Oleamide is an
organic compound with the formula CH3(CH2)7CH=CH(CH2)7CONH2.[3] It is the
amide derived from the
fatty acidoleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is
biosynthesized from N-oleoylglycine.[4]
It has been considered as a treatment for mood and sleep disorders, as well as
cannabinoid-regulated depression.[6][7]
In terms of its sleep inducing effects, it is speculated that oleamide interacts with multiple
neurotransmitter systems.[8][9] Some in-vitro studies show that cis-oleamide is an agonist for the
cannabinoid 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 an
endocannabinoid.[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 enhance
PPARα-dependent increase in
doublecortin, a marker of neurogenesis in the hippocampus[12]
Oleamide is rapidly metabolized by
fatty acid amide hydrolase (FAAH), the same enzyme that metabolizes
anandamide.[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 a
lubricant.[15]
Oleamide was found to be leaching out of
polypropylene plastics in laboratory experiments, affecting experimental results.[16] Since polypropylene is used in a wide number of food containers such as those for
yogurt, the problem is being studied.[17]
Oleamide is "one of the most frequent non-cannabinoid ingredients associated with
Spice 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.