CPCCOEt

CPCCOEt is a drug used in scientific research, which acts as a non-competitive antagonist at the metabotropic glutamate receptor subtype mGluR₁, with high selectivity although only moderate binding affinity.^[1]^[2] It is used mainly in basic research into the function of the mGluR₁ receptor,^[3]^[4] including the study of behavioural effects in animals including effects on memory and addiction.^[5]^[6]

CAS Number

179067-99-3^Y

PubChem CID

6278000

IUPHAR/BPS

1382

ChemSpider

23214736

Quick facts Identifiers, CAS Number ...

CPCCOEt
Identifiers

IUPAC name (−)-ethyl (7E)-7-hydroxyimino-1,7a-dihydrocyclopropa[b]chromene-1a-carboxylate
CAS Number	179067-99-3^Y
PubChem CID	6278000
IUPHAR/BPS	1382
ChemSpider	23214736
ChEBI	CHEBI:91562
ChEMBL	ChEMBL337583^N
Chemical and physical data
Formula	C₁₃H₁₃NO₄
Molar mass	247.250 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC(=O)[C@]12CC1/C(=N\O)c1ccccc1O2
InChI InChI=1S/C13H13NO4/c1-2-17-12(15)13-7-9(13)11(14-16)8-5-3-4-6-10(8)18-13/h3-6,9,16H,2,7H2,1H3/b14-11-/t9?,13-/m0/s1 Key:FXCTZFMSAHZQTR-ZBUQWEBQSA-N
^NY (what is this?) (verify)

[1]
Litschig S, Gasparini F, Rueegg D, Stoehr N, Flor PJ, Vranesic I, Prézeau L, Pin JP, Thomsen C, Kuhn R (March 1999). "CPCCOEt, a noncompetitive metabotropic glutamate receptor 1 antagonist, inhibits receptor signaling without affecting glutamate binding". Molecular Pharmacology. 55 (3): 453–61. doi:10.1016/S0026-895X(24)12169-4. PMID 10051528.
[2]
Ott D, Floersheim P, Inderbitzin W, Stoehr N, Francotte E, Lecis G, Richert P, Rihs G, Flor PJ, Kuhn R, Gasparini F (November 2000). "Chiral resolution, pharmacological characterization, and receptor docking of the noncompetitive mGlu1 receptor antagonist (+/-)-2-hydroxyimino- 1a, 2-dihydro-1H-7-oxacyclopropa[b]naphthalene-7a-carboxylic acid ethyl ester". Journal of Medicinal Chemistry. 43 (23): 4428–36. doi:10.1021/jm0009944. PMID 11087567.
[3]
Fukunaga I, Yeo CH, Batchelor AM (February 2007). "The mGlu1 antagonist CPCCOEt enhances the climbing fibre response in Purkinje neurones independently of glutamate receptors". Neuropharmacology. 52 (2): 450–8. doi:10.1016/j.neuropharm.2006.08.014. PMID 17045308. S2CID 40361285.
[4]
Sugiyama Y, Kawaguchi SY, Hirano T (February 2008). "mGluR1-mediated facilitation of long-term potentiation at inhibitory synapses on a cerebellar Purkinje neuron". The European Journal of Neuroscience. 27 (4): 884–96. doi:10.1111/j.1460-9568.2008.06063.x. PMID 18279362. S2CID 25581416.
[5]
Lominac KD, Kapasova Z, Hannun RA, Patterson C, Middaugh LD, Szumlinski KK (November 2006). "Behavioral and neurochemical interactions between Group 1 mGluR antagonists and ethanol: potential insight into their anti-addictive properties". Drug and Alcohol Dependence. 85 (2): 142–56. doi:10.1016/j.drugalcdep.2006.04.003. PMID 16697125.
[6]
Kim J, Lee S, Park H, Song B, Hong I, Geum D, Shin K, Choi S (March 2007). "Blockade of amygdala metabotropic glutamate receptor subtype 1 impairs fear extinction". Biochemical and Biophysical Research Communications. 355 (1): 188–93. Bibcode:2007BBRC..355..188K. doi:10.1016/j.bbrc.2007.01.125. PMID 17292864.

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