Oleamide

• Cis-9 ,10- octadecenoamide
• (Z) -9,10 - octadecenoamide
• Oleamide

75-76 ° C

Attention

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Oleamide is the carboxylic acid amide of oleic acid. It is formed in the body and is consequently to the endogenous substances. Where it is present as cis isomer, and is involved in a series of signal processes. Industrially it is esp. used in the manufacture of plastics.

Properties

Is oleamide - such as oleic acid or the related anandamide - a water-insoluble substance.

Biological Significance

Oleamide was found in the cerebrospinal fluid of cats that were kept under sleep deprivation. It was initially referred to as " Cerebrodien " because it was assumed that we are dealing with a diene. A short time later it was finally identified as the " cis " isomer oleic acid amide.

Oleamide shows sleep-inducing effect and hypomotility. It interacts with potassium channels and GABAA and 5- HT7 receptors. The interaction with the GABAA receptors seems to cause the sleep-inducing effect.

It could be shown that oleamide interacts directly with the cannabinoid receptor 1 (CB1 receptor). It also activates vanilloid TRPV1 receptors.

Whether it can be counted as endocannabinoid but, in spite of the cannabinoid -like effects ( increased appetite, hypothermia, hypoactivity ) is still controversial.

Oleic acid amide is degraded by the fatty acid amide hydrolase ( FAAH ).

Biochemical illustration

The exact de novo synthesis of oleamide is not fully understood. But it is believed that oleic acid amide is formed from oleoyl- CoA and glycine. Here, glycine and oleoyl -CoA are condensed to enzymatically Oleoylglycin which the bile acid CoA: amino acid N-acetyltransferase is catalyzed ( BACAT ) or a BACAT - like enzyme. Subsequently, Oleoylglycin be oxidatively converted to oleic acid amide by the enzyme PAM ( peptidylglycine α - amidating monooxygenase ). Alternatively could occur by direct reaction of oleamide oleoyl- CoA and ammonia, which is catalyzed by cytochrome c. You may also performs a combination of the two paths for the biosynthesis of oleic acid amide.

Whether the fatty acid amide hydrolase ( FAAH ) can form of oleic acid and ammonium (NH4 ) oleamide ( reverse reaction of degradation ) is doubted. The faces that both very high concentrations were required to NH4 , and the reaction has an optimum pH of more than 9. These conditions are physiologically very difficult to achieve.

Elaidinsäureamid

Elaidinsäureamid, the trans isomer of oleic acid amide, though is biologically active, but much less than the cis isomer. Many of the effects observed in the cis isomer are also not detectable in the trans isomer.

Technical use

Oleamide is used in the production of plastics. There it serves as a lubricant and facilitate for example the slide against each other by plastic sheets. It is also a hydrophobizing agent and can also be used as a raw material for cosmetics production. Finally, it is used as slip agents for polyethylene and (next erucamide ) in polypropylene products.

Recently it has been shown that oleic acid amide contained in reaction vessels can enter polypropylene in solution. This could then affect biochemical experiments.