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PHCCC

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Chemical compound

Pharmaceutical compound

PHCCC
Identifiers

IUPAC name (−)-N-Phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide
CAS Number	179068-02-1
PubChemCID	3579925
ChemSpider	2816644
Chemical and physical data
Formula	C₁₇H₁₄N₂O₃
Molar mass	294.310 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c4ccccc4NC(=O)C1(CC1C2=NO)Oc3ccccc23
InChI InChI=1S/C17H14N2O3/c20-16(18-11-6-2-1-3-7-11)17-10-13(17)15(19-21)12-8-4-5-9-14(12)22-17/h1-9,13,21H,10H2,(H,18,20) Key:FPXPIEZPAXSELW-UHFFFAOYSA-N
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PHCCC is a research drug which acts as aglutamate receptor ligand, particularly being apositive allosteric modulator at themGluR₄ subtype,^[1] as well as an agonist atmGluR₆.^[2] It has anxiolytic effects in animal studies.^[3] PHCCC and similar drugs have been suggested as novel treatments forParkinson's disease.^[4]

^Maj M, Bruno V, Dragic Z, Yamamoto R, Battaglia G, Inderbitzin W, Stoehr N, Stein T, Gasparini F, Vranesic I, Kuhn R, Nicoletti F, Flor PJ (December 2003). "(−)-PHCCC, a positive allosteric modulator of mGluR4: characterization, mechanism of action, and neuroprotection".Neuropharmacology.45 (7):895–906.doi:10.1016/S0028-3908(03)00271-5.PMID 14573382.S2CID 17446511.
^Beqollari D, Kammermeier PJ (July 2008). "The mGlu(4) receptor allosteric modulator N-phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide acts as a direct agonist at mGlu(6) receptors".European Journal of Pharmacology.589 (1–3):49–52.doi:10.1016/j.ejphar.2008.06.054.PMID 18593581.
^Stachowicz K, Kłak K, Kłodzińska A, Chojnacka-Wojcik E, Pilc A (September 2004)."Anxiolytic-like effects of PHCCC, an allosteric modulator of mGlu4 receptors, in rats".European Journal of Pharmacology.498 (1–3):153–6.doi:10.1016/j.ejphar.2004.07.001.PMID 15363989.
^Niswender CM, Johnson KA, Weaver CD, Jones CK, Xiang Z, Luo Q, Rodriguez AL, Marlo JE, de Paulis T, Thompson AD, Days EL, Nalywajko T, Austin CA, Williams MB, Ayala JE, Williams R, Lindsley CW, Conn PJ (November 2008)."Discovery, characterization, and antiparkinsonian effect of novel positive allosteric modulators of metabotropic glutamate receptor 4".Molecular Pharmacology.74 (5):1345–58.doi:10.1124/mol.108.049551.PMC 2574552.PMID 18664603.

mGluR₁Tooltip Metabotropic glutamate receptor 1	Agonists:ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01-6128 Ro67-4853 Ro67-7476 VU-71 Theanine Antagonists:BAY 36-7620 CPCCOEt Cyclothiazide LY-367,385 LY-456,236 MCPG NPS-2390
mGluR₅Tooltip Metabotropic glutamate receptor 5	Agonists:ACPD ADX-47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU-1545;Positive allosteric modulators:LSN2463359 Antagonists:CTEP DMeOB LY-344,545 Mavoglurant MCPG NPS-2390 Remeglurant SIB-1757 SIB-1893;Negative allosteric modulators:AZD9272 Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant

mGluR₂Tooltip Metabotropic glutamate receptor 2

mGluR₃Tooltip Metabotropic glutamate receptor 3

mGluR₄Tooltip Metabotropic glutamate receptor 4	Agonists:Glutamate L-AP4 LSP2-9166 PHCCC VU-001,171 VU-0155,041;Positive allosteric modulators:Foliglurax MPEP Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₆Tooltip Metabotropic glutamate receptor 6	Agonists:Glutamate L-AP4 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₇Tooltip Metabotropic glutamate receptor 7	Agonists:AMN082 Glutamate L-AP4 LSP2-9166 Antagonists:CPPG MAP4 MMPIP MPPG MSOP MTPG UBP-1112 XAP044;Negative allosteric modulators:ADX71743
mGluR₈Tooltip Metabotropic glutamate receptor 8	Agonists:DCPG Glutamate L-AP4;Positive allosteric modulators:AZ12216052 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112

See also:Receptor/signaling modulators •Ionotropic glutamate receptor modulators •Glutamate metabolism/transport modulators

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