Adverts

Open Access Articles- Top Results for Gacyclidine

Gacyclidine

</th></tr>
Gacyclidine
150px
Systematic (IUPAC) name
1-[(1R,2S)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine
Clinical data
Identifiers
68134-81-6 7pxY
None
PubChem CID 176265
ChemSpider 153540 7pxN
UNII 9290ND070R 7pxY
Chemical data
Formula C16H25NS
263.4414 g/mol
 14pxN (what is this?)  (verify)

Gacyclidine[1] (GK-11)[2] is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP).[3][4]

Synthesis

The condensation of 2-methylcyclohexanone (I) with 2-thienyllithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with sodium azide (NaN3) in trichloroacetic acid to yield the azide (V). The reduction of (V) with lithium aluminium hydride (LiAlH4) or Raney nickel in isopropanol affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of potassium carbonate (K2CO3) in acetonitrile to provide the target compound as a diastereomeric mixture.[5]

See also

References

  1. ^ US patent 6107495, Jean-Bernard Cazaux, Michel Dafniet, Jean-Marc Kamenka, Eric Manginot, "Thienylcyclohexane derivatives for thienylcyclohexyl synthesis" 
  2. ^ Jacques Hamon, Florence Espaze, Jacques Vignon & Jean-Marc Kamenka (1999). "The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum". Eur. J. Med. Chem. 34 (2): 125–135. doi:10.1016/S0223-5234(99)80046-4. 
  3. ^ Hirbec H, Gaviria M, Vignon J. (2001). "Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor". CNS Drug Reviews 7 (2): 172–98. PMID 11474423. doi:10.1111/j.1527-3458.2001.tb00194.x. 
  4. ^ Hirbec H, Mausset AL, Kamenka JM, Privat A, Vignon J (2002). "Re-evaluation of phencyclidine low-affinity or "non-NMDA" binding sites". J Neurosci Res 68 (3): 305–314. PMID 12111860. doi:10.1002/jnr.10203. 
  5. ^ US patent 5179109, Jean-Marc Kamenka et al, "Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines" 


Lua error in package.lua at line 80: module 'Module:Buffer' not found.