Gacyclidine

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Gacyclidine
Gacyclidine.png
Systematic (IUPAC) name
1-[(1R,2S)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine
Identifiers
CAS Number 68134-81-6 YesY
ATC code none
PubChem CID: 176265
ChemSpider 153540 N
UNII 9290ND070R YesY
ChEMBL CHEMBL1742478
Chemical data
Formula C16H25NS
Molecular mass 263.4414 g/mol
  • C[C@@H](CCCC1)[C@@]1(N2CCCCC2)C3=CC=CS3
  • InChI=1S/C16H25NS/c1-14-8-3-4-10-16(14,15-9-7-13-18-15)17-11-5-2-6-12-17/h7,9,13-14H,2-6,8,10-12H2,1H3/t14-,16+/m0/s1 N
  • Key:DKFAAPPUYWQKKF-GOEBONIOSA-N N
 NYesY (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]

Gacyclidine synthesis

See also

References

  1. ↑ US patent 6107495, Jean-Bernard Cazaux, Michel Dafniet, Jean-Marc Kamenka, Eric Manginot, "Thienylcyclohexane derivatives for thienylcyclohexyl synthesis" 
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ US patent 5179109, Jean-Marc Kamenka et al, "Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines" 


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