Allylamine is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C
3H
5NH
2. This colorless liquid is the simplest stable
unsaturated amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen
Hydrogen is the chemical element wi ...
.
Production and reactions
All three allylamines, mono-, di-, and
triallylamine
Triallylamine is the organic compound with the formula N(CH2CH=CH2)3. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a tertiary amine and three alkene groups. Triallylamine (and mono- and diallyl amines) is p ...
, are produced by the treating
allyl chloride
Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chl ...
with
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...
followed by distillation.
Or by the reaction of allyl chloride with Hexamine. Pure samples can be prepared by hydrolysis of
allyl isothiocyanate
Allyl isothiocyanate (AITC) is an organosulfur compound (formula CH2CHCH2NCS). This colorless oil is responsible for the pungent taste of mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated thr ...
. It behaves as a typical amine.
[Henk de Koning, W. Nico Speckamp "Allylamine" in ''Encyclopedia of Reagents for Organic Synthesis'', 2001, John Wiley & Sons, Weinheim. Article Online Posting Date: April 15, 2001]
Polymerization can be used to prepare the homopolymer (
polyallylamine) or copolymers. The polymers are promising membranes for use in
reverse osmosis.
[
]
Other allylamines
Diallylamine
Diallylamine is the organic compound with the formula HN(CH2CH=CH2)2. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a secondary amine and two alkene groups. Diallylamine is used in the production of ''N,N' ...
is a precursor to industrial products. Functionalized allylamines have pharmaceutical applications. Pharmaceutically important allylamines include flunarizine
Flunarizine, sold under the brand name Sibelium among others, is a drug classified as a calcium antagonist which is used for various indications. It is not available by prescription in the United States or Japan. The drug was discovered at Janss ...
and naftifine
Naftifine hydrochloride (brand names include Exoderil and Naftin) is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis (topical fungal infections).
Naftifine was invented at the Sandoz Researc ...
. Flunarizine aids in the relief of migraines while naftifine acts to fight common fungus
A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from t ...
causing infections such as athlete's foot
Athlete's foot, known medically as ''tinea pedis'', is a common skin infection of the feet caused by a fungus. Signs and symptoms often include itching, scaling, cracking and redness. In rare cases the skin may blister. Athlete's foot fungus ...
, jock itch
Jock may refer to:
Common meanings
* Jock (stereotype), a North American term for a stereotypical male athlete
* Jock, a derogatory term for Scottish people mostly used by the English
* Short for jockstrap, an item of male protective undergarm ...
, and ringworm
Dermatophytosis, also known as ringworm, is a fungal infection of the skin. Typically it results in a red, itchy, scaly, circular rash. Hair loss may occur in the area affected. Symptoms begin four to fourteen days after exposure. Multiple ar ...
.
Safety
Allylamine, like other allyl derivatives is a lachrymator
Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...
and skin irritant. Its oral is 106 mg/kg for rats.
References
External links
* at National Center for Biotechnology Information
The National Center for Biotechnology Information (NCBI) is part of the United States National Library of Medicine (NLM), a branch of the National Institutes of Health (NIH). It is approved and funded by the government of the United States. The ...
{{Authority control
Allylamines