3D model (JSmol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 and binds irreversibly (forming a covalent bond) to the PCP binding site on the NMDA receptor complex. 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. Metaphit was also shown to prevent d-amphetamine induced hyperactivity, while significantly depleting dopamine content in the nucleus accumbens. Metaphit was the first acylating ligand used to study the cocaine receptor. 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.
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- Schweri, MM; Thurkauf, A; Mattson, MV; Rice, KC. "Fourphit: a selective probe for the methylphenidate binding site on the dopamine transporter". J Pharmacol Exp Ther. 261: 936–42. PMID 1602399.