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Merck

77440

Phenacetin

≥98.0% (HPLC)

Synonym(s):

1-Acetyl-p-phenetidin, 4′-Ethoxyacetanilide, N-(4-Ethoxyphenyl)acetamide, p-Acetophenetidide, Acetophenetidin

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About This Item

Linear Formula:
CH3CONHC6H4OC2H5
CAS Number:
62-44-2
Molecular Weight:
179.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57652699
EC Number:
200-533-0
Beilstein/REAXYS Number:
1869238
MDL number:
MFCD00009094
Assay:
≥98.0% (HPLC)
Form:
crystals

Key Documents

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InChI key

CPJSUEIXXCENMM-UHFFFAOYSA-N

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)

SMILES string

CCOc1ccc(NC(C)=O)cc1

assay

≥98.0% (HPLC)

form

crystals

functional group

amide

Quality Level

200

mp

134-137 °C

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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.

signalword

Danger

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Muta. 2 - Skin Sens. 1 - Water-react. 2

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2199V
WXBD6341V
WXBD4498V
WXBD3429V
WXBD0648V

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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)
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
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
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