Oleamide 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 CH₃(CH₂)₇CH=CH(CH₂)₇CONH₂(. It is the

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 i ...

derived from the

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, ...

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omeg ...

. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is

biosynthesized Biosynthesis is a multi-step, enzyme- catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules ...

from N-oleoylglycine.

Biochemical and medical aspects

In terms of natural occurrence, oleamide was first detected in human plasma. It was later shown to accumulate in the

cerebrospinal fluid Cerebrospinal fluid (CSF) is a clear, colorless body fluid found within the tissue that surrounds the brain and spinal cord of all vertebrates. CSF is produced by specialised ependymal cells in the choroid plexus of the ventricles of the ...

during sleep deprivation and induces

sleep in animals Sleep in animals refers to a behavioral and physiological state characterized by altered consciousness, reduced responsiveness to external stimuli, and homeostatic regulation observed in various animals. Sleep has been observed in mammals, birds, ...

. It has been considered as a potential treatment for mood and sleep disorders, as well as

cannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

-regulated depression. In terms of its sleep inducing effects, it is speculated that oleamide interacts with multiple neurotransmitter systems. Some in-vitro studies show that the cis enantomer of oleamide is an agnoist for 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 recep ...

CB-1 with an affinity around 8 micromolar. However, given oleamide's relatively low affinity for CB-1 and uncertainty about the concentration and biological role of oleamide in-vivo, it has been argued that it is premature to classify oleamide as an

endocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

. At larger doses oleamide can lower the body temperature of mice by about 2 degrees, with the effect lasting about two hours. The mechanism for this remains unknown. Oleamide is rapidly metabolized 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''.; Fu ...

(FAAH), the same enzyme that metabolizes

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 ...

. It has been postulated that some effects of oleamide are caused by increased concentrations of anandamide brought about through the inhibition of FAAH.

Other occurrences

Synthetic oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a

corrosion inhibitor In chemistry, a corrosion inhibitor or anti-corrosive is a chemical compound that, when added to a liquid or gas, decreases the corrosion rate of a material, typically a metal or an alloy, that comes into contact with the fluid. The effectiveness ...

. Oleamide was found to be leaking out of

polypropylene Polypropylene (PP), also known as polypropene, is a thermoplastic polymer used in a wide variety of applications. It is produced via chain-growth polymerization from the monomer propylene. Polypropylene belongs to the group of polyolefins a ...

plastics in laboratory experiments, affecting experimental results. Since polypropylene is used in a wide number of food containers such as those for

yogurt Yogurt (; , from tr, yoğurt, also spelled yoghurt, yogourt or yoghourt) is a food produced by bacterial fermentation of milk. The bacteria used to make yogurt are known as ''yogurt cultures''. Fermentation of sugars in the milk by these bac ...

, the problem is being studied. Oleamide is "one of the most frequent non-cannabinoid ingredients associated with

Spice A spice is a seed, fruit, root, bark, or other plant substance primarily used for flavoring or coloring food. Spices are distinguished from herbs, which are the leaves, flowers, or stems of plants used for flavoring or as a garnish. Spice ...

products." Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of the products tested.

References

{{Cannabinoidergics Eicosanoids Endocannabinoids Fatty acid amides Hypnotics Lipids

Biochemical and medical aspects

Other occurrences

See also

References