Structure via PubChem · Public domain (PubChem)
anandamide
Sign in to saveAlso known as AEA, arachidonoyl ethanolamide, N-arachidonoylethanolamine, Arachidonylethanolamide, N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamide, N-arachidonoyl-2-hydroxyethylamide, (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide, (all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide
Anandamide (ANA), also referred to as '''N-arachidonoylethanolamine (AEA'), is a fatty acid neurotransmitter belonging to the fatty acid derivative group known as N-acylethanolamines (NAE). Anandamide takes its name from the Sanskrit word ananda'' (आनन्द), meaning "joy, bliss, delight," plus amide. Anandamide, the first discovered endocannabinoid, engages with the body's endocannabinoid system by binding to the same cannabinoid receptors that THC found in cannabis acts on. Anandamide can be found within tissues in a wide range of animals. It has also been found in plants, such as the cacao tre
Chemical data
- Formula
- C22H37NO2
- Molecular weight
- 347.5 g/mol
- IUPAC name
- (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
- SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
- InChIKey
- LGEQQWMQCRIYKG-DOFZRALJSA-N
- XLogP
- 5.4
- Polar surface area
- 49.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
5,296 papers- Anandamide and other N-acylethanolamines: A class of signaling lipids with therapeutic opportunities.Progress in lipid research · 2023
- Anandamide transport.Pharmacology & therapeutics · 2004
- Anandamide uptake explained?Trends in pharmacological sciences · 2012
- Anandamide receptor signal transduction.Vitamins and hormones · 2009
- Brain activity of anandamide: a rewarding bliss?Acta pharmacologica Sinica · 2019
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 347.282429
Show 7 more facts
- subject has role
- calcium channel blocker
- Commons category
- Anandamide
- chemical formula
- C₂₂H₃₇NO₂
- isomeric SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
- canonical SMILES
- CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO
- found in taxon
- Caenorhabditis elegans
- physically interacts with
- Transient receptor potential cation channel subfamily V member 1
Sources (6)
via Wikidata · CC0
~7 min read
Encyclopedic overview
11 sectionsContents
- Discovery
- Research
- Behavior
- Obesity and liver disease
- Topical effects
- Biosynthesis
- Metabolism
- Transport
- See also
- References
- External links
Anandamide (ANA), also referred to as '''N-arachidonoylethanolamine (AEA'), is a fatty acid neurotransmitter belonging to the fatty acid derivative group known as N-acylethanolamines (NAE). Anandamide takes its name from the Sanskrit word ananda'' (आनन्द), meaning "joy, bliss, delight," plus amide. Anandamide, the first discovered endocannabinoid, engages with the body's endocannabinoid system by binding to the same cannabinoid receptors that THC found in cannabis acts on. Anandamide can be found within tissues in a wide range of animals. It has also been found in plants, such as the cacao tree.
Anandamide is derived from the non-oxidative metabolism of arachidonic acid, an essential omega-6 fatty acid. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways. It is degraded primarily by the fatty acid amide hydrolase (FAAH) enzyme, which converts anandamide into ethanolamine and arachidonic acid. As such, inhibitors of FAAH lead to elevated anandamide levels and are being pursued for possible therapeutic use.
Excerpted from Wikipedia’s “anandamide” article, available under the CC BY-SA 4.0 licence.