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Ethanolamides are chemical compounds which 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
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...
s and
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 wi ...
. Some ethanolamides are naturally occurring, such as
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 r ...
,
palmitoylethanolamide Palmitoylethanolamide (PEA) is an endogenous fatty acid amide, and lipid modulator PEA has been studied in ''in vitro'' and ''in vivo'' systems using exogenously added or dosed compound; there is evidence that it binds to a nuclear receptor, th ...
and
prostamide Prostamides are a class of physiologically active, lipid-like substances chemically related to prostaglandins. They occur naturally in humans and other animals. The first prostamide, called prostamide E2, was discovered in 1997. Biochemistry Pro ...
s, which play physiological roles as lipid
neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell. Neur ...
s and
autacoid Autacoids or "autocoids" are biological factors (molecules) which act like local hormones, have a brief duration, and act near their site of synthesis. The word ''autacoid'' comes from the Greek words "autos" (self) and "acos" (relief; i.e., drug ...
s. The crystal structure of the membrane enzyme
NAPE-PLD NAPE-PLD may refer to: * N-acyl phosphatidylethanolamine-specific phospholipase D, an enzyme * N-acetylphosphatidylethanolamine-hydrolysing phospholipase D ''N''-acetylphosphatidylethanolamine-hydrolysing phospholipase D (EC 3.1.4.54, NAPE-PLD, a ...
has revealed how these endogenous ethanolamides are generated from cell membranes, and that
bile acid Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary ...
s play a role in their production. Ethanolamides can be prepared synthetically by heating
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
s with ethanolamine.


See also

*
Diethanolamide Diethanolamides are common ingredients used in cosmetics to act as a foaming agents or as emulsifiers. Chemically, they are amides formed from diethanolamine and carboxylic acids, typically fatty acid In chemistry, particularly in biochemistry ...
*
Docosatetraenoylethanolamide Docosatetraenoylethanolamide (DEA) (Adrenoyl-ethanolamide) (Adrenoyl-EA) is an endogenous ethanolamide that has been shown to act on the cannabinoid (CB1) receptor. DEA is similar in structure to anandamide (AEA, a recognized endogenous ligand fo ...
*
Oleoylethanolamide Oleoylethanolamide (OEA) is an endogenous peroxisome proliferator-activated receptor alpha (PPAR-α) agonist. It is a naturally occurring ethanolamide lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons. OEA ...


References


External links

{{wiktionary inline, ethanolamide, ethanolamides Fatty acid amides