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166100-37-4

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166100-37-4 Structure

166100-37-4 Structure
IdentificationBack Directory
[Name]

2'-FLUORO AEA
[CAS]

166100-37-4
[Synonyms]

AFEA
2'-FLUORO AEA
AEA, 2'-FLUORO
-fluoroethylamide
Arachidonyl-2&rsquo
2'-FLUORO ANANDAMIDE
Arachidonoyl-2&rsquo
ANANDAMIDE, 2'-FLUORO
FLUOROETHYLEICOSATETRAENAMIDE
Arachidonyl-2-fluoroethylamide
ARACHIDONOYL 2'-FLUOROETHYLAMIDE
N-(2-FLUOROETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
5,8,11,14-Eicosatetraenamide, N-(2-fluoroethyl)-, (5Z,8Z,11Z,14Z)-
[Molecular Formula]

C22H36FNO
[MDL Number]

MFCD02259376
[MOL File]

166100-37-4.mol
[Molecular Weight]

349.53
Chemical PropertiesBack Directory
[solubility ]

DMF: 10 mg/ml; DMSO: 7 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (1:1): 8 mg/ml
Safety DataBack Directory
[Symbol(GHS) ]


GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319
[Precautionary statements ]

P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Hazard InformationBack Directory
[Description]

Arachidonoyl-2'-fluoroethylamide (2-fluoro AEA) is an analog of anandamide in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution adds considerably increased binding affinity for the CB1 receptor (Kis = 26.7 and 908 nM for CB1 and CB2, respectively). It also contributes additional selectivity, in that binding to CB2 is decreased relative to AEA.1 However, the in vivo activity of 2-fluoro AEA is enhanced much less than the binding affinity, because the analog remains a good substrate for FAAH and is rapidly hydrolyzed by this enzyme.
[Uses]

Arachidonoyl-2'-fluoroethylamide is a CB1 receptor agonist and an analog of Anandamide (A637220), which is an endogenous cannabinoid and TRPV1 receptor agonist.
[References]

1. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability J. Med. Chem. 41(27),5353-5361(1998).
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