Basic information
- CAS
53847-30-6- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO- InChIKey
RCRCTBLIHCHWDZ-DOFZRALJSA-N- Molecular formula
- C23H38O4
- Average molar mass
- 378.5 g/mol
- Monoisotopic mass
- 378.2770097
Overview
2-arachidonoylglycerol is an endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol. It has a role as a human metabolite. It is a 2-acylglycerol 20:4 and an endocannabinoid. It is functionally related to an arachidonic acid.
Names & identifiers
- Preferred name
- 2-Arachidonylglycerol
- IUPAC
- 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
- English name
- 2-AG
- Molecular formula
- C23H38O4
- Molecular weight
- 378.55
Names & synonyms
Show more names
Database identifiers
- CAS
53847-30-6- PubChem CID
- 5282280
- DTXSID
DTXSID001017454- ChEMBL
CHEMBL122972- ChEBI
CHEBI:52392- UNII
- 8D239QDW64
- Nikkaji
- J671.147B
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 18
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 445
Experimental & physicochemical properties
Physicochemical properties
- Boiling point
- 508.6 · 508.6±50.0 °C(Predicted)
- Density
- 0.992 · 0.992±0.06 g/cm3(Predicted)
- Flash point
- 2 °C · 2 °C
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/ml; · DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): ~150 μg/ml
- form
- acetonitrile solution
- pka
- 13.54 · 13.54±0.10(Predicted)
- color
- Colorless to light yellow
- InChIKey
- RCRCTBLIHCHWDZ-DOFZRALJSA-N
- SMILES
- [H]C(CO)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO
- CAS DataBase Reference
- 53847 · 53847-30-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 D239QDW64 · 8D239QDW64
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302+H312+H332-H319
- Precautionary statements
- 210 · P210-P280-P301+P312-P303+P361+P353-P304+P340+P312-P305+P351+P338
- Hazard Codes
- F,Xn
- Risk Statements
- 11 · 11-20/21/22-36
- Safety Statements
- 26 · 26-36/37-16
- RIDADR
- 1648 · UN 1648 3/PG 2
- WGK Germany
- 2 · 2
- Storage Class
- 12 · 12 - Non Combustible Liquids
Safety & regulation
Safety data
- wgk
- 2
- ridadr
- UN 1648 3/PG 2
- risk_code
- 11-20/21/22-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn
- safety_code
- 26-36/37-16
- Storage Class
- 12 - Non Combustible Liquids
- Hazard statements
- H225-H302+H312+H332-H319
- Precautionary statements
- P210-P280-P301+P312-P303+P361+P353-P304+P340+P312-P305+P351+P338
Chemistry & industry
Pharmacology
Applications
Uses2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats.
General Description2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism. 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers46 total
Additional notes
DefinitionChEBI: An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.
Related reactions
Compound notes
Loading…