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Merck

1514008

USP

Phenacetin Melting Point Standard

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Phenacetin, 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:
41116107
NACRES:
NA.24
PubChem Substance ID:
329750741
EC Number:
200-533-0
Beilstein/REAXYS Number:
1869238
MDL number:
MFCD00009094

Product Name

Phenacetin Melting Point Standard, United States Pharmacopeia (USP) Reference Standard

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

SMILES string

CCOc1ccc(NC(C)=O)cc1

grade

pharmaceutical primary standard

API family

phenacetin

manufacturer/tradename

USP

mp

133-136 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Phenacetin Melting Point Standard USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.

Biochem/physiol Actions

Substrate of CYP1A2 and CYP2D6.

General description

Phenacetin Melting Point Standard (Phenacetin) is a lipid-soluble drug with moderate solubility with aqueous solvents. Its oral absorption is based on formulation factors like particle size. Its major metabolic route is O-dealkylation to paracetamol and its minor pathways are deacetylation and hydroxylation to form pphenetidine, 2-hydroxyphenetidine, 2- and 3-hydroxyphenacetin and N-hydroxyphenacetin.

Other Notes

Sales restrictions may apply.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Kinetics and metabolism of paracetamol and phenacetin
Prescott, L.F.
British Journal of Clinical Pharmacology (1980)
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)
Analgesic nephropathy: a reassessment of the role of phenacetin and other analgesics.
L F Prescott
Drugs, 23(1-2), 75-149 (1982-01-01)
Phenacetin abuse: a review.
G Carro-Ciampi
Toxicology, 10(4), 311-339 (1978-08-01)
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