Arachidonylcyclopropylamide

Arachidonylcyclopropylamide

Names
IUPAC name N-(Cyclopropyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Other names ACPA
Identifiers
CAS Number	229021-64-1
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL418353
ChemSpider	4470548
IUPHAR/BPS	739
PubChem	5311007
InChI InChI=1S/C23H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)24-22-20-21-22/h6-7,9-10,12-13,15-16,22H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15- Key: GLGAUBPACOBAMV-DOFZRALJSA-N InChI=1/C23H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)24-22-20-21-22/h6-7,9-10,12-13,15-16,22H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15- Key: GLGAUBPACOBAMV-DOFZRALJBJ
SMILES O=C(NC1CC1)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula	C23H37NO
Molar mass	343.56 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

Arachidonylcyclopropylamide (ACPA) is a synthetic agonist of the cannabinoid receptor 1 (CB1R). ACPA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the cannabinoid receptor 2 (CB2R) (K_i = 2.2 nM for CB1R; K_i = 700 nM for CB2R).^[1]

References

1. Hillard, CJ; et al. (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.