Metaphit

Metaphit
IUPAC name 1-[1-(3-isothiocyanatophenyl)cyclohexyl]piperidine
Identifiers
PubChem	114745
ChemSpider	102730 Y
ChEMBL	CHEMBL41541 Y
Jmol-3D images	Image 1
SMILES S=C=N\c1cccc(c1)C3(N2CCCCC2)CCCCC3
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
Properties
Molecular formula	C18H24N2S
Molar mass	300.462
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 & 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

1. ^ A specific acylating agent for the [3H]phencyclidine receptors in rat brain. Rafferty MF, Mattson M, Jacobson AE, Rice KC. FEBS Lett. 1985 Feb 25;181(2):318-22.
2. ^ Metaphit fails to antagonize PCP-induced passive avoidance deficit. Danysz W. Department of Pharmacology, Institute of Psychiatry & Neurology, Warsaw, Poland.
3. ^ Metaphit, a proposed phencyclidine (PCP) antagonist, prevents PCP-induced locomotor behavior through mechanisms unrelated to specific blockade of PCP receptors Edward D. French, Neuroscience Program, Maryland Psychiatric Research Center, Baltimore, MD, USA. Arthur E. Jacobson, Kenner C. Rice. National Institute of Diabetes, Digestive and Kidney Diseases, Laboratory of Chemistry, National Institutes of Health, Bethesda, MD, U.S.A.
4. ^ Cocaine Receptor: Biochemical Characterization and Structure-Activity Relationships of Cocaine Analogues at Dopamine Transporter. F. Ivy Carroll, Anita H. Lewin, John W. Boja, and Michael J. Kuhar. Journal of Medicinal Chemistry Volume 35, Number 6