235830

Sigma-Aldrich

Phenacetin

97%

Synonym(s):
p-Acetophenetidide, Acetophenetidin, 1-Acetyl-p-phenetidin, 4′-Ethoxyacetanilide, N-(4-Ethoxyphenyl)acetamide
Linear Formula:
CH3CONHC6H4OC2H5
CAS Number:
Molecular Weight:
179.22
Beilstein/REAXYS Number:
1869238
EC Number:
MDL number:
PubChem Substance ID:

assay

97%

mp

133-136 °C (lit.)

SMILES string

CCOc1ccc(NC(C)=O)cc1

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

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Biochem/physiol Actions

Substrate of CYP1A2 and CYP2D6.

Other Notes

This product has been replaced by 77440-ALDRICH | Phenacetin ≥98.0% (HPLC)

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

WGK Germany

3

S P Clissold
Drugs, 32 Suppl 4, 46-59 (1986-01-01)
Since their synthesis in the late 1800s paracetamol (acetaminophen) and phenacetin have followed divergent pathways with regard to their popularity as mild analgesic/antipyretic drugs. Initially, paracetamol was discarded in favour of phenacetin because the latter drug was supposedly less toxic....
[Phenacetin abuse I. Occurrence, per capita consumption and costs of treatment].
M J Mihatsch et al.
Schweizerische medizinische Wochenschrift, 110(4), 108-115 (1980-01-28)
J A Hinson
Environmental health perspectives, 49, 71-79 (1983-03-01)
Phenacetin can be metabolized to reactive metabolites by a variety of mechanisms. (1) Phenacetin can be N-hydroxylated, and the resulting N-hydroxyphenacetin can be sulfated or glucuronidated. Whereas phenacetin N-O sulfate immediately rearranges to form a reactive metabolite which may covalently...
Analgesic nephropathy: a reassessment of the role of phenacetin and other analgesics.
L F Prescott
Drugs, 23(1-2), 75-149 (1982-01-01)
Eslam Nouri-Nigjeh et al.
The Analyst, 136(23), 5064-5067 (2011-10-11)
Electrochemistry in combination with mass spectrometry is emerging as a versatile analytical technique in the imitation of oxidative drug metabolism during the early stages of drug discovery and development. Here, we present electrochemical O-dealkylation of phenacetin to acetaminophen by square-wave...

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