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:
Molecular Weight:
179.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
200-533-0
Beilstein/REAXYS Number:
1869238
MDL number:
Assay:
≥98.0% (HPLC)
Form:
crystals
Quality Level
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
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.
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signalword
Danger
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
hcodes
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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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.