LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

N-(2-fluoro-ethyl) 2-methyl-arachidonoyl amine

Systematic Name

N-(2-fluoro-ethyl)-2-methyl-5Z,8Z,11Z,14Z-eicosatetraenoyl amine

Synonyms

N-(2-fluoro-ethyl)2-methylarachidonoylamide
2-methylarachidonoyl-(2'-fluoroethyl)amide

LM ID

LMFA08020056

Formula

C₂₃H₃₈NOF

Exact Mass

Calculate m/z

363.293742

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

(±)-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 (Ki = 5.7 nM in rat brain). It also confers 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. 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.²

This information has been provided by Cayman Chemical

References

1. Ryan, W.J., Banner, K., Crocker, P.J., et al. Synthesis of (+)- and (−)-2-methylarachidonyl-2'-fluoroethylamide (O-689). Bioorg. Med. Chem. Lett. 7, 2669-2672 (1997).

2. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Evaluation of cannabinoid receptor binding and in vivo activities for anandamide analogs.,
J Pharmacol Exp Ther, 1995

Pubmed ID: 7791088

String Representations

InChiKey (Click to copy)

HMMNZALKMVCHHZ-ZKWNWVNESA-N

InChi (Click to copy)

InChI=1S/C23H38FNO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(2)23(26)25-21-20-24/h7-8,10-11,13-14,16-17,22H,3-6,9,12,15,18-21H2,1-2H3,(H,25,26)/b8-7-,11-10-,14-13-,17-16-

SMILES (Click to copy)

C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCC(C)C(=O)NCCF