N-Arachidonoyl Dopamine-d8

N-Arachidonoyl dopamine-d₈ contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of N-arachidonoyl dopamine by GC- or LC-mass spectrometry. Several different arachidonoyl amino acids, including NADA, have been isolated and characterized from bovine brain.¹ NADA is the amide of the neurotransmitter dopamine and arachidonic acid. NADA is a CB₁-selective cannabinoid agonist, inducing the typical tetrad of hypothermia, analgesia, catalepsy, and hypomotility in rats which exceeds that of anandamide (AEA).² NADA is a full agonist at the vanilloid receptor 1, but is inactive on the dopaminergic D₁ and D₂ receptors. NADA is also a potent inhibitor (IC₅₀ = 0.25 µM) of the proliferation of MCF-7 breast carcinoma cells. Recent reports of NADA's endothelium-dependent vasodilation indicate that some of its cannabinergic activities antagonized by SR141716A may be non-CB₁/CB₂ dependent.³

1.Huang, S.M., Bisogno, T., Petros, T.J., et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits painThe Journal of Biological Chemisty276(46)42639-42644(2001) 2.Bisogno, T., Melck, D., Bobrov, M.Y., et al.N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivoBiochem. J.351(Pt 3)817-824(2001) 3.Randall, M., and Maxey, K.M.Personal Communication(2003)