N-Arachidonoyl dopamine

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N-Arachidonoyl dopamine
N-Arachidonoyl dopamine.svg
Names
IUPAC name
(5Z,8Z,11Z,14Z)-N-[2-(3,4-dihydroxyphenyl)-ethyl]icosa-5,8,11,14-tetraenamide
Other names
NADA
Identifiers
199875-69-9 N
ChEMBL ChEMBL138921 YesY
ChemSpider 4445314 YesY
4261
Jmol 3D model Interactive image
PubChem 5282105
  • InChI=1S/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15- YesY
    Key: MVVPIAAVGAWJNQ-DOFZRALJSA-N YesY
  • InChI=1/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15-
    Key: MVVPIAAVGAWJNQ-DOFZRALJBM
  • CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCC1=CC(=C(C=C1)O)O
Properties
C28H41NO3
Molar mass 439.63 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

N-Arachidonoyl dopamine (NADA) is an endocannabinoid that acts as an agonist of the CB1 receptor and the transient receptor potential V1 (TRPV1) ion channel. NADA was first described as a putative endocannabinoid (agonist for the CB1 receptor) in 2000[1] and was subsequently identified as an endovanilloid (agonist for TRPV1) in 2002.[2] NADA is an endogenous arachidonic acid based lipid found in the brain of rats, with especially high concentrations in the hippocampus, cerebellum, and striatum.[2] It activates the TRPV1 channel with an EC50 of approximately of 50nM which makes it the putative endogenous TRPV1 agonist.[3]

In mice, NADA was shown to induce the tetrad of physiological paradigms associated with cannabinoids: hypothermia, hypo-locomotion, catalepsy, and analgesia.[1][4][5] NADA has been found to play a regulatory role in both the peripheral and central nervous systems, and displays antioxidant and neuroprotectant properties.[2][6][6][7][8] NADA has also been implicated in smooth muscle contraction and vasorelaxation in blood vessels.[9][10][11][12] Additionally, NADA has been observed to suppress inflammatory activation of human Jurkat T cells and to inhibit the release of prostaglandin E2 (PGE2) from lipopolysaccharide (LPS)-activated astrocytes, microglia and mouse brain ECs (MEC-Brain).[13][14][15] NADA also promotes the inflammatory resolution of human endothelial cells activated by both endogenous (i.e. TNF) and exogenous (i.e. bacterial derived LPS (TLR4 agonist) and FSL-1 (TLR2/6 agonist)) inflammatory mediators.[16] Furthermore, NADA also displays inhibitory activity in HIV-1 replication assays.[17] Finally, NADA can prevent the degranulation and release of TNF from RBL- 2H3 mast cells treated with an IgE-antigen complex.[18] Together, theses studies show that physiological functions attributed to NADA are multifaceted, and include the ability to modulate the immune response.

See also

References

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External links