pramocaine (CED0013482)

Record Information
Version1.0
Creation Date2016-06-03 10:24:00 UTC
Update Date2026-08-19 22:01:01 UTC
Accession NumberCHEM042893
Identification
Common Namepramocaine
ClassSmall Molecule
Description
Pramocaine is an organic compound with the chemical formula C17H27NO3 and an average molecular weight of 293.41 g/mol. It belongs to the phenol ethers, a class of benzenoids within the organic compounds. This compound is found in or released from nine recorded sources across several categories. In healthcare, pharmaceuticals, and veterinary products, it is used in antipruritics and vasoprotectives. Within food, food processing, and cookware, it is utilized for food preservation. It is also present in electrical and electronic equipment, specifically in electrically stimulated smoking devices and conductors or conductive bodies characterized by the conductive materials. Additionally, it is found in household cleaning and consumer products, including soap dispensers, perfumes within detergents and soaps, cigar cigarettes, and other smoking requisites. Recorded exposure routes for pramocaine include topical, oral, auricular, rectal, and vaginal administration. At the molecular level, pramocaine interacts with ten recorded protein targets. It acts as an inhibitor of several sodium channel proteins, specifically sodium channel protein type 1 subunit alpha (SCN1A), sodium channel protein type 4 subunit alpha (SCN4A), sodium channel protein type 5 subunit alpha (SCN5A), and sodium channel protein type 7 subunit alpha (SCN7A), as well as six other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
gamma-Morpholinopropyl 4-N-butoxyphenyl etherChEBI
p-Butoxyphenyl gamma-morpholinopropyl etherChEBI
PramocainumChEBI
PramoxineChEBI
ProxazocainChEBI
g-Morpholinopropyl 4-N-butoxyphenyl etherGenerator
Γ-morpholinopropyl 4-N-butoxyphenyl etherGenerator
p-Butoxyphenyl g-morpholinopropyl etherGenerator
p-Butoxyphenyl γ-morpholinopropyl etherGenerator
4-(3-(p-Butoxyphenoxy)propyl)morpholineMeSH
BalsabitMeSH
Itch-XMeSH
Pramoxine hydrochlorideMeSH
TronothaneMeSH
PramoxMeSH
TronolaneMeSH
Fleet pain reliefMeSH
ProctoFoamMeSH
4-(3-(4-Butoxyphenoxy)propyl)morpholineMeSH
PrameGelMeSH
Pramocaine hydrochlorideMeSH
PraxMeSH
Ascher brand OF pramoxine hydrochlorideMeSH
Isdin brand OF pramoxine hydrochlorideMeSH
Seid brand OF pramoxine hydrochlorideMeSH
Ferndale brand OF pramoxine hydrochlorideMeSH
Ross brand OF pramoxine hydrochlorideMeSH
GenDerm brand OF pramoxine hydrochlorideMeSH
Medicis brand OF pramoxine hydrochlorideMeSH
Abbott brand OF pramoxine hydrochlorideMeSH
Fleet brand OF pramoxine hydrochlorideMeSH
Schwarz brand OF pramoxine hydrochlorideMeSH
PramocaineKEGG
Chemical FormulaC17H27NO3
Average Molecular Mass293.407 g/mol
Monoisotopic Mass293.199 g/mol
CAS Registry Number140-65-8
IUPAC Name4-[3-(4-butoxyphenoxy)propyl]morpholine
Traditional Namepramoxine
SMILESCCCCOC1=CC=C(OCCCN2CCOCC2)C=C1
InChI IdentifierInChI=1S/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3
InChI KeyDQKXQSGTHWVTAD-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
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Morpholine
  • Oxazinane
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.22 g/LALOGPS
logP3.03ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.93 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.82 m³·mol⁻¹ChemAxon
Polarizability35.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0ufu-5900000000-594926332aad338cf632Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0fb9-0920000000-809db2c1fd1e2472e79cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f9m-9670000000-7f949734e83956a1ce28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-7c9bc5e2393574b551acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0290000000-4c336a718a063e0c4bd2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0910000000-5d6f0b2eda70998496cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-6dba3652b26250fc34b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3900000000-cb727bd5218a44669d18Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-6900000000-d132e77318e9757c12bcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zmi-9400000000-4e4a238aa95af1cb797eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-9100000000-e81d251a19a7e8af2df6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-3c9f67d2e404ef8d5770Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2390000000-5d913724471bdf19da51Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-5930000000-da5ece8fe013935326f9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9300000000-d92eb3b5437acc2a91d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1490000000-171288be014cfa876ecfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-4960000000-700f9211a5a7f0ceba3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-3900000000-74f77092f7ec618ffb1aNot 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
1022.0Log mg/kg[570:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
292VasoprotectivesHealthcare, pharmaceuticals & veterinary productsNot Available
304AntipruriticsHealthcare, pharmaceuticals & veterinary productsNot 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
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)11.0546
Click to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8K424Mus musculusPredicted (SEA)1.08989
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)20.7079
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)24.1333
Click to view 3D structureHistamine H3 receptorQ9QYN8Rattus norvegicusPredicted (SEA)6.77288
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)22.6541
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)71.777
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)96.4552
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)78.6277
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)67.9624
Click to view 3D structureD(4) dopamine receptorP30729Rattus norvegicusPredicted (SEA)7.16213
Click to view 3D structureSigma intracellular receptor 2Q5U3Y7Rattus norvegicusPredicted (SEA)10.6653
Histamine H2 receptor structureClick to view 3D structureHistamine H2 receptorP25021HumansPredicted (SEA)8.95266
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)47.7216
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)41.8829
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)44.6076
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)32.2296
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)28.0257
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)121.6
Histamine H4 receptor structureClick to view 3D structureHistamine H4 receptorQ9H3N8HumansPredicted (SEA)18.3724
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)207.546
D(1B) dopamine receptor structureClick to view 3D structureD(1B) dopamine receptorP21918HumansPredicted (SEA)33.1638
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)31.7625
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)67.3396
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)74.7353
Concentrations
Not Available
External Links
DrugBank IDDB09345
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPramocaine
Chemspider IDNot Available
ChEBI ID8357
PubChem Compound ID4886
Kegg Compound IDC07892
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17244091
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24819289
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8150879