Gacyclidine

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Gacyclidine
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Systematic (IUPAC) name
1-[(1R,2S)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine
Identifiers
CAS Number 68134-81-6
ATC code none
PubChem CID 176265
Chemical data
Formula C16H25NS
Molar mass 263.4414 g/mol[[Script error: No such module "String".]]
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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).[1][2]

Synthesis

Gacyclidine 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. [3]

See also

References

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Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
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Morphinans: Dextrallorphan • Dextromethorphan • Dextrorphan • Methorphan (Racemethorphan) • Morphan (Racemorphan);
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3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299
Miscellaneous
Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2
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  1. ↑ 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.
  2. ↑ 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.
  3. ↑ Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines. Jean-Marc Kamenka et al, 1993. "[1]"
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