60902-27-4

Basic information

• Product Name: Phenacetin-d3
• Synonyms: 2,2,2-trideuterio-N-(4-ethoxyphenyl)acetamide
• CAS NO: 60902-27-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 182.234205334
• Mol File: 60902-27-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenacetin-d3(CAS DataBase Reference)
• NIST Chemistry Reference: Phenacetin-d3(60902-27-4)
• EPA Substance Registry System: Phenacetin-d3(60902-27-4)

Safety Data

• Hazardous Substances Data: 60902-27-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Phenacetin-d3 is used as a research compound for investigating the pharmacological properties and potential health risks associated with Phenacetin. Its deuterated nature allows for the study of metabolic pathways, drug interactions, and the development of safer alternatives to Phenacetin.
Used in Analytical Chemistry:
Phenacetin-d3 is employed as an internal standard in analytical chemistry, particularly in the quantification of Phenacetin and related compounds in biological samples. The use of deuterated analogues helps to improve the accuracy and precision of analytical measurements by providing a stable reference point for comparison.
Used in Toxicology Studies:
Phenacetin-d3 is utilized in toxicology research to better understand the mechanisms of action and potential carcinogenic effects of Phenacetin. By comparing the behavior of Phenacetin-d3 with its non-deuterated counterpart, researchers can gain insights into the factors contributing to its toxicity and develop strategies to mitigate these risks.
Used in Drug Development:
Phenacetin-d3 serves as a valuable tool in the development of new drugs with improved safety profiles. By studying the structural and functional differences between Phenacetin and its deuterated analogue, researchers can identify potential modifications that may reduce the risk of adverse effects while maintaining therapeutic efficacy.

Upstream product

• 62-44-2 4-ethoxyacetanilide 
• 60902-28-5 Paracetamol-C⁽²⁾H₃ 
• 75-03-6 ethyl iodide 

Downstream Products

• 60902-28-5 Paracetamol-C⁽²⁾H₃ 

Relevant articles and documents

Preparation of labeled human drugmetabolites and drug-drug interaction-probes with fungal peroxygenases

Enzymatic conversion of a drug can be an efficient alternative for the preparation of a complex metabolite compared with a multi-step chemical synthesis approach. Limitations exist for chemical methods for direct oxygen incorporation into organic molecule

NMR spectroscopic studies on the metabolism and futile deacetylation of phenacetin in the rat

1. 1H-NMR spectroscopy of urine was used to determine the % deacetylation and re-acetylation of 2H-labelled (in the acetyl) phenacetin metabolites in the rat. 2. Male Sprague-Dawley rats were each dosed with either phenacetin or phenacetin-C2H3, at 50 mg kg-1. The total urinary recoveries for phenacetin and phenacetin-C2H3, were 47·6±16·7 and 50·1±16·2% respectively (not significantly different, p > 0·05). Paracetamol sulphate and glucuronide are the major urinary metabolites of both protio and deuteriophenacetin. 2. The futile deacetylation given by the urinary recovery of protio-acetyl metabolites of phenacetin-C2H3, was 29·6±0·9% for paracetamol sulphate and 36·6±3·1% for paracetamol glucuronide. These observations demonstrate a high level of futile deacetylation in the paracetamol conjugates formed by metabolism of phenacetin-C2H3, and this may indicate a high metabolic flux through the nephrotoxic intermediate 4-aminophenol. 4. The level of futile deacetylation for phenacetin was significantly higher than that found previously in studies of labelled paracetamol in rat or man, and may be important in understanding the higher nephrotoxicity of phenacetin as compared with paracetamol.