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Cinchonidine

CAT: 0013-GTR19175697-02Size: 2 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19175697-02Size:2 g
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Description
Cinchonidine is a natural alkaloid isolated from Cinchona officinalis and serves as a pseudo-enantiomer of cinchonine. This small molecule is utilized in asymmetric synthesis research and has been investigated in vitro for its potential biological activities.
CAS Number
485-71-2
Product Name Alternative
A-Quinidine, 5HT Receptor, 5HTReceptor, alpha-Quinidine, Cinchonidine, L-Cinchonidine, Parasite, SERT, SerotoninTransporter, Serotonin Transporter, α-Quinidine
Field of Research
Infectious Disease & Virology, Neuroscience, Pharmacology & Drug Discovery
Purity
94.96% (May vary between batches)
Solubility
H2O:< 1 mg/mL (insoluble or slightly soluble) ; DMSO:8.57 mg/mL (29.11 mM) ;10% DMSO+40% PEG300+5% Tween 80+45% Saline:1 mg/mL (3.4 mM) ; Ethanol:55 mg/mL (186.83 mM)
Smiles
[C@H] (O) ([C@]1 ([N@@]2C[C@H] (C=C) [C@] (C1) (CC2) [H]) [H]) C=3C4=C (N=CC3) C=CC=C4
Molecular Formula
C19H22N2O
Molecular Weight
294.39
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Cinchonidine

Cinchonidine is 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis. It has a role as a metabolite. It is an (8xi)-cinchonan-9-ol and a cinchona alkaloid. It derives from a hydride of an (8S)-cinchonan.

CAS Number485-71-2
PubChem CID101744
IUPAC Name(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
Molecular FormulaC19H22N2O
Molecular Weight294.4
XLogP2.7
Topological Polar Surface Area36.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Heavy Atom Count22
Formal Charge0
Complexity412
SMILES
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O
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
Chemical Structure
2D Structure
2D structure of Cinchonidine
CAS: 485-71-2
CID: 101744
Formula: C19H22N2O
MW: 294.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight294.4
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass294.173213330
Monoisotopic Mass294.173213330
Topological Polar Surface Area36.4 Ų
Heavy Atom Count22
Formal Charge0
Complexity412
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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