To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
Live Statistics
English Articles
Improved in 24 Hours
Added in 24 Hours
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
.
Leo
Newton
Brights
Milds

From Wikipedia, the free encyclopedia

Gacyclidine
Gacyclidine.png
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H25NS
Molar mass263.4414 g/mol g·mol−1
3D model (JSmol)
 ☒N☑Y (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. doi:10.1111/j.1527-3458.2001.tb00194.x. PMC 6741685. PMID 11474423.
  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. doi:10.1002/jnr.10203. PMID 12111860.
  5. ^ US patent 5179109, Jean-Marc Kamenka et al, "Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines" 


This page was last edited on 27 September 2019, at 16:02
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.