PHCCC

PHCCC
Identifiers
	IUPAC name (−)-N-Phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide;
CAS Number	179068-02-1;
PubChem CID	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;
	(verify)

PHCCC is a research drug which acts as a glutamate receptor ligand, particularly being a positive allosteric modulator at the mGluR₄ subtype,^[1] as well as an agonist at mGluR₆.^[2] It has anxiolytic effects in animal studies.^[3] PHCCC and similar drugs have been suggested as novel treatments for Parkinson's disease.^[4]

References

^ 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.

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Identifiers

IUPAC name (−)-N-Phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide
CAS Number	179068-02-1
PubChem CID	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
(verify)