Arachidonoyl serotonin

Names

[ Name ]:
Arachidonoyl serotonin

[Synonym ]:
(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-icosatetraenamide
Arachidonoyl serotonin
AA-5-HT N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenamide
(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]icosa-5,8,11,14-tetraenamide
Arachidonyl serotonin,N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide
5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-
Arachidonyl serotonin
N-Arachidonoylserotonin

Biological Activity

[Description]:

N-Arachidonoylserotonin (Arachidonyl serotonin; AA-5-HT) is a potent fatty acid amide hydrolase (FAAH) inhibitor with an IC50 value of 1~12 µM. N-Arachidonoylserotonin acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels (IC50=70~100 nM). N-Arachidonoylserotonin is analgesic in rodents [1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Signaling Pathways >> Metabolic Enzyme/Protease >> FAAH

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> FAAH

[Target]

IC50: 1~12 µM (FAAH), 70~100 nM (TRPV1 channels)[1]

[References]

[1]. Ortar G, et al. New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. J Med Chem. 2007;50(26):6554-6569.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
680.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₀H₄₂N₂O₂

[ Molecular Weight ]:
462.667

[ Flash Point ]:
365.3±31.5 °C

[ Exact Mass ]:
462.324615

[ PSA ]:
65.12000

[ LogP ]:
7.16

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.574

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Anticonvulsant effects of N-arachidonoyl-serotonin, a dual fatty acid amide hydrolase enzyme and transient receptor potential vanilloid type-1 (TRPV1) channel blocker, on experimental seizures: the roles of cannabinoid CB1 receptors and TRPV1 channels.

Basic Clin Pharmacol Toxicol. 115(4) , 330-4, (2014)

Selective blockade of anandamide hydrolysis, through the inhibition of the FAAH enzyme, has anticonvulsant effects, which are mediated by CB1 receptors. Anandamide, however, also activates TRPV1 chann...

The dual fatty acid amide hydrolase/TRPV1 blocker, N-arachidonoyl-serotonin, relieves carrageenan-induced inflammation and hyperalgesia in mice.

Pharmacol. Res. 61 , 537-46, (2010)

Given that the pharmacological or genetic inactivation of fatty acid amide hydrolase (FAAH) counteracts pain and inflammation, and on the basis of the established involvement of transient receptor pot...

The blockade of the transient receptor potential vanilloid type 1 and fatty acid amide hydrolase decreases symptoms and central sequelae in the medial prefrontal cortex of neuropathic rats de Novellis, V., et al.

Mol. Pain 17 , 7, (2011)