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Anandamide (AEA, N-arachidonoylethanolamine)

The body's own cannabinoid.

The body's own cannabinoid. The 3D structure of the molecule, how it was discovered, and how it relates to the cannabinoid receptors; at three levels for Everyone, Students and Experts, with sources.

MoleculePubChem 5281969Last updated:

What's on this page?

Interactive 3D · real anatomy and real data

Where in your body are the cannabinoid receptors?

About 1.4 MB to download.

Level
Reproductive organs

Regions

How to read it Choose a region, or tap a glowing point on the map.

  • Solid light is the CB1 receptor, a ring is CB2. Each region has its own color; the color only tells regions apart.
  • The strength of the light is the receptor gene level measured in human tissue (Human Protein Atlas). That is why the liver’s point is dim: a healthy liver has few receptors.
  • With the layer selector above you can also see other receptors, the enzymes that make and break down endocannabinoids, and the liver enzymes that break down CBD and THC.
  • Every piece of information shows its source and the type of evidence (human, animal, cell). You can change the reading level above.
  • Drag to rotate. Use the + and − buttons to zoom; on a computer, Ctrl or ⌘ with the scroll wheel, on a phone, two fingers.

C22H37NO2 · 347.5 g/mol · PubChem 5281969

Anandamide is a fat-derived messenger molecule that the body makes itself. It was found in pig brain in 1992, during a search for a substance that binds to the receptor that compounds in cannabis bind to. It switches the receptor on, but not at full strength. When its job is done, an enzyme called FAAH breaks it down and ends its effect. Devane 1992AnimalChemistry labSugiura 2006ReviewCravatt 1996AnimalLu and Mackie 2016ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labPDB 6BTIMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)

Student level

Anandamide is an amide formed by the fatty acid arachidonic acid and ethanolamine. Its structure was determined by mass spectrometry and NMR and confirmed by synthesis; it competed with a labeled cannabinoid for receptor binding, and in mouse muscle tissue it showed an effect typical of the psychoactive cannabinoids in cannabis. At cannabinoid receptors, it behaves like a partial agonist in most experiments. In the brain, it is broken down to arachidonic acid mainly by FAAH. Devane 1992AnimalChemistry labSugiura 2006ReviewCravatt 1996AnimalLu and Mackie 2016ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labPDB 6BTIMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)

Expert level: method notes and numbers

Anandamide is an amide formed by the fatty acid arachidonic acid and ethanolamine. Its structure was determined by mass spectrometry and NMR and confirmed by synthesis; it competed with a labeled cannabinoid for receptor binding, and in mouse muscle tissue it showed an effect typical of the psychoactive cannabinoids in cannabis. At cannabinoid receptors, it behaves like a partial agonist in most experiments. In the brain, it is broken down to arachidonic acid mainly by FAAH. Devane 1992AnimalChemistry labSugiura 2006ReviewCravatt 1996AnimalLu and Mackie 2016ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labPDB 6BTIMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)Efficacy depends on the assay system: at human CB2, both endocannabinoids behaved like full agonists in Sf9 membranes, while in CHO-hCB2 membranes anandamide was a weak partial agonist (34 ± 4% of the maximal response) and reduced the effect of 2-AG. It was also a partial agonist in the CB1-dependent calcium response in NG108-15 cells. FAAH also breaks down other fatty acid amides; inhibiting FAAH raises the levels of other molecules too. Its only experimental bound form was solved in a retinol-binding protein (CRBP2, PDB 6BTI); there is no structure of it bound to a cannabinoid receptor in the PDB.

PubChem does not provide a 3D structure for this flexible molecule; the shape on the map is just one of the possible shapes generated by computer from its chemical description. PubChemComputer modelBolton 2011Computer model

Identifiers and citation

IUPAC name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
InChIKey
LGEQQWMQCRIYKG-DOFZRALJSA-N
Formula and weight
C22H37NO2 · 347.5 g/mol

How to cite: cbd.school editorial team. Anandamide (AEA, N-arachidonoylethanolamine). Endocannabinoid system 3D map, cbd.school. Last updated October 24, 2026. https://cbd.school/learn/endocannabinoid-system-map/molekuller/anandamid/

Molecule identifiers from the PubChem (NCBI) record; 3D shape is one of the possible shapes generated with RDKit. The map, text and downloaded images are CC BY-SA 4.0. An independent expert review has not been done yet. All licenses

Other pages of the map

Overview: what the endocannabinoid system is, the feedback brake at the synapse, CBD's targets, lesson mode, data and licenses.

Sources

Show 10 references
  1. National Center for Biotechnology Information. PubChem Compound database: anandamide (CID 5281969), 2-AG (CID 5282280), Δ9-THC (CID 16078), cannabidiol (CID 644019), cannabinol (CID 2543). Formula, molecular weight, IUPAC name and InChIKey are values computed by PubChem. A 3D conformer exists only for THC, CBD and CBN; it is not experimental but a model computed by PubChem. PubChem does not generate conformers for anandamide and 2-AG, which have more than 15 rotatable bonds. Accessed October 24, 2026. Source Computer model
  2. Bolton EE, Chen J, Kim S et al. PubChem3D: a new resource for scientists. J Cheminform. 2011;3(1):32. PMID 21933373 · doi:10.1186/1758-2946-3-32 Computer model
  3. Devane WA, Hanus L, Breuer A et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 1992;258(5090):1946-9. PMID 1470919 · doi:10.1126/science.1470919 AnimalChemistry lab
  4. Sugiura T, Kishimoto S, Oka S, Gokoh M. Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Prog Lipid Res. 2006;45(5):405-46. PMID 16678907 · doi:10.1016/j.plipres.2006.03.003 Review
  5. Cravatt BF, Giang DK, Mayfield SP et al. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 1996;384(6604):83-7. PMID 8900284 · doi:10.1038/384083a0 Animal
  6. Lu HC, Mackie K. An Introduction to the Endogenous Cannabinoid System. Biol Psychiatry. 2016;79(7):516-25. PMID 26698193 · doi:10.1016/j.biopsych.2015.07.028 Review
  7. Gonsiorek W, Lunn C, Fan X et al. Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor: antagonism by anandamide. Mol Pharmacol. 2000;57(5):1045-50. PMID 10779390 Cell / lab
  8. Sugiura T, Kodaka T, Nakane S et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem. 1999;274(5):2794-801. PMID 9915812 · doi:10.1074/jbc.274.5.2794 Cell / lab
  9. RCSB Protein Data Bank, entry 6BTI: Crystal structure of human cellular retinol binding protein 2 (CRBP2) in complex with N-arachidonoylethanolamine (AEA) (X-ray crystallography, 1.45 Å; bound E7Y = anandamide). doi:10.2210/pdb6BTI/pdb. PDB data CC0 1.0. · doi:10.2210/pdb6BTI/pdb Molecular structure (lab)
  10. Lee SA, Yang KJZ, Brun PJ et al. Retinol-binding protein 2 (RBP2) binds monoacylglycerols and modulates gut endocrine signaling and body weight. Sci Adv. 2020;6(11):eaay8937. PMID 32195347 · doi:10.1126/sciadv.aay8937 AnimalMolecular structure (lab)