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77440

Sigma-Aldrich

Phenacetin

≥98.0% (HPLC)

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Synonym(s):
1-Acetyl-p-phenetidin, 4′-Ethoxyacetanilide, N-(4-Ethoxyphenyl)acetamide, p-Acetophenetidide, Acetophenetidin
Linear Formula:
CH3CONHC6H4OC2H5
CAS Number:
62-44-2
Molecular Weight:
179.22
Beilstein:
1869238
EC Number:
200-533-0
MDL number:
MFCD00009094
PubChem Substance ID:
57652699
NACRES:
NA.22

Assay

≥98.0% (HPLC)

form

crystals

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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Application

Phenacetin (phen) can be used to synthesize the charge-transfer (CT) complex [(phen)(TCNE)12] by reacting with tetracyanoethylene (TCNE) in dichloromethane.

Biochem/physiol Actions

Substrate of CYP1A2 and CYP2D6.

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H350

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Spectroscopic investigation of the novel charge-transfer complex [(phen)(TCNE)12] formed in the reaction of phenacetin with tetracyanoethylene.
AlQaradawi SY and Nour EM
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 62(1-3), 578-581 (2005)
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
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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