Names | |||
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Preferred IUPAC name N-Phenylacetamide [1] | |||
Other names Acetanilide [1] N-Phenylethanamide | |||
Identifiers | |||
3D model (JSmol) | |||
606468 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.864 | ||
EC Number |
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82833 | |||
KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
CompTox Dashboard (EPA) | |||
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Properties [2] [3] | |||
C8H9NO | |||
Molar mass | 135.166 g·mol−1 | ||
Odor | Odorless | ||
Density | 1.219 g/cm3 | ||
Melting point | 113–115 °C (235–239 °F; 386–388 K) | ||
Boiling point | 304 °C (579 °F; 577 K) | ||
<0.56 g/100 mL (25 °C) | |||
Solubility | Soluble in ethanol, diethyl ether, acetone, benzene | ||
log P | 1.16 (23 °C) | ||
Vapor pressure | 2 Pa (20 °C) | ||
Acidity (pKa) | 0.5 (25 °C, H2O) (conjugate acid) [4] | ||
2.71 | |||
Hazards [5] [6] | |||
GHS labelling: | |||
Warning | |||
H302 | |||
P264, P270, P301+P312, P330, P501 | |||
Flash point | 174 °C (345 °F; 447 K) | ||
545 °C (1,013 °F; 818 K) | |||
Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. It is the N-acetylated derivative of aniline. [7] It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
Acetanilide can be produced by reacting acetic anhydride with aniline: [7]
The preparation used to be a traditional experiment in introductory organic chemistry lab classes, [8] but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen.
Acetanilide is slightly soluble in water, and stable under most conditions. [5] Pure crystals are plate shaped and appear colorless, white, or in between.
Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. [7] It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. [9] Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs. [10]
In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the names of Antifebrin by A. Cahn and P. Hepp in 1886. [11] But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia and ultimately liver and kidney damage, [12] prompted the search for supposedly less toxic aniline derivatives such as phenacetin. [13] After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties. [12] [14] The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body.
An antipyretic is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which results in a reduction in fever.
Paracetamol (acetaminophen) is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely used over-the-counter medication. Common brand names include Tylenol and Panadol.
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
A patent medicine is a non-prescription medicine or medicinal preparation that is typically protected and advertised by a trademark and trade name, and claimed to be effective against minor disorders and symptoms, as opposed to a prescription drug that could be obtained only through a pharmacist, usually with a doctor's prescription, and whose composition was openly disclosed. Many over-the-counter medicines were once ethical drugs obtainable only by prescription, and thus are not patent medicines.
Phenacetin is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s.
Hepatotoxicity implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn from the market after approval.
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.
Pyroglutamic acid is a ubiquitous but understudied natural amino acid derivative in which the free amino group of glutamic acid or glutamine cyclizes to form a lactam. The names of pyroglutamic acid conjugate base, anion, salts, and esters are pyroglutamate, 5-oxoprolinate, or pidolate.
Cyclooxygenase-3 (COX-3) is an enzyme that is encoded by the PTGS1 (COX1) gene, but is not functional in humans. COX-3 is the third and most recently discovered cyclooxygenase (COX3050) isozyme, while the first two to be discovered were COX-1 and COX-2. The COX-3 isozyme is encoded by the same gene as COX-1, with the difference that COX-3 retains an intron that is not retained in COX-1.
Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.
4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.
NAPQI, also known as NAPBQI or N-acetyl-p-benzoquinone imine, is a toxic byproduct produced during the xenobiotic metabolism of the analgesic paracetamol (acetaminophen). It is normally produced only in small amounts, and then almost immediately detoxified in the liver.
Hydrocodone/paracetamol is the combination of the pain medications hydrocodone and paracetamol (acetaminophen). It is used to treat moderate to severe pain. It is taken by mouth. Recreational use is common in the United States.
AM404, also known as N-arachidonoylphenolamine, is an active metabolite of paracetamol (acetaminophen), responsible for all or part of its analgesic action and anticonvulsant effects. Chemically, it is the amide formed from 4-aminophenol and arachidonic acid.
N-Methylphenethylamine (NMPEA) is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into phenylacetaldehyde which is further broken down into phenylacetic acid by monoamine oxidase. When this is inhibited by monoamine oxidase inhibitors, it allows more of the PEA to be metabolized into nymphetamine (NMPEA) and not wasted on the weaker inactive metabolites.
Paracetamol poisoning, also known as acetaminophen poisoning, is caused by excessive use of the medication paracetamol (acetaminophen). Most people have few or non-specific symptoms in the first 24 hours following overdose. These symptoms include feeling tired, abdominal pain, or nausea. This is typically followed by absence of symptoms for a couple of days, after which yellowish skin, blood clotting problems, and confusion occurs as a result of liver failure. Additional complications may include kidney failure, pancreatitis, low blood sugar, and lactic acidosis. If death does not occur, people tend to recover fully over a couple of weeks. Without treatment, death from toxicity occurs 4 to 18 days later.
Bernard Beryl Brodie was a founding scientist in the area of biochemical and neurochemical pharmacology whose work in the 1940s and 1950s had great impact. He was a major figure in the fields of drug metabolism and drug therapy, studying how the absorption and interactions of drugs in the body. Brodie helped to found and lead the Laboratory of Chemical Pharmacology at the National Heart Institute in Bethesda, Maryland, one of the National Institutes of Health. He was a member of the United States National Academy of Sciences.
David Lester was an American biochemist who did extensive studies of alcoholism and was a professor at Rutgers University.
Aspirin/paracetamol/caffeine is a combination drug for the treatment of pain, especially tension headache and migraine. It contains aspirin, a non-steroidal anti-inflammatory drug; paracetamol (acetaminophen), an analgesic; and caffeine, a stimulant.
An endocannabinoid enhancer (eCBE) is a type of cannabinoidergic drug that enhances the activity of the endocannabinoid system by increasing extracellular concentrations of endocannabinoids. Examples of different types of eCBEs include fatty acid amide hydrolase (FAAH) inhibitors, monoacylglycerol lipase (MAGL) inhibitors, and endocannabinoid transporter (eCBT) inhibitors. An example of an actual eCBE is AM404, the active metabolite of the analgesic paracetamol and a dual FAAH inhibitor and eCBRI.
N-Phenyl derivatives of primary amides are called 'anilides' and may be named using the term 'anilide' in place of 'amide' in systematic or retained names of amides. (…) However, names expressing N-substitution by a phenyl group on an amide are preferred IUPAC names.
"Making an old pain and fever medication" by NileRed. YouTube . May 21, 2017.