NADA Chemical Properties

Boiling point:

640.0±55.0 °C(Predicted)

Density 

1.023±0.06 g/cm3(Predicted)

Flash point:

14 °C

storage temp. 

−20°C

solubility 

Soluble in DMSO (up to 50 mg/ml).

pka

9.79±0.10(Predicted)

form 

ethanol solution

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.

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1170 3/PG 2

WGK Germany 

1

MSDS

• Language:English Provider:SigmaAldrich

NADA Usage And Synthesis

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] SUSAN M. HUANG. An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors[J]. Proceedings of the National Academy of Sciences of the United States of America, 2002, 99 1: 8400-8405. DOI:10.1073/pnas.122196999
[2] T BISOGNO. N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo.[J]. Biochemical Journal, 2000, 351 Pt 3: 817-824.
[3] WILLIAM J. REDMOND. Identification of N-arachidonoyl dopamine as a highly biased ligand at cannabinoid CB1 receptors[J]. British Journal of Pharmacology, 2015, 173 1: 115-127. DOI:10.1111/bph.13341
[4] LUCIANO DE PETROCELLIS . Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity[J]. FEBS Letters, 2000, 483 1: Pages 52-56. DOI:10.1016/s0014-5793(00)02082-2
[5] SAMIRA K LAWTON. N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1.[J]. Journal of immunology, 2017: 1465-1475. DOI:10.4049/jimmunol.1602151

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