hydroquinine
quinine, 10,11-dihydro-
Identification
| Name | hydroquinine |
| IUPAC | (R)-(5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol |
| CAS Number | 522-66-7 |
| EINECS | 208-334-0 |
| FDA UNII | 31J3Q51T6L |
| Molecular Formula | C20 H26 N2 O2 |
| Molecular Weight | 326.43962000 |
| MDL Number | MFCD00151107 |
| Beilstein | 091444 |
| XlogP3 | 3.10 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 172.50 °C. @ 760.00 mm Hg |
| Boiling Point | 498.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 491.00 °F. TCC ( 255.20 °C. ) (est) |
| logP (o/w) | 3.770 (est) |
| Soluble in | water, 290 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for hydroquinine usage levels up to | not for fragrance use. |
| Recommendation for hydroquinine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cinchonan-9-ol, 10,11-dihydro-6'-methoxy-, (8alpha,9R)- (9CI)
dihydroquinine
(R)-(5-
ethyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol
(9R)-6'-
methoxy-10,11-dihydrocinchonan-9-ol
quinine, 10,11-dihydro-
PubMed:
Silver(I)-directed growth of metal-organic complex nanocrystals with bidentate ligands of hydroquinine anthraquinone-1,4-diyl diethers as linkers at the water-chloroform interface.
PubMed:
The molecular phenotype of endocapillary proliferation: novel therapeutic targets for IgA nephropathy.
PubMed:
Catalytic and asymmetric fluorolactonisations of carboxylic acids through anion phase transfer.
PubMed:
How do pseudoenantiomers structurally differ in the gas phase? An IR/UV spectroscopy study of jet-cooled hydroquinine and hydroquinidine.
PubMed:
Interfacial self-assembly and characterization of chiral coordination polymer multilayers with bidentate ligands of hydroquinine anthraquinone-1,4-diyl diether as linkers.
PubMed:
Enantioselective α-hydroxylation of β-ketoamides.
PubMed:
Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine.
PubMed:
Mutation in the Plasmodium falciparum CRT protein determines the stereospecific activity of antimalarial cinchona alkaloids.
PubMed:
Modified asymmetric Strecker reaction of aldehyde with secondary amine: a protocol for the synthesis of S-clopidogrel (an antiplatelet agent).
PubMed:
Microwave-assisted organocatalytic enantioselective intramolecular aza-Michael reaction with α,β-unsaturated ketones.
PubMed:
Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.
PubMed:
Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids.
PubMed:
A hybrid process for chiral separation of compound-forming systems.
PubMed:
Preparation of heteroaryloxetanes and heteroarylazetidines by use of a Minisci reaction.
PubMed:
Asymmetric synthesis of an N-acylpyrrolidine for inhibition of HCV polymerase.
PubMed:
The role of contact chemoreception in egg-laying behaviour of locusts.
PubMed:
Characterization of phenoloxidase activity in Sydney rock oysters (Saccostrea glomerata).
PubMed:
[Adverse drug reactions in three older patients, even without changes in medication].
PubMed:
Proliferation and morphological transformation of RMK cells exposed to hydroquinine containing ionomers.
PubMed:
Prostaglandin biosynthesis by midgut tissue isolated from the tobacco hornworm, Manduca sexta.
PubMed:
Hydroquinine pharmacokinetics after oral administration in adult patients with muscle cramps.
PubMed:
Stage-specific effects of antimalarials on an Indian isolate of Plasmodium falciparum.
PubMed:
Randomised controlled trial of hydroquinine in muscle cramps.
PubMed:
Randomised controlled trial of hydroquinine in muscle cramps.
PubMed:
Randomised controlled trial of hydroquinine in muscle cramps.
PubMed:
Randomised controlled trial of hydroquinine in muscle cramps.
PubMed:
Efficacy of hydroquinine in preventing frequent ordinary muscle cramp outlasts actual administration.
PubMed:
[No difference in efficacy of hydroquinine and placebo in restless legs syndrome].
PubMed:
Liquid chromatographic determination of quinine, hydroquinine, saccharin, and sodium benzoate in quinine beverages.
PubMed:
[Study of antiviral effect of chlorine-substituted benzoquinine and hydroquinine].
PubMed:
STUDY OF THE ACTION OF FOUR AROMATIC CINCHONA DERIVATIVES ON PNEUMOCOCCUS. A COMPARISON WITH OPTOCHIN.