Mefloquine (CED0003094)

Record Information
Version1.0
Creation Date2016-05-25 18:19:53 UTC
Update Date2026-05-14 16:36:25 UTC
Accession NumberCHEM022096
Identification
Common NameMefloquine
ClassSmall Molecule
Description
Mefloquine is an organic compound with the chemical formula C17H16F6N2O and an average molecular weight of 378.31 g/mol. Mefloquine belongs to the 4-quinolinemethanols, a subclass of quinolines and derivatives within the organic compounds. This substance is classified as an organoheterocyclic compound. The compound is found in or released from 13 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antiprotozoal. It is also associated with food preservation in the category of food, food processing, and cookware. Other recorded sources include indoor air via air, dust, and atmospheric transport, as well as household cleaning and consumer products such as perfumes within detergents and soaps, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. Additionally, it is linked to electrical and electronic equipment, including antennas, auxiliary devices, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, hybrid capacitors, and one other source. Recorded exposure routes for mefloquine include oral and inhalation. Regarding its biological activity, mefloquine acts as an antagonist of the adenosine receptor A2a (ADORA2A), which is its only recorded protein target.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanolChEBI
a-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanolGenerator
Α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanolGenerator
MefloquinoneHMDB
Hoffmann la roche brand OF mefloquine hydrochlorideHMDB
Hoffmann-la roche brand OF mefloquine hydrochlorideHMDB
Mefloquine hydrochlorideHMDB
Roche brand OF mefloquine hydrochlorideHMDB
LariamHMDB
MephloquineHMDB
MefloquineHMDB
Chemical FormulaC17H16F6N2O
Average Molecular Mass378.312 g/mol
Monoisotopic Mass378.117 g/mol
CAS Registry Number53230-10-7
IUPAC Name[2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol
Traditional Namemefloquine
SMILESOC(C1CCCCN1)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F
InChI IdentifierInChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2
InChI KeyXEEQGYMUWCZPDN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-quinolinemethanols. These are organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub Class4-quinolinemethanols
Direct Parent4-quinolinemethanols
Alternative Parents
Substituents
  • 4-quinolinemethanol
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Alcohol
  • Aromatic alcohol
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP3.1ALOGPS
logP4.11ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area45.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.58 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9025000000-bd2efec95144343a1b49Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9880700000-0d7f5ede34418b735bf8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-0009000000-f63c2940b613df55b83dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-4029000000-054581384c6b5a51066dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9041000000-1e6b869ab2fa3ffa6785Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-f43f6cd574501c04be1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2019000000-deffba940fff3f2a8a5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9042000000-cda7cad59a1c31fcc399Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-0c5583423999f9b76541Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-1009000000-c8c4028b3773cf47d2c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0536-9067000000-f1c1030c0e913181f813Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-826539601dd4ffcd5accNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0029000000-cab8b26d4d2c51fe26efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1059000000-9cd7452365f680e2e6a5Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
175.0Log mg/kg[100:310]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)26.9358
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)149.471
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)77.6157
Glycine receptor subunit alpha-1 structureClick to view 3D structureGlycine receptor subunit alpha-1P23415HumansPredicted (SEA)0.622794
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)839.993
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3328.21
Click to view 3D structureObtusifoliol 14-alpha demethylaseP93846Sorghum bicolorPredicted (SEA)9.6533
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)2651.62
Click to view 3D structureMitogen-activated protein kinase kinase kinase kinase 2Q12851HumansPredicted (SEA)2198.93
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)2523.48
Mitogen-activated protein kinase kinase kinase kinase 4 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase kinase 4O95819HumansPredicted (SEA)2370.04
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)2332.83
Click to view 3D structureMitogen-activated protein kinase kinase kinase kinase 5Q9Y4K4HumansPredicted (SEA)1961.96
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)2781.01
MAP kinase-interacting serine/threonine-protein kinase 2 structureClick to view 3D structureMAP kinase-interacting serine/threonine-protein kinase 2Q9HBH9HumansPredicted (SEA)1982.82
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)2659.49
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)3623.26
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)2994.63
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)2487.75
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)3799.43
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)3605.66
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)2861.27
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)2804.52
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)3572.89
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)3144.25
Concentrations
Not Available
External Links
DrugBank IDDB00358
HMDB IDHMDB0243550
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMefloquine
Chemspider ID3906
ChEBI ID63681
PubChem Compound ID4046
Kegg Compound IDC07633
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.