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quinine

Chemical Structure

General Material Information

Preferred name quinine
Trivial Name Quinine
Short Description cinchonan-9-ol, 6'-methoxy-, (8a,9R)-
Formula C20 H24 N2 O2
CAS Number 130-95-0
Deleted CAS Number 12239-42-8
ECHA Number 205-003-2
FDA UNII A7V27PHC7A
Nikkaji Number J654.524F
Beilstein Number 91867
MDL MFCD00198096
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • chinin
  • cinchonan-9-ol, 6'-methoxy-, (3a,8a,9R)-
  • cinchonan-9-ol, 6'-methoxy-, (8a,9R)-
  • (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
  • (R)-(6-methoxy-4-chinolinyl)[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol
  • (R)-(6-methoxy-4-quinolinyl)[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol
  • (3a,8a,9R)-6'- methoxycinchonan-9-ol
  • (8a,9R)-6'- methoxycinchonan-9-ol
  • 6'- methoxycinchonan-9-ol
  • (8S,9R)- quinine
  • (R)-(-)- quinine
  • Cinchonan-9-ol, 6′-methoxy-, (8α,9R)-
  • (8α,9R)-6′-Methoxycinchonan-9-ol
  • 6′-Methoxycinchonidine
  • (-)-Quinine
  • (8S,9R)-Quinine
  • (R)-(-)-Quinine
  • NSC 192949
  • WR297608
  • Qualaquin
  • Mosgard
  • Quinlup
  • Quine 9
  • Cinkona
  • Quinex
  • Quinlex
  • Rezquin
  • QSM
  • SW 85833
  • (R)-(6-Methoxy-4-quinolyl)[(2S)-5-vinylquinuclidin-2-yl]methanol
  • MeSH ID: D011803

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Literature & References

(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:130-95-0
Pubchem (cid):3034034
Pubchem (sid):134973208
Publications by Info
Quinine
Publications by PubMed
[Kansei biosensors to reproduce gustatory and olfactory senses].
Role of NMDA, opioid and dopamine D1 and D2 receptor signaling in the acquisition of a quinine-conditioned flavor avoidance in rats.
Taste loss in hospitalized multimorbid elderly subjects.
Genetic analysis of chemosensory traits in human twins.
Somatosensory factors in taste perception: effects of active tasting and solution temperature.
[Functional MRI investigation of brain activity triggered by taste stimulation].
Rational development of taste masked oral liquids guided by an electronic tongue.
Evidence for an integrated oral sensory module in the human anterior ventral insula.
The role of transient receptor potential vanilloid-1 on neural responses to acids by the chorda tympani, glossopharyngeal and superior laryngeal nerves in mice.
Structural analogues of homoeriodictyol as flavor modifiers. Part III: short chain gingerdione derivatives.
Potentiation of taste and extract stimuli in conditioned flavor preference learning.
New bitter-masking compounds: hydroxylated benzoic acid amides of aromatic amines as structural analogues of homoeriodictyol.
Hunger alters the expression of acquired hedonic but not sensory qualities of food-paired odors in humans.
Olfactory influences on appetite and satiety in humans.
Olfactory influences on appetite and satiety in humans.
Taste masking analysis in pharmaceutical formulation development using an electronic tongue.
Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification.
'Thermal taste' predicts higher responsiveness to chemical taste and flavor.
Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer.
Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
An opioid receptor antagonist, naltrexone, does not alter taste and smell responses in humans.
The representation of umami taste in the taste cortex.
Glutamate and the flavor of foods.
Factors affecting the perception of naturalness and flavor strength in citrus drinks.
The neurophysiology of taste and olfaction in primates, and umami flavor.
Flavor avoidance learning and its implications in reducing strychnine baiting hazards to nontarget animals.
Glucose- and fructose-conditioned flavor preferences in rats: taste versus postingestive conditioning.
Oral caffeine consumption by rats: the role of flavor history, concentration, concurrent food, and an adenosine agonist.
Preference of Old World monkeys for amino acids and other gustatory stimuli: the influence of monosodium glutamate.
Influence of the sense of taste on broiler chick feed consumption.
Conditioned flavor preferences based on delayed caloric consequences.
Norepinephrine-facilitated eating: reduction in saccharin preference and conditioned flavor preferences with increase in quinine aversion.
Rats learn to like the taste of morphine.
Use of taste repellants and emetics to prevent accidental poisoning of dogs.
Developmental flavor experience affects utilization of odor, not taste in toxiphobic conditioning.
Flavor enhances the antidipsogenic effect of naloxone.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06526
HMDB (The Human Metabolome Database):HMDB14611
FooDB:FDB002087
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 324.42367553711
Boiling Point 495 to 496°C @ 760 mm Hg
Flash Point TCC Value 253.7 °C TCC
logP (o/w) 3.44
Solubility
alcohol Yes
water, 500 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Odorless
odorless
Flavor Type: Bitter
bitter
General comment Bitter

Occurrences

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-cat LDLo 100 mg/kg
Rivista di Malariologia. Vol. 11, Pg. 3, 1932.

intramuscular-frog LDLo 400 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.

oral-frog LDLo 1500 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.

oral-guinea pig LD50 1800 mg/kg
Schweizerische Medizinische Wochenschrift. Vol. 84, Pg. 351, 1954.

unreported-man LDLo 294 mg/kg
"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.

intraperitoneal-mouse LD50 115 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 1760, 1985.

intravenous-mouse LD50 68 mg/kg
Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.

intravenous-rabbit LDLo 70 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.

oral-rabbit LDLo 500 mg/kg
Rivista di Malariologia. Vol. 11, Pg. 3, 1932.

intraperitoneal-rat LD > 100 mg/kg
Cancer Research. Vol. 52, Pg. 2797, 1992.

oral-rat LDLo 800 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 100, Pg. 408, 1950.

Dermal Toxicity:
subcutaneous-cat LDLo 100 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.

subcutaneous-dog LDLo 180 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.

subcutaneous-frog LDLo 200 mg/kg
BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.

subcutaneous-mouse LDLo 200 mg/kg
BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA BLOOD: OTHER CHANGES CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.

subcutaneous-rabbit LDLo 231 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.

subcutaneous-rat LDLo 200 mg/kg
CARDIAC: OTHER CHANGES BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA BLOOD: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic agents
Recommendation for quinine usage levels up to:
not for fragrance use.
Recommendation for quinine flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):130-95-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3034034
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Chemidplus:0000130950
RTECS:VA6020000 for cas# 130-95-0