Acetanilide

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Acetanilide

Acetanilide is an odourless solid

Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
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

Trade name

A trade name, also known as a trading name or a business name, is the name which a business trades under for commercial purposes, although its registered, Legal name , used for contracts and other formal situations, may be another....
Antifebrin.

Properties
Acetanilide is slightly soluble in water.

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Formation

Acetanilide can be produced by reacting acetic anhydride

Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
with either aniline

Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
or phenylammonium chloride

Properties

Acetanilide is slightly soluble in water. It has the ability to self-ignite if it reaches a temperature of 545 °C

Celsius

Celsius is a temperature scale that is named after the Swedish astronomer Anders Celsius , who developed a similar temperature scale two years before his death....
, but is otherwise stable under most conditions. Pure crystals are plate shaped, white in colour, and have a sugary aftertaste.

Applications

Acetanilide is used as an inhibitor

Reaction inhibitor

A reaction inhibitor is a chemical substance that decreases the rate of, or prevents, a chemical reaction....
in hydrogen peroxide

Hydrogen peroxide

Hydrogen peroxide is a very pale blue liquid which appears colorless in a dilute solution, slightly more viscous than water. It is a weak acid....
and is used to stabilize cellulose

Cellulose

File:Cellulose Sessel.svgCellulose is an organic compound with the chemical formula , a polysaccharide consisting of a linear chain of several hundred to over ten thousand ? linked D-glucose units....
ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
varnish

Varnish

Varnish is a Transparency , hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a Turpentine substitute or solvent....
es. It has also found uses in the intermediation in rubber

Rubber

Natural rubber is an elastomer?an Elasticity_ hydrocarbon polymer?that was originally derived from a milky colloidal suspension, or latex , found in the sap of some plants....
accelerator synthesis, dyes and dye

Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
intermediate synthesis, and camphor

Camphor

Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula carbon10hydrogen16oxygen....
synthesis. Acetanilide was used as a precursor in penicillin

Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
synthesis and other pharmaceuticals and its intermediates.

Acetanilide is a prodrug

Prodrug

A prodrug is a Pharmacology substance that is administered in an inactive form. Once administered, the prodrug is drug metabolism in vivo into an active metabolite....
with analgesic

Analgesic

An analgesic is any member of the diverse group of Medication used to relieve pain . The word analgesic derives from Greek an- and algos ....
and antipyretic

Antipyretic

Antipyretics are drugs that reduce body temperature in situations such as fever. However, they will not affect the normal body temperature if one does not have a fever....
(fever

Fever

Fever is a frequent medical sign that describes an increase in internal body temperature to levels above normal. Fever is most accurately characterized as a temporary elevation in the body's thermoregulatory set-point, usually by about 1?2 ?C ....
-reducing) properties; it is in the same class of drugs as acetaminophen (paracetamol

Paracetamol

Paracetamol or acetaminophen is a widely used over-the-counter drug analgesic and antipyretic . It is commonly used for the relief of fever, headaches, and other minor aches and pains, and is a major ingredient in numerous common cold and Influenza remedies....
). Under the name acetanilid it formerly figured in the formula of a number of patent medicine

Patent medicine

Patent medicine is the somewhat misleading term given to various medical compounds sold under a variety of names and labels, though they were, for the most part, actually medicines with trademarks, not patented medicines....
s and over the counter drugs. In 1948, Julius Axelrod

Julius Axelrod

Julius Axelrod was an United States biochemistry. He won a share of the Nobel Prize in Physiology or Medicine in 1970 along with Bernard Katz and Ulf von Euler....
and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia

Methemoglobinemia

Methemoglobinemia is a disorder characterized by the presence of a higher than normal level of methemoglobin in the blood. Methemoglobin is a form of hemoglobin that does not bind oxygen....
and ultimately doing damage to the liver

Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
and kidney

Kidney

The kidneys are Organ that have numerous biological roles. Their primary role is to maintain the homeostasis balance of bodily fluids by filtering and secreting Metabolomics#Metabolitess and minerals from the blood and excreting them, along with water , as urine....
s. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite

Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
of acetanilide and whose use Axelrod and Brodie suggested in the same study.

In the 19th century it was one of a large number of compounds used as experimental photographic developer

Photographic developer

In the Photographic processing, plates or papers, the photographic developer is a chemical that makes the latent image on the film or print visible....
s.

Commonly used in organic chemistry labs for recrystallization experiments.

Acetanilide

Formation

Properties

Applications

External links