Acetaldehyde is the most abundant carcinogen in tobacco smoke, and it readily dissolves into saliva during smoking. Fermented food and many alcoholic beverages can also contain significant amounts of acetaldehyde.
What are the hazards of acetanilide?
Hazards. ACETANILIDE is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5...
Does acetanilide have aniline?
You see, it was found that acetanilide samples always had an impurity of aniline in them, which is what acetanilide was made from. The problem with aniline being present as an impurity is that aniline is a carcinogen (cancer-causing agent).
What is acetanilide named after?
Acetanilide is named after acetamides and aniline. It has a benzene ring and is derived from acetic acid and that is why is it called acetamidobenzine. The first aniline derivative is acetanilide. When a hydrogen atom that is found on nitrogen is replaced by an acetyl group, it forms acetanilide.
What is the melting point of acetanilide?
So with the above experiment we get the following observations: The resulting acetanilide crystals weighed as the preparation element quantities. It has a melting point of 114.5 degrees Celsius. Because aniline is a carcinogen, it must be handled with extreme caution. Avoid inhaling acetic anhydride vapors.
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What is acetanilide used for?
It has been used in the manufacture of colored dyes for fabrics and textiles, as a reagent in the production of rubber, and as a hydrogen peroxide decomposition inhibitor. Probably what it's best known for however is its role in the pharmaceutical field. In the late 1800s, acetanilide was found to possess painkilling properties, and was introduced as an analgesic under the name Antifebrin.
What is the structure of acetanilide?
Acetanilide has an amide functional group, meaning it has a nitrogen atom bonded directly to a carbonyl (carbon-oxygen double bond). Acetanilide can be described by two resonance structures, with the one that places a positive charge on the nitrogen atom helping to explain why it is non-basic.
What is the name of the compound that is synthesized by reacting aniline with?
Acetanilide is commonly synthesized by reacting aniline with either acetyl chloride or acetic anhydride, with acetic anhydride being preferred over acetyl chloride due to corrosiveness and toxicity concerns.
How is acetanilide synthesized?
Structure and resonance forms of acetanilide. In terms of how acetanilide is synthesized, it's most commonly made by reacting aniline with either acetyl chloride or a cetic anhydride. Although both methods work equally well, the preparation from acetic anhydride tends to be preferred due to the corrosiveness and toxicity of acetyl chloride. ...
What is the reaction of acetanilide to chlorosulfonic acid?
When acetanilide is reacted with chlorosulfonic acid (HSO 3 Cl), it produces 4-acetamidobenzenesulfonyl chloride, which is then reacted with ammonia or organic primary amines to make sulfonamides. We talked earlier about the fact that acetanilide was introduced as a pain relief agent in the late 1800's.
Is acetanilide an analgesic?
Finally, we saw that although acetanilide was once used as an analgesic, the toxicity concerns due to aniline impurities caused it to be unpopular due to the carcinogenic properties of aniline. To unlock this lesson you must be a Study.com Member. Create your account.
Is acetanilide a cancer causing compound?
So although your headache may get better, you run the risk of contaminating yourself with a cancer-causing compound, which is of much greater concern. Acetanilide is a derivative of aniline, where one of the hydrogen atoms on the nitrogen atom has been replaced with an acetyl group.
Why was phenacetin removed from the market?
Phenacetin is linked to hypertension, cardiovascular disease, and cancer, but was removed from the market primarily due to induction of chronic renal disease. View chapter Purchase book. Read full chapter. URL: https://www.sciencedirect.com/science/article/pii/B012369400000747X.
What is the most abundant P450?
P450 3A4 is, on the average, the most abundant P450 in human liver and small intestine and is of interest because of its prominence in the oxidation of a great variety of drugs, procarcinogens, and steroids ( Guengerich et al. 1994 ). Many years went into the development of assays, and some proved better than others.
What are the functions of P450?
Historically a number of in vivo assays have been used as measures of human P450 function. These have included antipyrine clearance , hexobarbital metabolism , and phenacetin O-deethylation ( Distlerath and Guengerich 1987 ). With the development of knowledge about which human P450 enzymes are involved in the oxidation of particular drugs, it has become possible to develop non-invasive assays that predict levels of individual P450 enzymes ( Table 2 ), particularly the major ones involved in the metabolism of drugs and protoxicants/procarcinogens. This information is usually derived from in vitro studies on particular P450s coupled with pharmacokinetic work in humans. General conclusions are presented in Table 6.
When was phenacetin first used?
Phenacetin was developed in 1878 by an American chemist, Harmon Northrop Morse. It was introduced into the pharmaceutical market in 1887. However, it was withdrawn in 1983 in the United States due to unacceptable levels of interstitial nephritis in patients and potential risks of tumorigenicity.
Is phenacetin a carcinogen?
Phenacetin is group 2A (reasonably anticipated to be a human carcinogen) based on sufficient evidence of carcinogenicity in experimental animals according to the IARC Working Group noted above. The same group found that analgesic mixtures containing phenacetin are known to be human carcinogens based on sufficient evidence of carcinogenicity in humans. The Human Health Assessment Group in (US) Environmental Protection Agency's Office of Health and Environmental Assessment has evaluated phenacetin for carcinogenicity. According to their analysis, the weight of evidence for phenacetin is group B2 (considered probably carcinogenic to humans), which is based on inadequate evidence in humans and sufficient evidence in animals.
Is deacetylase present in renal cortex?
Deacetylase enzymes are also present in higher levels in renal cortex, the target for acetaminophen nephrotoxicity, than in liver or renal medulla and there is a positive correlation between renal cortex deacetylase activity and susceptibility to acetaminophen nephrotoxicity in various animal models.
When was acetanilide first introduced?
The introduction of acetanilide in 1886 and phenacetin the following year opened up the road to paracetamol’s discovery. The structural similarity of these three drugs is shown in Figure 10.39.
Which chemical structure retains antibiotic activity?
FIGURE 16.3. Chemical structures of chloramphenicol and thiamphenicol. Thiamphenicol, in which the nitro group of chloramphenicol is replaced by a methylsulfone group, retains antibiotic activity, but does not cause the aplastic anemia that is a major concern with chloramphenicol therapy.
When was paracetamol first used?
Paracetamol should have been introduced earlier than 1953, when Sterling & Winthrop marketed it for the first time. Acetanilide and phenacetin were effective in reducing fever and relieving pain, but they had a high incidence of toxic side effects. The former was more toxic, causing cyanosis resulting from methemoglobinemia. It was reported that French chemist Charles Gerhardt synthesized paracetamol in 1852 but did not test it for medical use. Later, in 1878, American chemist Harmon N. Morse also synthesized paracetamol by reducing p-nitrophenol, using tin and glacial acetic acid. Once again, the scientific community did not work to discover the medical uses of the product.
Is acetaminophen an analgesic?
Acetaminophen is an acetanilide widely used as an antipyretic and analgesic drug, which can cause hepatocellular necrosis in man and experimental animals [115,116 ]. Evidence from a variety of studies has indicated a model where the microsomal cytochrome P450-dependent system plays an important role in the oxidation of the drug to a chemically reactive and potentially toxic metabolite, highly reactive both as an electrophile and as reactive oxidant [ 117 ].
