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Quinine

Athanor · official

C20H24N2O2 · 324.4 g/mol

IUPAC name: (5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol

Also called cinchona alkaloid, antimalarial, tonic water

Natural productsDrugsRings
Open in Athanor
The structure of Quinine
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol
Synonyms
cinchona alkaloid, antimalarial, tonic water
+ 39 more

(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol, Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-, (5-ethenyl-1-azabicyclo(2.2.2)octan-2-yl)-(6-methoxyquinolin-4-yl)methanol, RefChem:577168, Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-, 6'-Methoxycinchonan-9-ol, Quniacridine, Quinine anhydrous, {5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(6-methoxyquinolin-4-yl)methanol, Quinidine anhydrous, (6-methoxy-4-quinolyl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol, (1R)((2S,4S,5R)-5-vinylquinuclidin-2-yl)(6-methoxy(4-quinolyl))methan-1-ol, [5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol, 9-epi-Quinine, (+)-Chinidin, QUININE MONO HCL, SCHEMBL25528, (R)-(6-methoxy-4-quinolyl)-(5-vinylquinuclidin-2-yl)methanol, CHEMBL15088, 2-Quinuclidinemethanol, .alpha.-(6-methoxy-4-quinolyl)-5-vinyl-, orb1226574, SCHEMBL29645229, CHEBI:94416, GNF-PF-5473, (6-methoxy-4-quinolyl)-(5-vinylquinuclidin-2-yl)methanol, DTXSID40903283, (R)-[(2S,4S,5R)-1-Aza-5-vinylbicyclo[2.2.2]-oct-2-yl](6-methoxyquinolin-4-yl)methanol, HMS3369K22, HMS3373C19, HMS3751O13, HMS5086D14, EBC-06043, NSC131458, SBB006500, STL356793, AKOS015909346, NSC-131458, PB48768, NCGC00015871-03

Molecular formula
C20H24N2O2
Empirical formula
C10H12NO
Molecular weight
324.4 g/mol
Exact mass
324.18378
CAS number
130-95-0
PubChem CID
1065
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
Isomeric SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
InChI
InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3
InChIKey
LOUPRKONTZGTKE-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
24
Rings
5
Aromatic rings
2
Fraction sp³ carbons (Fsp3)
0.45
H-bond donors
1
H-bond acceptors
4
Rotatable bonds
4
TPSA (Ų)
45.6
Formal charge
0
XLogP3
2.9 PubChem
Complexity
457 PubChem
Stereocenters
0 defined, 5 undefinedCIP: C11: undefined · C13: undefined · C15: undefined · N18: undefined · C20: undefined
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C74.05%
  • H7.46%
  • N8.63%
  • O9.86%

Isotope pattern

100%324.18423%325.1872.9%326.190327.193

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
3.17 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-3.89 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
4.52 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 324.42
  • log P ≤ 5 (Crippen): 3.17
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Synblock Inc, Thermo Fisher Scientific, CAPOT.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  7. ·Literature on PubChem

Data last updated 2026-10-14.