CP 55,940

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Cat.No. 0949 - CP 55,940 | C24H40O3 | CAS No. 83002-04-4
Description: Potent and non-selective CB agonist
Chemical Name: (-)-cis-3-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol
Purity: ≥98% (HPLC)
Datasheet
Citations (51)
Reviews
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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 37.66 100
DMSO 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 the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

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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References

References are publications that support the biological activity of the product.

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: CP 55,940, CP 55,940 supplier, Potent, non-selective, cannabinoids, receptors, agonists, Non-Selective, CP55940, cb2r, cb1r, Pfizer, Non-selective, Cannabinoids, 0949, Tocris Bioscience

51 Citations for CP 55,940

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

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

You et al (2011) Functional characterization and analgesic effects of mixed cannabinoid receptor/T-type channel ligands. Mol Pain 7 89 PMID: 22093952

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

Tucker et al (2001) The endogenous cannabinoid agonist, anandamide stimulates sensory nerves in guinea-pig airways. Br J Pharmacol 132 1127 PMID: 11226144

Christopoulos et al (2001) Pharmacological analysis of cannabinoid receptor activity in the rat vas deferens. Br J Pharmacol 132 1281 PMID: 11250879

White and Hiley (1998) The actions of some cannabinoid receptor ligands in the rat isolated mesenteric artery. Br J Pharmacol 125 533 PMID: 9806337

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

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

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

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

Ford (2017) Characterization of structurally novel G protein biased CB1 agonists: implications for drug development. Pharmacol Res 125 161 PMID: 28838808

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

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

Gangarossa et al (2011) Convulsant doses of a DA 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

Vinod et al (2008) Genetic and pharmacological manipulations of the CB(1) receptor alter ethanol preference and dependence in ethanol preferring and nonpreferring mice. Synapse 62 574 PMID: 18509854

Naguib et al (2008) MDA7: a novel selective agonist for CB2 receptors that prevents allodynia in rat neuropathic pain models. Br J Pharmacol 155 1104 PMID: 18846037

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

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

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

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

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

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

Vincent et al (2016) Cannabinoid receptor-specific mechanisms to alleviate pain in sickle cell anemia via inhibition of mast cell activation and neurogenic inflammation. Haematologica 101 566 PMID: 26703965

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

Petrov et al (2013) Mastering tricyclic ring systems for desirable functional cannabinoid activity. Eur J Med Chem 69 881 PMID: 24125850

Gadotti et al (2013) Analgesic effect of a mixed T-type channel inhibitor/CB2 receptor agonist. Mol Pain 9 32 PMID: 23815854

Hayase (2013) Working memory- and anxiety-related behavioral effects of repeated nicotine as a stressor: the role of cannabinoid receptors. BMC Neurosci 14 20 PMID: 23394117

Cawston et al (2013) Real-time characterization of cannabinoid receptor 1 (CB1 ) allosteric modulators reveals novel mechanism of action. Br J Pharmacol 170 893 PMID: 23937487

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

Cain et al (2012) Mouse models for studying pain in sickle disease: effects of strain, age, and acuteness. Br J Haematol 156 535 PMID: 22171826

Vannacci et al (2004) The endocannabinoid 2-arachidonylglycerol decreases the immunological activation of Guinea pig mast cells: involvement of nitric oxide and eicosanoids. J Pharmacol Exp Ther 311 256 PMID: 15187170

Godlewski et al (2003) Cannabinoid receptor-independent inhibition by cannabinoid agonists of the peripheral 5-HT3 receptor-mediated von Bezold-Jarisch reflex. Br J Pharmacol 138 767 PMID: 12642377

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

Barann et al (2002) Direct inhibition by cannabinoids of human 5-HT3A receptors: probable involvement of an allosteric modulatory site. Br J Pharmacol 137 589 PMID: 12381672


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