CP 55,940

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Cat.No. 0949 - CP 55,940 | C24H40O3 | CAS No. 83002-04-4
Description: Potent, non-selective cannabinoid receptor agonist
Chemical Name: (-)-cis-3-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol
Purity: ≥98% (HPLC)
Datasheet
Citations (35)
Literature

Biological Activity

Cannabinoid agonist which is considerably more potent than Δ9-THC in both behavioral tests and receptor binding assays. Displays high and roughly equal affinity for both central and peripheral cannabinoid receptors (Ki = 0.6 - 5.0 and 0.7 - 2.6 nM at CB1 and CB2 respectively; EC50 values are 0.2, 0.3 and 5 nM at CB1, CB2 and GRP55 respectively).

Licensing Information

Sold for research purposes under agreement from Pfizer Inc.

Technical Data

M. Wt 376.58
Formula C24H40O3
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 83002-04-4
PubChem ID 104895
InChI Key YNZFFALZMRAPHQ-SYYKKAFVSA-N
Smiles O[C@H]1C[C@@H]([C@]2=CC=C(C(C)(C)CCCCCC)C=C2O)[C@H](CCCO)CC1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.66 100
ethanol 37.66 100

Preparing Stock Solutions

The following data is based on the product molecular weight 376.58. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.66 mL 13.28 mL 26.55 mL
5 mM 0.53 mL 2.66 mL 5.31 mL
10 mM 0.27 mL 1.33 mL 2.66 mL
50 mM 0.05 mL 0.27 mL 0.53 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Griffin et al (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5'-O-(3-[35S]thio)-triphosphate binding assay in rat cerebellar membranes. J.Pharmacol.Exp.Ther. 285 553 PMID: 9580597

Thomas et al (1998) Comparative receptor binding analyses of cannabinoid agonists and antagonists. J.Pharmacol.Exp.Ther. 285 285 PMID: 9536023

Wiley et al (1995) Discriminative stimulus effects of CP 55,940 and structurally dissimilar cannabinoids in rats. Neuropharmacology 34 669 PMID: 7566504

Avdesh (2011) Corticosteroid dependent and independent effects of a cannabinoid agonist on core temperature, motor activity, and prepulse inhibition of the acoustic startle reflex in Wistar rats. Psychopharmacology Epub ahead of print PMID: 21947354


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Keywords: Potent non-selective cannabinoids receptors agonists Non-Selective CP55940 cb2r cb1r Pfizer Non-selective Cannabinoids

35 Citations for CP 55,940

Citations are publications that use Tocris products. Selected citations for CP 55,940 include:

Mahmoud et al (2015) (4-(Bis(4-fluorophenyl)methyl)piperazin-1-yl)(cyclohexyl)methanone hydrochloride (LDK1229): a new cannabinoid CB1 receptor inverse agonist from the class of benzhydryl piperazine analogs. Mol Pharmacol 87 197 PMID: 25411367

Mounsey et al (2015) Increasing levels of the endocannabinoid 2-AG is neuroprotective in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mouse model of Parkinson's disease. Pharmacol Res Perspect 273 36 PMID: 26244281

Presley et al (2015) Preclinical evaluation of SMM-189, a cannabinoid receptor 2-specific inverse agonist. Eur J Pharmacol 3 e00159 PMID: 26196013

Tarawneh et al (2014) Flavanones from Miconia prasina. Phytochem Lett 7 130 PMID: 24976876

Thomazeau et al (2014) Prefrontal deficits in a murine model overexpressing the down syndrome candidate gene dyrk1a. J Neurosci 34 1138 PMID: 24453307

Häggström et al (2014) Potential upstream regulators of cannabinoid receptor 1 signaling in prostate cancer: a Bayesian network analysis of data from a tissue microarray. J Biol Chem 74 1107 PMID: 24913716

Hruba and McMahon (2014) The cannabinoid agonist HU-210: pseudo-irreversible discriminative stimulus effects in rhesus monkeys. Br J Pharmacol 727 35 PMID: 24486701

Baillie et al (2013) CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity. Mol Pharmacol 83 322 PMID: 23160940

Marcu et al (2013) Novel insights into CB1 cannabinoid receptor signaling: a key interaction identified between the extracellular-3 loop and transmembrane helix 2. J Pharmacol Exp Ther 345 189 PMID: 23426954

Tambaro et al (2013) Long-term CB1 receptor blockade enhances vulnerability to anxiogenic-like effects of cannabinoids. Neuropharmacology 70 268 PMID: 23462228

Marini et al (2013) Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors. Br J Pharmacol 169 887 PMID: 23711022

Prather et al (2013) CB1 and CB2 receptors are novel molecular targets for Tamoxifen and 4OH-Tamoxifen. Biochem Biophys Res Commun 441 339 PMID: 24148245

Rajasekaran et al (2013) Human metabolites of synthetic cannabinoids JWH-018 and JWH-073 bind with high affinity and act as potent agonists at cannabinoid type-2 receptors. Toxicol Appl Pharmacol 269 100 PMID: 23537664

Seillier et al (2013) Phencyclidine-induced social withdrawal results from deficient stimulation of cannabinoid CB1 receptors: implications for schizophrenia. Eur J Pharmacol 38 1816 PMID: 23563893

Bolognini et al (2012) AM630 behaves as a protean ligand at the human cannabinoid CB2 receptor. Br J Pharmacol 165 2561 PMID: 21615724

Chimalakonda et al (2012) Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug Metab Dispos 40 2174 PMID: 22904561

Laricchiuta et al (2012) CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation. PLoS One 7 e42111 PMID: 22848724

Brents et al (2012) Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem Pharmacol 83 952 PMID: 22266354

Horváth et al (2012) A new cannabinoid CB2 receptor agonist HU-910 attenuates oxidative stress, inflammation and cell death associated with hepatic ischaemia/reperfusion injury. J Physiol 165 2462 PMID: 21449982

Gangarossa et al (2011) Convulsant doses of a dopamine D1 receptor agonist result in Erk-dependent increases in Zif268 and Arc/Arg3.1 expression in mouse dentate gyrus. PLoS One 6 e19415 PMID: 21559295

Brents et al (2011) Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity. PLoS One 6 e21917 PMID: 21755008

Holderith et al (2011) Cannabinoids attenuate hippocampal γ oscillations by suppressing excitatory synaptic input onto CA3 pyramidal neurons and fast spiking basket cells. Br J Pharmacol 589 4921 PMID: 21859823

García et al (2011) Symptom-relieving and neuroprotective effects of the phytocannabinoid △9-THCV in animal models of Parkinson's disease. J Cell Mol Med 163 1495 PMID: 21323909

Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. J Biol Chem 32 43101 PMID: 19907129

Kimura et al (2009) Location, structure, and dynamics of the synthetic cannabinoid ligand CP-55,940 in lipid bilayers. Biophys J 96 4916 PMID: 19527650

Kapur et al (2008) Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction. J Pharmacol Exp Ther 325 341 PMID: 18174385

Georgieva et al (2008) Unique agonist-bound cannabinoid CB1 receptor conformations indicate agonist specificity in signaling. Neuropsychopharmacology 581 19 PMID: 18162180

Giannini et al (2008) Activation of cannabinoid receptors prevents antigen-induced asthma-like reaction in guinea pigs. Prostate 12 2381 PMID: 18266975

Pertwee et al (2007) The psychoactive plant cannabinoid, Delta9-tetrahydrocannabinol, is antagonized by Delta8- and Delta9-tetrahydrocannabivarin in mice in vivo. Br J Pharmacol 150 586 PMID: 17245367

Kokkola et al (2005) S-nitrosothiols modulate G protein-coupled receptor signaling in a reversible and highly receptor-specific manner. BMC Cell Biol 6 21 PMID: 15850493

Ehrhart et al (2005) Stimulation of cannabinoid receptor 2 (CB2) suppresses microglial activation. J Neuroinflammation 2 29 PMID: 16343349

Savinainen et al (2005) Identification of WIN55212-3 as a competitive neutral antagonist of the human cannabinoid CB2 receptor. Br J Pharmacol 145 636 PMID: 15852035

Thomas et al (2005) Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist. Br J Pharmacol 146 917 PMID: 16205722

Savinainen et al (2003) An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors. Br J Pharmacol 140 1451 PMID: 14623770

Hilairet et al (2003) Hypersensitization of the Orexin 1 receptor by the CB1 receptor: evidence for cross-talk blocked by the specific CB1 antagonist, SR141716. Exp Neurol 278 23731 PMID: 12690115


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