Gacyclidine
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| Systematic (IUPAC) name | |
| 1-[(1R,2S)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 68134-81-6 |
| ATC code | None |
| PubChem | CID 176265 |
| ChemSpider | 153540 |
| UNII | 9290ND070R  |
| Chemical data | |
| Formula | C16H25NS |
| Mol. mass | 263.4414 g/mol |
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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]
[edit] Synthesis
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. [5]
[edit] See also
[edit] References
- ^ US Patent US 6107495
- ^ 'The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum' Jacques Hamon, Florence Espaze, Jacques Vignon & Jean-Marc KamenkaEur. (J. Med. Chem. 34 (1999) 125−135)
- ^ 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. "[1]"
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