Phenacetin (CHEM003665)

Record Information
Version1.0
Creation Date2014-09-11 02:05:50 UTC
Update Date2026-08-18 00:30:27 UTC
Accession NumberCHEM003665
Identification
Common NamePhenacetin
ClassSmall Molecule
Description
Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Analgesic, Non-Narcotic
  • Drug
  • Ether
  • Human Neurotoxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Acetamido-4-ethoxybenzeneChEBI
4-EthoxyacetanilideChEBI
AcetophenetidinChEBI
AcetophenetidineChEBI
AcetophenetinChEBI
AcetphenetidinChEBI
AchrocidinChEBI
CodempiralChEBI
CommotionalChEBI
ContradolChEBI
ContradouleurChEBI
FenacetinaChEBI
N-(4-Ethoxyphenyl)acetamideChEBI
PhenacetineChEBI
PhenacetinumChEBI
Chemical FormulaC10H13NO2
Average Molecular Mass179.216 g/mol
Monoisotopic Mass179.095 g/mol
CAS Registry Number62-44-2
IUPAC NameN-(4-ethoxyphenyl)acetamide
Traditional Namephenacetin
SMILESCCOC1=CC=C(NC(C)=O)C=C1
InChI IdentifierInChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
InChI KeyCPJSUEIXXCENMM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • Acetanilide
  • N-acetylarylamine
  • Phenoxy compound
  • Phenol ether
  • N-arylamide
  • Alkyl aryl ether
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point137.5°C
Boiling PointNot Available
Solubility766 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility1.78 g/LALOGPS
logP1.62ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.13 m³·mol⁻¹ChemAxon
Polarizability19.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityPhenacetin's analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia.
MetabolismMetabolised in the body to paracetamol.
Toxicity ValuesAcute oral toxicity (LD50): 866 mg/kg [Mouse].
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (5)
Uses/SourcesUsed principally as an analgesic.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03783
HMDB IDHMDB0256387
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenacetin
Chemspider ID4590
ChEBI ID8050
PubChem Compound IDNot Available
Kegg Compound IDC07591
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ernst Bocker, Wolfgang Kracht, Roland Rupp, Erhard Schellmann, Viktor Trescher, Martin Ullrich, “Preparation of melt-sprayed spherical phenacetin granules.” U.S. Patent US4086346, issued October, 1972.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24201458
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24447449