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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}{{Drugbox
| IUPAC_name = 2-[(1''R'',2''R'',5''R'')-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
| image = CP 55,940-2D-skeletal.svg
| image_class = skin-invert-image
| width = 200px

| tradename =
| legal_status =
| legal_CA = Schedule II
| routes_of_administration =

| metabolism =
| elimination_half-life =
| excretion =

| CAS_number = 83002-04-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KFY70972J5
| PubChem = 3086156
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 559612
| ChemSpiderID = 94668


| C=24 | H=40 | O=3
| StdInChI = 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
| StdInChIKey = YNZFFALZMRAPHQ-SYYKKAFVSA-N
| smiles = O[C@H]1C[C@@H](C2=CC=C(C(C)(C)CCCCCC)C=C2O)[C@H](CCCO)CC1
}}

'''CP 55,940''' is a [[synthetic cannabinoid]] which mimics the effects of naturally occurring [[Tetrahydrocannabinol|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]].<ref>{{cite journal | vauthors = Glass M, Dragunow M, Faull RL | title = Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain | journal = Neuroscience | volume = 77 | issue = 2 | pages = 299–318 | date = March 1997 | pmid = 9472392 | doi = 10.1016/s0306-4522(96)00428-9 | s2cid = 40213209 }}</ref>

== Pharmacology ==

CP 55,940 is 45 times more potent than Δ9-THC, and fully antagonized by [[rimonabant]] (SR141716A).<ref>{{cite journal | vauthors = Rinaldi-Carmona M, Pialot F, Congy C, Redon E, Barth F, Bachy A, Brelière JC, Soubrié P, Le Fur G | display-authors = 6 | title = Characterization and distribution of binding sites for [3H]-SR 141716A, a selective brain (CB1) cannabinoid receptor antagonist, in rodent brain | journal = Life Sciences | volume = 58 | issue = 15 | pages = 1239–47 | year = 1996 | pmid = 8614277 | doi = 10.1016/0024-3205(96)00085-9 }}</ref> It is considered a full agonist at both CB1 and CB2 receptors and has [[Disassociation constant#Protein-ligand binding|Ki]] values of 0.58 nM and 0.68 nM respectively, but is an antagonist at [[GPR55]], the putative "CB3" receptor.<ref>{{cite journal | vauthors = Kapur A, Zhao P, Sharir H, Bai Y, Caron MG, Barak LS, Abood ME | title = Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands | journal = The Journal of Biological Chemistry | volume = 284 | issue = 43 | pages = 29817–27 | date = October 2009 | pmid = 19723626 | pmc = 2785612 | doi = 10.1074/jbc.M109.050187 | doi-access = free }}</ref> CP 55,940 binding has been detected in the cytosol of rat brain cerebral cortex.<ref>{{cite journal | vauthors = Qureshi J, Saady M, Cardounel A, Kalimi M | title = Identification and characterization of a novel synthetic cannabinoid CP 55,940 binder in rat brain cytosol | journal = Molecular and Cellular Biochemistry | volume = 181 | issue = 1–2 | pages = 21–27 | date = April 1998 | pmid = 9562238 | doi = 10.1023/A:1006855504094 | s2cid = 6200670 }}</ref> It can upregulate [[5-HT2A receptor|5-HT2A]] receptors in mice.<ref>{{cite journal | vauthors = Franklin JM, Carrasco GA | title = Cannabinoid receptor agonists upregulate and enhance serotonin 2A (5-HT(2A)) receptor activity via ERK1/2 signaling | journal = Synapse | volume = 67 | issue = 3 | pages = 145–59 | date = March 2013 | pmid = 23151877 | pmc = 3552103 | doi = 10.1002/syn.21626 }}</ref>

== 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.<ref>{{cite journal | vauthors = Tomiyama K, Funada M | title = Cytotoxicity of synthetic cannabinoids found in "Spice" products: the role of cannabinoid receptors and the caspase cascade in the NG 108-15 cell line | journal = Toxicology Letters | volume = 207 | issue = 1 | pages = 12–7 | date = November 2011 | pmid = 21907772 | doi = 10.1016/j.toxlet.2011.08.021 }}</ref><ref>{{ cite web | url = http://www.hpacultures.org.uk/products/celllines/generalcell/detail.jsp?refId=88112302&collection=ecacc_gc | title = General Cell Collection: NG108-15 | publisher = Public Health England Culture Collections }}</ref>

== In vivo studies ==

CP 55,940 showed protective effects on rat brain mitochondria upon paraquat exposure.<ref>{{cite journal | vauthors = Velez-Pardo C, Jimenez-Del-Rio M, Lores-Arnaiz S, Bustamante J | title = Protective effects of the synthetic cannabinoids CP55,940 and JWH-015 on rat brain mitochondria upon paraquat exposure | journal = Neurochemical Research | volume = 35 | issue = 9 | pages = 1323–32 | date = September 2010 | pmid = 20514518 | doi = 10.1007/s11064-010-0188-1 | hdl-access = free | hdl = 11336/67604 | s2cid = 821457 }}</ref>

It also showed neuroprotective effects by reducing intracellular calcium release and reducing hippocampal cell death in cultured neurons subjected to high levels of [[NMDA]].<ref>{{cite journal | vauthors = Zhuang SY, Bridges D, Grigorenko E, McCloud S, Boon A, Hampson RE, Deadwyler SA | title = Cannabinoids produce neuroprotection by reducing intracellular calcium release from ryanodine-sensitive stores | journal = Neuropharmacology | volume = 48 | issue = 8 | pages = 1086–96 | date = June 2005 | pmid = 15910885 | doi = 10.1016/j.neuropharm.2005.01.005 | s2cid = 14953725 }}</ref>

== See also ==
* [[CP 42,096]]
* [[CP 47,497]]
* [[CP 55,244]]
* [[Cycloheptyl CP 55,940]]

== References ==
{{reflist}}

{{Cannabinoids}}
{{Hallucinogens}}
{{Cannabinoidergics}}

[[Category:Primary alcohols]]
[[Category:Cyclohexanols]]
[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Drugs developed by Pfizer]]
[[Category:Phenols]]
[[Category:CB1 receptor agonists]]
[[Category:CB2 receptor agonists]]

CP 55,940 - Revision history

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