Phenacetin
Synonyms: phenacetin; acetyl p-aminophenylethyl ether; acetoethoxy aniline; acetoethoxyaniline; acetamidophenylether; phenacetin; acetooxyethylaniline; 4-ethoxyacetyl Aniline
English name: Phenacetin
CAS Number: 62-44-2
Content of 99%
Molecular formula: C10H13NO2
Molecular weight: 179.22
Chemical properties: white shiny scaly crystal or white crystalline powder. Melting point 137-138 ° C, refractive index of 1.571. Insoluble in water, slightly soluble in ether, slightly soluble in boiling water, soluble in ethanol and chloroform. Dissolved in concentrated sulfuric acid when no color, to the solution after the drop of nitric acid was orange. Odorless, slightly bitter taste.
Uses: antipyretic analgesics for the treatment of fever headache, neuralgia and so on
Also known as acetooxyethylaniline. Shiny lobes or scaly crystals, odorless, slightly bitter taste. Melting point 134 ~ 137 ℃. Stable in the air, very slightly soluble in water, slightly soluble in boiling water, slightly soluble in ether, soluble in ethanol, chloroform. By p-nitrochlorobenzene by etherification, reduction and acetylation reaction in the system. For acetanilide antipyretic analgesics. Apply to fever, headache, neuralgia and other drugs dubbed compound tablets.
Antipyretic effect is stronger than analgesic effect. Pharmacodynamic intensity and aspirin rather, the role of slow and lasting, low toxicity. Studies have shown that: the goods and its metabolites paracetamol have antipyretic effect. Because the use of enzyme inhibitors to phenacetin can not be converted into paracetamol, can still show a significant antipyretic effect. So the line after the antipyretic effect is not only by its active product paracetamol produced. Phenylephrine mild analgesic effect, generally able to maintain 3-4 hours; and salicylic acid combination of synergies, so that the effect of analgesic enhancement. Clinically used mainly for small animals, antipyretic analgesia. This product is also one of the components of APC tablets.
Packing: 25KG cardboard drum
Preparation
Method 1
Fenoxetine can be prepared by synthesizing Williamson in methyl ethyl ketone by refluxing with acetaminophen and iodine in the presence of anhydrous potassium carbonate. The crude product was recrystallized from water.
Method 2
By p-aminophenylethyl ether by acetylation derived
A mixture of benzene, acetic anhydride and p-aminophenylethyl ether was heated and heated in an oil bath for 4 hours. After completion of the reaction, the reaction product was cooled, that was precipitated with fentaine, filtered and washed with cold benzene. The yield was theoretical Of the 86%.
Fenapine was invented in 1878, mainly used as an analgesic. Usually daily 300 to 500 mg dose will achieve analgesic effect. It also has a fever effect.
Phenacetin use and synthesis methods
Antipyretic analgesic analgesic effect of phenacetin is similar to that of "acetylsalicylic acid", which is mainly used as antipyretic analgesic, which is slow and lasting. For the treatment of headache, neuralgia, joint pain and fever Have a better effect, but the anti-rheumatic, anti-inflammatory effect is weak. Excessive dose can lead to methemoglobinemia, resulting in hypoxia, long-term medication can damage the kidneys, and even cause nipple necrosis, should be used with caution. Because of its toxic side effects and the rapid development of other similar drugs, the drug has ceased to be used alone, but as a raw material and other drugs with recipe. Often with aspirin, caffeine together to form compound aspirin, its composition is phenacetin 0.162 grams, 0.227 grams of aspirin, caffeine 0.035 grams, less toxic, for the treatment of colds. Such as the addition of a small amount of chlorpheniramine in the drug, but also made of chlorpheniramide tablets, can be used to treat cold headache, neuralgia, rheumatism and so on.
Phenacetin itself does not antipyretic analgesic effect, in the body, after metabolizing the decomposition of acetaminophen that paracetamol, only to play the effect of antipyretic analgesic. But also decomposition of p-phenylethyl ether, p-phenylethyl ether is not only antipyretic analgesic effect, and is the main factor in the side effects of phenacetin.
China in 1954 began production of phenacetin, nitrochlorobenzene and ethanol by etherification reaction of p-nitrophenylether, and then reduced to p-aminophenylethyl ether and acetic acid acetylation reaction in the system.
Side effects Long-term use of tablets containing phenacetin can cause renal papillary necrosis, interstitial nephritis, and may even induce renal pelvic cancer and bladder cancer. Phenacetin is also easy to make hemoglobin to form methemoglobin, the blood oxygen carrying capacity decreased, causing cyanosis reaction. In addition, phenacetin can also cause hemolytic and hemolytic anemia, and the retina has a certain toxicity. Long-term use of phenacetin, but also can cause dependence on drugs. Foreign countries such as the United States, Britain, Germany, Japan and other countries have decided to cancel phenacetin, or provided in its packaging should be marked "can not take long-term or high-dose taking."
Chemical properties of white shiny scaly crystal or white crystalline powder. Melting point 137-138 ° C, refractive index of 1.571. Insoluble in water, slightly soluble in ether, slightly soluble in boiling water, soluble in ethanol and chloroform. Dissolved in concentrated sulfuric acid when no color, to the solution after the drop of nitric acid was orange. Odorless, slightly bitter taste.
Use Acetaminophenylethyl ether used as organic synthesis of raw materials and pharmaceutical intermediates.
Use antipyretic analgesics for the treatment of fever headache, neuralgia and so on
Use of raw materials for scientific research
Production method (1) from p-aminophenylethyl ether by acetylation derived A mixture of benzene, acetic anhydride and p-aminophenylethyl ether was heated and heated in an oil bath for 4 hours. After completion of the reaction, the reaction product was cooled, that was precipitated with fentaine, filtered and washed with cold benzene. The yield was theoretical Of the 86%. (2) by the addition of acetaminophen and sodium ethanol role: first acetamidophenol added to sodium ethoxide, and then slowly adding ethyl iodide, heating reflux 1h, cooling, filtration, the crude product dissolved in ethanol, Filter, the filtrate diluted with hot water, and then by cooling, filtration, drying, and finished products, the yield of 80% of the theoretical amount. The first method can also be used as a solvent, but with acetic acid instead, the process is as follows. 40% of dilute acetic acid heated to boiling, put p-aminophenylether, steamed water, to the temperature rose to 150 ° C by adding glacial acetic acid, reflux 1h, continue to steam, until the temperature rose above 150 ℃, sampling determination of free amino benzene Ether, according to the amount of residual aminophenylethyl ether added acetic anhydride, reflux reaction 0.5h, check the end, qualified after decompression, recovery of acetic acid to amino content below 0.046, acid 0.2% or less, the reaction liquid into the hot refining mother liquor, Stir to cool to 40 ° C, filter, to be non-septine crude. Refined, fenapine crude plus boiling water or refined mother liquor, heated and stirred to dissolve, filter, the filtrate adjusted to pH = 4.5-4.7 with acid, adding activated carbon and sodium thiosulfate stirring decolorization, filtration, filtrate cooling crystallization, Dry, was phenacetin.
Category of toxic substances
Toxic grading poisoning
Acute toxicity Oral-rat LD50: 3600 mg / kg; Oral-mouse LD50: 866 mg / kg
Flammable hazardous characteristics open flame combustible; heating decomposition of the release of toxic nitrogen oxide gas; the drug side effects: pale, liver damage, hemoglobin
Storage and storage characteristics of the warehouse ventilation low temperature drying; and reducing agent, food additives stored separately
Fire extinguishing agent spray water, foam, carbon dioxide, sand.
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