2-Arachidonoylglycerol, an endocannabinoid compound, is an endogenous agonist for the cannabinoid (CB1) receptor in the central nervous system. Through a CB1 receptor-dependent mechanism, 2-Arachidonoylglycerol at a concentration of 0.3nM induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells.
Physicochemical Properties
| Molecular Formula | C23H38O4 |
| Molecular Weight | 378.55 |
| Exact Mass | 378.277 |
| Elemental Analysis | C, 72.98; H, 10.12; O, 16.91 |
| CAS # | 53847-30-6 |
| Related CAS # | 53847-30-6 |
| PubChem CID | 5282280 |
| Appearance | Colorless to light yellow liquid |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 508.6±50.0 °C at 760 mmHg |
| Flash Point | 163.0±23.6 °C |
| Vapour Pressure | 0.0±3.0 mmHg at 25°C |
| Index of Refraction | 1.508 |
| LogP | 6.24 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 18 |
| Heavy Atom Count | 27 |
| Complexity | 445 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(OC(CO)CO)=O |
| InChi Key | RCRCTBLIHCHWDZ-DOFZRALJSA-N |
| InChi Code | InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15- |
| Chemical Name | 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate |
| Synonyms | 2-AG; 2AG; 2 AG; 2-Arachidonoylglycerol; 2-Arachidonoyl Glycerol; 2 Arachidonoylglycerol; 2Arachidonoylglycerol |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Human Endogenous Metabolite |
| ln Vitro | 2-Arachidonylglycerol (2-AG) is a ligand that is isolated from intestinal tissue that is related to cannabis. 2-Arachidonoylglycerol inhibits the induction of long-term potentiation at CA3-CA1 synapses and fully agonistically activates neuronal cannabinoid receptors. 2. Arachidonoylglycerol binds to cannabinoid receptors and produces a number of effects that are common to drugs containing cannabinoids[1]. |
| References |
[1]. A second endogenous cannabinoid that modulates long-term potentiation. Nature. 1997 Aug 21;388(6644):773-8. |
| Additional Infomation |
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 an endocannabinoid and a 2-acylglycerol 20:4. It is functionally related to an arachidonic acid. 2-Arachidonoylglycerol has been reported in Homo sapiens and Apis cerana with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6417 mL | 13.2083 mL | 26.4166 mL | |
| 5 mM | 0.5283 mL | 2.6417 mL | 5.2833 mL | |
| 10 mM | 0.2642 mL | 1.3208 mL | 2.6417 mL |