Metaphit

Metaphit (1-[1-(3-Isothiocyanato)phenyl]cyclohexylpiperidine) is a research chemical that acts as an acylator of NMDARAn, sigma and DAT binding sites in the CNS. It is the m-isothiocyanate derivative of phencyclidine (PCP) and binds irreversibly (forming a covalent bond) to the PCP binding site on the NMDA receptor complex.^[1] However, later studies suggest the functionality of metaphit is mediated by sites not involved in PCP-induced passive avoidance deficit, and not related to the NMDA receptor complex.^[2] Metaphit was also shown to prevent d-amphetamine induced hyperactivity, while significantly depleting dopamine content in the nucleus accumbens.^[3] Metaphit was the first acylating ligand used to study the cocaine receptor.^[4] It is a structural isomer of the similar research compound fourphit, as it and metaphit both are isothiocyanate substituted derivatives of an analogous scaffold shared with PCP.^[5]

Metaphit

Names
Preferred IUPAC name 1-[1-(3-Isothiocyanatophenyl)cyclohexyl]piperidine
Identifiers
CAS Number	96316-00-6 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL41541 Y
ChemSpider	102730 Y
PubChem CID	114745
UNII	NFS3HJC8WD Y
CompTox Dashboard (EPA)	DTXSID00914572
InChI InChI=1S/C18H24N2S/c21-15-19-17-9-7-8-16(14-17)18(10-3-1-4-11-18)20-12-5-2-6-13-20/h7-9,14H,1-6,10-13H2 Y Key: FGSGBQAQSPSRJK-UHFFFAOYSA-N Y InChI=1/C18H24N2S/c21-15-19-17-9-7-8-16(14-17)18(10-3-1-4-11-18)20-12-5-2-6-13-20/h7-9,14H,1-6,10-13H2 Key: FGSGBQAQSPSRJK-UHFFFAOYAE
SMILES S=C=N\c1cccc(c1)C3(N2CCCCC2)CCCCC3
Properties
Chemical formula	C18H24N2S
Molar mass	300.462
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Metaphit as a methanesulfonate salt

See also

• RTI-76
• p-ISOCOC
• Methocinnamox