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N-Arachidonoyldopamine

BML-VR104

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Activator of CB₁ receptor and TRPV1

Endogenous, specific ligand for the CB₁ receptor (CB₁: K_i=250nM; CB₂: K_i=12µM) [1] and TRPV1 [2] (EC₅₀=50nM) found in nervous tissues [3, 4]. Immunosuppressant inhibiting T cell proliferation and phosphorylation of the NF-κB p65 subunit [5]. Potent vasorelaxant [6] and inhibitor of HIV-1 [7].

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Product Details

Alternative Name	N-Arachidonoyl-3-hydroxytyramine, NADA, AA-DA
Appearance	Viscous oil.
CAS	199875-69-9
Couple Target	Cannabinoid receptor, TRP channel
Couple Type	Activator, Ligand
Formula	C₂₈H₄₁NO₃
MW	439.6
Purity	≥98% (TLC)
Solubility	Soluble in DMSO.

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. Stable for at least 1 year after receipt when stored, as supplied, at -20°C. Stock solutions are stable for up to 3 months at -20°C.
Handling	Protect from oxygen. Keep under inert gas.
Long Term Storage	-20°C
Shipping	Dry Ice

Regulatory Status	RUO – Research Use Only

Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine: R. Sancho, et al.; J. Immunol. 175, 3990 (2005), Abstract
Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels: L. De Petrocellis, et al.; Br. J. Pharmacol. 143, 251 (2004), Abstract — Full Text
Modulation of trigeminal sensory neuron activity by the dual cannabinoid-vanilloid agonists anandamide, N-arachidonoyl-dopamine and arachidonyl-2-chloroethylamide: T.J. Price, et al.; Br. J. Pharmacol. 141, 1118 (2004), Abstract
Characterisation of the vasorelaxant properties of the novel endocannabinoid N-arachidonoyl-dopamine (NADA): S.E. O’Sullivan, et al.; Br. J. Pharmacol. 141, 803 (2004), Abstract
Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways: R. Sancho, et al.; J. Immunol. 172, 2341 (2004), Abstract
Arachidonyl dopamine as a ligand for the vanilloid receptor VR1 of the rat: A. Toth, et al.; Life Sci. 73, 487 (2003), Abstract
N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia: C.J. Chu, et al.; J. Biol. Chem. 278, 13633 (2003), Abstract
An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors: S.M. Huang, et al.; PNAS 99, 8400 (2002), Abstract
Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine: V. Bezuglov, et al.; Bioorg. Med. Chem. Lett. 11, 447 (2001), Abstract
N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo: T. Bisogno, et al.; Biochem. J. 351, 817 (2000), Abstract — Full Text

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N-Arachidonoyldopamine

BML-VR104

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