Description
N-Arachidonoyldopamine (199875-69-9) is an endogenous conjugate of arachidonic acid and dopamine.1?May be the “endogenous capsaicin like substance” in the CNS acting at TRPV1 channels, EC50~ 50 nM1. Also acts as a selective cannabinoid CB1 agonist (Ki=0.25 and 15 μM for CB1 and CB2 respectively)2?and results in a distinct signaling profile from any known cannabinoid3. Competitive inhibitor of FAAH and anandamide transport.4. Modulates acute systemic inflammation via non-hematopoietic TRPV1.5
Uses
NADA is a endogenous CB1 agonist, as well as a vanilloid agonist and inhibitor of FAAH and AMT.
Definition
ChEBI: Arachidonoyl dopamine is a fatty amide, a member of catechols, a secondary carboxamide and a N-(fatty acyl)-dopamine. It is functionally related to a dopamine and an arachidonic acid.
Biological Activity
Potent endogenous cannabinoid and vanilloid receptor agonist, with no action at dopamine receptors. Selective for CB 1 over CB 2 receptors (K i values are 0.25 and 12 μ M respectively), and potent agonist at TRPV1 (VR1) receptors (EC 50 ~ 50 nM). Metabolically stable and competitively inhibits FAAH and anandamide transport. Has cannabinoid and vanilloid actions in vivo . Also available as part of the Endocannabinoid Tocriset™ .
References
1) Huang?et al.?(2002),?An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors; Proc. Natl. Acad. Sci. USA,?99?8400
2) Bisogno?et al.?(2000),?N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo; Biochem. J.,?351 Pt 3?817
3) Redmund?et al.?(2016),?Identification of N-arachidonoyl dopamine as a highly biased ligand at cannabinoid CB1 receptors; Br. J. Pharmacol.,?173?115
4) Petrocellis?et al.?(2000),?Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity; FEBS Lett.,?483?52
5) Lawton?et al.?(2017),?N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1; J. Immunol.,?199?1465
