Virodhamine (''O''-arachidonoyl ethanolamine; O-AEA) is an

endocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

and a nonclassic eicosanoid, derived from

arachidonic acid Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the New Latin word ''ara ...

. ''O''-Arachidonoyl ethanolamine is

and ethanolamine joined by an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

linkage, the opposite of the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...

linkage found in

anandamide Anandamide (ANA), also known as ''N''-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter. Anandamide was the first endocannabinoid to be discovered: it participates in the body's endocannabinoid system by binding to cannabinoid r ...

. Based on this opposite orientation, the molecule was named virodhamine from the

Sanskrit Sanskrit (; attributively , ; nominally , , ) is a classical language belonging to the Indo-Aryan languages, Indo-Aryan branch of the Indo-European languages. It arose in South Asia after its predecessor languages had Trans-cultural diffusion ...

word ''virodha'', which means opposition. It acts as an

antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, ri ...

of the CB₁ receptor and

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ag ...

of the CB₂ receptor. Concentrations of virodhamine in the human hippocampus are similar to those of

, but they are 2- to 9-fold higher in peripheral tissues that express CB₂. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity ''in vivo''.

References

Eicosanoids Endocannabinoids Fatty acid esters CB1 receptor antagonists CB2 receptor agonists {{cannabinoid-stub

See also

References