analog. Lysosomotropic agent.
Basic Description
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
Specifications & Purity
Moligand™, ≥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
Grade
Moligand™
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.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Alkaloids and derivatives
Class
Cinchona alkaloids
Subclass
Not available
Intermediate Tree Nodes
Not available
Direct Parent
Cinchona alkaloids
Alternative Parents
4-quinolinemethanols Quinuclidines Aralkylamines Pyridines and derivatives Piperidines Benzenoids Heteroaromatic compounds Trialkylamines Secondary alcohols 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols
Molecular Framework
Aromatic heteropolycyclic compounds
Substituents
Cinchonan-skeleton - 4-quinolinemethanol - Quinoline - Quinuclidine - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Alcohol - Aromatic alcohol - Aromatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
External Descriptors
cinchona alkaloid - (8xi)-cinchonan-9-ol
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
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
InChIKey
KMPWYEUPVWOPIM-KODHJQJWSA-N
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
Molecular Weight
294.39
Beilstein
89690
Reaxy-Rn
89687
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=89687&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
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
Molecular Weight
294.400 g/mol
XLogP3
2.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
294.173 Da
Monoisotopic Mass
294.173 Da
Topological Polar Surface Area
36.400 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
412.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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,
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).
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).
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).
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4 Citations
D2410264