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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:
Molecular Weight:
179.22
Beilstein/REAXYS Number:
1869238
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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1 of 4

This Item
P14815A5000100528
Phenacetin ≥98.0% (HPLC)

77440

Phenacetin

4-Ethoxyaniline 98%

P14815

4-Ethoxyaniline

Acetaminophen meets USP testing specifications, 98.0-102.0%, powder

A5000

Acetaminophen

4′-Aminoacetanilide 99%

100528

4′-Aminoacetanilide

mp

133-136 °C (lit.)

mp

2-5 °C (lit.)

mp

168-172 °C (lit.)

mp

164-167 °C (lit.)

form

crystals

form

-

form

powder

form

solid

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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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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)
Heloisa N Bordallo et al.
Molecular pharmaceutics, 9(9), 2434-2441 (2012-07-25)
This study centers on the use of inelastic neutron scattering as an alternative tool for physical characterization of solid pharmaceutical drugs. On the basis of such approach, relaxation processes in the pharmaceutical compound phenacetin (p-ethoxyacetanilide, C(10)H(13)NO(2)) were evidenced on heating
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

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