Description

 

Phenacetin powder, appears as a white crystalline powder or white, lustrous, scaly crystals. Its crystalline structure gives it a unique shine and texture. It is poorly soluble in water, with a solubility of approximately 0.076 g per 100 mL of water. However, it is slightly soluble in boiling water. Additionally, it is micro-soluble in diethyl ether but soluble in ethanol and chloroform. Phenacetin is incompatible with strong oxidizing agents and strong acids. Mixing it with these substances may lead to chemical reactions and potential safety hazards. It is classified as a carcinogen by the International Agency for Research on Cancer (IARC). Long-term or high-dose use of phenacetin may pose a risk of cancer.

Chemical Formula

C10H13NO2

Exact Mass

179

Molecular Weight

179

m/z

179 (100.0%), 180 (10.8%)

Elemental Analysis

C, 67.02; H, 7.31; N, 7.82; O, 17.85

Synthesis Methods

1. Phenolic acetic acid method

The phenol acetic acid method was one of the earliest synthesis methods of phenacetin powder. It starts with the preparation of phenacetin from para acetyl angelic acid (PAA). The following are the specific steps:

Step 1: N-acetylation reaction: Acetoacetic acid can be prepared by adding ethylamine to acetic acid for N-acetylation.

PAA + CH3CO2H + C2H5NH2 → CH3CONHC2H5 + CH3CO2H + H2O

Step 2: Esterification reaction: Next, in the presence of sulfuric acid, acetylated ethyl acetate and phenol undergo esterification reaction in carbon tetrachloride to generate Phenacetin.

CH3CONHC2H5 + C6H5OH → C6H5OCONHC2H5 + H2O

C6H5OCONHC2H5 + H2SO4 → C6H

2. Phenylacetic acid method

Due to the complex preparation process of PAA, the phenylacetic acid method has gradually become the main method for synthesizing phenacetin. This method is prepared using phenylacetic acid as the raw material. The following are the specific steps:

Step 1: Condensation reaction between phenylacetic acid and N-formylaniline: The condensation reaction between phenylacetic acid and N-formylaniline is catalyzed by sulfuric acid to produce N – (phenylacetyl) – N ‘- methylaniline.

C6H5CH2COOH + C6H5NH(CO)CH3 → C6H5CH2NHCOCH2C6H5 + H2O

Step 2: Acetylation reaction of N – (phenylacetyl) – N ‘- methylaniline: N – (phenylacetyl) – N’ – methylaniline undergoes acetylation reaction in acetic acid to produce N – (phenylacetyl) – N ‘- methylaniline acetate.

C6H5CH2NHCOCH3 + CH3CO2H → C6H5CH2NHCOCH2C6H5·CH3CO2H

Step 3: N – (phenylacetyl) – N ‘- methylaniline acetate esterification reaction: N – (phenylacetyl) – N’ – methylaniline acetate and phenol undergo esterification reaction in carbon tetrachloride to generate Phenacetin.

C6H5CH2NHCOCH2C6H5·CH3CO2H + C6H5OH → C6H5OCONHC2H5 + C6H5CH2NHCOCH2C6H5·CH3CO2H

C6H5OCONHC2H5 + CH3CO2HSO4H → C6H5OC2H5 + CH3CO2H2SO4

The discovery process of Phenacetin

In 1873, scientists first synthesized Phenacetin through a reaction between p-nitrophenol and glacial acetic acid catalyzed by tin. However, this product did not receive much attention at that time.

Years later, in 1887, Phenacetin, also known as acetophenetidin, was introduced as a medication for fever reduction and pain relief. It was the first synthetic analgesic and antipyretic drug on the market. Its mechanism of action was believed to be related to its ability to lower the body’s temperature set-point in the brain and produce analgesic effects.

Unfortunately, Phenacetin was soon found to have significant side effects. Prolonged or excessive use of Phenacetin could lead to various health issues, including anemia, cyanosis, hypoxia, kidney damage, and even cancer. In particular, the use of Phenacetin was linked to a significant increase in kidney disease cases in the 1950s, leading to its eventual ban in many countries.

Despite its drawbacks, the discovery of Phenacetin was crucial in the development of modern pharmacology. Researchers soon realized that Phenacetin was metabolized in the body to form Paracetamol (acetaminophen), which had similar analgesic and antipyretic properties but with fewer side effects. This led to the development and widespread use of Paracetamol as a safer alternative to Phenacetin.

In summary, while Phenacetin’s discovery marked an important milestone in the history of pharmacology, its significant side effects ultimately led to its replacement by safer alternatives like Paracetamol. The story of Phenacetin serves as a reminder of the importance of rigorous testing and continuous research in drug development.

Phenacetin, though no longer widely used due to its adverse side effects, played a significant role in the early history of pharmaceutical analgesics and antipyretics. Its applications were primarily focused on pain relief and fever reduction.

Pain Relief

Phenacetin was effective in relieving a wide range of pain, from mild to moderate. It was commonly used to treat headaches, toothaches, menstrual cramps, muscle pain, and other painful conditions. The analgesic properties of Phenacetin were attributed to its ability to inhibit prostaglandin synthesis, thereby reducing inflammation and pain.

Fever Reduction

Phenacetin Powder CAS 62-44-2 Applications | Shaanxi BLOOM Tech Co., Ltd

In addition to its analgesic properties, Phenacetin was also effective in reducing fever. It lowered the body’s temperature set-point in the brain, allowing the body to cool itself naturally. This made it a valuable medication for treating various febrile conditions.

However, it’s important to note that Phenacetin’s use has been largely discontinued due to its association with adverse side effects such as kidney damage, anemia, and cancer. As a result, safer alternatives like Paracetamol (acetaminophen) have been developed and are now widely used for pain relief and fever reduction.

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