quinine
cinchonan-9-ol, 6'-methoxy-, (8a,9R)-
 
Notes:
an alkaloid derived from the bark of the cinchona tree. it is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. it was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. the mechanisms of its antimalarial effects are not well understood. Used in tonics and bitter drinks Quinine is a natural white crystalline alkaloid having antipyretic, antimalarial, analgesic, anti-inflammatory properties and a bitter taste. It is a stereoisomer of quinidine which, unlike quinine, is an anti-arrhythmic. Though it has been synthesized in the lab, the bark of the cinchona tree is the only known natural source of quinine. Quinine was the first effective treatment for malaria caused by Plasmodium falciparum, appearing in therapeutics in the 17th century. It remained the antimalarial drug of choice until the 1940s, when other drugs replaced it. (Wikipedia)
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      17-29910 QUININE ANHYDROUS, Kosher
       
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(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol (Click)
CAS Number: 130-95-0Picture of molecule
Other: 12239-42-8
ECHA EINECS - REACH Pre-Reg: 205-003-2
FDA UNII: A7V27PHC7A
Nikkaji Web: J654.524F
Beilstein Number: 91867
MDL: MFCD00198096
XlogP3: 2.90 (est)
Molecular Weight: 324.42368000
Formula: C20 H24 N2 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: pale yellow to brown needles (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 177.00 °C. @ 760.00 mm Hg
Boiling Point: 495.00 to  496.00 °C. @ 760.00 mm Hg (est)
Flash Point: 489.00 °F. TCC ( 253.70 °C. ) (est)
logP (o/w): 3.440
Soluble in:
 alcohol
 water, 500 mg/L @ 25 °C (exp)
Insoluble in:
 water
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Organoleptic Properties:
Odor Type: odorless
 odorless  
Odor Description:
odorless
 bitter  
Taste Description:
bitter
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: denaturants
hair conditioning
masking agents
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Suppliers:
Atlantic Chemicals
Quinine
ExtraSynthese
For experimental / research use only.
Quinine (HPLC) ≥90%
Penta International
QUININE ANHYDROUS, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
Quinine
Sigma-Aldrich: Sigma
For experimental / research use only.
Quinine suitable for fluorescence, anhydrous, ≥98.0% (dried material, NT)
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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
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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.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: 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
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (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
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cinchona bark
Search  Picture
 red bark
Search  Picture
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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
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Articles:
Info: Quinine
PubMed: [Kansei biosensors to reproduce gustatory and olfactory senses].
PubMed: Role of NMDA, opioid and dopamine D1 and D2 receptor signaling in the acquisition of a quinine-conditioned flavor avoidance in rats.
PubMed: Taste loss in hospitalized multimorbid elderly subjects.
PubMed: Genetic analysis of chemosensory traits in human twins.
PubMed: Somatosensory factors in taste perception: effects of active tasting and solution temperature.
PubMed: [Functional MRI investigation of brain activity triggered by taste stimulation].
PubMed: Rational development of taste masked oral liquids guided by an electronic tongue.
PubMed: Evidence for an integrated oral sensory module in the human anterior ventral insula.
PubMed: The role of transient receptor potential vanilloid-1 on neural responses to acids by the chorda tympani, glossopharyngeal and superior laryngeal nerves in mice.
PubMed: Structural analogues of homoeriodictyol as flavor modifiers. Part III: short chain gingerdione derivatives.
PubMed: Potentiation of taste and extract stimuli in conditioned flavor preference learning.
PubMed: New bitter-masking compounds: hydroxylated benzoic acid amides of aromatic amines as structural analogues of homoeriodictyol.
PubMed: Hunger alters the expression of acquired hedonic but not sensory qualities of food-paired odors in humans.
PubMed: Olfactory influences on appetite and satiety in humans.
PubMed: Olfactory influences on appetite and satiety in humans.
PubMed: Taste masking analysis in pharmaceutical formulation development using an electronic tongue.
PubMed: Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification.
PubMed: 'Thermal taste' predicts higher responsiveness to chemical taste and flavor.
PubMed: Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer.
PubMed: Interaction of gustatory and lingual somatosensory perceptions at the cortical level in the human: a functional magnetic resonance imaging study.
PubMed: An opioid receptor antagonist, naltrexone, does not alter taste and smell responses in humans.
PubMed: The representation of umami taste in the taste cortex.
PubMed: Glutamate and the flavor of foods.
PubMed: Factors affecting the perception of naturalness and flavor strength in citrus drinks.
PubMed: The neurophysiology of taste and olfaction in primates, and umami flavor.
PubMed: Flavor avoidance learning and its implications in reducing strychnine baiting hazards to nontarget animals.
PubMed: Glucose- and fructose-conditioned flavor preferences in rats: taste versus postingestive conditioning.
PubMed: Oral caffeine consumption by rats: the role of flavor history, concentration, concurrent food, and an adenosine agonist.
PubMed: Preference of Old World monkeys for amino acids and other gustatory stimuli: the influence of monosodium glutamate.
PubMed: Influence of the sense of taste on broiler chick feed consumption.
PubMed: Conditioned flavor preferences based on delayed caloric consequences.
PubMed: Norepinephrine-facilitated eating: reduction in saccharin preference and conditioned flavor preferences with increase in quinine aversion.
PubMed: Rats learn to like the taste of morphine.
PubMed: Use of taste repellants and emetics to prevent accidental poisoning of dogs.
PubMed: Developmental flavor experience affects utilization of odor, not taste in toxiphobic conditioning.
PubMed: Flavor enhances the antidipsogenic effect of naloxone.
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