Allylamine is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula C₃H₅NH₂. This colorless liquid is the simplest stable unsaturated

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

Production and reactions

All three allylamines, mono-, di-, and triallylamine, 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 c ...

with

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

followed by distillation. Or by the reaction of allyl chloride with

hexamine Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and p ...

. Pure samples can be prepared by hydrolysis of

allyl isothiocyanate Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymato ...

. 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 Reverse osmosis (RO) is a water purification process that uses a partially permeable membrane, semi-permeable membrane to separate water molecules from other substances. RO applies pressure to overcome osmotic pressure that favors even distribu ...

Other allylamines

Diallylamine is a precursor to industrial products. Functionalized allylamines have pharmaceutical applications. Pharmaceutically important allylamines include flunarizine 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 Resear ...

; the latter spurred the development of Petasis' ''borono''-Mannich reaction. Flunarizine aids in the relief of migraines while naftifine acts to fight common

fungus A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...

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 undergarmen ...

, and

ringworm Dermatophytosis, also known as tinea and ringworm, is a mycosis, fungal infection of the skin (a dermatomycosis), that may affect skin, hair, and nails. Typically it results in a red, itchy, scaly, circular rash. Hair loss may occur in the a ...

Safety

Allylamine, like other allyl derivatives is a

lachrymator Tear gas, also known as a lachrymatory agent or lachrymator (), sometimes colloquially known as "mace" after the Mace (spray), early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the ey ...

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 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 NCBI is lo ...

{{Authority control Allylamines