ContaminantDB: Phenacetin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:50 UTC

Update Date

2026-05-14 17:53:16 UTC

Accession Number

CHEM003665

Identification

Common Name

Phenacetin

Class

Small 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Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Acetamido-4-ethoxybenzene	ChEBI
4-Ethoxyacetanilide	ChEBI
Acetophenetidin	ChEBI
Acetophenetidine	ChEBI
Acetophenetin	ChEBI
Acetphenetidin	ChEBI
Achrocidin	ChEBI
Codempiral	ChEBI
Commotional	ChEBI
Contradol	ChEBI
Contradouleur	ChEBI
Fenacetina	ChEBI
N-(4-Ethoxyphenyl)acetamide	ChEBI
Phenacetine	ChEBI
Phenacetinum	ChEBI

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Mass

179.216 g/mol

Monoisotopic Mass

179.095 g/mol

CAS Registry Number

62-44-2

IUPAC Name

N-(4-ethoxyphenyl)acetamide

Traditional Name

phenacetin

SMILES

CCOC1=CC=C(NC(C)=O)C=C1

InChI Identifier

InChI=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 Key

CPJSUEIXXCENMM-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Acetanilides

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:8050 )
acetamides (CHEBI:8050 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	137.5°C
Boiling Point	Not Available
Solubility	766 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	1.78 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.41	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.13 m³·mol⁻¹	ChemAxon
Polarizability	19.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-001i-0900000000-335c6f93c6c61172faca	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r09-1900000000-693fadbb890b194d9f4b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-6900100000-e5425770c8b511b991fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-ff1bc2f7f827dd1711f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01qi-0900000000-8d7f58b56528e6f12b90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-632d2f940d3bf1e4b090	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-2900000000-a8b75ec081cf2f9bd170	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0c03-2900000000-115f1b03c65a7dc2e1e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0900000000-375522dc595b7e227b62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-6900100000-e5425770c8b511b991fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-698cff42b1b6605dd2c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-03xr-8900000000-c35af434bc3a9f36b748	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03di-3900000000-8363e8eced8d1e99af1d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2900000000-a894326d86b9ce21e136	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-03di-0900000000-ace73eb8b42719a7c2c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0900000000-676cc1faca1027bed0ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0c03-2900000000-115f1b03c65a7dc2e1e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-8d1dd9759f580c330fd0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-03ei-0900000000-922db44266944eac53c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2900000000-a8b75ec081cf2f9bd170	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-632d2f940d3bf1e4b090	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-0900000000-06f027a46bdc57e87bce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c452f944a1db68cee3c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0api-5900000000-f70777770ccda7bb06c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-cd4d0176028d2239a02b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kbr-1900000000-ffdf4ba50461a7f4a9e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3900000000-b21ee1fba6c9e0e2a84f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-a251ba59f8f792deb3e1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Phenacetin'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.

Metabolism

Metabolised in the body to paracetamol.

Toxicity Values

Acute oral toxicity (LD50): 866 mg/kg [Mouse].

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (5)

Uses/Sources

Used principally as an analgesic.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB03783

HMDB ID

HMDB0256387

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Phenacetin

Chemspider ID

4590

ChEBI ID

8050

PubChem Compound ID

Not Available

Kegg Compound ID

C07591

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24201458

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24447449

Phenacetin (CHEM003665)

Structure for CHEM003665: Phenacetin