2-LG.2-linoleoylglycerol

2-LG is an endogenous 2-monoacylglycerol, co-isolated with 2-AG in spleen, gut and brain. The founding paper by Ben-Shabat and Mechoulam (1998) describes it as devoid of direct binding to the CB1 and CB2 receptors, yet able to potentiate the effects of 2-AG in animals and, alone among the esters tested, to slow its inactivation by neuronal and basophilic cells: this is the origin of the phrase « entourage effect ». Later work strongly qualifies that account. Murataeva and colleagues (2016) found no potentiation and describe instead the behaviour of a functional antagonist; Lu, Williams and Doherty (2019) measure a very weak partial agonist activity at human CB1, EC50 close to 17 µM and maximal efficacy well below that of 2-AG, while observing an attenuation of responses to 2-AG and anandamide. The most credible residual mechanism remains indirect: competition for the hydrolases that degrade 2-AG. Human data are entirely lacking, no clinical study or controlled exposure data having been published, and no therapeutic benefit can be put forward.

Source

An endogenous mammalian lipid, absent from hemp. It is formed by diacylglycerol lipases from diacylglycerols carrying linoleic acid, and it is also a major product of the intestinal digestion of dietary triglycerides, linoleic acid frequently occupying the sn-2 position of vegetable oils. Ben-Shabat et al. (1998) co-isolated it with 2-AG in spleen, brain and gut, where it ranks among the most abundant 2-acylglycerols accompanying 2-AG.

Diacylglycerol lipase pathway: a diacylglycerol bearing a linoleic acid at the sn-2 position is hydrolysed into 2-linoleoylglycerol. Pancreatic lipase produces the same molecule from the triglycerides of a meal, which makes it as much a digestive metabolite as an endogenous lipid mediator.

European Union

Not controlled in the European Union. The substance appears neither in the international narcotics conventions nor in the notifications of the EUDA (formerly EMCDDA), and it has never been the subject of a risk assessment under the new psychoactive substances regime. The fatty acid monoglycerides to which it belongs moreover form a class of lipids commonly present in the diet.

France

No narcotic status in France. 2-LG is an endogenous lipid and a normal product of the digestion of fats: it is named by no ANSM list, and nor does it fall under the generic clause of annex III of the decree of 22 February 1990 covering tetrahydrocannabinols, their esters, ethers and salts, since it derives from no tetrahydrocannabinol. Its possession as a laboratory reagent or its presence as a lipid constituent are therefore not restricted on that basis.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Family

Endocannabinoid or related mediator › Putative

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

No dedicated article.

1. 1Ben-Shabat S. et al., An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity, Eur J Pharmacol 1998 (new tab)PMID 9721036
2. 2Murataeva N. et al., Where's my entourage? The curious case of 2-oleoylglycerol, 2-linolenoylglycerol, and 2-palmitoylglycerol, Pharmacol Res 2016 (new tab)PMID 27117667
3. 3Lu L., Williams G., Doherty P., 2-Linoleoylglycerol Is a Partial Agonist of the Human Cannabinoid Type 1 Receptor that Can Suppress 2-Arachidonoylglycerol and Anandamide Activity, Cannabis Cannabinoid Res 2019 (new tab)PMID 31872059
4. 4PubChem, 2-Linoleoylglycerol, CID 5365676 (National Library of Medicine) (new tab)
5. 5Syed S.K. et al., Regulation of GPR119 receptor activity with endocannabinoid-like lipids, Am J Physiol Endocrinol Metab 2012 (new tab)PMID 23074242
6. 6LIPID MAPS LipidWeb, Monoacylglycerols: structure, occurrence, biochemistry and function (new tab)

SMILES

CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC(CO)CO

Machine-readable entry (JSON)

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