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]
^Danysz, Wojciech (1991). "Metaphit fails to antagonize PCP-induced passive avoidance deficit". Pharmacology Biochemistry and Behavior. 38 (1): 231–3.
doi:
10.1016/0091-3057(91)90618-C.
PMID1826788.
^French, Edward D.; Jacobson, Arthur E.; Rice, Kenner C. (1987). "Metaphit, a proposed phencyclidine (PCP) antagonist, prevents PCP-induced locomotor behavior through mechanisms unrelated to specific blockade of PCP receptors". European Journal of Pharmacology. 140 (3): 267–74.
doi:
10.1016/0014-2999(87)90283-4.
PMID2820762.
^Carroll, F. Ivy; Lewin, Anita H.; Boja, John W.; Kuharf, Michael J. (1992). "Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogs at the dopamine transporter". Journal of Medicinal Chemistry. 35 (6): 969–81.
doi:
10.1021/jm00084a001.
PMID1552510.
^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.
PMID1602399.