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Gacyclidine (GK-11) 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).
The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with Na-N3 in trichloroacetic acid to yield the azide (V). The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrile to provide the target compound as a diastereomeric mixture. 
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- ↑ Hirbec H, Gaviria M, Vignon J. Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor. CNS Drug Reviews. 2001 Summer;7(2):172-98.
- ↑ Hirbec H, Mausset AL, Kamenka JM, Privat A, Vignon J. Re-evaluation of phencyclidine low-affinity or "non-NMDA" binding sites. J Neurosci Res. 2002 May 1;68(3):305-14.
- ↑ Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines.
Jean-Marc Kamenka et al, 1993. ""