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77440

Sigma-Aldrich

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
Beilstein:
1869238
EC Number:
200-533-0
MDL number:
MFCD00009094
UNSPSC Code:
12352100
PubChem Substance ID:
57652699
NACRES:
NA.22

Quality Level

200

Assay

≥98.0% (HPLC)

form

crystals

mp

133-136 °C (lit.)

functional group

amide

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

Health hazardExclamation mark
GHS08,GHS07

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2199V
WXBD6341V
WXBD4498V
WXBD3429V
WXBD0648V

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Paracetamol British Pharmacopoeia (BP) Reference Standard

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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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