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130-95-0 molecular structure
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(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

ChemBase ID: 130392
Molecular Formular: C20H24N2O2
Molecular Mass: 324.41676
Monoisotopic Mass: 324.18377802
SMILES and InChIs

SMILES:
O(c1cc2c(nccc2[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](C=C)C3)cc1)C
Canonical SMILES:
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)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/t13-,14-,19-,20+/m0/s1
InChIKey:
LOUPRKONTZGTKE-WZBLMQSHSA-N

Cite this record

CBID:130392 http://www.chembase.cn/molecule-130392.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
IUPAC Traditional name
quinine
Brand Name
Qualaquin
Synonyms
Quinine
Quinine
奎宁
CAS Number
130-95-0
EC Number
205-003-2
MDL Number
MFCD00198096
Beilstein Number
91867
PubChem SID
24848751
162224671
24853550
PubChem CID
3034034
8549
CHEBI ID
15854
ATC CODE
M09AA01
P01BC01
CHEMBL
170
Chemspider ID
84989
DrugBank ID
DB00468
IUPHAR ligand ID
2510
KEGG ID
D08460
Unique Ingredient Identifier
A7V27PHC7A
Wikipedia Title
Quinine
Medline Plus
a682322

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.892048  H Acceptors
H Donor LogD (pH = 5.5) -0.7213722 
LogD (pH = 7.4) 0.863951  Log P 2.513464 
Molar Refractivity 94.6936 cm3 Polarizability 38.350784 Å3
Polar Surface Area 45.59 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
173-175 °C(lit.) expand Show data source
177°C (350.6°F) expand Show data source
Optical Rotation
[α]20/D -126±5°, c = 1% in chloroform expand Show data source
[α]25/D -165°, c = 2 in ethanol expand Show data source
Fluorescence
λex 347 nm; λem 448 nm in 0.5 M sulfuric acid expand Show data source
RTECS
VA6020000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38-42/43 expand Show data source
Safety Statements
22-26-36/37-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H317-H319-H334-H335 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338-P342 + P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Bioavailability
76 to 88% expand Show data source
Excretion
Renal (20%) expand Show data source
Half Life
~18 hours expand Show data source
Metabolism
Hepatic (mostly CYP3A4 and CYP2C19-mediated) expand Show data source
Protein Bound
~70% expand Show data source
Legal Status
Rx-only USA expand Show data source
Pregnancy Category
C (USA), D (Au) expand Show data source
Gene Information
human ... ABCB1(5243), CYP2C9(1559), CYP2D6(1565)rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522) expand Show data source
Purity
≥98.0% (dried material, NT) expand Show data source
90% expand Show data source
Grade
certified reference material expand Show data source
TraceCERT® expand Show data source
Suitability
suitable for fluorescence expand Show data source
Impurities
≤5% dihydroquinine (HPLC) expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Loss on Drying
≤1% loss on drying, 110 °C expand Show data source
Empirical Formula (Hill Notation)
C20H24N2O2 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - Q1878 external link
Biochem/physiol Actions
Potassium channel blocker
Sigma Aldrich - 22620 external link
Biochem/physiol Actions
Potassium channel blocker
Other Notes
Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions1,2; In additions of diethylzinc to aldehydes.3
Sigma Aldrich - 145904 external link
Biochem/physiol Actions
Potassium channel blocker
Other Notes
remainder hydroquinine
Packaging
10, 50 g in poly bottle
Application
Resolving agent for carboxylic acids.1 Catalyzes the kinetic resolution of furanones.2
Sigma Aldrich - 69311 external link
Biochem/physiol Actions
钾通道阻断剂。
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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