Metaphit

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Metaphit
Metaphit.svg
Names
IUPAC name
1-[1-(3-isothiocyanatophenyl)cyclohexyl]piperidine
Identifiers
ChEMBL ChEMBL41541 YesY
ChemSpider 102730 YesY
Jmol interactive 3D Image
PubChem 114745
Properties
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).
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Infobox references
Metaphit as a methanesulfonate salt

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 & 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]

References[edit]

  1. ^ Rafferty, Michael F.; Mattson, Mariena; Jacobson, Arthur E.; Rice, Kenner C. (1985). "A specific acylating agent for the [3H]phencyclidine receptors in rat brain". FEBS Letters 181 (2): 318–22. doi:10.1016/0014-5793(85)80284-2. PMID 2982662. 
  2. ^ 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. PMID 1826788. 
  3. ^ 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. PMID 2820762. 
  4. ^ 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. PMID 1552510.