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From the body

2-AG2-Arachidonoylglycerol

An endocannabinoid present in brain in far greater amounts than anandamide, a full CB1 agonist, hydrolysed mainly by MAGL.

Endogenous
Level of detail

C₂₃H₃₈O₄

CAS 53847-30-6

Family
Endocannabinoid or related mediatorEstablished
Origin
Endogenous (established endocannabinoid)
First described
1995
Molar mass
378.55 g/mol

Updated on

In plain terms

2-AG is the other major messenger of the endocannabinoid system, present in the brain in much larger amounts than anandamide. The body makes it when needed from membrane lipids, then an enzyme called MAGL breaks it down.

Receptors and activity

Target network

CB1AgonistKi = 472 nM · not specifiedmembranes of CB1-transfected cells (isolation study)
  • Activates

The lower the cited value, the closer the target sits to 2-AG: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of 2-AG.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1AgonistKi = 472 nM · not specified39 out of 100

    Mechoulam et al. 1995, Biochem Pharmacol 50:83 (isolation, dog intestine; Ki CB1/CB2) (new tab) · membranes of CB1-transfected cells (isolation study)

  2. CB2AgonistKi = 1.4 µM · not specified31 out of 100

    Mechoulam et al. 1995, Biochem Pharmacol 50:83 (isolation, dog intestine; Ki CB1/CB2) (new tab) · membranes of CB2-transfected cells (isolation study)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

2-Arachidonoylglycerol was described in 1995 by two teams: Raphael Mechoulam's, which isolated it from dog intestine and measured Ki values of 472 nM (CB1) and 1400 nM (CB2) on membranes of transfected cells (Mechoulam et al. 1995), and Takayuki Sugiura's, which showed its binding to the cannabinoid receptor of synaptosomes (Sugiura et al. 1995). In rat, its brain content is about 170 times that of anandamide; its formation is calcium-dependent and goes through phospholipase C and diacylglycerol lipase, and it behaves there as a full agonist at neuronal receptors (Stella et al. 1997). In a calcium assay, its maximal response at CB1 exceeded that of the other agonists tested, whereas anandamide behaved as a partial agonist (Sugiura et al. 1999); at the CB2 receptor of HL-60 cells it was the most potent of the natural ligands tested (Sugiura et al. 2000). Unlike anandamide, it does not activate TRPV1 (Pertwee et al. 2010). In mice, knocking out DGLα abolishes endocannabinoid-mediated retrograde suppression of synaptic transmission in the cerebellum, hippocampus and striatum (Tanimura et al. 2010). About 85 % of its brain hydrolysis is due to MAGL (Blankman et al. 2007). In vitro, 2-AG isomerises to 1-arachidonoylglycerol by acyl migration, which complicates its measurement (Higuchi et al. 2010). A MAGL inhibitor, Lu AG06466 (formerly ABX-1431), showed no efficacy on tics in a 12-week randomised trial in 49 adults with Gilles de la Tourette syndrome (Müller-Vahl et al. 2021).

Key sources.

Biosynthetic pathway

In vivo

Formed on demand from arachidonic-acid-containing membrane diacylglycerols by the diacylglycerol lipases DAGLα and DAGLβ (Bisogno et al. 2003). In mouse brain, about 85 % of 2-AG hydrolase activity is due to MAGL, the rest mainly to ABHD6 and ABHD12 (Blankman et al. 2007).

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Established

Chemistry

2-monoacylglycerol (MAG 20:4)

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

2-Arachidonoylglycerol (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Mechoulam et al. 1995, Biochem Pharmacol 50:83 (isolation, dog intestine; Ki CB1/CB2) (new tab)PMID 7605349
  2. Sugiura et al. 1995, Biochem Biophys Res Commun 215:89 (binding to the brain receptor) (new tab)PMID 7575630
  3. Stella, Schweitzer & Piomelli 1997, Nature 388:773 (170 × anandamide, full agonist) (new tab)PMID 9285589
  4. Sugiura et al. 1999, J Biol Chem 274:2794 (CB1, maximal response) (new tab)PMID 9915812
  5. Blankman, Simon & Cravatt 2007, Chem Biol 14:1347 (MAGL ≈ 85%, ABHD6, ABHD12) (new tab)PMID 18096503
  6. Pertwee et al. 2010, Pharmacol Rev 62:588 (IUPHAR LXXIX) (new tab)PMID 21079038
  7. Tanimura et al. 2010, Neuron 65:320 (DGLα and retrograde signalling) (new tab)PMID 20159446
  8. Müller-Vahl et al. 2021, Mov Disord (Lu AG06466/ABX-1431, Tourette, 12-week trial) (new tab)PMID 34117788

Identifiers

Names

Common name
2-Arachidonoylglycerol
IUPAC name
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Other names
Sn-2-AG

Identifiers

Formula
C₂₃H₃₈O₄
CAS
53847-30-6
PubChem CID
5282280(new tab)
ChEBI
CHEBI:52392(new tab)
InChIKey
RCRCTBLIHCHWDZ-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.