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2-AG (2-arachidonoylglycerol)

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 5282280Last 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.

C23H38O4 · 378.5 g/mol · PubChem 5282280

2-AG is the second of the body's own cannabinoids. It was found in 1995 by two separate teams working independently: one in dog intestine, the other in rat brain. In most experiments, it switches cannabinoid receptors on at full strength, and when its job is done it is broken down mainly by an enzyme called MAGL. Mechoulam 1995AnimalCell / labSugiura 1995AnimalSugiura 2006ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labLu and Mackie 2016ReviewDinh 2002AnimalPDB 6BTHMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)

Student level

2-AG is a monoacylglycerol in which arachidonic acid is attached to the middle (2nd) carbon of glycerol. 2-AG isolated from dog intestine bound to CB1 and CB2 and produced four THC-like effects in mice (reduced pain sensitivity, immobility, reduced spontaneous movement and lowered body temperature). Unlike anandamide, it is a full agonist in most experiments. The two endocannabinoids are made and broken down through separate enzyme pathways; in neurons, 2-AG is broken down mainly by MAGL. Mechoulam 1995AnimalCell / labSugiura 1995AnimalSugiura 2006ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labLu and Mackie 2016ReviewDinh 2002AnimalPDB 6BTHMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)

Expert level: method notes and numbers

2-AG is a monoacylglycerol in which arachidonic acid is attached to the middle (2nd) carbon of glycerol. 2-AG isolated from dog intestine bound to CB1 and CB2 and produced four THC-like effects in mice (reduced pain sensitivity, immobility, reduced spontaneous movement and lowered body temperature). Unlike anandamide, it is a full agonist in most experiments. The two endocannabinoids are made and broken down through separate enzyme pathways; in neurons, 2-AG is broken down mainly by MAGL. Mechoulam 1995AnimalCell / labSugiura 1995AnimalSugiura 2006ReviewGonsiorek 2000Cell / labSugiura 1999Cell / labLu and Mackie 2016ReviewDinh 2002AnimalPDB 6BTHMolecular structure (lab)Lee 2020AnimalMolecular structure (lab)Mechoulam 1995: in transiently transfected cell membranes, Ki 472 ± 55 nM for CB1 and 1,400 ± 172 nM for CB2; less potent than THC in mouse vas deferens. Sugiura 1995: binding increased markedly in the presence of the esterase inhibitor DFP or at 0 °C; the molecule breaks down easily in the assay medium. In the CB1-dependent calcium response in NG108-15 cells, 2-AG gave the highest response; the authors proposed that CB1 is essentially a 2-AG receptor. Besides MAGL, ABHD6 and ABHD12 also take part in its breakdown in the brain. Its only experimental bound form is in the CRBP2 protein (PDB 6BTH).

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
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
InChIKey
RCRCTBLIHCHWDZ-DOFZRALJSA-N
Formula and weight
C23H38O4 · 378.5 g/mol

How to cite: cbd.school editorial team. 2-AG (2-arachidonoylglycerol). Endocannabinoid system 3D map, cbd.school. Last updated October 24, 2026. https://cbd.school/learn/endocannabinoid-system-map/molekuller/2ag/

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 11 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. Mechoulam R, Ben-Shabat S, Hanus L et al. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol. 1995;50(1):83-90. PMID 7605349 · doi:10.1016/0006-2952(95)00109-d AnimalCell / lab
  4. Sugiura T, Kondo S, Sukagawa A et al. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun. 1995;215(1):89-97. PMID 7575630 · doi:10.1006/bbrc.1995.2437 Animal
  5. 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
  6. 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
  7. 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
  8. 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
  9. Dinh TP, Carpenter D, Leslie FM et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci U S A. 2002;99(16):10819-24. PMID 12136125 · doi:10.1073/pnas.152334899 Animal
  10. RCSB Protein Data Bank, entry 6BTH: Crystal structure of human cellular retinol binding protein 2 (CRBP2) in complex with 2-arachidonoylglycerol (2-AG) (X-ray crystallography, 1.35 Å; bound ECB = 2-AG). doi:10.2210/pdb6BTH/pdb. PDB data CC0 1.0. · doi:10.2210/pdb6BTH/pdb Molecular structure (lab)
  11. 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)