Fatty acid amides (FAAs) are
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
s formed from a
fatty acid
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...
and an
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 Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
. In nature, many FAAs have
ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid wit ...
as the amine component. Also known as
''N''-acylethanolamines, they contain the functionality RC(O)N(H)CH
2CH
2OH. A well known example is
anandamide
Anandamide (ANA), also known as ''N''-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter. Anandamide was the first endocannabinoid to be discovered: it participates in the body's endocannabinoid system by binding to cannabinoid rec ...
. Other fatty acid amides are fatty acid primary amides (FAPAs). They contain the functionality RC(O)NH
2). Oleamide is an example of this class of FAPAs.
[
]
Natural occurrences
FAAs play a role in intracellular signalling. The signalling is controlled in part by fatty acid amide hydrolase
Fatty acid amide hydrolase or FAAH (, oleamide hydrolase, anandamide amidohydrolase) is a member of the serine hydrolase family of enzymes. It was first shown to break down anandamide in 1993. In humans, it is encoded by the gene ''FAAH''.;
Fun ...
s, which convert the amide to the parent fatty acid. One example of signaling is induced by the binding of anandamide to the cannabinoid receptor
Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid recepto ...
s.
Aliphatic amides can be found in ''Zanthoxylum
''Zanthoxylum'' is a genus of about 250 species of deciduous and evergreen trees, shrubs and climbers in the family Rutaceae that are native to warm temperate and subtropical areas worldwide. It is the type genus of the tribe Zanthoxyleae in ...
'' species found in Nigeria.[The Nigerian Zanthoxylum; Chemical and biological values. S. K. Adesina, Afr. J. Trad. CAM, 2005, volume 2, issue 3, pages 282-301]
article
See also
* Fatty acid ester Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary f ...
References
Further reading
*
{{Commonscat, Fatty acid amides