oleamide
{{short description|Chemical compound}}
{{chembox
| ImageFile = Oleamide.svg
| ImageSize =
| PIN = (9Z)-Octadec-9-enamide
| OtherNames = oleoyl-amide
Oleylamide
9-Octadecenamide
(Z)-9-Octadecenamide
9,10-Octadecenoamide
Oleic acid amide
Cis-9,10-octadecenoamide
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4446508
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7L25QK8BWO
| InChI = 1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
| InChIKey = FATBGEAMYMYZAF-KTKRTIGZBR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15927
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FATBGEAMYMYZAF-KTKRTIGZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 301-02-0
| PubChem = 5283387
| IUPHAR_ligand = 284
| EINECS = 206-103-9
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 116314
| SMILES = O=C(N)CCCCCCC\C=C/CCCCCCCC
}}
|Section2={{Chembox Properties
| C=18 | H=35 | N=1 | O=1
| Appearance = Creamy solid[http://www.chemicalland21.com/arokorhi/specialtychem/perchem/OLEAMIDE.htm# Oleamide] at chemicalland21.com
| Density = 0.879 g/cm3
| MeltingPtC = 70
| MeltingPt_ref = <{{Cite web | url=http://www.chemspider.com/Chemical-Structure.4446508.html | title=(9Z)-9-Octadecenamide | C18H35NO | ChemSpider}}
| BoilingPt = >
| BoilingPtC = 200
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt = >
| FlashPtC = 200
| AutoignitionPt =
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
}}
}}
Oleamide is an organic compound with the formula {{chem2|CH3(CH2)7CH\dCH(CH2)7CONH2}}.{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Oleamide |title = Oleamide}} It is the amide derived from the fatty acid oleic 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.
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 during sleep deprivation and induces sleep in animals.{{cite journal |last1=McKinney |first1=Michele K. |last2=Cravatt |first2=Benjamin F. |title=Structure and Function of Fatty Acid Amide Hydrolase |journal=Annual Review of Biochemistry |date=June 2005 |volume=74 |issue=1 |pages=411–432 |doi=10.1146/annurev.biochem.74.082803.133450 |pmid=15952893 |s2cid=23571858 }}{{cite journal |last1=Cravatt |first1=B. |last2=Prospero-Garcia |first2=O |last3=Siuzdak |first3=G |last4=Gilula |first4=N. |last5=Henriksen |first5=S. |last6=Boger |first6=D. |last7=Lerner |first7=R. |title=Chemical characterization of a family of brain lipids that induce sleep |journal=Science |date=9 June 1995 |volume=268 |issue=5216 |pages=1506–1509 |doi=10.1126/science.7770779 |pmid=7770779 |bibcode=1995Sci...268.1506C |s2cid=32070839 }}
It has been considered as a treatment for mood and sleep disorders, as well as cannabinoid-regulated depression.[http://www.patentstorm.us/patents/6359010/claims.html Methods of treating anxiety and mood disorders with oleamide – US Patent 6359010] {{webarchive|url=https://web.archive.org/web/20110612185115/http://www.patentstorm.us/patents/6359010/claims.html |date=2011-06-12 }}{{cite journal |last1=Mechoulam |first1=Raphael |last2=Fride |first2=Ester |last3=Hanu |first3=Lumir |last4=Sheskin |first4=Tzviel |last5=Bisogno |first5=Tiziana |last6=Di Marzo |first6=Vincenzo |last7=Bayewitch |first7=Michael |last8=Vogel |first8=Zvi |title=Anandamide may mediate sleep induction |journal=Nature |date=September 1997 |volume=389 |issue=6646 |pages=25–26 |doi=10.1038/37891 |pmid=9288961 |bibcode=1997Natur.389R..25M |s2cid=26371103 }}
In terms of its sleep inducing effects, it is speculated that oleamide interacts with multiple neurotransmitter systems.{{cite journal |last1=Fedorova |first1=I |last2=Hashimoto |first2=A |last3=Fecik |first3=RA |last4=Hedrick |first4=MP |last5=Hanus |first5=LO |last6=Boger |first6=DL |last7=Rice |first7=KC |last8=Basile |first8=AS |title=Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems |journal=The Journal of Pharmacology and Experimental Therapeutics |date=October 2001 |volume=299 |issue=1 |pages=332–42 |pmid=11561096 }}{{cite journal |last1=Hiley |first1=C. Robin |last2=Hoi |first2=Pui Man |title=Oleamide: A Fatty Acid Amide Signaling Molecule in the Cardiovascular System?: OLEAMIDE |journal=Cardiovascular Drug Reviews |date=13 April 2007 |volume=25 |issue=1 |pages=46–60 |doi=10.1111/j.1527-3466.2007.00004.x |pmid=17445087 }} Some in-vitro studies show that cis-oleamide is an agonist for the cannabinoid receptor CB-1 with an affinity around 8 micromolar.{{cite journal |last1=Leggett |first1=JD |last2=Aspley |first2=S |last3=Beckett |first3=SR |last4=D'Antona |first4=AM |last5=Kendall |first5=DA |last6=Kendall |first6=DA |title=Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors. |journal=British Journal of Pharmacology |date=January 2004 |volume=141 |issue=2 |pages=253–62 |doi=10.1038/sj.bjp.0705607 |pmid=14707029|pmc=1574194 }} 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.{{cite journal |last1=Fowler |first1=Christopher J |title=Oleamide: a member of the endocannabinoid family?: Commentary |journal=British Journal of Pharmacology |date=January 2004 |volume=141 |issue=2 |pages=195–196 |doi=10.1038/sj.bjp.0705608|pmid=14691053 |pmc=1574195 }} 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 has been found to enhance PPARα-dependent increase in doublecortin, a marker of neurogenesis in the hippocampus{{cite journal |last1=Roy |first1=Avik |last2=Kundu |first2=Madhuchhanda |last3=Chakrabarti |first3=Sudipta |last4=Patel |first4=Dhruv R |last5=Pahan |first5=Kalipada |title=Oleamide, a Sleep-Inducing Supplement, Upregulates Doublecortin in Hippocampal Progenitor Cells via PPARα |journal=J Alzheimers Dis|date=December 2021 |volume=84|issue=4 |pages=1747–1762 |doi=10.3233/JAD-215124 |pmid=34744082|pmc=10075226}}
Oleamide is rapidly metabolized by fatty acid amide hydrolase (FAAH), the same enzyme that metabolizes anandamide.{{cite journal |last1=Maurelli |first1=Stefano |last2=Bisogno |first2=Tiziana |last3=De Petrocellis |first3=Luciano |last4=Di Luccia |first4=Aldo |last5=Marino |first5=Gennaro |last6=Di Marzo |first6=Vincenzo |title=Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase' |journal=FEBS Letters |date=11 December 1995 |volume=377 |issue=1 |pages=82–86 |doi=10.1016/0014-5793(95)01311-3|pmid=8543025 |s2cid=7461775 |doi-access=free |bibcode=1995FEBSL.377...82M }} It has been postulated that some effects of oleamide are caused by increased concentrations of anandamide brought about through the inhibition of FAAH.
It has been claimed that oleamide increases the activity of choline acetyltransferase, an enzyme that is critical in the production of acetylcholine.{{cite journal |last1=Heo |first1=Ho-Jin |last2=Park |first2=Young-June |last3=Suh |first3=Young-Min |last4=Choi |first4=Soo-Jung |last5=Kim |first5=Mi-Jeong |last6=Cho |first6=Hong-Yon |last7=Chang |first7=Yun-Jeong |last8=Hong |first8=Bumshik |last9=Kim |first9=Hye-Kyung |last10=Kim |first10=Eunki |last11=Kim |first11=Chang-Ju |last12=Kim |first12=Byung-Gee |last13=Shin |first13=Dong-Hoon |title=Effects of Oleamide on Choline Acetyltransferase and Cognitive Activities |journal=Bioscience, Biotechnology, and Biochemistry |date=January 2003 |volume=67 |issue=6 |pages=1284–1291 |doi=10.1271/bbb.67.1284|doi-access=free |pmid=12843655 }}
Other occurrences
Oleamide has been found in Ziziphus jujuba, also known as Jujube fruit.
Synthetic oleamide has a variety of industrial uses, including as a lubricant.[http://www.wrchem.com/Products/OLEAMIDE.htm Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films] {{webarchive |url=https://web.archive.org/web/20070127054121/http://www.wrchem.com/Products/OLEAMIDE.htm |date=January 27, 2007 }}
Oleamide was found to be leaching out of polypropylene plastics in laboratory experiments, affecting experimental results.{{cite journal |last1=McDonald |first1=G. R. |last2=Hudson |first2=A. L. |last3=Dunn |first3=S. M. J. |last4=You |first4=H. |last5=Baker |first5=G. B. |last6=Whittal |first6=R. M. |last7=Martin |first7=J. W. |last8=Jha |first8=A. |last9=Edmondson |first9=D. E. |last10=Holt |first10=A. |title=Bioactive Contaminants Leach from Disposable Laboratory Plasticware |journal=Science |date=7 November 2008 |volume=322 |issue=5903 |pages=917 |doi=10.1126/science.1162395 |pmid=18988846 |bibcode=2008Sci...322..917M |s2cid=35526901 }} Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.{{cite news|url=https://www.theglobeandmail.com/news/national/researchers-raise-alarm-after-chemical-leak-found-in-common-plastic/article1065340/|title=Researchers Raise Alarm After Chemical Leak Found In Common Plastic |last=Mittelstaedt|first=Martin|date=6 November 2008|work=Globe and Mail|access-date=10 June 2013}}
Oleamide is "one of the most frequent non-cannabinoid ingredients associated with Spice products."{{cite journal |last1=Fattore |first1=Liana |last2=Fratta |first2=Walter |title=Beyond THC: The New Generation of Cannabinoid Designer Drugs |journal=Frontiers in Behavioral Neuroscience |date=21 September 2011 |volume=5 |pages=60 |doi=10.3389/fnbeh.2011.00060 |pmid=22007163 |pmc=3187647 |doi-access=free }} Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of the products tested.{{cite journal |last1=Uchiyama |first1=Nahoko |last2=Kikura-Hanajiri |first2=Ruri |last3=Ogata |first3=Jun |last4=Goda |first4=Yukihiro |title=Chemical analysis of synthetic cannabinoids as designer drugs in herbal products |journal=Forensic Science International |date=May 2010 |volume=198 |issue=1–3 |pages=31–38 |doi=10.1016/j.forsciint.2010.01.004 |pmid=20117892 }}
See also
References
{{Reflist|2}}
{{Cannabinoids}}
{{Neurotransmitters}}
{{Cannabinoidergics}}