Structure via PubChem · Public domain (PubChem)
phenacetin
Sign in to saveAlso known as Acetophenetin, Acetphenetidin, Acetophenetidine, Acetophenetidin, N-(4-ethoxyphenyl)acetamide
Phenacetin (; acetophenetidin, '''N-(4-ethoxyphenyl)acetamide''') is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn in Canada in 1973, and by the U.S. Food and Drug Administration in 1983).
Chemical data
- Formula
- C10H13NO2
- Molecular weight
- 179.22 g/mol
- IUPAC name
- N-(4-ethoxyphenyl)acetamide
- SMILES
- CCOC1=CC=C(C=C1)NC(=O)C
- InChIKey
- CPJSUEIXXCENMM-UHFFFAOYSA-N
- XLogP
- 1.6
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
3,257 papers- Phenacetin.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1980
- Phenacetin abuse: a review.Toxicology · 1978
- Phenacetin: an update.Journal of endodontics · 1979
- Reactive metabolites of phenacetin and acetaminophen: a review.Environmental health perspectives · 1983
- Phenacetin.Report on carcinogens : carcinogen profiles · 2002
via PubMed
Wikidata facts
- Mass
- 179.094629
Show 7 more facts
- defined daily dose
- 1.8
- chemical formula
- C₁₀H₁₃NO₂
- canonical SMILES
- CCOC1=CC=C(C=C1)NC(=O)C
- World Health Organisation international non-proprietary name
- fenacetin
- isomeric SMILES
- CCOC1=CC=C(C=C1)/N=C(\C)/O
- melting point
- 135.0
- Commons category
- Phenacetin
via Wikidata · CC0
~7 min read
Article
11 sectionsContents
- History
- Known mechanism of action
- Preparation
- Uses
- Medical
- Other
- Safety
- In popular culture
- See also
- References
- External links
Phenacetin (; acetophenetidin, '''N-(4-ethoxyphenyl)acetamide''') is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn in Canada in 1973, and by the U.S. Food and Drug Administration in 1983).
==History== Phenacetin was introduced in 1887 in Elberfeld, Germany by German company Bayer, and was used principally as an analgesic; it was one of the first synthetic fever reducers to go on the market. It is also known historically to be one of the first non-opioid analgesics without anti-inflammatory properties. Although paracetamol (acetaminophen) was produced earlier, a historical accident saw it ignored after Joseph von Mering's 1893 assessment.