An analog of anandamide that binds CB receptors
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Arachidonoyl-2'-Fluoroethylamide

Item No. 90054

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-fluoroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
166100-37-4
Synonyms
  • 2'-fluoro AEA
  • 2'-fluoro Anandamide
Molecular Formula
C22H36FNO
Formula Weight
349.5
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 7 mg/mlEthanol: 15 mg/mlEthanol:PBS (1:1): 8 mg/ml
SMILES
O=C(N(CCF)[H])CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
InChi Code
InChI=1S/C22H36FNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-
InChi Key
DOGHEWWVBBVYEY-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $53

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    10 mg

    $98

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    50 mg

    $409

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    100 mg

    $711

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    Product 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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).