2'-FLUORO AEA

2'-FLUORO AEA Property

Boiling point:

496.0±45.0 °C(Predicted)

Density 

0.925±0.06 g/cm3(Predicted)

solubility 

DMF: 10 mg/ml; DMSO: 7 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (1:1): 8 mg/ml

pka

15.24±0.46(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

2'-FLUORO AEA Chemical Properties,Usage,Production

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 (K_is = 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.

in vivo

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).