Description
Cinchonidine (α-Quinidine) is a cinchona alkaloid found in Cinchona officinalis and Gongronema latifolium. A building block used in asymmetric synthesis in organic chemistry. Weak inhibitor of serotonin transporter (SERT) with Kis of 330, 4.2, 36, 196, 15 μM for dSERT, hSERT, hSERT I172M, hSERT S438T, hSERT Y95F, respectively. Antimalarial activities.
Synonyms
Cinchonidinederivedcatalyst
IUPAC Name
(R)-[(2S,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
Molecular Weight
294.39
Molecular Formula
C19H22N2O
Canonical SMILES
C=CC1CN2CCC1CC2C(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
InChI Key
KMPWYEUPVWOPIM-KODHJQJWSA-N
Boiling Point
436.16 °C
Melting Point
204-206 °C(lit.)
Flash Point
234.7 °C
Purity
94%
Density
1.0863 g/cm³
Solubility
Insoluble in water
Appearance
Crystalline powder
Storage
Keep in dark place, inert atmosphere, room temperature
Complexity
412
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
4
EC Number
207-622-3
Exact Mass
294.173213330
H-Bond Acceptor
3
H-Bond Donor
1
Heavy Atom Count
22
Isomeric SMILES
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O
Monoisotopic Mass
294.173213330
NSC Number
757800
Physical State
Crystalline powder
Rotatable Bond Count
3
Topological Polar Surface Area
36.4 Ų
UNII
1U622LRA8Z
