EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

quinacrine dihydrochloride
cinchonan-9-ol, 6'-methoxy-, (8a,9R)-, hydrochloride (1:2)

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Name:(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;dihydrochloride
CAS Number: 60-93-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:200-493-4
FDA UNII: 8C3EMH7D9X
Beilstein Number:4834013
MDL:MFCD00012659
Molecular Weight:397.34362000
Formula:C20 H26 Cl2 N2 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 495.90 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000000 mmHg @ 25.00 °C. (est)
Flash Point: 489.00 °F. TCC ( 253.70 °C. ) (est)
logP (o/w): 3.440 (est)
Soluble in:
 water, 1.594e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
quinine dihydrochloride 95%
Odor: characteristic
Use: Primary alkaloid of various species of Cinchona (Rubiaceae). Optical isomer of Quinidine. Antimalarial; muscle r
Penta International
QUINACRINE DIHYDROCHLORIDE
Sigma-Aldrich: Sigma
For experimental / research use only.
Quinacrine Dihydrochloride ≥90%
 
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-child TDLo 630 mg/kg/1W-I
SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" GASTROINTESTINAL: NAUSEA OR VOMITING
Japanese Journal of Ophthalmology. Vol. 28, Pg. 409, 1984.

intravenous-guinea pig LD50 57 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

intravenous-mouse LD50 86 mg/kg
Biochemical Journal. Vol. 28, Pg. 426, 1934.

oral-mouse LD50 660 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

intravenous-rabbit LD50 35 mg/kg
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

oral-rabbit LD50 641 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

intravenous-rat LD50 78 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

oral-rat LD50 1392 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.

Dermal Toxicity:
subcutaneous-guinea pig LDLo 199 mg/kg
Proceedings of the Society for Experimental Biology and Medicine. Vol. 32, Pg. 595, 1935.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for quinacrine dihydrochloride usage levels up to:
 not for fragrance use.
 
Recommendation for quinacrine dihydrochloride flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):60-93-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91429
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;dihydrochloride
Chemidplus:0000060935
RTECS:AR7875000 for cas# 60-93-5
 
References:
 (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;dihydrochloride
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:60-93-5
Pubchem (cid):91429
Pubchem (sid):135048003
 
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
CHEMBL:View
HMDB (The Human Metabolome Database):Search
MedlinePlusSupp:View
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 cinchonan-9-ol, 6'-methoxy-, (8a,9R)-, hydrochloride (1:2)
 cinchonan-9-ol, 6'-methoxy-, dihydrochloride, (8a,9R)-
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;dihydrochloride
(8a,9R)-6'-methoxycinchonan-9-ol dihydrochloride
 quinine bihydrochloride
 quinine bimuriate
 quinine dihydrochloride
(-)-quinine dihydrochloride
 

Articles:

PubMed:Phospholipase A2-responsive antibiotic delivery via nanoparticle-stabilized liposomes for the treatment of bacterial infection.
PubMed:Dexmedetomidine-induced contraction involves c-Jun NH2 -terminal kinase phosphorylation through activation of the 5-lipoxygenase pathway in the isolated endothelium-denuded rat aorta.
PubMed:Gender determination from pulpal tissue.
PubMed:Mepivacaine-induced contraction involves phosphorylation of extracellular signal-regulated kinase through activation of the lipoxygenase pathway in isolated rat aortic smooth muscle.
PubMed:A novel method using an acedan-based Zn(DPA) probe to monitor ATP localization in an in vivo system.
PubMed:Determination of quinacrine dihydrochloride dihydrate stability and characterization of its degradants.
PubMed:Evaluation of phenolphthalein, diazepam and quinacrine dihydrochloride in the in vitro mammalian cell micronucleus test in Chinese hamster ovary (CHO) and TK6 cells.
PubMed:Determination of sex from tooth pulp tissue.
PubMed:The direct effect of levobupivacaine in isolated rat aorta involves lipoxygenase pathway activation and endothelial nitric oxide release.
PubMed:Direct effect of ropivacaine involves lipoxygenase pathway activation in rat aortic smooth muscle.
PubMed:Direct effect of dexmedetomidine on rat isolated aorta involves endothelial nitric oxide synthesis and activation of the lipoxygenase pathway.
PubMed:Variability in cytogenetic adaptive response of cultured human lymphocytes to mitomycin C, bleomycin, quinacrine dihydrochloride, Co60 gamma-rays and hyperthermia.
PubMed:A one-year neonatal mouse carcinogenesis study of quinacrine dihydrochloride.
PubMed:2n-fatty acids from phosphatidylcholine label sphingolipids--a novel role of phospholipase A2?
PubMed:The effect of chloroquine, quinacrine, and metronidazole on both soybean plants and soil microbiota.
PubMed:4-Bromophenacyl bromide induces Ca2+ influx in human gingival fibroblasts.
PubMed:Re-evaluation of the mutagenic potential of quinacrine dihydrochloride dihydrate.
PubMed:Quinacrine dihydrochloride, the non-surgical female sterilant induces dicentrics, rings, and marker chromosomes in human peripheral blood lymphocytes treated in vitro: a preliminary report.
PubMed:The pathway of cell senescence: WI-38 cells arrest in late G1 and are unable to traverse the cell cycle from a true G0 state.
PubMed:Scaling lichenoid eruptions and Sjögren-like syndrome: manifestations of nonfatal postoperative transfusion-associated graft-versus-host disease?
PubMed:Nuclear matrix condensation and c-myc and c-fos expression are specifically altered in culture rat hepatocytes after exposure to cyproterone acetate and phenobarbital.
PubMed:Quinacrine staining of marginal cells in the stria vascularis of the guinea-pig cochlea: a possible source of extracellular ATP?
PubMed:Coronary vasoconstriction is the most probable cause of death of rats intoxicated with botulinolysin, a hemolysin produced by Clostridium botulinum.
PubMed:Conductometric study of interaction between dyes and surface active agents.
PubMed:Nongenotoxic carcinogens shift cultured rat hepatocytes into G1 cell cycle phase: influence of tissue oxygen tension on cells with different ploidy.
PubMed:Studies of lysophospholipids related to the hamster sperm acrosome reaction in vitro.
PubMed:Application of image analysis on monolayer cultures of rat hepatocytes: assessment of a chemically inducible G0-G1 cell cycle phase shift.
PubMed:Cytogenetics of bisexual/unisexual species of Poecilia. III. The karyotype of Poecilia formosa, a gynogenetic species of hybrid origin.
PubMed:Antimalarial activity of optical isomers of quinacrine dihydrochloride against chloroquine-sensitive and -resistant Plasmodium falciparum in vitro.
PubMed:[Acquired hydrocele in the adult: sclerotherapy].
PubMed:Micronucleus test on quinacrine dihydrochloride in mice: a comparison of dosage regimens.
PubMed:Sex chromatin analysis of lymphocytes invading host organs in transfusion-associated graft-versus-host disease.
PubMed:Distinction between the G0 and the late G1 phase of rat cells in vivo and in vitro with the nuclear QDH-fluorescence pattern.
PubMed:Analysis of the G1 arrest position of senescent WI38 cells by quinacrine dihydrochloride nuclear fluorescence. Evidence for a late G1 arrest.
PubMed:Proton translocation coupled to dimethyl sulfoxide reduction in anaerobically grown Escherichia coli HB101.
PubMed:Drug-induced immunogenic changes of murine leukemia cells: dissociation of onset of resistance and emergence of novel immunogenicity.
PubMed:Double Y as an indicator in a test of mitotic nondisjunction in cultured human lymphocytes.
PubMed:G0-G1 transition of rat hepatocytes detected by changes in nuclear chromatin condensation after in vivo treatment with phenobarbital.
PubMed:Induction of micronuclei in the mouse. Revised timing of the final stage of erythropoiesis.
PubMed:Mechanisms involved in the synthesis of disaturated phosphatidylcholine by alveolar type II cells isolated from adult rat lung.
PubMed:Improved fluorescence method for identifying sex chromatin in formalin-fixed tissue.
PubMed:Fluorimetric measurements and chromatin condensation patterns of nuclei from 3T3 cells throughout G1.
PubMed:Feasibility of testing DNA repair inhibitors for mutagenicity by a simple method.
PubMed:Drug-mediated antigenic changes in murine leukemia cells: antagonistic effects of quinacrine, an antimutagenic compound.
PubMed:Frequency of evident Barr and "F" corpuscles in tetraploid Purkinje neurons.
PubMed:The mutagenic activity of 61 agents as determined by the micronucleus, Salmonella, and sperm abnormality assays.
PubMed:Detection of aneuploidy in human sperm.
PubMed:Metmyoglobin reductase. Identification and purification of a reduced nicotinamide adenine dinucleotide-dependent enzyme from bovine heart which reduces metmyoglobin.
PubMed:Cell cycle dependent changes of chromosomes in mouse fibroblasts.
PubMed:[Transvaginal sterilization of women--a review].
PubMed:Cytogenetic assays of chemical clastogens using mammalian cells in culture.
PubMed:A cytological procedure to screen mammalian temperature-sensitive mutants for cell-cycle-related defects.
PubMed:A simple fluorescence staining technique for the differentiation of human tissue transplanted into nude mice.
PubMed:Effect of Hoechst 33258 on Chinese hamster chromosomes.
PubMed:Prenatal sex determination by demonstration of Y body using fluorescent stain.
PubMed:Fluorescent (F) bodies in the spermatozoa of man and the great apes.
PubMed:[Identification of the XYY syndrome by quinacrine dihydrochloride fluorescence staining].
PubMed:Y bodies and similar fluorescent chromocentres in human tumours including teratomata.
PubMed:Effects of pH on the migration of X and Y sperm.
PubMed:Testing the hypothesis of Y translocation in XX males by fluorescence microscopy after quinacrine-dihydrochloride staining.
PubMed:Identification of G group anomalies in Down's syndrome by quinacrine dihydrochloride fluorescence staining.
 
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.
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