2-Arachidonoylglycerol
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IUPAC name
2-O-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyl]glycerol
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Systematic IUPAC name
1,3-Dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate | |
Other names
2-AG, 2-arachidonoylglycerol
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
IUPHAR/BPS |
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PubChem CID
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UNII | |
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Properties | |
C23H38O4 | |
Molar mass | 378.3 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Arachidonoylglycerol (2-AG) is an
CB1 receptor and the primary endogenous ligand for the CB2 receptor.[1][2] 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.[3] 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.[4] 2-AG is synthesized from arachidonic acid-containing diacylglycerol (DAG)
.
Occurrence
2-AG, unlike
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][5] 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.[6][7][8]
Discovery
2-AG was discovered by
endocannabinoid discovered. The cannabinoid established the existence of a cannabinoid neuromodulatory system in the nervous system.[13]
Pharmacology
Unlike
transport proteins for 2-arachidonoylglycerol and anandamide. These include the heat shock proteins (Hsp70s) and fatty acid binding proteins (FABPs).[18][19]
Biosynthesis
2-Arachidonoylglycerol is synthesized from arachidonic acid-containing diacylglycerol (DAG), which is derived from the increase of inositol phospholipid metabolism by the action of diacylglycerol lipase. The molecule can also be formed from pathways like the hydrolysis derived (by diglyceride) from both phosphatidylcholine (PC) and phosphatidic acid (PAs) by the action of DAG lipase and the hydrolysis of arachidonic acid-containing lysophosphatidic acid by the action of a phosphatase.[20]
See also
- 2-Arachidonoyl glyceryl ether
- Endocannabinoid transporters
References
Notes
- S2CID 4422311.
- ^ PMID 9915812.
- S2CID 39220005.
- PMID 14976257.
- S2CID 10583431.
- S2CID 25430588.
- ^ The Endocannabinoid-CB Receptor System: Importance for development and in pediatric disease Neuroendocrinology Letters Nos.1/2, Feb-Apr Vol.25, 2004.
- ^ Cannabinoids and Feeding: The Role of the Endogenous Cannabinoid System as a Trigger for Newborn Suckling Archived 2020-10-01 at the Wayback Machine Women and Cannabis: Medicine, Science, and Sociology, 2002 The Haworth Press, Inc.
- ^ Pizzorno, Lara; MDiv; MA; LMT. "New Developments in Cannabinoid-Based Medicine: An Interview with Dr. Raphael Mechoulam" Archived 2018-06-19 at the Wayback Machine. Longevity Medicine Review. Retrieved 2011-05-26.
- ^ Sugiura T, Itoh K, Waku K, Hanahan DJ (1994) Proceedings of Japanese conference on the Biochemistry of Lipids, 36, 71-74 (in Japanese)
- PMID 7575630.
- PMID 7605349.
- ISBN 978-0-306-48228-1.
- PMID 11588122.
- PMID 26989199.
- PMID 18096503.
- PMID 21418147.
- PMID 19307565.
- PMID 19481477.
- PMID 24102242.
General references
- Dinh TP, Carpenter D, Leslie FM, et al. (August 2002). "Brain monoglyceride lipase participating in endocannabinoid inactivation". Proceedings of the National Academy of Sciences of the United States of America. 99 (16): 10819–24. PMID 12136125.