Endocannabinoid
Endogenous2-AG2-Arachidonoylglycerol
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Aliases.2-Arachidonoylglycerol · Sn-2-AG
The principal endocannabinoid by brain concentration, a full CB1/CB2 agonist. Target of the MAGL inhibitors in clinical development.
Updated on
Level of detail
Identifiers
- Formula
- C₂₃H₃₈O₄
- Molar mass
- 378.55 g·mol⁻¹
- CAS
- 53847-30-6
- PubChem CID
- 5282280
- First described
- 1995
- Origin
- Endocannabinoid
- InChIKey
- RCRCTBLIHCHWDZ-DOFZRALJSA-N
In plain terms
2-AG is the other natural messenger of your endocannabinoid system - produced in far greater quantity than anandamide. It acts strongly and briefly, then is broken down within minutes by an enzyme called MAGL.
Receptors and activity
- CB1Ki ≈ 472 nM (Sugiura 1995)Agonist
- CB2Ki ≈ 1400 nMAgonist
- Agonist
- Partial agonist
- Antagonist
- Modulator
- Inverse agonist
Hover over a row for the precise value (Ki, EC50…)
Subjective signature
Hover over an axis to read its definition.
- Calm65
- Clarity60
- Sleep45
- Appetite70
- High60
Editorial estimate, not clinical.
Pharmacology
2-AG (2-arachidonoylglycerol) is the most abundant endocannabinoid in the brain (≈ 200× the concentration of AEA). Sutton et al. (1995) and Mechoulam et al. (1995) characterised it independently. Unlike anandamide, it is a full agonist - not a partial one - at CB1, which makes it the principal messenger of retrograde depression of neurotransmission at the synapse. It is degraded by MAGL; the MAGL inhibitors (KML29, MJN110, ABX-1431) are in clinical development for chronic pain and Tourette syndrome.
Biosynthetic pathway (in vivo)
Hydrolysed on demand from membrane DAG by the diacylglycerol lipases α/β (DAGLα/β), degraded mainly by MAGL (~85%) and secondarily by ABHD6/ABHD12
Legal framework
International
Endogène, non régulé
European Union
Endogène, non régulé
France
Endogène, non régulé
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Endocannabinoid
- Origin
- Endocannabinoid
- Status
- Endogenous
References
- 1.Sugiura · BBRC 1995PMID 7575630
- 2.Mechoulam · Biochem Pharmacol 1995PMID 7605349
Structured data
- InChIKey
- RCRCTBLIHCHWDZ-DOFZRALJSA-N
- SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
- Formula
- C23H38O4
- Molar mass
- 378.55 g·mol⁻¹
- CAS
- 53847-30-6
- PubChem CID
- 5282280
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.