Document Detail

Synaptamide, endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function.
MedLine Citation:
PMID:  22959887     Owner:  NLM     Status:  MEDLINE    
Docosahexaenoylethanolamide, the structural analog of the endogenous cannabinoid receptor ligand anandamide, is synthesized from docosahexaenoic acid (DHA) in the brain. Although docosahexaenoylethanolamide binds weakly to cannabinoid receptors, it stimulates neurite growth, synaptogenesis and glutamatergic synaptic activity in developing hippocampal neurons at concentrations of 10-100 nM. We have previously proposed the term synaptamide for docosahexaenoylethanolamide to emphasize its potent synaptogenic activity and structural similarity to anandamide. Synaptamide is subjected to hydrolysis by fatty acid amide hydrolase, and can be oxygenated to bioactive metabolites. The brain synaptamide content is dependent on the dietary DHA intake, suggesting an endogenous mechanism whereby diets containing adequate amounts of omega-3 fatty acids improve synaptogenesis in addition to well-recognized anti-inflammatory effects.
Hee-Yong Kim; Arthur A Spector
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Intramural; Review     Date:  2012-09-05
Journal Detail:
Title:  Prostaglandins, leukotrienes, and essential fatty acids     Volume:  88     ISSN:  1532-2823     ISO Abbreviation:  Prostaglandins Leukot. Essent. Fatty Acids     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-01-09     Completed Date:  2013-07-03     Revised Date:  2014-01-09    
Medline Journal Info:
Nlm Unique ID:  8802730     Medline TA:  Prostaglandins Leukot Essent Fatty Acids     Country:  Scotland    
Other Details:
Languages:  eng     Pagination:  121-5     Citation Subset:  IM    
Copyright Information:
Published by Elsevier Ltd.
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MeSH Terms
Arachidonic Acids / metabolism
Cannabinoid Receptor Agonists / metabolism,  pharmacology
Cannabinoid Receptor Antagonists / metabolism,  pharmacology
Cannabinoids / metabolism
Docosahexaenoic Acids / analogs & derivatives,  metabolism
Endocannabinoids / metabolism
Ethanolamines / metabolism
Glutamine / physiology
Hippocampus / cytology,  drug effects,  metabolism*
Neurites / drug effects,  metabolism*
Neurogenesis* / drug effects
Neurons / cytology,  drug effects,  metabolism*
Polyunsaturated Alkamides / metabolism
Receptors, Cannabinoid / metabolism
Synaptic Transmission* / drug effects
Terminology as Topic
Grant Support
Reg. No./Substance:
0/Arachidonic Acids; 0/Cannabinoid Receptor Agonists; 0/Cannabinoid Receptor Antagonists; 0/Cannabinoids; 0/Endocannabinoids; 0/Ethanolamines; 0/N-docosahexaenoylethanolamide; 0/Polyunsaturated Alkamides; 0/Receptors, Cannabinoid; 0RH81L854J/Glutamine; 25167-62-8/Docosahexaenoic Acids; 94421-68-8/anandamide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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