Epiquinidine
Basic information
- CAS
572-59-8- Standard SMILES
C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](O)c1ccnc2ccc(OC)cc12- InChIKey
LOUPRKONTZGTKE-AFHBHXEDSA-N- Molecular formula
- C20H24N2O2
- Average molar mass
- 324.4 g/mol
- Monoisotopic mass
- 324.18377801
Names & identifiers
- Preferred name
- Epiquinidine
- IUPAC
- (R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
- English name
- (9R)-6'-methoxycinchonan-9-ol
- Molecular formula
- C20H24N2O2
- Molecular weight
- 324.42
Names & synonyms
Epiquinidine572-59-8(9R)-6'-Methoxycinchonan-9-ol9-epi-Quinidine9-EpiquinidineRN974X9U97EINECS 209-340-6EPIQUINIDINE [MI]ICQ-12DTXSID40205835Cinchonan-9-al, 6'-methoxy-, (9R)-CINCHONAN-9-OL, 6'-METHOXY-, (9R)-
Show more names
(9R)-Epiquindine(8R,9R)-6'-Methoxycinchonan-9-ol(R)-(6-methoxy-4-quinolyl)-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol(R)-[(4S,5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol
RefChem:590941DTXCID70128326209-340-6GNF-Pf-180(R)-[(2R,4S,5R)-5-ETHENYL-1-AZABICYCLO[2.2.2]OCTAN-2-YL](6-METHOXYQUINOLIN-4-YL)METHANOL(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanolEpichinidin.beta.-Quinine
Database identifiers
- CAS
572-59-8- PubChem CID
- 94175
- DTXSID
DTXSID40205835- ChEMBL
CHEMBL576997- UNII
- RN974X9U97
- EC Number
- 209-340-6
- Nikkaji
- J6.544G
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 45.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 457
Physicochemical properties
- Melting point
- 111 · 111-113°
- alpha
- 25 · D25 +107.8° (c = 1.02 in ethanol)
- Boiling point
- 462.75 °C · 462.75°C (rough estimate)
- Density
- 1.1294 · 1.1294 (rough estimate)
- refractive index
- 1.57 · 1.5700 (estimate)
- storage temp.
- 2 · 2-8°C
- form
- Solid-Liquid Mixture
- pka
- 12.8 · 12.80±0.20(Predicted)
- color
- White to off-white
- FDA UNII
- 974 X9U97 · RN974X9U97
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H317-H334
- Precautionary statements
- 261 · P261-P280-P342+P311
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-42/43
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- risk_code
- 22-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-36/37-45
- Hazard statements
- H302-H317-H334
- Precautionary statements
- P261-P280-P342+P311
Chemistry & industry
Applications
DescriptionThis alkaloid is stereoisomeric with epiQuinine and occurs in 'Quinoidine', the mixture of amorphous bases left after extraction of the four primary alkaloids of Cinchona bark. It crystallizes in colourless leaflets from Et20 and is fluorescent in dilute H2S04, It is dextrorotatory with [α]19D + 102.4° (c 0.8648, EtOH) and furnishes a dihydrochloride, m.p. 195-6°C (dec.); [α]20D + 45.5° (c 0.8012, EtOH); a hydrobromide, m.p. 240°C; thiocyanate, m.p. 193°C; [α]20D + 44.5° (H20) and the dibenzoyl-(+)-tartrate, m.p. 167°C; [α]201D + 3.7° (c 0.8068, EtOH-CHCI 3 ). Catalytic hydrogenation with Pd gives the dihydro derivative, m.p. 122°C; [α]22D + 73.1° (c 0.766, EtOH).
UsesThe 9-epimer of Quinidine (Q685000). Antimalarial.
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Related reactions
1 records
Compound notes
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