Arachidonyl-2'-chloroethylamide

Arachidonyl-2'-chloroethylamide (ACEA) is a synthetic agonist of the CB1 (CB1R). ACEA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the CB2 (CB2R) (Ki = 1.4 nM for CB1R; Ki = 3100 nM for CB2R). [1]

Arachidonyl-2'-chloroethylamide
Arachidonyl-2-chloroethylamide.svg
Names
Preferred IUPAC name
(5Z,8Z,11Z,14Z)-N-(2-Chloroethyl)icosa-5,8,11,14-tetraenamide
Other names
Arachidonyl-2'-chloroethylamide; ACEA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C22H36ClNO/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- checkY
    Key: SCJNCDSAIRBRIA-DOFZRALJSA-N checkY
  • InChI=1/C22H36ClNO/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-
    Key: SCJNCDSAIRBRIA-DOFZRALJBU
  • ClCCNC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
C22H36ClNO
Molar mass 365.99 g·mol−1
Solubility in other solvents soluble in ethanol, chloroform, THF and DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

ReferencesEdit

  1. ^ Hillard, CJ; Manna, S; Greenberg, MJ; Dicamelli, R; Ross, RA; Stevenson, LA; Murphy, V; Pertwee, RG; Campbell, WB (1999). "Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1)". The Journal of Pharmacology and Experimental Therapeutics. 289 (3): 1427–33. PMID 10336536.