N-Arachidonoyl dopamine

N-Arachidonoyl dopamine
	IUPAC name (5Z,8Z,11Z,14Z)-N-[2-(3,4-dihydroxyphenyl)-ethyl]icosa-5,8,11,14-tetraenamide
	Other names NADA
Identifiers
CAS number	199875-69-9
PubChem	5282105
ChemSpider	4445314
ChEMBL	CHEMBL138921
Jmol-3D images	Image 1
	SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCC1=CC(=C(C=C1)O)O ;
	InChI 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- ; Key: MVVPIAAVGAWJNQ-DOFZRALJSA-N 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 ;
Properties
Molecular formula	C28H41NO3
Molar mass	439.63 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

N-Arachidonoyl dopamine (NADA) is an endocannabinoid which acts as an agonist of the CB₁ receptor^[1] and the transient receptor potential V1 (TRPV1) ion channel. Its discovery was described in 2002 by an academic research group from Italy and the USA. It was found in the brain of rats, with especially high concentrations in the hippocampus, cerebellum and striatum. It activates the TRPV1 channel with an EC₅₀ of approximately of 50nM. The high potency makes it the putative endogenous TRPV1 agonist.^[2]

References[edit]

^ Ralevic V (July 2003). "Cannabinoid modulation of peripheral autonomic and sensory neurotransmission". European Journal of Pharmacology 472 (1–2): 1–21. doi:10.1016/S0014-2999(03)01813-2. PMID 12860468.
^ Huang SM, Bisogno T, Trevisani M, Al-Hayani A, De Petrocellis L, Fezza F, Tognetto M, Petros TJ, Krey JF, Chu CJ, Miller JD, Davies SN, Geppetti P, Walker JM, Di Marzo V (June 2002). "An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors". Proceedings of the National Academy of Sciences of the United States of America 99 (12): 8400–5. doi:10.1073/pnas.122196999. PMC 123079. PMID 12060783.