CP 55,940

CP 55,940

Legal status
Legal status	CA: Schedule II
Identifiers
IUPAC name 2-[(1R,2R,5R)-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
CAS Number	83002-04-4
PubChem CID	3086156
ChemSpider	94668
UNII	KFY70972J5
ChEMBL	ChEMBL559612 Y
CompTox Dashboard (EPA)	DTXSID80875516
Chemical and physical data
Formula	C24H40O3
Molar mass	376.581 g·mol−1
3D model (JSmol)	Interactive image
SMILES O[C@H]1C[C@@H](C2=CC=C(C(C)(C)CCCCCC)C=C2O)[C@H](CCCO)CC1
InChI InChI=1S/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1 Key:YNZFFALZMRAPHQ-SYYKKAFVSA-N

CP 55,940 is a synthetic cannabinoid which mimics the effects of naturally occurring THC (one of the psychoactive compounds found in cannabis). CP 55,940 was created by Pfizer in 1974 but was never marketed. It is currently used as a research tool to study the endocannabinoid system.

Pharmacology

CP 55,940 is 45 times more potent than Δ⁹-THC, and fully antagonized by rimonabant (SR141716A). It is considered a full agonist at both CB₁ and CB₂ receptors and has K_i values of 0.58 nM and 0.68 nM respectively, but is an antagonist at GPR55, the putative "CB₃" receptor. CP 55,940 binding has been detected in the cytosol of rat brain cerebral cortex. It can upregulate 5-HT_2A receptors in mice.

In vitro studies

CP 55,940 induced cell death in NG 108-15 Mouse neuroblastoma x Rat glioma hybrid brain cancer (genetically engineered mouse x rat brain cancer) cells.

In vivo studies

CP 55,940 showed protective effects on rat brain mitochondria upon paraquat exposure.

It also showed neuroprotective effects by reducing intracellular calcium release and reducing hippocampal cell death in cultured neurons subjected to high levels of NMDA.

See also

• CP 47,497
• CP 55,244