O-689 Chemical Properties

Boiling point:

503.6±50.0 °C(Predicted)

Density 

0.921±0.06 g/cm3(Predicted)

Flash point:

14 °C

storage temp. 

−20°C

solubility 

DMF: >10 mg/ml; DMSO: >30 mg/ml; Ethanol: >100 mg/ml; Ethanol:PBS (1:2): 8.5 mg/ml; PBS (pH 7.2): <100 μg/ml

form 

ethanol solution

pka

14.98±0.46(Predicted)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

7-16-26-36

RIDADR 

UN 1170 3/PG 2

WGK Germany 

1

MSDS

• Language:English Provider:SigmaAldrich

O-689 Usage And Synthesis

Description

(±)-2-Methyl arachidonoyl-2''-fluoroethylamide (2-Methyl-2''-fluoro AEA) is an analog of anandamide (AEA) in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution confers considerably increased binding affinity for the CB₁ receptor (K_i = 5.7 nM in rat brain). It also confers additional selectivity, in that binding to CB₂ is decreased relative to AEA. 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. 2-Methyl-2''-fluoro AEA is further modified by the addition of an α-methyl group at the C-2 position of arachidonic acid. This substitution confers enhanced metabolic stability. 2-Methyl-2''-fluoro AEA can fully substitute for Δ⁹-THC in animal self-administration tests, whereas AEA and 2-fluoro AEA cannot.

O-689(166100-39-6)Related Product Information

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