Procainamide (CED0003972)

Record Information
Version1.0
Creation Date2016-05-22 03:45:21 UTC
Update Date2026-08-19 02:23:24 UTC
Accession NumberCHEM016847
Identification
Common NameProcainamide
ClassSmall Molecule
Description
Procainamide is an organic compound with the formula C13H21N3O and an average molecular weight of 235.33 g/mol. Procainamide belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from 30 different sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antiarrhythmic of class I and III. Other recorded sources include building and construction materials such as ceilings, household items like credit card holders, and various household cleaning and consumer products, including soap detergents, bleaching agents, perfumes within detergents and soaps, and other smoking requisites such as cigar cigarettes. It is also associated with food processing and cookware, specifically in the processing of meats and fish, the preparation of wort, food preservation, and molasses and the treatment of molasses. Furthermore, it is found in electrical and electronic equipment, including antennas, amplifiers, adjustable resistors, colour television systems, and conductors or conductive bodies characterised by the conductive materials, among 10 others. The compound is administered through oral, intravenous, and intramuscular exposure routes. Procainamide interacts with three recorded protein targets, acting as an inhibitor or other modulator of the sodium channel protein type 5 subunit alpha (SCN5A), the voltage-gated inwardly rectifying potassium channel KCNH2, and DNA (cytosine-5)-methyltransferase 1 (DNMT1).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
BiocorylChEBI
p-Amino-N-(2-diethylaminoethyl)benzamideChEBI
p-Aminobenzoic diethylaminoethylamideChEBI
ProcainamidaChEBI
ProcainamidumChEBI
Apo-procainamideHMDB
Parke davis brand OF procainamide hydrochlorideHMDB
Procainamide hydrochlorideHMDB
ProcamideHMDB
ProcanbidHMDB
Apotex brand OF procainamide hydrochlorideHMDB
Hydrochloride, procainamideHMDB
ProcanHMDB
Uriach brand OF procainamide hydrochlorideHMDB
Apothecon brand OF procainamide hydrochlorideHMDB
NovocainamideHMDB
NovocamidHMDB
Pfizer brand OF procainamide hydrochlorideHMDB
Procaine amideHMDB
Procan SRHMDB
PronestylHMDB
RhythminHMDB
Sidmark brand OF procainamide hydrochlorideHMDB
Amide, procaineHMDB
Bristol-myers squibb brand OF procainamide hydrochlorideHMDB
Monarch brand OF procainamide hydrochlorideHMDB
Chemical FormulaC13H21N3O
Average Molecular Mass235.325 g/mol
Monoisotopic Mass235.168 g/mol
CAS Registry Number51-06-9
IUPAC Name4-amino-N-[2-(diethylamino)ethyl]benzamide
Traditional Nameprocainamide
SMILESCCN(CC)CCNC(=O)C1=CC=C(N)C=C1
InChI IdentifierInChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)
InChI KeyREQCZEXYDRLIBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzamides
Alternative Parents
Substituents
  • Aminobenzamide
  • Benzamide
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • 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 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 Solubility3.02 g/LALOGPS
logP1.42ALOGPS
logP0.95ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)15.75ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.25 m³·mol⁻¹ChemAxon
Polarizability27.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dr-9700000000-95dbcabafddc689c7c51Not 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 Spectrumsplash10-03dr-1940000000-b9d8d6702d2ec39984a3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-1940000000-b9d8d6702d2ec39984a3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-5900000000-c7352292c2ca704d6892Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1090000000-bef3da50733e1140e14aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-0940000000-98ab06e1b8550215cdaaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-3c9d04ec798748cc957aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-a32b895dd0eb19dc8813Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9110000000-20900032e174aab10a1bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ri-1790000000-c34ddbb3ff1c0983adcbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-2910000000-eade1dffa69e386cc91eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9400000000-40f1c1ebcfeb2029c8d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0190000000-ec82e6634f5291088253Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-6690000000-309e42ec6748fb795a10Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-0b46b12a4a8fed4dd328Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01p9-0970000000-f20ad5a122356337eb22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0229-1900000000-554557c10d38fea3d2b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-8900000000-016dd1ee9cecc2bf22e2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-b59dd73be5c5027352ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-4390000000-a08741c73eb9ea2fcfdcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-800956671d0607615bddNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot 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
1212.0Log mg/kg[680:2200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
285Antiarrhythmics, class i and iiiHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 1Q63089Rattus norvegicusPredicted (SEA)0.0778492
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)56.7521
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)166.909
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)227.32
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)130.553
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)379.359
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)89.7602
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)170.568
Click to view 3D structureAcetylcholinesteraseP23795Bos taurusPredicted (SEA)18.061
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)123.157
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)120.9
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)400.456
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)286.174
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)577.486
5'-AMP-activated protein kinase catalytic subunit alpha-1 structureClick to view 3D structure5'-AMP-activated protein kinase catalytic subunit alpha-1Q13131HumansPredicted (SEA)301.977
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)590.876
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)469.976
Focal adhesion kinase 1 structureClick to view 3D structureFocal adhesion kinase 1Q05397HumansPredicted (SEA)356.238
Cyclin-dependent kinase 8 structureClick to view 3D structureCyclin-dependent kinase 8P49336HumansPredicted (SEA)212.061
Mitogen-activated protein kinase 8 structureClick to view 3D structureMitogen-activated protein kinase 8P45983HumansPredicted (SEA)406.451
Serine/threonine-protein kinase PAK 4 structureClick to view 3D structureSerine/threonine-protein kinase PAK 4O96013HumansPredicted (SEA)363.556
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)372.82
Tyrosine-protein kinase JAK3 structureClick to view 3D structureTyrosine-protein kinase JAK3P52333HumansPredicted (SEA)547.124
G protein-coupled receptor kinase 5 structureClick to view 3D structureG protein-coupled receptor kinase 5P34947HumansPredicted (SEA)127.05
Calcium/calmodulin-dependent protein kinase type II subunit alpha structureClick to view 3D structureCalcium/calmodulin-dependent protein kinase type II subunit alphaQ9UQM7HumansPredicted (SEA)168.232
Concentrations
Not Available
External Links
DrugBank IDDB01035
HMDB IDHMDB0015169
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProcainamide
Chemspider ID4744
ChEBI ID8428
PubChem Compound ID4913
Kegg Compound IDC07401
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16230360
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2494958
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=29276243
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29494946