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Changing Medicine Together
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~ 2-AG, Endocannabiniod: Overview ~
Note:
- Cannabinoids produced by the cannabis plant are called phytocannabinoids. For quick reference, endo- refers to inside the body, while phyto- refers to plants.
- Cannabiniods produced by the human body are called Endo-cannabiniods.
Both endocannabinoids and phytocannabinoids are messaging molecules used by the larger endocannabinoid system (ECS).
the cannabis molecule is a Isomer (molecular copy) of the natural bodily cannabinoids
- Cannabinoids produced by the cannabis plant are called phytocannabinoids. For quick reference, endo- refers to inside the body, while phyto- refers to plants.
- Cannabiniods produced by the human body are called Endo-cannabiniods.
Both endocannabinoids and phytocannabinoids are messaging molecules used by the larger endocannabinoid system (ECS).
the cannabis molecule is a Isomer (molecular copy) of the natural bodily cannabinoids
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Chemical Name: 2-Arachidonoylglycerol (2-AG)
IUPAC name 1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z) - 5,8,11,14-eicosatetraenoate Molecular Formula: C23H38O4 Molar Mass: 378.3/g/mol |
Science, Cannabiniods 101: What is 2-AG
2-Arachidonoylglycerol (2-AG) is the other main endocannabinoid, that along with anandamide, has an effect on the CB receptors in the central and peripheral nervous system. Specifically, 2-AG is a full agonist of both CB receptors, and is the primary ligand (binding molecule) for the CB2 receptor. 2-AG It is an ester formed from the omega-6 fatty acid arachidonic acid and glycerol. It is present at relatively high levels in the central nervous system, with cannabinoid neuromodulatory effects. It has been found in maternal bovine and human milk. The chemical was first described in 1994-1995, although it had been discovered some time before that. The activities of Phospholipase C (PLC) and diacylglycerol lipase (DAGL) mediate its formation. 2-AG is synthesized from arachidonic acid-containing diacylglycerol (DAG).
2-AG, unlike anandamide (another endocannabinoid), 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).[2][3] Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. It has been found in maternal bovine as well as human milk.[4][5][6]
2-AG, unlike anandamide (another endocannabinoid), 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).[2][3] Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. It has been found in maternal bovine as well as human milk.[4][5][6]
Chemical properties of 2-AG2-AG is a member of a group of molecules that derive from arachidonic acid or two other 20-carbon essential fatty acids (EFAs) known as EPA and DGLA. These molecules, known as eicosanoids, are all oxidised versions of these 20-carbon (containing 20 carbon atoms per molecule) EFAs, and play a complex and important role in various bodily processes including immunity and inflammation.
The chemical formula for 2-AG, which can be classed as a fatty acid ester of glycerol as it converts the hydroxyl group of glycerol into a carboxyl group, has the molecular formula C23H38O4 and a molar mass of 378.3 g/mol. Due to its long hydrocarbon tail, the molecule can easily be broken down by the actions of lipid metabolism enzymes.
The chemical formula for 2-AG, which can be classed as a fatty acid ester of glycerol as it converts the hydroxyl group of glycerol into a carboxyl group, has the molecular formula C23H38O4 and a molar mass of 378.3 g/mol. Due to its long hydrocarbon tail, the molecule can easily be broken down by the actions of lipid metabolism enzymes.
Synthesis and degradation of 2-AG
2-AG synthesis from precursor phospholipids, effected through the actions of the DAG lipase2-AG is formed similarly to anandamide—through the reaction of arachidonic acid with another endogenous molecule—although unlike anandamide, 2-AG requires glycerol rather than a free amine to make the chemical changes required.
However, rather than directly synthesising from the degradation of arachidonic acid, 2-AG is formed when the arachidonic acid-containing phospholipid diacylglycerol (DAG) reacts with glycerol. The enzyme that facilitates this process is known as the DAG lipase.
2-AG is degraded by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH, also responsible for the degradation of anandamide) and several uncharacterised enzymes. It is believed that MAGL is responsible for up to 85% of this degradation process.
Physiological effects of 2-AG
2-AG is the most abundant endocannabinoid found in the body, and like anandamide, is thought to play an important role in the regulation of appetite, immune system functions and pain management. It is also thought that 2-AG may also play a role in the inhibition of cancer cell proliferation.
However, rather than directly synthesising from the degradation of arachidonic acid, 2-AG is formed when the arachidonic acid-containing phospholipid diacylglycerol (DAG) reacts with glycerol. The enzyme that facilitates this process is known as the DAG lipase.
2-AG is degraded by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH, also responsible for the degradation of anandamide) and several uncharacterised enzymes. It is believed that MAGL is responsible for up to 85% of this degradation process.
Physiological effects of 2-AG
2-AG is the most abundant endocannabinoid found in the body, and like anandamide, is thought to play an important role in the regulation of appetite, immune system functions and pain management. It is also thought that 2-AG may also play a role in the inhibition of cancer cell proliferation.
- Lower inflammatory proteins like cytokines
- neuroprotectant
- strengthen blood brain barrier
- cerebroprotection
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