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Phenacetin

Non-opioid analgesic CAS# 62-44-2

Phenacetin

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Quality Control of Phenacetin

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Chemical structure

Phenacetin

3D structure

Chemical Properties of Phenacetin

Cas No. 62-44-2 SDF Download SDF
PubChem ID 4754 Appearance Powder
Formula C10H13NO2 M.Wt 179.22
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Acetophenetidin
Solubility DMSO : ≥ 100 mg/mL (557.97 mM)
H2O : 0.67 mg/mL (3.74 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name N-(4-ethoxyphenyl)acetamide
SMILES CCOC1=CC=C(C=C1)NC(=O)C
Standard InChIKey CPJSUEIXXCENMM-UHFFFAOYSA-N
Standard InChI 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)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Phenacetin

DescriptionPhenacetin is a non-opioid analgesic without anti-inflammatory properties. Target: COX Phenacetin is a pain-relieving and fever-reducing drug, Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy. the clinical and laboratory data were compatible with phenacetin nephritis as described in Europe and Australia and recently in the United States and Canada. This report evaluates the findings in the 23 cases and cautions against the use of phenacetin, particularly in patients with impaired renal function [1]. Phenacetin has been linked to renal papillary necrosis in human beings [2, 3].

References:
[1]. Tan, G.H., M.D. Rabbino, and J. Hopper, Jr., Is Phenacetin a Nephrotoxin?A Report on Twenty-Three Users of the Drug. Calif Med, 1964. 101: p. 73-7. [2]. Brix, A.E., Renal papillary necrosis. Toxicol Pathol, 2002. 30(6): p. 672-4. [3]. Dubach, U.C., B. Rosner, and T. Sturmer, An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987). N Engl J Med, 1991. 324(3): p. 155-60.

Phenacetin Dilution Calculator

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Phenacetin Molarity Calculator

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Preparing Stock Solutions of Phenacetin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.5797 mL 27.8987 mL 55.7973 mL 111.5947 mL 139.4934 mL
5 mM 1.1159 mL 5.5797 mL 11.1595 mL 22.3189 mL 27.8987 mL
10 mM 0.558 mL 2.7899 mL 5.5797 mL 11.1595 mL 13.9493 mL
50 mM 0.1116 mL 0.558 mL 1.1159 mL 2.2319 mL 2.7899 mL
100 mM 0.0558 mL 0.279 mL 0.558 mL 1.1159 mL 1.3949 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Phenacetin

Phenacetin is a non-opioid analgesic without anti-inflammatory properties.Phenacetin is a pain-relieving and fever-reducing drug, Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy. the clinical and labora

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References on Phenacetin

IRMS to study a common cocaine cutting agent: phenacetin.[Pubmed:27860349]

Drug Test Anal. 2017 Mar;9(3):479-484.

Phenacetin is a pharmaceutical closely related to acetaminophen that has been banned in France for a long time due to its nephritic and carcinogenic adverse effects. It frequently appears in cocaine seizures as a cutting agent. Following both sanitary and intelligence motivations, this molecule was chosen for this study, and stable isotopes seemed to be the most appropriate tool. A total of 228 seized samples were collected over a 6-year period, and 8 standards of known origin were purchased. They were submitted to gas chromatography (GC) or elemental analysis - isotope ratio mass spectrometry (EA-IRMS) measurements, depending on their complexity. Stable isotope ratios of carbon, hydrogen, and nitrogen for a part of the sample set, were acquired. The isotopic values of Phenacetin standards acquired from various providers located worldwide are quite spread, which indicates that stable isotopes could be used to discriminate manufacturers. However, the measured values of most of the seized samples are concentrated in a narrow range, tending to demonstrate that Phenacetin is smuggled from a single source or similar ones. Consequently, stable isotopes could only be used to exclude that several samples come from a common source. Copyright (c) 2016 John Wiley & Sons, Ltd.

Thermodynamics of dissolution and infrared-spectroscopy of solid dispersions of phenacetin.[Pubmed:26955604]

J Adv Pharm Technol Res. 2016 Jan-Mar;7(1):6-12.

In this work enthalpies of dissolution in water of polyethylene glycols (PEGs) having an average molecular weight of 1000 and 1400, Pluronic-F127, Phenacetin as well as the composites prepared from them were measured using solution calorimetry at 298.15 K. Intermolecular interaction energies of polymer-Phenacetin were calculated on the basis of an additive scheme. It was shown that for mixtures with high content of polymer (>90 wt%) Pluronic-F127 has the highest solubilizing effect, while for mixtures with (4-6):1 polymer: Phenacetin ratio the best solubilizing agent is PEG-1400. Infrared-spectra showed a decrease of the number of self-associated molecules of Phenacetin with increasing of polymer content in the composites. The obtained results enabled us to identify the features of intermolecular interactions of polymers with a model hydrophobic drug and may be used for optimizing the conditions for preparing solid dispersions based on hydrophilic polymers.

Electro-catalytic oxidation of phenacetin with a three-dimensional reactor: Degradation pathway and removal mechanism.[Pubmed:26950512]

Chemosphere. 2016 Jun;152:17-22.

Phenacetin is a common analgesic, anti-arthritic and anti-rheumatic drug. This study dealt with the degradation of Phenacetin in alkaline media using a three-dimensional reactor with particle electrodes. Particular attention was paid to the degradation pathway and the reaction mechanism in the system. Liquid chromatography coupled with time-of-flight mass spectrometry was used to identify the intermediates. The Phenacetin was observed to be firstly cut off the branch chains main by direct oxidation, and then the intermediates further degraded to ring opening products by hydroxyl radical resulting from indirect oxidation and finally mineralized to CO2, H2O. A possible removal mechanism was proposed that direct and indirect oxidation together did effect on the pollutants with oxygen.

A study of the formation of magnetically active solid dispersions of phenacetin using atomic and magnetic force microscopy.[Pubmed:28217547]

J Adv Pharm Technol Res. 2017 Jan-Mar;8(1):2-7.

A lot of pharmaceutical substances have a poor solubility that limits their absorption and distribution to the targeted sites to elicit the desired action without causing untoward effects on healthy cells or tissues. For such drugs, new modes of delivery have to be developed for efficient and effective delivery of the drug to the target site. Formation of magnetically active solid dispersion of such drugs could be a useful approach to addressing this problem because they combine targeted delivery and good solubility. In this work, the distribution of superparamagnetic nanoparticles in the solid dispersion of polyethylene glycol with average molecular weight 950-1050 g/mol and Phenacetin was studied using atomic force and magnetic force microscopy. The distribution of nanoparticles was found to be uniform in studied composites. Magnetically active solid dispersions may find application in the production of the capsulated drug delivery systems with enhanced solubility parameters.

Description

Phenacetin is a non-opioid analgesic without anti-inflammatory properties, inhibits COX-3 activity.

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