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77440

Sigma-Aldrich

Phenacetin

≥98.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula lineal:
CH3CONHC6H4OC2H5
Número de CAS:
62-44-2
Peso molecular:
179.22
Beilstein/REAXYS Number:
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

signalword

Danger

hcodes

H302,H350

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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Certificados de análisis (COA)

Lot/Batch Number
WXBF4290V
WXBF1391V
WXBD8312V
WXBD2199V

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Paracetamol British Pharmacopoeia (BP) Reference Standard

BP371

Paracetamol

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
Kazuo Takayama et al.
Journal of hepatology, 57(3), 628-636 (2012-06-05)
Hepatocyte-like cells differentiated from human embryonic stem cells (hESCs) and induced pluripotent stem cells (hiPSCs) can be utilized as a tool for screening for hepatotoxicity in the early phase of pharmaceutical development. We have recently reported that hepatic differentiation is
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