Mexiletine (CED0004467)

Record Information
Version1.0
Creation Date2016-05-25 18:20:05 UTC
Update Date2026-08-18 12:03:27 UTC
Accession NumberCHEM022103
Identification
Common NameMexiletine
ClassSmall Molecule
Description
Mexiletine belongs to the phenol ethers, a class of benzenoids within the organic compounds. It has the chemical formula C11H17NO and an average molecular weight of 179.26 g/mol. The compound functions as a biological drug (PMC7426781). Its recorded protein targets include the Aryl hydrocarbon receptor (AHR) and the Sodium channel protein type 5 subunit alpha (SCN5A), for which it acts as an agonist or inhibitor. Mexiletine is found in or released from ten recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is used as an antiarrhythmic of class I and III. It is also associated with food preservation in the context of food, food processing, and cookware. Other recorded sources include electrical and electronic equipment, such as antennas, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Additionally, it is found in household cleaning and consumer products, specifically perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. The recorded route of exposure for this compound is oral.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(+-)-1-(2,6-Dimethylphenoxy)propan-2-amineChEBI
(2Rs)-1-(2,6-Dimethylphenoxy)-2-aminopropaneChEBI
1-(2',6'-Dimethylphenoxy)-2-aminopropaneChEBI
1-(2,6-Dimethylphenoxy)-2-propanamineChEBI
1-Methyl-2-(2,6-xylyloxy)ethanamineChEBI
MexiletinaChEBI
MexiletinumChEBI
MexilitineHMDB
MexileteneHMDB
Mexitil PLHMDB
Novo mexiletineHMDB
Novo-mexiletineHMDB
MexitilHMDB
MexitylHMDB
Boehringer ingelheim brand OF mexiletine hydrochlorideHMDB
Mexiletine hydrochlorideHMDB
Novopharm brand OF mexiletine hydrochlorideHMDB
Chemical FormulaC11H17NO
Average Molecular Mass179.259 g/mol
Monoisotopic Mass179.131 g/mol
CAS Registry Number31828-71-4
IUPAC Name1-(2,6-dimethylphenoxy)propan-2-amine
Traditional Name1-(2,6-dimethylphenoxy)propan-2-amine
SMILESCC(N)COC1=C(C)C=CC=C1C
InChI IdentifierInChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3
InChI KeyVLPIATFUUWWMKC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Xylene
  • M-xylene
  • Phenoxy compound
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
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 Solubility0.54 g/LALOGPS
logP2.17ALOGPS
logP2.46ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.25 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.97 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-9100000000-6d40293ed4e486f9cf9eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-9300000000-147905f020f0139cfe20Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-9100000000-6d40293ed4e486f9cf9eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-9300000000-147905f020f0139cfe20Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-9400000000-e9948c49f03b5a215db0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-0900000000-083bab651324c62f4cd5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-0900000000-feace6e16ed93a4bd13eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-d9f9d0eeea2a47e42771Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-76838bfcf2fd2b0e2b17Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-c5920fd67439f418b86fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-b5f13a7a078d1c192691Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-24a61cef86793ffcf760Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-d740cc5fc7a9b2b380a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-0900000000-083bab651324c62f4cd5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-0900000000-feace6e16ed93a4bd13eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-94985b5db6692d615971Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-c1e103780c7df279dc6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-d077857c1d4a1d567c03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-9ef54de393ed768d242fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-9a364fda721f96e6e368Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-6b280de493776a9dc242Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-be0a7f708a3a6a0bccd0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-bacd798fb57178717712Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-320ad3be57ff9aced9a9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9500000000-fcf382c7be2dce359603Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-19467960da04d559b6bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-939b7c3be7e71365188cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9400000000-16d73c9c92a1487bbc7cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9200000000-9a25be6ae97cd157924eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-3aee50267bd861738c2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-d552a69206ce56dd07b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-3900000000-c2586c04dbdd926fce0cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-4308c43f1886c6a0f8baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9800000000-aa44f825fd30f7141c70Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-4900000000-a769f9a616166f7b84b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-647dfa982977df5e264bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9700000000-48182f10e3e560cae33fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5900000000-55dc4fc5ebb39a0c447cNot 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
254.0Log mg/kg[140:450]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
285Antiarrhythmics, class i and iiiHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & 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
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)49.2007
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)249.118
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)56.285
Potassium channel subfamily K member 2 structureClick to view 3D structurePotassium channel subfamily K member 2O95069HumansPredicted (SEA)0.934191
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)70.9985
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)123.469
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)21.9535
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)110.001
Click to view 3D structureTrace amine-associated receptor 1Q8HZ64Macaca mulattaPredicted (SEA)1.32344
Sodium channel protein type 9 subunit alpha structureClick to view 3D structureSodium channel protein type 9 subunit alphaQ15858HumansPredicted (SEA)135.925
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)14.8692
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)20.0072
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)213.307
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)245.069
Sodium channel protein type 2 subunit alpha structureClick to view 3D structureSodium channel protein type 2 subunit alphaQ99250HumansPredicted (SEA)71.4656
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)362.388
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)669.114
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)332.183
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)117.163
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)870.121
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)677.288
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)289.91
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)753.503
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)897.602
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)37.4455
Concentrations
Not Available
External Links
DrugBank IDDB00379
HMDB IDHMDB0014523
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMexiletine
Chemspider ID4034
ChEBI ID6916
PubChem Compound ID4178
Kegg Compound IDC07220
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10883344
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11009230