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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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Quality Level

200

assay

≥98.0% (HPLC)

form

crystals

mp

134-137 °C

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

77440-1KG: + 77440-50G: + 77440-BULK: + 77440-250G: + 77440-6X1KG: + 77440-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
0000502533
0000502533
WXBF4290V
WXBF1391V
0000161459

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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.
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
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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