| Identification | Back Directory | [Name]
NADA | [CAS]
199875-69-9 | [Synonyms]
NADA
AA-DA
Arachidonyl dopamine
ARACHIDONOYLDOPAMIDE
ARACHIDONOYL DOPAMINE
N-arachidonyldopamine
N-ARACHIDONOYLDOPAMINE
NADA (Arachidonoyl dopamine)
N-Arachidonoyl Dopamine (NADA)
N-ARACHIDONOYL-3-HYDROXYTYRAMINE
N-(3,4-Dihydroxyphenethyl)acetamide
N-[2-(3,4-Dihydroxyphenyl)ethyl]acetamide
N-[2-(3,4-DIHYDROXYPHENYL)ETHYL]-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
(5Z,8Z,11Z,14Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
5,8,11,14-Eicosatetraenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-, (5Z,8Z,11Z,14Z)-
AA-DA, Arachidonyl dopamine, NADA, N-[2,3-(4-Dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide | [Molecular Formula]
C28H41NO3 | [MDL Number]
MFCD03412031 | [MOL File]
199875-69-9.mol | [Molecular Weight]
439.63 |
| Chemical Properties | Back Directory | [Boiling point ]
640.0±55.0 °C(Predicted) | [density ]
1.023±0.06 g/cm3(Predicted) | [Fp ]
14 °C | [storage temp. ]
−20°C | [solubility ]
Soluble in DMSO (up to 50 mg/ml). | [form ]
ethanol solution | [pka]
9.79±0.10(Predicted) | [color ]
Pale yellow | [Sensitive ]
Air Sensitive | [Stability:]
Stable for 2 years from date of purchase as supplied. Subject to air oxidation Solutions in DMSO may be stored at -80° under an inert atmosphere for up to 1 month. |
| Hazard Information | Back Directory | [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™ . | [IC 50]
CB1: 250 nM (Ki); TRPV1: ~50 nM (EC50) | [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 |
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