Oleamide is anorganic compound with the formulaCH3(CH2)7CH=CH(CH2)7CONH2.[3] It is theamide derived from thefatty acidoleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it isbiosynthesized fromN-oleoylglycine.[4]
It has been considered as a treatment for mood and sleep disorders, as well ascannabinoid-regulated depression.[6][7]
In terms of its sleep inducing effects, it is speculated that oleamide interacts with multipleneurotransmitter systems.[8][9] Some in-vitro studies show thatcis-oleamide is an agonist for thecannabinoid receptorCB-1 with an affinity around 8 micromolar.[10] 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 anendocannabinoid.[11] At larger doses oleamide can lower the body temperature of mice by about 2 degrees, with the effect lasting about two hours.[9] The mechanism for this remains unknown.[9]
Oleamide has been found to enhancePPARα-dependent increase indoublecortin, a marker of neurogenesis in the hippocampus[12]
Oleamide is rapidly metabolized byfatty acid amide hydrolase (FAAH), the same enzyme that metabolizesanandamide.[13] It has been postulated that some effects of oleamide are caused by increased concentrations of anandamide brought about through the inhibition of FAAH.[9]
It has been claimed that oleamide increases the activity of choline acetyltransferase, an enzyme that is critical in the production of acetylcholine.[14]
Synthetic oleamide has a variety of industrial uses, including as alubricant.[15]
Oleamide was found to be leaching out ofpolypropylene plastics in laboratory experiments, affecting experimental results.[16] Since polypropylene is used in a wide number of food containers such as those foryogurt, the problem is being studied.[17]
Oleamide is "one of the most frequent non-cannabinoid ingredients associated withSpice products."[18] Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of the products tested.[19]
^Fedorova, I; Hashimoto, A; Fecik, RA; Hedrick, MP; Hanus, LO; Boger, DL; Rice, KC; Basile, AS (October 2001). "Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems".The Journal of Pharmacology and Experimental Therapeutics.299 (1):332–42.PMID11561096.
^abcdHiley, C. Robin; Hoi, Pui Man (13 April 2007). "Oleamide: A Fatty Acid Amide Signaling Molecule in the Cardiovascular System?: OLEAMIDE".Cardiovascular Drug Reviews.25 (1):46–60.doi:10.1111/j.1527-3466.2007.00004.x.PMID17445087.
^McDonald, G. R.; Hudson, A. L.; Dunn, S. M. J.; You, H.; Baker, G. B.; Whittal, R. M.; Martin, J. W.; Jha, A.; Edmondson, D. E.; Holt, A. (7 November 2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware".Science.322 (5903): 917.Bibcode:2008Sci...322..917M.doi:10.1126/science.1162395.PMID18988846.S2CID35526901.
