CP 55,940 Legal status
2-[(1R ,2R ,5R )-5-Hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) Formula C 24 H 40 O 3 Molar mass 376.581 g·mol−1 3D model (JSmol )
O[C@H]1C[C@@H](C2=CC=C(C(C)(C)CCCCCC)C=C2O)[C@H](CCCO)CC1
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 to study the endocannabinoid system .
A study found that CP 55,940 can upregulate 5-HT2A receptors in mice.[1]
CP 55,940 is 45 times more potent than Δ9 -THC, and fully antagonized by rimonabant (SR141716A).[2]
CP 55,940 is considered a full agonist at both CB1 and CB2 receptors and has Ki values of 0.58 nM and 0.68 nM respectively, but is an antagonist at GPR55 , the putative "CB3 " receptor.[3]
CP 55,940 showed protective effects on rat brain mitochondria upon paraquat exposure.[4]
It also showed neuroprotective effects by reducing intracellular calcium release and reducing hippocampal cell death in cultured neurons subjected to high levels of NMDA .[5]
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.[6] [7]
See also [ ]
References [ ]
^ Franklin JM, Carrasco GA (March 2013). "Cannabinoid receptor agonists upregulate and enhance serotonin 2A (5-HT(2A)) receptor activity via ERK1/2 signaling" . Synapse . 67 (3): 145–59. doi :10.1002/syn.21626 . PMC 3552103 . PMID 23151877 .
^ Rinaldi-Carmona M, Pialot F, Congy C, Redon E, Barth F, Bachy A, et al. (1996). "Characterization and distribution of binding sites for [3H]-SR 141716A, a selective brain (CB1) cannabinoid receptor antagonist, in rodent brain". Life Sciences . 58 (15): 1239–47. doi :10.1016/0024-3205(96)00085-9 . PMID 8614277 .
^ Kapur A, Zhao P, Sharir H, Bai Y, Caron MG, Barak LS, Abood ME (October 2009). "Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands" . The Journal of Biological Chemistry . 284 (43): 29817–27. doi :10.1074/jbc.M109.050187 . PMC 2785612 . PMID 19723626 .
^ Velez-Pardo C, Jimenez-Del-Rio M, Lores-Arnaiz S, Bustamante J (September 2010). "Protective effects of the synthetic cannabinoids CP55,940 and JWH-015 on rat brain mitochondria upon paraquat exposure". Neurochemical Research . 35 (9): 1323–32. doi :10.1007/s11064-010-0188-1 . hdl :11336/67604 . PMID 20514518 . S2CID 821457 .
^ Zhuang SY, Bridges D, Grigorenko E, McCloud S, Boon A, Hampson RE, Deadwyler SA (June 2005). "Cannabinoids produce neuroprotection by reducing intracellular calcium release from ryanodine-sensitive stores". Neuropharmacology . 48 (8): 1086–96. doi :10.1016/j.neuropharm.2005.01.005 . PMID 15910885 . S2CID 14953725 .
^ Tomiyama K, Funada M (November 2011). "Cytotoxicity of synthetic cannabinoids found in "Spice" products: the role of cannabinoid receptors and the caspase cascade in the NG 108-15 cell line". Toxicology Letters . 207 (1): 12–7. doi :10.1016/j.toxlet.2011.08.021 . PMID 21907772 .
^ "General Cell Collection: NG108-15" . Public Health England Culture Collections.
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
Cyclohexylphenols Eicosanoids
ACEA
ACPA
Methanandamide (AM-356)
O-1812
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
AM-251
AM-630
AM-6545
BML-190
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LY-320,135
MK-9470
NESS-0327
O-1918
O-2050
Otenabant (CP-945,598)
PF-514273
PipISB
PSB-SB-487
Rimonabant (SR141716)
Rosonabant (E-6776)
SR-144,528
Surinabant (SR147778)
Taranabant (MK-0364)
TM-38837
VCHSR
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
Hallucinogens
Psychedelics (5-HT2A agonists)
Benzofurans
2C-B-FLY
2CBFly-NBOMe
5-MeO-BFE
5-MeO-DiBF
Bromo-DragonFLY
F-2
F-22
TFMFly
Lyserg‐ amides
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1cP-LSD
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2-Butyllysergamide
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alpha -alkyltryptamines
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5-MeO-α-MT
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α-MT
x -DALT
(Daltacetin) 4-AcO-DALT
5-MeO-DALT
DALT
x -DET
(Ethacetin) 4-AcO-DET
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(T-9) DET
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x -DiPT
(Ipracetin) 4-AcO-DiPT
(Iprocin) 4-HO-DiPT
5-MeO-DiPT
DiPT
x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4-Propionyloxy-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT
(Deprocin) 4-HO-DPT
5-MeO-DPT
(The Light) DPT
Ibogaine-related
18-MAC
18-MC
Coronaridine
Ibogaine
Ibogamine
ME-18-MC
Noribogaine
Tabernanthine
Voacangine
x -MET
(Metocin) 4-HO-MET
(Metocetin) 4-AcO-MET
5-MeO-MET
MET
x -MiPT
(Mipracetin) 4-AcO-MiPT
(Miprocin) 4-HO-MiPT
5-Me-MiPT
(Moxy) 5-MeO-MiPT
MiPT
Others
4-HO-DBT
4-HO-EPT
4-HO-McPT
(Lucigenol) 4-HO-MPMI
(Meprocin) 4-HO-MPT
5-MeO-EiPT
5-MeO-MALT
5-MeO-MPMI
Aeruginascin
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DBT
EiPT
EPT
MPT
PiPT
Others
AL-38022A
ALPHA
Dimemebfe
Efavirenz
Glaucine
Lorcaserin
M-ALPHA
RH-34 Also empathogens in general (e. g.: 5-APB , 5-MAPB , 6-APB and other substituted benzofurans ).
Dissociatives (NMDAR antagonists )
Arylcyclo‐ hexylamines
Ketamine-related
2-Fluorodeschloroketamine
Arketamine ((R)-ketamine)
Deschloroketamine
Ethketamine (N-Ethylnorketamine)
Esketamine ((S)-ketamine)
Ketamine
Methoxetamine
Methoxmetamine
Methoxyketamine
MXiPr
Norketamine
Tiletamine
PCP-related Others
Diarylethylamines Morphinans
Dextrallorphan
Dextromethorphan
Dextrorphan
Racemethorphan
Racemorphan
Others
2-EMSB
2-MDP
8A-PDHQ
Aptiganel
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RB-64
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Selfotel
Xenon
Deliriants (mAChR antagonists )
Atropine
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BZ
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,668
Chloropyramine
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CS-27349
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EA-3167
EA-3443
EA-3580
EA-3834
Elemicin
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JB-318
JB-336
Meclozine
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Myristicin
Orphenadrine
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Pheniramine
Phenyltoloxamine
Procyclidine
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Scopolamine
Tolterodine
Trihexyphenidyl
Tripelennamine
Triprolidine
WIN-2299
Others
Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG
2-AGE (noladin ether)
11-Hydroxy-THC
α-Amyrin · β-Amyrin
AB-CHMINACA
AM-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
Gallocatechol (gallocatechin)
Honokiol
HU-210
JWH-007
JWH-015
JWH-018
JWH-073
Kavain
L-759,633
Levonantradol
Menabitan
Nabilone
Nabitan
NADA
O-1812
Oleamide
Pravadoline
Serinolamide A
THC (dronabinol)
UR-144
WIN 55,212-2
Yangonin
Antagonists: AM-251
AM-6545
Cannabidiol
Cannabigerol
Drinabant
Falcarinol (carotatoxin)
Hemopressin
Ibipinabant
LY-320,135
MK-9470
NESS-0327
O-2050
Otenabant
PF-514273
PipISB
Rimonabant
Rosonabant
Surinabant
Taranabant
THCV
TM-38837
VCHSR
Virodhamine
CB2
Agonists: 2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Virodhamine
Antagonists: 4-O-Methylhonokiol
AM-630
BML-190
Cannabidiol
Honokiol
JTE-907
SR-144,528
WIN 54,461
WIN 56,098
NAGly (GPR18 )
Agonists: Abnormal cannabidiol
ACPA
AM251
Anandamide
Cannabidiol
NADGly
THC (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)