Metaphit
| Metaphit | ||
|---|---|---|
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| IUPAC name 1-[1-(3-isothiocyanatophenyl)cyclohexyl]piperidine | ||
| Identifiers | ||
| PubChem | 114745 | |
| ChemSpider | 102730  | |
| ChEMBL | CHEMBL41541 | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C18H24N2S | |
| Molar mass | 300.462 | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Metaphit (1-[1-(3-Isothiocyanato)phenyl]cyclohexylpiperidine) is a research chemical that acts as an acylator of NMDARAn, sigma & 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
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.